DE102006017000A1 - New chiral perylenes, perylene anhydride imides, perylene acetamimides and chiral naphthalene bisimides are useful e.g. as vat dyes e.g. to color textiles and in data memory devices - Google Patents

Abstract

Chiral perylene dyes (I-II), chiral perylene anhydride imides (III), chiral perylene acetamimides (IV) and chiral naphthalene bisimide compound (V), are new. Chiral perylene dye of formula (I-II), chiral perylene anhydride imide compound of formula (III), chiral perylene acetamimide compound of formula (IV) and chiral naphthalene bisimide compound of formula (V), are new. R1-R8H, F, Cl, Br, I or 1-37C alkyl (optionally interrupted by 1-10 T) (optionally substituted by 1-12 F, Cl, Br, I, CN or 1-18C-alkyl (optionally interrupted by 1-6 T) (optionally substituted by 1-12 F, Cl, Br, I, CN or 1-18C alkyl (optionally interrupted by 1-6 T))); and T : carbonyl, O, S, Se, Te, cis or trans-CH=CH- (where one CH is optionally replaced by N), Ctriple boundC, 1,2-, 1,3 - or 1,4-phenylene, 2,3-, 2,4-, 2,5-, 2,6-, 3,4 - or 3,5-pyridinediyl, 2,3-, 2,4-, 2,5- or 3,4-thiophenediyl, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-naphthalenediyl (where 1-2 ring C atoms is optionally replaced by N), 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-anthracenediyl (where 1-2 ring C atoms is optionally replaced by N). Preferably R1 and R2 are different and not H. Free valences of methine groups and/or quaternary carbon atoms may join to form a ring, e.g. cyclohexane.

Description

State of technology

chiral Dyes are gaining a growing interest in the art because with them on the one hand in principle unmistakable visual effects can be achieved and to another functional units their chirality e.g. transferred to liquid crystals can. In this way, the structure of a matrix can be controlled, e.g. in ferroelectric liquid crystals, while the light absorption and light emission with the arrangement of the chromophores is controlled. The perylene dyes [1,2], perylene-3,4: 9,10-tetracarboxylic bisimides (1), indicate good conditions for such applications her big one stability and high fluorescence quantum yields. The fact that at they have only one electron transition in the visible range [3], is one good condition for a targeted control of the optical properties. The nitrogen atoms of 1 are ideal positions to introduce chirality, because with them in the HOMO and in the LUMO orbital node [4], so that substituents on electronically efficiently decoupling these positions from the chromophore become. This combination of a chromophore with a chiral moiety allows it, both functionalities independently from each other.

task

The inventive task consisted in specifically targeted in light-absorbing compounds in certain Wavelength ranges induce strong CD effects so that they do not directly copy the UV / Vis absorption are thereby a unique, unmistakable Color effect arises, the e.g. For Safety markings can be used. In addition, should with such dyes the chiral information in ordered, microscopic Structures, such as liquid crystals imprinted can be.

description

A convenient starting material for the perylene dyes 1 is the perylene-3,4: 9,10-tetracarboxylic bisanhydride (2), correspondingly 1 directly with primary amines (R ¹ -NH ₂ ) can be condensed to bisimides 1. The synthesis problem is thus attributed to the representation of chiral, primary amines. For this purpose, the natural amino acids 4 are suitable as "chiral pool compounds" suitable starting materials.They are reduced with lithium alanate to the amino alcohols 5. For further reduction to the amines they are converted into the bis-tosylate 6, which with lithium aluminum hydride to the tosylamides Hydrogen bromide and phenol release amines 8. Condensation of these amines with bisanhydride 2 leads to symmetrically substituted perylene dyes 1 with two centers of chirality, but the vast majority of such perylene dyes are poorly soluble, so that they are only partially soluble For a wider application of chiral perylene dyes in homogeneous solution, one of the two nitrogen atoms of 1 is substituted with a solubility enhancing sec-alkyl radical ("dovetail radical"), such as the 1-hexylheptyl radical, and the chiral structure in the second introduced. For this purpose, the corresponding, at both nitrogen atoms symmetrically substituted perylenebisimide 1 is first synthesized and this then partially saponified to 9. The condensation of the anhydride imide 9 with the chiral amines then provides chiral, readily soluble perylenebisimides 10.

The chiral perylenebisimides 1 can also be partially hydrolyzed to the chiral anhydride imides 3, as e.g. For 1f or 1k has been shown, with the respective ring narrowed Lactams [5] were obtained as a by-product. The anhydride imides can in turn with any primary Amines to the unsymmetrically substituted, chiral Fabstoffen 3 are condensed.

The UV / Vis absorption and fluorescence spectra of the perylene dyes 1 and 10 with aliphatic chiral radicals R ¹ and R ² are as expected congruent with those with achiral, aliphtic radicals - see 5 -, so that these dyes are also visually indistinguishable. The CD effects of these chiral dyes are surprisingly small, despite the strong color. This is possible make it plausible on the basis of the type of electron excitation, which in the case of perylene dyes is a virtually pure π-π * excitation [6]. This results in a vanishingly small magnetic transition moment [7], so that a coupling of the electron system to the chiral information is without any significance. Add to this the flat geometry of the chromophore. This applies to both mobile chiral aliphatic radicals as in 1a and rigid radicals such as 1j. Hereby, one of the stated objectives is reached surprisingly efficiently. It is thus possible to use the UV / Vis absorption and the chiral information independently of one another in the case of dyes such as 1a to 1f or 1j.

If For perylene dyes CD effects are desired, then the chirality with a additional Mechanism can be induced in the chromophore. Ask for this Exciton interactions a suitable way, for which so far only two identical Perylenbisimid units in interaction have been brought and strong CD effects in the absorption range which have yielded dyes [8].

However, exciton effects are also expected in the interaction of different π systems [9,10,11]. We have therefore linked a 1-naphthyl residue via a tetravalent C atom as an electronic insulator with the nitrogen atoms of 1 and 3, respectively, and provided this C atom with a methyl group to generate the chirality, so that the chirality on a carboxylic imide N atom , the C atom 1 of the naphthyl residue, the C atom of the methyl group and a hydrogen atom is formed. In the thus designed dye 1h or 1i, which has been obtained by the condensation of 1- (1-Napthyl) ethylamine (8f or 8g) with 2, you will find the surprising CD spectra of 6 , In the strongly color-determining part of the spectrum of 1h or 1i, at about 530 nm, hardly any CD effect is observed. In the shorter-wavelength part of the spectrum, at 320 nm, on the other hand, considerably stronger CD effects occur, although the perylene bisimide chromophore absorbs the light considerably less - here, both the perylenebisimide chromophore and the 1-naphthyl radical absorb. To prove that the CD effect actually originates from an exciton interaction, the unsymmetrically substituted dye 10h or 10i has been synthesized analogously, which carries the achiral, solubility-enhancing residue 1-hexylheptyl on the second nitrogen atom. The CD spectrum of these dyes is very similar to the spectra of 1h or 1i, but with the difference that all CD effects are only half as large; this corresponds to half the number of 1-naphthyl radicals per perylenebisimide unit. To further prove the relationships, the analog naphthalene bisimide derivatives have been synthesized, which absorb shorter wavelengths compared to the perylene bisimides, in the ultraviolet range [12]. Accordingly, the spectral distance of these bisimides for absorption of the 1-naphthyl radical is smaller. It is consistently observed, in the short-wave range at 300 nm, similar CD effects, as in the Perylenbisimiden. The CD effects in the region of the longest wavelength absorption of the bisimides at 380 nm, however, are considerably stronger than for the perylene dyes at 530 nm as a result of the lower spectral distance of the absorptions.

These Results prove that maximum CD effects over the Exciton interactions of two different chromophores then expect if these light in a similar spectral range absorb. With increasing spectral distance of the absorption sites then the exciton effects become smaller. One can order the size of exciton effects over the Controlling the position of the absorption of side chains - by an absorption in the Shortwave range can be a chiral information in the visible range hide, since the effects only occur in the UV range, or you can use her strength systematically as needed by the location of the absorption of the side chain to adjust. Such possibilities are for Some technical applications of interest, as needed Systematically designing dyes. On the one hand, this is for things like security markings of interest, where a covert feature required is; the CD effect can be used in the ultraviolet range of polarizing filters, if necessary using λ / 4-plate or detected other optical components in a conventional manner be while in the visible range the conspicuous coloring the dyes does not give a CD effect. On the other hand, the dyes but also in applications such as in liquid crystals of interest, at which are e.g. the "helical-twisting power" regardless of the light absorption is to be adjusted. This has e.g. for liquid crystal displays Importance.

experimental part

L - (+) - isoleucineol (5b):

L - (+) - isoleucine (4b, 30.2 g, 229 mmol) was added in small portions with stirring under N ₂ atmosphere to a mixture of LiAlH ₄ powder (96%, 25.0 g, 586 mmol) and tert-butyl methyl ether (600 mL, 2 L flask), boiled under reflux for 24 h, cooled to room temperature, diluted with tert-butyl methyl ether (400 mL), carefully hydrolyzed with aqueous sodium hydroxide solution (30 mL, 10%) with cooling and stirred for 1 h. Of the The solid was filtered off with suction and washed three times with hot ether. The combined organic phases were dried with MgSO ₄ , the solvent was stripped off in vacuo and the residue was distilled under a fine vacuum. Y. 21.0 g (78.5%) of colorless, scaly leaflets of pentane, b.p. 66 ° C / 8 mbar, mp 38-39 ° C, [α] _D ²⁰ = + 2.08 ° (c = 2.07, in methanol); IR (KBr): ν ~ = 3348 cm ^-1 (s, NH ₂ ), 3259 (s, NH ₂ ), 3130 (m, OH), 2964 (s, CH ₂ / CH ₃ ), 2935 (s, CH ₂ / CH ₃ ), 2879 (s, CH ₂ / CH ₃ ), 1621 (s, NH ₂ ), 1578 (m), 1571 (m), 1467 (s, CH ₂ / CH ₃ ), 1436 (m) , 1403 (s, OH), 1355 (w), 1072 (s, CO), 1049 (m), 1032 (m); ¹ H NMR (CDCl _3): δ = 0.89 (d, 3 H, _CH3), 0.91 (t, 3 H, _CH3), 1.18 (m, 1 H, CH), 1:40 (m, 1 H, CH ₂ ), 1.50 (m, 1H, CH ₂ ), 2.70 (m, 1H, CH), 2.90 (s, 3H, NH ₂ / OH), 3.35 (dd, 1H, CH ₂ ), 3.65 (d. dd, 1 H, CH ₂ ); ¹³ C NMR (CDCl ₃ ): δ = 11.18 (1 C, CH ₃ ), 14.96 (1 C, CH ₃ ), 25.22 (1 C, CH ₂ ), 37.91 (1 C, CH), 56.91 (1 C, CH), 63.77 (1 C, CH ₂ ); MS (70 eV)): m / z (%) = 118 (1) [M ⁺ + H], 87 (5), 86 (100) [M ⁺ -CH ₂ OH], 69 (19), 60 ( 97) [M ⁺ -C ₄ H ₉ ], 56 (6), 44 (45), 42 (14), 41 (15), 30 (26), 28 (5).

L - (+) - Leucinol (5d):

L - (+) - leucine (4d, 30.2 g, 229 mmol) was reacted and worked up according to L - (+) - isoleucinol. Y. 20.2 g (75.2%) of colorless, viscous liquid, bp 78-82 ° C / 5 torr (ref. [13]: 100-105 ° C / 10 torr), [α] _D ²⁰ = + 4.38 ° (c = 2.19, in ethanol) (ref. [13]: [α] _D ¹⁷ = + 4.15 ° in ethanol); IR (film): ν ~ = 3353 cm ^-1 (s, NH ₂ ), 3277 (s, NH ₂ ), 3180 (s, OH), 2957 (s, CH ₂ / CH), 2915 (s, CH ₂ / CH ₃ ), 2871 (s, CH ₂ / CH ₃ ), 1593 (m, NH ₂ ), 1468 (s, CH ₂ / CH ₃ ), 1385 (m), 1367 (s, OH), 1171 (w ), 1150 (w), 1130 (w), 1058 (s, CO), 1021 (m), 940 (m), 885 (w), 837 (w), 811 (w), 668 (w), 465 (w); ¹ H NMR (CDCl ₃ ): δ = 0.76 (d, 3H, CH ₃ ), 0.77 (d, 3H, CH ₃ ), 1.04 (t, 2H, CH ₂ ), 1.56 (m, 1H, CH), 2.62 (br., 3H, NH ₂ / OH), 2.76 (m, 1H, CH), 3.09 (dd, 1H, CH ₂ ), 3.40 (dd, 1H, CH ₂ ); ¹³ C NMR (CDCl ₃ ): δ = 21.94 (1 C, CH ₃ ), 23.11 (1 C, CH ₃ ), 24.43 (1 C, CH ₂ ), 43.00 (1 C, CH), 50.36 (1 C, CH), 66.48 (1 C, CH ₂ ); MS (70 eV): m / z (%) = 118 (1) [M ⁺ + H], 87 (6), 86 (100) [M ⁺ -CH ₂ OH], 60 (35) [M ⁺ - C ₄ H ₉ ], 56 (3), 44 (55), 43 (17), 42 (12), 41 (11), 39 (4), 31 (2), 30 (48), 29 (2) , 28 (5), 27 (4).

L - (+) - valinol (5c):

L - (+) - valine (4c, 26.9 g, 230 mmol) was reacted and worked up according to L - (+) - isoleucinol. Y. 12.8 g (54%) of colorless, viscous liquid, bp 44 ° C / 0.25 torr (ref. [13]: 95-100 ° C / 10 torr), [α] _D ²⁰ = + 17.18 ° (c = 2.34, in ethanol) (ref. [14]: [α] _D ²⁰ = + 15.6 ° in ethanol); IR (film): ν ~ = 3353 cm ^-1 (s, NH ₂ ), 3290 (s, NH ₂ ), 3180 (s, OH), 2960 (s, CH ₂ / CH ₃ ), 2875 (s, CH ₂ / CH ₃ ), 1592 (m, NH ₂ ), 1466 (m, CH ₂ / CH ₃ ), 1388 (m), 1368 (m, OH), 1103 (w), 1055 (s, CO), 1012 (w), 933 (w), 874 (m), 615 (m); ¹ H NMR (CDCl ₃ ): δ = 0.80 (d, 3H, CH ₃ ), 0.82 (d, 3H, CH ₃ ), 1.49 (m, 1H, CH), 2.41 (br., 3H, NH ₂ / OH), 2.46 (m, 1 H, CH), 3.20 (dd, 1 H, CH ₂ ), 3.52 (dd, 1 H, CH ₂ ); ¹³ C NMR (CDCl ₃ ): δ = 18.20 (1 C, CH ₃ ), 19.16 (1 C, CH ₃ ), 30.96 (1 C, CH), 58.25 (1 C, CH), 64.35 (1 C, CH ); MS (70 eV): m / z (%) = 104 (2) [M ⁺ ], 73 (5), 72 (100) [M ⁺ -CH ₂ OH], 70 (2), 60 (68) [ M ⁺ -C ₃ H ₇ ], 57 (7), 56 (7), 55 (36), 44 (3), 43 (4), 42 (17), 41 (6), 39 (5), 31 (3), 30 (10), 29 (4), 28 (7), 27 (4).

N- (p-toluenesulfonyl) -L-isoleucinol-p-toluenesulfonic acid (6b):

Pyridine (47.5 g, 600 mmol) was added dropwise to an ice-cooled, stirred mixture of isoleucinol (5b, 11.7 g, 100 mmol) toluenesulfonyl chloride (57.2 g, 300 mmol) and chloroform (120 mL), stirred for 4 h at room temperature, with Ice (300 g) and conc. Hydrochloric acid (100 mL) was added and stirred until the ice had melted. The chloroform phase was separated, washed three times with water, dried with magnesium sulfate, evaporated in vacuo and the residue recrystallized. Y. 35.6 g (83.5%) of colorless crystals of methanol / n-pentane 10: 3, mp. 93-94.5 ° C, [α] _D ²⁰ = -29.81 ° (c = 2.10, in methanol); IR (KBr): ν ~ = 3276 (s, NH), 3041 (w, aryl), 2970 (s, CH ₂ / CH ₃ ), 2935 (m, CH ₂ / CH ₃ ), 2882 (m, CH ₂ / CH ₃ ), 1600 (m, aryl), 1498 (w, aryl), 1447 (s, CH ₂ / CH ₃ ), 1356 (s, SO ₂ -O), 1318 (s, SO ₂ -N), 1301 (s), 1193 (s), 1178 (s, SO ₂ -O), 1159 (s, SO ₂ -N), 1095 (s, CO), 1021 (m), 998 (s), 977 (s ), 945 (s), 901 (s), 841 (s), 814 (s, aryl), 668 (s), 627 (m), 557 (s), 535 (s) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0.73 (d, 3 H, _CH3), 0.75 (t, 3 H, _CH3), 0.94 (m, 1 H, CH), 1:40 (m, 1 H, CH _2), 1:59 (m, 1 H, CH _2), 2:41 (s, 3 H, _CH3), 2:45 (s, 3 H, _CH3), 3.22 (br., 1 H, CH), 3.82 (dd , 1 H, O-CH ₂ ), 3.98 (dd, 1 H, O-CH ₂ ), 4.88 (br., 1 H, NH), 7.25 (d, 2 H, O-Tos), 7.33 (d, 2 H, O-tosyl), 7.68 (d, 2 H, N-tosyl), 7.70 (d, 2 H, N-tosyl); ¹³ C NMR (CDCl ₃ ): δ = 11.05 (1 C, CH ₃ ), 14.89 (1 C, CH ₃ ), 21.47 (1 C, aryl-CH ₃ ), 21.61 (1 C, aryl-CH ₃ ), 24.52 (1 C, CH ₂ ), 35.73 (1 C, CH), 56.50 (1 C, N-CH), 69.06 (1 C, O-CH ₂ ), 127.02 (2 C, N-tosyl), 127.90 ( 2C, O-tosyl), 129.62 (2C, N-tosyl), 129.88 (2C, O-tosyl), 132.32 (1C, O-tosyl), 137.48 (1C, N-tosyl), 143.44 ( 1 C, N-tosyl), 145.07 (1 C, O-tosyl); MS (70 eV): m / z (%) = 369 (7), 368 (35) [M ⁺ -C ₄ H ₉ ], 240 (60) [M ⁺ -CH ₂ SO ₃ C ₆ H ₄ CH ₃ ], 196 (6), 184 (10), 157 (6), 155 (58) [SO ₂ C ₆ H ₄ CH ₃ ⁺ ], 139 (25), 99 (6), 98 (88) [C ₆ H ₁₂ N ⁺ ], 92 (16), 91 (100) [CH ₃ -C ₆ H ₄ ⁺ ], 89 (8), 70 (14), 69 (38), 65 (26) [C ₅ H ₅ ⁺ ], 63 (5), 56 (21), 42 (36) [C ₂ H ₄ N ⁺ ], 41 (28), 39 (13), 30 (20), 29 (9), 27 (6) ,

N- (p-toluenesulfonyl) -L-leucinol-p-toluenesulfonic acid (6d):

Leucinol (5d, 11.7 g, 100 mmol) was reacted and worked up corresponding to N- (p-toluenesulfonyl) -L-isoleucinol-p-toluenesulfonic acid ester. Y. 31.0 g (73%) of colorless crystals of toluene / petroleum ether 10: 1, mp. 99.5-102 ° C (ref. [15]: 103-104 ° C from ether / petroleum ether), [α] _D ²⁰ = -49.26 ° (c = 2.16, in ethanol) (ref. [15]: [α] _D ²⁰ = -55.4 ° in ethanol); IR (KBr): ν ~ = 3267 (s, NH), 2962 (s, CH ₂ / CH ₃ ), 1602 (w, aryl), 1496 (w, aryl), 1463 (m), 1455 (m, CH ₂ / CH ₃ ), 1431 (m, CH ₂ / CH ₃ ), 1327 (s, C-SO ₂ ), 1308 (m), 1289 (m), 1164 (s, C-SO ₂ ), 1095 (m , CO), 1069 (m), 949 (m), 816 (m), 808 (m), 697 (m), 676 (s), 575 (m), 547 (s) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0:54 (d, 3 H, _CH3), 0.70 (d, 3 H, _CH3), 1.21 (tt, 2 H, CH _2), 1:35 (m, 1 H, CH), 2:36 (s, 3 H, _CH3), 2:40 (s, 1 H, _CH3), 3:36 (m, 1 H, CH), 3.77 (dd, 1 H, CH _2), 3.88 (dd, 1 H, CH ₂ ), 4.74 (br., 1 H, NH), 7.21 (d, 2H, O-tosyl), 7.29 (d, 2H, O-tosyl), 7.64 (d, 2H, N Tosyl), 7.67 (d, 2H, N-tosyl); ¹³ C NMR (CDCl ₃ ): δ = 21.46 (2 C, aryl-CH ₃ ), 21.61 (1 C, CH ₃ ), 22.64 (1 C, CH ₃ ), 24.01 (1 C, CH ₂ ), 40.77 ( 1 C, CH), 50.62 (1 C, N-CH), 71.55 (1 C, O-CH ₂ ), 127.01 (2 C, O -tosyl), 127.92 (2 C, N -tosyl), 129.65 (2 C, O-tosyl), 129.90 (2 C, N -tosyl), 132.38 (1 C, O -tosyl), 137.49 (1 C, N -tosyl), 143.53 (1 C, O-tosyl), 145.07 (1 C, N-tosyl); MS (70 eV): m / z (%) = 425 (0.2) [M ⁺ ], 368 (2) [M ⁺ -C ₄ H ₉ ], 242 (5), 241 (13), 240 (100) [M ⁺ -CH ₂ SO ₃ C ₆ H ₄ CH ₃ ], 210 (3), 184 (14), 157 (2), 156 (4), 155 (45) [SO ₂ C ₆ H ₄ CH ₃ ⁺ ], 139 (7), 125 (3), 111 (5), 109 (4), 98 (26) [C ₆ H ₁₂ N ⁺ ], 97 (7), 95 (5), 92 (10), 91 (63) [CH ₃ -C ₆ H ₄ ^+], 89 (4) 85 (4), 83 (6), 82 (5), 81 (6), 71 (6), 69 (9) 67 (4), 65 (12) [C ₅ H ₅ ⁺ ], 64 (3), 57 (9), 56 (3), 56 (10), 55 (9), 43 (11), 42 (57 ) [C ₂ H ₄ N ⁺ ], 41 (13), 39 (6), 28 (3), 27 (4).

N- (p-toluenesulfonyl) -L-valinol-p-toluenesulfonic acid (6c):

Valinol (5c, 10.3 g, 100 mmol) was reacted and worked up corresponding to N- (p-toluenesulfonyl) -L-isoleucinol-p-toluenesulfonic acid ester. Y. 32.3 g (79%) of colorless needles of toluene / petroleum ether 10: 1, mp 104-106 ° C (ref. [15]: 110-111 ° C in ethanol), [α] _D ²⁰ = -33.90 ° (c = 1.60 in ethanol) (ref. [15]): [α] D ²⁰ = -57.2 ° in chloroform); IR (KBr): ν ~ = 3279 (m, NH), 2966 (m, CH ₂ / CH ₃ ), 1599 (m, aryl), 1444 (m, aryl), 1361 (s, SO ₂ -O), 1324 (m, SO ₂ -N), 1309 (w), 1191 (m), 1179 (s, SO ₂ -O), 1160 (s, SO ₂ -N), 1093 (m), 983 (m), 964 (m), 952 (m), 848 (w), 815 (m), 668 (s), 572 (w), 557 (m) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0.74 (d, 3 H, _CH3), 0.76 (d, 3 H, _CH3), 2:07 (m, 1 H, CH), 2:41 (s, 3 H, CH _3), 2:45 (s, 3 H, _CH3), 3.15 (m, 1 H, CH), 3.81 (dd, 1 H, CH _2), 3.99 (dd, 1 H, CH _2), 4.94 (d, 1H, NH), 7.26 (d, 2H, tosyl), 7.33 (d, 2H, tosyl), 7.69 (d, 2H, tosyl), 7.71 (d, 2H, tosyl); ¹³ C NMR (CDCl _3): δ = 17.77 (1 C, CH _3), 18.90 (1 C, CH _3), 21:53 (1 C, CH _3), 21.66 (1 C, CH _3), 28.92 (1 C , CH), 57.64 (1 C, CH), 69.31 (1 C, CH ₂ ), 127.07 (2 C, tosyl), 127.96 (2 C, tosyl), 129.67 (2 C, tosyl), 129.95 (2 C, Tosyl), 132.35 (1 C, tosyl), 137.50 (1 C, tosyl), 143.51 (1 C, tosyl), 145.13 (1 C, tosyl); MS (70 eV): m / z (%) = 412 (0.2) [M ⁺ + H], 370 (5), 369 (9), 368 (43) [M ⁺ -C ₃ H ₇ ], 228 ( 5), 227 (13), 226 (100) [M ⁺ -CH ₂ SO ₃ C ₆ H ₄ CH ₃ ], 196 (8), 157 (8), 156 (7), 155 (68) [SO ₂ C ₆ H ₄ CH ₃ ^+], 140 (3), 139 (33), 92 (12), 91 (75) [CH ₃ -C ₆ H ₄ ^+], 90 (3) 89 (3), 84 (31) [C ₅ H ₁₀ N ⁺ ], 70 (3), 65 (11) [C ₅ H ₅ ⁺ ], 64 (3), 56 (5), 55 (8), 42 (3) [C ₂ H ₄ N ⁺ ], 41 (5), 39 (4).

N- (p-toluenesulfonyl) -L-2-amino-1-butanol p-toluenesulfonic (6a):

L-2-amino-1-butanol (5a, 8.91 g, 100 mmol, [α] _D ²⁰ = -9.50 °) was reacted and worked up in accordance with N- (p-toluenesulfonyl) -L-isoleucinol-p-toluenesulfonic acid ester. Y. 33.1 g (83%) of colorless, finely powdered crystals of methanol / n-pentane 10: 4, mp. 94-95 ° C, [α] _D ²⁰ = + 55.82 ° (c = 2.14, in methanol); IR (KBr): ν ~ = 3350 (s, NH), 3070 (w, aryl), 2978 (m, CH ₂ / CH ₃ ), 2944 (m, CH ₂ / CH ₃ ), 2886 (w, CH ₂ / CH ₃ ), 1598 (s, aryl), 1498 (m, aryl), 1460 (m, CH ₂ / CH ₃ ), 1432 (m, CH ₂ / CH ₃ ), 1400 (m), 1359 (s, SO ₂ -O), 1341 (m), 1323 (s, SO ₂ -N), 1191 (s), 1180 (s, SO ₂ -O), 1165 (s, SO ₂ -N), 1147 (m) , 1092 (s, CO), 1025 (m), 975 (s), 953 (m), 880 (m), 823 (s), 818 (s, aryl), 784 (m), 772 (m), 663 (s), 579 (m), 552 (s) cm ^-1 ; ¹ H NMR (CDCl ₃ ): δ = 0.70 (t, 3H, CH ₃ ), 1.39 (m, 1H, CH ₂ ), 1.52 (m, 1H, CH ₂ ), 2.41 (s, 3H, CH _3), 2:45 (s, 3 H, _CH3), 3.29 (m, 1 H, N-CH), 3.83 (dd, 1 H, O-CH _2), 3.97 (dd, 1 H, O-CH ₂ ), 5.01 (d, 1H, NH), 7.26 (d, 2H, O-tosyl), 7.33 (d, 2H, O-tosyl), 7.70 (d, 2H, N-tosyl), 7.72 (d, 2H, N-tosyl); ¹³ C NMR (CDCl ₃ ): δ = 9.68 (1 C, CH ₃ ), 21.43 (1 C, aryl-CH ₃ ), 21.56 (1 C, aryl-CH ₃ ), 24.62 (1 C, CH ₂ ), 53.84 (1C, N-CH), 70.71 (1C, O-CH ₂ ), 126.93 (2C, N-tosyl), 127.87 (2C, O-tosyl), 129.62 (2C, N-tosyl). , 129.88 (2C, O-tosyl), 132.33 (1C, O-tosyl), 11.9 (1C, N-tosyl), 143.44 (1C, N-tosyl), 145.04 (1C, O-tosyl). , - MS (70 eV): m / z (%) = 397 [M ⁺ ], 368 (0.5) [M ⁺ -C ₂ H ₅ ], 242 [M ⁺ -SO ₂ C ₆ H ₄ CH ₃ ], 213 (2), 212 (22) [M ⁺ -CH ₂ SO ₃ C ₆ H ₄ CH ₃ ], 155 (13) [SO ₂ C ₆ H ₄ CH ₃ ⁺ ], 139 (3), 105 (2) 92 (5), 91 (31) [CH ₃ -C ₆ H ₄ ⁺ ], 89 (3), 71 (5), 70 (100) [C ₄ H ₈ N ⁺ ], 65 (11) [C ₅ H ₅ ⁺ ], 63 (2), 44 (16), 42 (16) [C ₂ H ₄ N ⁺ ], 41 (15), 39 (4), 28 (2).

N- (p-toluenesulfonyl) -L-2-amino-3-methyl-pentane (7b):

N- (p-toluenesulfonyl) -L-isoleucinol p-toluenesulfonic acid ester (6b, 42.5 g, 200 mmol) in tert-butyl methyl ether (600 mL) was added dropwise under N ₂ atmosphere to lithium aluminum hydride powder (96%, 11.0 g, 278 mmol) in tert-butyl methyl ether (500 mL), refluxed for 24 h with stirring, allowed to cool, hydrolyzed by careful addition of 10% aqueous NaOH (15 mL) and stirred for 1 h. The solid was separated and extracted three times with hot tert-butyl methyl ether. The combined organic phases were dried with magnesium sulfate and evaporated. The oily residue was recrystallized from low boiling petroleum ether. Y. 9.06 g (36%) of colorless plates mp 39-40 ° C, [α] _D ²⁰ = + 30.90 ° (c = 2.09, in methanol); IR (KBr): ν ~ = 3307 (s, NH), 2970 (s, CH ₂ / CH ₃ ), 2913 (m, CH ₂ / CH ₃ ), 2879 (m, CH ₂ / CH ₃ ), 1599 ( w, aryl), 1495 (w, aryl), 1460 (m, CH ₂ / CH ₃ ), 1430 (m, CH ₃ ), 1383 (m), 1334 (s, SO ₂ -N), 1303 (s) , 1288 (m), 1162 (s, SO ₂ -N), 1113 (m), 1092 (s), 946 (w), 816 (s, aryl), 668 (s), 608 (w), 556 ( s), 545 (s) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0.78 (d, 3 H, _CH3), 0.81 (t, 3 H, _CH3), 0.90 (d, 3 H, _CH3), 1:02 (m, 1 H, CH), 1:35 (m, 2 H, CH _2), 2:42 (s, 3 H, _CH3), 3.26 (m, 1 H, N-CH), 4.71 (d, 1 H, NH), 7.29 (d , 2H, tosyl), 7.77 (d, 2H, tosyl); ¹³ C NMR (CDCl ₃ ): δ = 11.65 (1 C, CH ₃ ), 13.92 (1 C, CH ₃ ), 16.81 (1 C, CH ₃ ), 21.45 (1 C, aryl-CH ₃ ), 25.57 ( 1 C, CH ₃ ), 40.02 (1 C, CH), 53.42 (1 C, N-CH), 127.02 (2 C, tosyl), 129.54 (2 C, tosyl), 138.33 (1 C, tosyl), 143.03 (1C, tosyl); MS (70 eV): m / z (%) = 255 (0.2) [M ⁺ ], 240 (0.6) [M ⁺ -CH ₃ ], 200 (5) 199 (11), 198 (100) [M ⁺ -C ₄ H ₉ ], 157 (3), 156 (5), 155 (59) [SO ₂ C ₆ H ₄ CH ₃ ⁺ ], 92 (4), 91 (41) [CH ₃ -C ₆ H ₄ ⁺ ], 65 (6) [C ₅ H ₅ ⁺ ], 44 (2), 42 (1), 41 (3), 39 (2), 29 (1).

N-p-toluenesulfonyl-L-2-amino-4-methyl-pentane (7d):

N- (p-toluenesulfonyl) -L-leucinol-p-toluenesulfonic acid ester (6d, 42.6 g, 100 mmol) in tert-butyl methyl ether (200 mL), lithium aluminum hydride powder (96%, 10.6 g, 280 mmol) in tert-butyl methyl ether ( 220 mL) and aqueous NaOH (10%, 15 mL) were reacted corresponding to N- (p-toluenesulfonyl) -L-2-amino-3-methyl-pentane and worked up. Y. 20.7 g (81%) of colorless crystal needles of low-boiling petroleum ether, mp 59-61 ° C (ref. [16] 62-63 ° C, [α] _D ²⁰ = + 4.14 ° (c = 2.03, in ethanol) (ref [16] [α] _D ¹⁸ = + 1.4 ° in ethanol) IR (KBr): ν ~ = 3242 (s, NH), 3068 (w, aryl), 3050 (w, aryl), 3034 (w, Aryl), 2973 (s, CH ₂ / CH ₃ ), 2955 (s, CH ₂ / CH ₃ ), 2868 (m, CH ₂ / CH ₃ ), 1602 (m, aryl), 1497 (m, aryl), 1464 (m, CH ₂ / CH ₃ ), 1454 (m, CH ₂ / CH ₃ ), 1329 (s), 1317 (s, SO ₂ -N), 1306 (s), 1169 (s, SO ₂ -N ), 1150 (s), 1096 (s), 1028 (s), 962 (s), 901 (m), 816 (s), 709 (m), 681 (s), 578 (s), 515 (s ) cm ^{-1; 1} H NMR (CDCl _3): δ = 0.67 (d, 3 H, _CH3), 0.74 (d, 3 H, _CH3), 0.95 (d, 3 H, _CH3) 1.08 ( dd, 1 H, CH _2), 1.22 (dd, 1 H, CH _2), 1:53 (m, 1 H, CH), 2:37 (s, 3 H, _CH3), 3.82 (m, 1 H, CH) , 4.75, 7.25 (d, 2H, aryl), 7.74 (d, 2H, aryl); ¹³ C NMR _(CDCl3) (br, 1H, NH.): δ = 21:40 (1 C, _CH3) , 22.6 (2 C, CH _3), 22:47 (1 C, CH _3), 24.46 (1C, CH _2), 46.93 (1 C, CH), 48.14 (1 C, CH), 126.99 (2 C, tosyl ) 129.49 (2C, tosyl), 138.35 (1C, tosyl), 142.99 (1C, tosyl); MS (70 eV): m / z (%) = 255 (0.2) [M ⁺ ], 240 (4) [M ⁺ -CH ₃ ], 200 (4), 199 (9), 198 (100) [M ⁺ -C ₄ H ₉ ], 171 (2), 156 (3), 155 (5) [SO ₂ C ₆ H ₄ CH ₃ ⁺ ], 154 (71), 92 (6), 91 (57) [CH ₃ -C ₆ H ₄ ⁺ ], 88 (3), 84 (3), 65 (8) [C ₅ H ₅ ⁺ ], 44 (3), 43 (3), 42 (3), 41 (5) , 39 (4), 28 (2).

N-p-toluenesulfonyl-L-2-amino-3-methylbutane (7c):

N- (p-toluenesulfonyl) -L-valinol p-toluenesulfonic acid ester (6c, 25.0 g, 61.8 mmol) in tert-butyl methyl ether (200 mL), lithium aluminum hydride powder (96%, 7.00 g, 177 mmol) in tert-butyl methyl ether ( 300 ml) and aqueous NaOH (10%, 10 ml) were reacted in accordance with N- (p-toluenesulfonyl) -L-2-amino-3-methylpentane and worked up and recrystallized from low-boiling petroleum ether. Y. 10.3 g (69%) of colorless platelets, mp 43-45 ° C from ethanol (Ref. [16] 44-46 ° C), [α] _D ²⁰ = + 18.16 ° (c = 2.07 in ethanol) (ref. [16] [α] _D ²⁰ = 22.6 ° in ethanol); IR (KBr): ν ~ = 3280 (s, NH), 3258 (s, NH), 3068 (w, aryl), 3052 (w, aryl), 2963 (s, CH ₃ ), 2876 (m, CH ₃ ), 1598 (m, aryl), 1497 (w, aryl), 1466 (m, CH ₃ ), 1431 (m, CH ₃ ), 1415 (m, CH ₃ ), 1323 (s, SO ₂ -N), 1305 (s), 1290 (m), 1166 (s, SO ₂ -N), 1119 (w), 1094 (s), 1036 (m), 967 (m), 815 (m), 708 (w), 670 (s), 593 (s), 555 (s), 540 (m) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0.81 (d, 6 H, _CH3), 0.91 (d, 3 H, _CH3), 1.63 (m, 1 H, CH), 2:42 (s, 3 H, CH ₃ ), 3.15 (m, 1H, CH), 4.94 (d, 1H, NH), 7.29 (d, 2H, tosyl), 7.79 (d, 2H, tosyl); ¹³ C NMR (CDCl _3): δ = 17.87 (1 C, CH _3), 17.96 (1 C, CH _3), 18:15 (1 C, CH _3), 21:49 (1 C, CH _3), 33.40 (1 C , CH), 54.91 (1 C, CH), 127.06 (2 C, tosyl), 129.56 (2 C, tosyl), 138.42 (1 C, tosyl), 143.03 (1 C, tosyl); MS (70 eV): m / z (%) = 241 (0.3) [M ⁺ ], 200 (5), 199 (10), 198 (100) [M ⁺ -C ₃ H ₇ ], 157 (4) , 156 (6), 155 (75) [SO ₂ C ₆ H ₄ CH ₃ ⁺ ], 92 (6), 91 (55) [CH ₃ -C ₆ H ₄ ⁺ ], 89 (2), 65 (8 ) [C ₅ H ₅ ⁺ ], 43 (2), 41 (3), 39 (3), 28 (6).

N- (p-toluenesulfonyl) -L-2-aminobutane (7a):

N- (p-toluenesulfonyl) -L-2-amino-1-butanol-p-toluenesulfonic acid ester (6a, 50.1 g, 126 mmol) in tert-butyl methyl ether (750 mL), lithium aluminum hydride powder (96%, 13.8 g, 349 mmol ) in tert-butyl methyl ether (650 ml) and aqueous NaOH (10%, 20 ml) were correspondingly N- (p-toluenesulfonyl) -L-2-amino-3-methylpentane reacted and worked up. Y. 19.0 g (66%) colorless prisms of petroleum ether / ether 1: 4, mp. 59-60 ° C, [α] _D ²⁰ = + 1.06 ° (c = 2.08, in methanol); IR (KBr): ν ~ = 3287 (s, NH), 3060 (w, aryl), 2965 (m, CH ₂ / CH ₃ ), 2933 (m, CH ₂ / CH ₃ ), 2874 (m, CH ₂ / CH ₃ ), 1597 (w, aryl), 1494 (w, aryl), 1463 (m, CH ₂ / CH ₃ ), 1455 (m), 1434 (m, CH ₃ ), 1424 (m), 1376 ( w), 1339 (m), 1317 (s, SO ₂ -N), 1305 (s), 1154 (s, SO ₂ -N), 1142 (s), 1094 (s), 1038 (s), 1010 ( s), 961 (m), 816 (m, aryl), 665 (s), 582 (s), 553 (m) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0.79 (t, 3 H, _CH3), 1:01 (d, 3 H, _CH3), 1:40 (quint, 2 H, CH _2), 2:42 (s, 3 H, CH ₃ ), 3.22 (quint, 1H, N-CH), 4.93 (d, 1H, NH), 7.29 (d, 2H, tosyl), 7.79 (d, 2H, tosyl); ¹³ C NMR (CDCl ₃ ): δ = 9.82 (1 C, CH ₃ ), 20.95 (1 C, CH ₃ ), 21.40 (1 C, aryl-CH ₃ ), 30.12 (1C, CH _2), 51.28 (1 C, N-CH), 126.94 (2 C, tosyl), 129.49 (2 C, tosyl), 138.31 (1 C, tosyl), 142.97 (1 C, tosyl) ; MS (70 eV): m / z (%) = 227 (0.6) [M ⁺ ], 212 (5) [M ⁺ -CH ₃ ], 199 (11), 198 (100) [M ⁺ -C ₂ H ₅ ], 157 (5), 156 (7), 155 (93) [SO ₂ C ₆ H ₄ CH ₃ ⁺ ], 92 (7), 91 (72) [CH ₃ -C ₆ H ₄ ⁺ ], 89 (3), 65 (10) [C ₅ H ₅ ⁺ ], 39 (2).

L-2-amino-3-methyl pentan-hydrobromide (8b):

N- (p-toluenesulfonyl) -L-2-amino-3-methylpentane (7b, 5.11 g, 20.0 mmol), phenol (4.00 g, 42.5 mmol) and 30% hydrobromic acid in glacial acetic acid (40 mL) were added under exclusion of atmospheric moisture (CaCl ₂ tube) 8d reacted at 40 ° C, poured into anhydrous ether (150 mL), allowed to stand for 3 d at -30 ° C, filtered off, washed with anhydrous ether and dried in vacuo; the crystals are very hygroscopic. Y. 1.35 g (37%) of colorless, flaky crystals, mp 139 ° C, [α] _D ²⁰ = -0.78 ° (c = 2.05, in methanol); IR (KBr): ν ~ = 2997 (s, br., NH ₃ ⁺ ), 2713 (w, CH ₂ / CH ₃ ), 2671 (w, CH ₂ / CH ₃ ), 2567/2503 (w, NH ₃ ⁺ ), 1949 (w, NH ₃ ⁺ ), 1596/1585 (s, NH ₃ ⁺ ), 1499 (s, NH ₃ ⁺ ), 1461 (m, CH ₂ / CH ₃ ), 1394 (m, CH ₃ ) , 1212 (m), 1177 (w), 1132 (w), 1120 (m), 1077 (w), 957 (w) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0.95 (t, 3 H, _CH3), 1:04 (d, 3 H, _CH3), 1.28 (m, 1 H, CH _2), 1:37 (d, 3 H, CH ₃ ), 1.52 (m, 1H, CH ₂ ), 1.87 (m, 1H, CH), 3.40 (br., 1H, N-CH), 8.07 (br., 3H, NH ₃ ⁺ ) ; ¹³ C NMR (CDCl _3): δ = 11:35 (1 C, CH _3), 13.86 (1 C, CH _3), 14:47 (1 C, CH _3), 25.91 (1C, CH _2), 37.80 (1 C , CH), 52.47 (1 C, N-CH); MS (70 eV): m / z (%) = 283 (0.1) [2 (M ⁺ +1) + Br], 102 (0.4) [M ⁺ + H], 100 (0.4) [M ⁺ -H] , 86 (1) [M ⁺ -CH ₃ ], 82 (2) [HBr], 81 (1) [Br], 80 (2) [HBr], 79 (1) [Br], 72 (1), 70 (1), 69 (2) [86-NH ₃ ], 57 (1), 56 (1), 55 (2), 45 (2), 44 (100) [M ⁺ -C ₄ H ₉ ], 43 (2), 42 (3), 41 (3), 39 (1), 30 (2), 29 (1).

L-2-amino-4-methylpentane hydrobromide (8d):

N- (p-toluenesulfonyl) -L-2-amino-4-methylpentane (7d, 5.11 g, 20.0 mmol), phenol (4.00 g, 42.5 mmol) and hydrobromic acid in glacial acetic acid (30%, 40 mL) were 2-amino-3-methylpentane hydrobromide reacted and worked up to form colorless crystals after 3 h. Y. 2.11 g (58%) of colorless, small, matted needles, mp 178-179 ° C; [α] _D ²⁰ = + 5.66 ° (c = 2.05, in methanol); IR (KBr): ν ~ = 3036 (s, NH ₃ ⁺ ), 2964/2919 (s, CH ₂ / CH ₃ ), 2782 (w), 2698 (w), 2551 (w, NH ₃ ⁺ ), 1985 (w, br., NH ₃ ⁺ ), 1608/1595 (m, NH ₃ ⁺ ), 1505 (s, NH ₃ ⁺ ), 1472 (m), 1464 (m, CH ₂ / CH ₃ ), 1436 (w ), 1391 (m, CH ₃ ), 1368 (w), 1179 (w), 1156 (w) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 0.93 (d, 3 H, _CH3), 0.97 (d, 3 H, _CH3), 1:46 (d, 3 H, _CH3), 1:51 (q, 1 H, CH ₂ ), 1.75 (q, 1H, CH ₂ ), 1.81 (o, 1H, CH), 3.51 (m, 1H, N-CH), 8.04 (br., 3H, NH ₃ ⁺ ); ¹³ C NMR (CDCl _3): δ = 18.87 (1 C, CH _3), 21.89 (1 C, CH _3), 22:53 (1 C, CH _3), 24.52 (1C, CH _2), 43.79 (1 C , CH), 47.31 (1 C, N-CH); MS (70 eV): m / z (%) = 102 (0.5) [M ⁺ +1], 101 (1) [M ⁺ ], 100 (1) [M ⁺ -H], 86 (4) [M ⁺ -CH ₃ ], 82 (6) [HBr], 81 (2) [Br], 80 (6) [HBr], 79 (2) [Br], 69 (2) [86-NH ₃ ], 58 (2), 57 (1), 45 (2), 44 (100) [M ⁺ -C ₄ H ₉ ], 43 (4), 42 (4), 41 (5), 39 (3), 30 ( 5), 28 (2), 27 (2) [44-NH ₃ ].

L-2-amino-3-methylbutanoic acid hydrobromide (8c):

N-Toluenesulfonyl-L-2-amino-3-methylbutane (7c, 3.02 g, 12.5 mmol), phenol (2.00 g, 21.2 mmol) and hydrobromic acid in glacial acetic acid (30%, 20 mL) were analogous to L-2-amino 3-methyl-pentane-hydrobromide reacted and worked up to form a colorless solid after 3 h. Y. 1.27 g (63%) colorless, small, matted needles, mp 215-218 ° C; [α] _D ²⁰ = + 1.13 ° (c = 1.95, in methanol); IR (KBr): ν ~ = 3032 (s, NH ₃ ⁺ ), 2967/2924 (s, CH ₂ / CH ₃ ), 2530 (w, NH ₃ ⁺ ), 1616/1597 (m, NH ₃ ⁺ ), 1503 (s, NH ₃ ⁺ ), 1472/1459 (m, CH ₂ / CH ₃ ), 1398 (m, CH ₃ ), 1390 (m) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 1:05 (d, 3 H, _CH3), 1:09 (d, 3 H, _CH3), 1:42 (d, 3 H, _CH3), 2:05 (oct, 1 H, CH), 3.26 (quint, 1H, N-CH), 8.07 (br., 3H, NH ₃ ⁺ ); ¹³ C NMR (CDCl ₃ ): δ = 15.42 (1 C, CH ₃ ), 17.73 (1 C, CH ₃ ), 18.97 (1 C, CH ₃ ), 31.64 (1 C, CH), 54.15 (1 C, N-CH); MS (70 eV): m / z (%) = 86 (1) [M ⁺ -H], 82 (6) [HBr], 81 (2) [Br], 80 (6) [HBr], 79 ( 2) [Br], 72 (4) [M ⁺ -CH ₃ ], 71 (1), 70 (2), 69 (1), 57 (2), 56 (2), 55 (8) [72- NH ₃ ], 45 (2), 44 (100) [M ⁺ -C ₃ H ₇ ], 43 (3), 42 (4), 41 (3), 39 (2), 30 (1), 28 ( 2), 27 (2) [44-NH ₃ ].

L-2-aminobutane hydrobromide (8a):

N-Toluenesulfonyl-L-2-aminobutane (7a, 20.0 g, 87.9 mmol), phenol (17.0 g, 181 mmol) and hydrobromic acid in glacial acetic acid (30%, 170 mL) were prepared according to L-2-amino-3-methylpentane. implemented hydrobromide and worked up. Y. 9.70 g (72%) of colorless, fibrous crystals, mp 147-149 ° C, [α] _D ²⁰ = -1.30 ° (c = 2.00, in methanol); IR (KBr): ν ~ = 3030/2968 (s, br., NH ₃ ⁺ ), 2788 (m, CH ₂ / CH ₃ ), 2702 (w, CH ₂ / CH ₃ ), 2517 (w, NH ₃ ⁺ ), 2010 (w, NH ₃ ⁺ ), 1616 (m, NH ₃ ⁺ ), 1503 (s, NH ₃ ⁺ ), 1462 (m, CH ₂ / CH ₃ ), 1391 (m, CH ₃ ), 1194 (w), 1150 (w), 1010 (w) cm ^-1 ; ¹ H NMR (CDCl _3): δ = 1:06 (t, 3 H, _CH3), 1:47 (d, 3 H, _CH3), 1.73 (m, 1 H, CH _2), 1.91 (m, 1 H, CH ₂ ), 3.41 (m, 1H, CH), 8.03 (br., 3H, NH ₃ ⁺ ); ¹³ C NMR (CDCl ₃ ): δ = 10.14 (1 C, CH ₃ ), 18.26 (1 C, CH ₃ ), 27.95 (1 C, CH ₂ ), 50.44 (1 C, CH); MS (70 eV): m / z (%) = 229 (0.2) [2 (M ⁺ +1) + Br], 227 (0.2) [2 (M ⁺ +1) + Br], 82 (15) [ HBr], 81 (5) [Br], 80 (15) [HBr], 79 (5) [Br], 74 (1) [M ⁺ + H], 73 (1) [M ⁺ ], 72 (3 ) [M ⁺ -H], 58 (12) [M ⁺ -CH ₃ ], 57 (3), 56 (3), 54 (4), 45 (3), 44 (100) [M ⁺ -C ₂ H ₅ ], 43 (3), 42 (6), 41 (9) [58-NH ₃ ], 39 (2), 30 (3), 29 (2).

N, N'-di- (L-1-methyl-2-phenylethyl) pearl-3,4: 9,10-tetracarbonsäurebisimid (1g):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (2.00 g, 5.10 mmol, L - (-) - 2-amino-1-phenylpropane (1.50 g, 11.1 mmol, [α] _D ²⁰ = -34.40 ° at c = 1.50 in ethanol) and imidazole (20 g) were heated under argon at 160 ° C for 1 h, cooled, with ethanol (200 mL) to form a homogeneous suspension, then with 2N HCl (400 mL), 1 h stirred, filtered off with suction (D4 glass filter), boiled with aqueous K ₂ CO ₃ (10%, 1 L), filtered off, washed with distilled water, dried at 120 ° C in air, dissolved in chloroform, filtered and purified by column chromatography (silica gel, Chloroform) 2.82 g (88.2%) of chloroform extractively [17] recrystallized, mp> 330 ° C; R _f (silica gel, CHCl ₃ ): 0.15; IR (KBr): ν ~ = 3070 (w, aryl ), 3030 (w, aryl), 2970/2940 (w, CH ₂ / CH ₃ ), 1695 (s, C = O), 1655 (s, C = O), 1595/1580 (s, aryl), 1435 (m), 1405 (s, CH ₂ / CH ₃ ), 1342 (s, CH ₃ ), 1258 (s, CN), 1180 (m), 1130 (w), 812 (s, aryl), 749 (s , Aryl), 702 (s, aryl) cm ^-1 , UV / Vis (CHCl _3): λ _max (ε) = 459.5 (18450), 490.5 (51410), 527.0 nm (86480); Fluorescence (CHCl ₃ ): λ _max = 541.5, 573.0 nm; ¹ H NMR (CDCl ₃ ): δ = 1.66 (d, 6H, CH ₃ ), 3.30 (dd, 2H, CH ₂ ), 3.50 (dd, 2H, CH ₂ ), 5.62 (sec., 2H , N-CH), 7.10 (t, 2H, phenyl), 7.19 (t, 4H, phenyl), 7.27 (d, 4H, phenyl), 8.53 (d, 4H, perylene), 8.60 (d, 4H, perylene); ¹³ C NMR (CDCl ₃ ): δ = 17.74 (2 C, CH ₃ ), 39.81 (2 C, CH ₂ ), 50.89 (2 C, N-CH), 122.98 (4 CH, aryl), 124.43 (4C , Aryl), 126.29 (2 CH, phenyl), 126.34 (2 C, aryl), 128.33 (4 CH, phenyl), 129.10 (4 CH, phenyl), 129.40 (2 C, perylene), 131.37 (4 CH, perylene ), 134.50 (4 C, perylene), 139.05 (2 C, phenyl), 163.80 (4 C = O, perylene); MS (70 eV): m / z (%) = 627 (9), 626 (19) [M ⁺ ], 536 (9), 535 (24) [M ⁺ -C ₆ H ₅ CH ₂ ], 510 ( 3), 509 (11), 508 (22) [M ⁺ -C ₆ H ₅ C ₃ H ₅ ], 418 (7), 417 (22) [508-C ₆ H ₅ CH ₂ ], 392 (6) , 391 (34), 390 (100) [508-C ₆ H ₅ C ₃ H _5], 374 (4), 373 (17) [390-OH], 346 (4), 345 (10) [373- CO], 320 (2), 289 (2), 200 (2), 178 (3), 118 (7), 117 (8), 115 (4), 98 (4), 91 (4), 73 ( 3), 69 (3), 60 (4), 57 (4), 55 (4), 44 (12), 43 (4), 41 (5), 36 (5), 28 (7); C ₄₂ H ₃₀ N ₂ O ₄ (626.7): calc. C 80.49, H 4.82, N 4.47; gef. C 80.29, H 5.01, N 4.31.

N, N'-di- (R-1-cyclohexylethyl) 3.4 to 9.10 Pearl-tetracarbonsäurebisimid (1e):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (2.00 g, 5.10 mmol) and R - (-) - 1-cyclohexylethylamine (1.53 g, 12.0 mmol, [α] _D ²⁰ = -4.7 °, in substance) were correspondingly N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide reacted and worked up. Y. 2.90 g (93%), mp> 330 ° C; R _f (silica gel, CHCl ₃ ): 0.34; IR (KBr): ν ~ = 2927 (m, CH ₂ / CH ₃ ), 2851 (m, CH ₂ / CH ₃ ), 1697 (s, C = O), 1658 (s, C = O), 1595 ( s, aryl), 1579 (m, aryl), 1448 (w), 1436 (w), 1406 (m, CH ₂ / CH ₃ ), 1375 (w), 1354 (w), 1338 (s, CH ₃ ) , 1256 (m, CN), 1197 (w), 1177 (w), 859 (w), 811 (m, aryl), 748 (m), 468 (w) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 457.5 (20520), 489.0 (52470), 525.5 nm (85970); Fluorescence (CHCl ₃ ): λ _max = 532.5, 572.5 nm; ¹ H NMR (CDCl _3): δ = 0.92-1.24 (m, 8 H, CH _2), 1:33 (m, 2 H, CH _2), 1:51 (m, 2 H, CH _2), 1.62 (m, 4 H, CH _2), 1.64 (d, 6 H, _CH3), 1.82 (m, 2 H, CH _2), 2:05 (m, 2 H, CH _2), 2:37 (m, 2 H, CH), 4.97 (m, 2H, N-CH), 8.44 (d, 4H, perylene), 8.57 (d, 4H, perylene); ¹³ C NMR (CDCl _3): δ = 16:49 (2 C, CH _3), 25.84 (2 C, CH _2), 26.02 (2 C, CH _2), 26.27 (2 C, CH _2), 30.05 (2 C , CH ₂ ), 31.12 (2 C, CH ₂ ), 39.34 (2 C, CH), 54.93 (2 C, N-CH), 122.85 (4 CH, perylene), 123.59 (4 C, perylene), 126.20 ( 2 C, perylene), 129-37 (2 C, perylene), 131.28 (4 CH, perylene), 134.24 (4 C, perylene), 163.72 (4 C = O, perylene); MS (70 eV): m / z (%) = 611 (15), 610 (35) [M ⁺ ], 593 (4) [M ⁺ -OH], 527 (7) [M ⁺ -C ₆ H ₁₁ ], 503 (5), 502 (24), 501 (74), 500 (36) [M ⁺ -C ₈ H ₁₄ ], 483 (6) [593-C ₈ H ₁₄ ], 418 (7), 417 (13) [500-C ₆ H ₁₁ ], 393 (6), 392 (34), 391 (83), 390 (100) [500-C ₈ H ₁₄ ], 374 (6), 373 (22) [ 390-OH], 346 (7), 345 (13) [373-CO], 289 (2), 167 (3), 124 (2), 81 (5), 67 (3), 55 (3), 41 (3); C ₄₀ H ₃₈ N ₂ O ₄ (610.8): calc. C 78.66, H 6.27, N 4.59; gef. C 78.63, H 6.24, N 4.59.

N, N'-di- (S-1-cyclohexylethyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (1f):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (2.00 g, 5.10 mmol) and S - (+) - 1-cyclohexylethylamine (1.53 g, 12.0 mmol, [α] ₅₄₆ ²⁰ = + 4.7 °, in substance) were correspondingly N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide reacted and worked up. Y. 2.89 g (93%), mp> 330 ° C; R _f (silica gel, CHCl ₃ ): 0.35; IR (KBr): ν ~ = 2928 (m, CH ₂ / CH ₃ ), 2852 (m, CH ₂ / CH ₃ ), 1697 (s, C = O), 1658 (s, C = O), 1595 ( s, aryl), 1579 (m, aryl), 1448 (w), 1436 (w), 1406 (s, CH ₂ / CH ₃ ), 1375 (w), 1354 (m), 1340 (s, CH ₃ ) , 1256 (m, CN), 1212 (w), 1197 (w), 1177 (w), 859 (m), 811 (s, aryl), 748 (s) cm ^-1 ; UV / Vis (CHCl _3): λ _max (ε) = 457.5 (21020), 489.0 (53730), 525.5 nm (88305); Fluorescence (CHCl ₃ ): λ _max = 531.5, 572.0 nm; ¹ H NMR (CDCl ₃ ): δ = 0.94-1.23 (m, 8 H, CH ₂ ), 1.33 (m, 2 H, CH ₂ ), 1.51 (m, 2 H, CH ₂ ), 1.62 (m, 4 H, CH _2), 1.66 (d, 6 H, _CH3), 1.81 (m, 2 H, CH _2), 2:05 (m, 2 H, CH _2), 2:37 (m, 2 H, CH), 4.97 (m, 2H, N-CH), 8.37 (d, 4H, perylene), 8.53 (d, 4H, perylene); ¹³ C NMR (CDCl _3): δ = 16:48 (2 C, CH _3), 25.84 (2 C, CH _2), 26.02 (2 C, CH _2), 26.27 (2 C, CH _2), 30.06 (2 C , CH ₂ ), 31.12 (2 C, CH ₂ ), 39.34 (2 C, CH), 54.94 (2 C, N-CH), 122.78 (4 CH, perylene), 123.59 (4 C, perylene), 126.11 ( 2 C, perylene), 129.30 (2 C, perylene), 131.18 (4 CH, perylene), 134.14 (4 C, perylene), 163.72 (4 C = O, perylene); MS (70 eV): m / z (%) = 611 (12), 610 (28) [M ⁺ ], 593 (4) [M ⁺ -OH], 527 (6), 502 (22), 501 ( 63), 500 (31) [M ⁺ -C ₈ H ₁₄ ], 483 (6) [593-C ₈ H ₁₄ ], 418 (7), 417 (12) [500-C ₆ H ₁₁ ] 393 (7 ), 392 (35), 391 (84), 390 (100) [500-110], 374 (7), 373 (27) [390-OH], 346 (10), 345 (18) [373-CO ], 320 (5), 289 (4), 275 (4), 274 (4), 167 (5), 137 (4), 124 (5), 123 (5), 81 (7), 67 (6 ), 57 (5), 55 (5), 41 (5); C ₄₀ H ₃₈ N ₂ O ₄ (610.8): calc. C 78.66, H 6.27, N 4.59; gef. C 78.70, H 6.17, N 4.42.

N, N'-di- [R-1- (1-naphthyl) ethyl] perylene-3,4: 9,10-tetracarbonsäurebisimid (1h):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (500 mg, 1.27 mmol) and R - (+) - 1- (1-naphthyl) ethylamine (450 mg, 2.63 mmol, [α] ₅₄₆ ²⁰ = + 54 °, c = 2.0 in ethanol) were reacted and worked up according to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide. Y. 770 mg (87%), mp> 330 ° C; R _f (silica gel, CHCl ₃ ): 0.28; IR (KBr): ν ~ = 3050 (w, aryl), 2970/2940 (w, CH ₃ ), 1698 (s, C = O), 1660 (s, C = O), 1594 (s, aryl), 1578 (m, aryl), 1511 (w), 1434 (w), 1405 (m, CH _3), 1372 (w), 1356 (w), 1336 (s, CH _3), 1253 (m, CN), 1208 (w), 1195 (w), 1171 (w), 810 (m, aryl), 797 (w), 777 (m, aryl), 750 (m, aryl) cm ^-1 ; UV / Vis (CHCl _3): λ _max (ε) = 460.5 (22240), 492.5 (56350), 529.5 nm (91380); Fluorescence (CHCl ₃ ): λ _max = 544.5, 573.5 nm; ¹ H NMR (CDCl _3): δ = 2.17 (d, 6 H, _CH3), 7:09 (q, 2 H, N-CH), 7:40 (t, 2 H, Naph.), 7:47 (d, 4 H , Perylene), 7.52 (t, 2H, naph.), 7.64 (t, 2H, naph.), 7.86 (d, 4H, naph.), 8.04 (d, 4H, naph.), 8.15 ( d, 4H, perylene); ¹³ C NMR (CDCl ₃ ): δ = 17.19 (2 C, CH ₃ ), 48.23 (2 C, N-CH), 122.33 (4 CH, Per), 123.15 (4 C, perylene), 123.28 (2 CH, Naph.), 125.13 (2 CH, Naph.), 125.37 (2 CH, Naph.), 125.45 (2 C, perylene), 126.59 (2 CH, Naph.), 128.23 (2 CH, Naph.), 128.51 ( 2 CH, naph.), 128.74 (2 C, perylene), 129.19 (2 CH, naph.), 131.06 (4 CH, perylene), 131.88 (2 C, naph.), 133.65 (4 C, perylene), 133.76 (2C, Naph.), 135.03 (2C, Naph.), 163.06 (4C = O, perylene); MS (70 eV): m / z (%) = 698 (5) [M ⁺ ], 546 (4), 545 (9) [M ⁺ -C ₁₀ H ₇ C ₂ H ₂ ], 392 (7), 391 (15) [545-C ₁₀ H ₇ C ₂ H ₃ ], 390 (5), 373 (3) [391-OH], 346 (4), 155 (12), 154 (71), 153 (100 ) [C ₁₀ H ₇ C ₂ H ₂ ⁺ ], 152 (51), 151 (17), 150 (8), 128 (3), 127 (4), 126 (5), 77 (6), 76 ( 17), 75 (5), 74 (3), 63 (7), 51 (4), 44 (4); C ₄₈ H ₃₀ N ₂ O ₄ (698.8): calc. C 82.50, H 4.33, N 4.01; gef. C 82.34, H 4.33, N 3.97.

N, N'-di- [5-1- (1-naphthyl) ethyl] perylene-3,4: 9,10-tetracarbonsäurebisimid (1i):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (500 mg, 1.27 mmol) and S - (-) - 1- (1-naphthyl) ethylamine (450 mg (2.63 mmol, [α] ₅₄₆ ²⁰ = -54 °); c = 2.0 in ethanol) were reacted and worked up correspondingly to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide, yielding 750 mg (85%), Mp> 330 ° C, R _f (silica gel, CHCl ₃ ): 0.25, IR (KBr): ν ~ = 3055 (w, aryl), 2980/2945 (w, CH ₃ ), 1697 (s, C = O ), 1658 (s, C = O), 1594 (s, aryl), 1577 (s, aryl), 1434 (w), 1512 (w), 1405 (s, CH ₃ ), 1373 (w), 1356 ( m), 1336 (s, CH _3), 1253 (m, CN), 1208 (w), 1197 (w), 1171 (w), 810 (s, aryl), 797 (w), 777 (m, aryl ), 753 (m, aryl) cm ^-1 , UV / Vis (CHCl ₃ ): λ _max (ε) = 460.5 (21160), 492.5 (55110), 529.5 nm (90610) nm, fluorescence (CHCl ₃ ): λ _max = 531.0, 549.0 nm; ¹ H NMR (CDCl _3): δ = 2.16 (d, 6 H, _CH3), 7:08 (q, 2 H, N-CH), 7:40 (t, 2 H, Naph). , 7.41 (d, 4H, perylene), 7.52 (t, 2H, naph.), 7.64 (t, 2H, naph.), 7.86 (d, 4H, naph.), 8.01 (d, 4H , Naph.), 8.15 (d, 4 H, perylene); ¹³ C NMR (CDCl ₃ ): δ = 17.14 (2 C, CH ₃ ), 48.16 (2 C, N-CH), 122.16 (4 CH, perylene), 123.03 (4 C, perylene), 123.25 (2 CH, Naph.), 125.09 (2 CH, naph.), 125.26 (2 C, perylene), 125.33 (2 CH, naph.), 126.56 (2 CH, naph.), 128.23 (2 CH, naph ), 128.46 (2 CH, naph), 128.57 (2 C, perylene), 129.14 (2 CH, naph), 130.91 (4 CH, perylene), 131.84 (2 C, naph.), 133.46 (4C , Perylene), 133.71 (2 C, Naph.), 134.96 (2 C, Naph.), 162.93 (4 C = O, perylene); MS (70 eV): m / z (%) = 699 (3), 698 (6) [M ⁺ ], 546 (4), 545 (10) [M ⁺ -C ₁₀ H ₇ C ₂ H ₂ ], 392 (7), 391 (16) [545 C ₁₀ H ₇ C ₂ H _3], 390 (5), 373 (3) [391-OH], 346 (4), 155 (11), 154 (68 ), 153 (100) [C ₁₀ H ₇ C ₂ H ₂ ⁺ ], 152 (49), 151 (16), 150 (7), 127 (4), 126 (4), 77 (5), 76 ( 16), 75 (4), 63 (6), 51 (3); C ₄₈ H ₃₀ N ₂ O ₄ (698.8): calc. C 82.50, H 4.33, N 4.01; gef. C 82.40, H 4.34, N 3.85.

N, N'-di (dehydroabietyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (1k):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (1.00 g, 2.55 mmol) and (+) - dehydroabietylamine (1.72 g, 6.00 mmol, [[α] ₅₄₆ ²⁰ = + 41.0 °, c = 1.0 in ethanol) were corresponding N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide reacted and worked up. Y. 2.13 g (90%), mp> 310 ° C; R _f (silica gel, CHCl ₃ ): 0.28; IR (KBr): ν ~ = 3035 cm ^-1 (w, aryl), 2958 (s, CH ₃ ), 2928 (s, CH ₂ / CH ₃ ), 2867 (m, CH ₂ ), 1701 (s, C = O), 1662 (s, C = O), 1596 (s, aryl), 1580 (m, aryl), 1498 (w), 1438 (m), 1405 (s, CH ₂ / CH ₃ ), 1378 ( w), 1334 (s, CH _3), 1252 (m, CN), 1161 (w), 1108 (w), 852 (w), 821 (w), 811 (s, aryl), 754 (m); UV / Vis (CDCl ₃ ): λ _max (ε) = 458.2 (17770), 489.1 (47870), 526.2 nm (75700); Fluorescence (CHCl ₃ ): λ _max = 535.5, 573.5 nm; ¹ H NMR (CDCl ₃ ): δ = 1.09 (s, 6H, CH ₃ ), 1.21 (s, 6H, CH ₃ ), 1.235 (d, 12H, CH ₃ ), 1.30-1.45 (m, 4 H, CH _2), 1.53-1.74 (m, 8 H, CH _2), 1.82-1.95 (m, 2 H, CH _2), 2.23 (dd, 2 H, CH), 2:30 to 2:38 (m, 2 H , CH ₂ ), 2.82 (sept, 2H, CH), 2.98-3.12 (m, 4H, CH ₂ ), 4.20 (d, 2H, N-CH ₂ ), 4.30 (d, 2H, N- CH ₂ ), 6.94 (s, 2H, aryl), 6.95 (d, 2H, aryl), 7.13 (d, 2H, aryl), 8.39 (d, 4H, perylene), 8.50 (d, 4H , Perylene); ¹³ C NMR (CDCl _3): δ = 18.63 (2 C, CH _2), 7:24 p.m. (2 C, CH _3), 19.88 (2 C, CH _2), 23.99 (4 C, CH _3), 26.05 (2 C , CH ₃ ), 30.52 (2 C, CH ₂ ), 33.46 (2 C, CH), 37.51 (2 C, CH ₂ ), 37.85 (2 C, C), 38.18 (2 C, CH ₂ ), 40.05 ( 2 C, C), 50.03 (2 C, N-CH ₂ ), 122.87 (4 CH, perylene), 123.32 (4 C, perylene), 123.70 (2 CH, aryl), 123.88 (2 CH, aryl), 126.12 (2 C, perylene), 126.99 (2 CH, aryl), 129.08 (2 C, perylene), 131.40 (4 CH, perylene), 134.26 (4 C, perylene), 135.07 (2 C, aryl), 145.53 (2 C, aryl), 147.51 (2 C, aryl), 164.27 (4 C = O, perylene); MS (70 eV): m / z (%) = 929 (8), 928 (22), 927 (31) [M ⁺ ], 912 (3) [M ⁺ -CH ₃ ], 725 (2), 674 (3) 673 (10), 672 (21) [M ⁺ -C ₁₉ H ₂₇ ], 671 (6), 661 (4), 660 (12), 659 (10) [M ⁺ -C ₂₀ H ₂₈ ], 657 ( 3), 471 (3), 420 (5), 419 (26), 418 (92) [672-C ₁₉ H ₂₆ ], 417 (14), 416 (4), 407 (3), 406 (13) , 405 (26) [659-C ₁₉ H ₂₆ ], 404 (25) [672-C ₂₀ H ₂₈ ], 403 (6), 392 (8), 391 (10), 390 (8), 388 (3 ), 387 (11), 376 (3), 373 (8), 359 (7), 346 (4), 345 (5), 268 (6), 267 (4), 255 (11), 254 (7 ) [C ₁₉ H ₂₆ ⁺ ], 253 (19), 240 (5), 239 (23) [C ₁₈ H ₂₃ ⁺ ], 237 (7), 225 (7), 213 (4), 211 (10) , 209 (5), 200 (7), 199 (9), 197 (16) [C ₁₅ H ₁₇ ^+], 195 (7), 186 (8), 185 (35), 183 (11), 174 ( 15), 173 (100), 171 (16), 169 (13), 167 (13), 165 (11), 159 (18), 157 (16), 155 (17), 143 (21), 141 ( 17), 135 (13), 131 (29), 129 (19), 128 (17), 119 (12), 117 (16), 115 (17), 109 (14), 107 (15), 105 ( 15), 97 (11), 95 (33), 93 (20), 91 (29), 83 (15), 81 (20), 79 (21), 77 (18), 71 (14), 69 ( 22), 67 (21), 57 (28), 56 (12), 55 (37), 51 (11); C ₆₄ H ₆₆ N ₂ O ₄ (927.2): calc. C 82.90, H 7.18, N 3.02; gef. C 83.00, H 7.32, N 3.15.

N, N'-di- (L-1,2-dimethylpropyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (1b):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (500 mg, 1.27 mmol) and L - (+) - 2-amino-3-methylbutane hydrobromide (8c, 460 mg, 2.75 mmol, [α] ₅₄₆ ²⁰ = + 0.96 °, c = 1.95 in methanol) were reacted according to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide and worked up. Y. 440 mg (65%), mp> 300 ° C; R _f (silica gel, CHCl ₃ ): 0.24; IR (KBr): ν ~ = 2964 (m, CH ₂ / CH ₃ ), 2873 (w, CH ₂ / CH ₃ ), 1698 (s, C = O), 1660 (s, C = O), 1595 ( s, aryl), 1579 (m, aryl), 1461 (w), 1435 (w), 1406 (m, CH ₃ / CH _3), 1385 (w), 1339 (s, CH _3), 1254 (m, CN), 1176 (w), 1083 (w), 811 (w, aryl), 748 (m) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 458.2 (17740), 489.1 (49475), 525.6 nm (82780); Fluorescence (CHCl ₃ ): λ _max = 532.0, 573.0 nm; ¹ H NMR (CDCl ₃ ): δ = 0.85 (d, 6H, CH ₃ ), 1.11 (d, 6H, CH ₃ ), 1.62 (d, 6H, CH ₃ ), 2.72 (m, 2H, CH), 4.90 (m, 2H, N-CH), 8.57 (d, 4H, perylene), 8.65 (d, 4H, perylene); ¹³ C NMR (CDCl ₃ ): δ = 16.85 (2 C, CH ₃ ), 20.13 (2 C, CH ₃ ), 20.81 (2 C, CH ₃ ), 30.37 (2 C, CH), 56.23 (2 C, N-CH), 122.98 (4 CH, perylene), 123.62 (4 C, perylene), 126.39 (2 C, perylene), 129.51 (2 C, perylene), 131.42 (4 CH, perylene), 134.45 (4 C, Perylene), 163.89 (4 C = O, perylene); MS (70 eV): m / z (%) = 531 (10), 530 (28) [M ⁺ ], 488 (5), 487 (16) [M ⁺ -C ₃ H ₇ ], 462 (7) , 461 (27), 460 (23) [M ⁺ -C ₅ H ₁₀ ], 418 (6), 417 (17) [460-C ₃ H ₇ ], 392 (12), 391 (52), 390 ( 100) [460-C ₅ H ₁₀ ], 374 (7), 373 (21) [390-OH], 346 (7), 345 (13) [373-CO], 320 (4), 289 (3) , 275 (3), 200 (2), 178 (3), 167 (2), 124 (2), 55 (3), 28 (5); C ₃₄ H ₃₀ N ₂ O ₄ (530.6): calc. C 76.96, H 5.70, N 5.28; gef. C 77.00, H 5.61, N 5.35.

N, N'-di (L- (perylene-3,4 1,3-dimethylbutyl): 9,10-tetracarbonsäurebisimid (1d):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (500 mg, 1.27 mmol) and L - (+) - 2-amino-4-methylpentane hydrobromide (8d, 500 mg, 2.75 mmol, [α] _D ²⁰ = + 5.68 °, c = 2.05 in methanol) were reacted and worked up according to N, N'-di- (L- (1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide. 68%), mp> 300 ° C, R _f (silica gel, CHCl ₃ ): 0.27, IR (KBr): ν ~ = 2959 (m, CH ₂ / CH ₃ ), 2872 (w, CH ₂ / CH ₃ ), 1698 (s, C = O), 1658 (s, C = O), 1595 (s, aryl), 1579 (m, aryl), 1464 (w), 1436 (w), 1406 (m, CH ₂ / CH ₃ ), 1386 (w), 1340 (s, CH ₃ ), 1263 (m, CN), 1212 (w), 1198 (w), 810 (m, aryl), 747 (m) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 457.0 (19800), 488.0 (50820), 524.5 nm (83270), fluorescence (CHCl ₃ ): λ _max = 532.0, 572.0 nm, ¹ H NMR (CDCl ₃ ): δ = 0.94 (d, 6 H, _CH3), 0.96 (d, 6 H, _CH3), 1:54 (m, 2 H, CH), 1.61 (d, 6 H, _CH3), 1.75 (m , 2H, CH ₂ ), 2.21 (m, 2H, CH ₂ ), 5.40 (m, 2H, N-CH), 8.57 (d, 4H, perylene), 8.65 (d, 4H, perylene) ¹³ C NMR (CDCl ₃ ): δ = 18.63 (2 C, CH ₃ ), 22.62 (2 C, CH ₃ ), 22.94 (2 C, CH ₃ ), 25.84 (2 C, CH ₂ ), 42.74 (2 C, CH), 48.18 (2 C, N-CH), 123.00 (4 CH, perylene), 123.75 (4 C, perylene), 126.41 (2 C, perylene), 129.49 (2 C, perylene), 131.37 (4 CH, perylene), 134.46 (4 C, perylene), 163.85 (4 C = O, perylene); MS (70 eV): m / z (%) = 560 (9), 559 (42), 558 (100) [M ⁺ ], 542 (3), 541 (9), 516 (4), 515 (12 ), 502 (6), 501 (8) [M ⁺ -C ₄ H ₉ ], 477 (3), 476 (16), 475 (47), 474 (29) [M ⁺ -C ₆ H ₁₂ ], 458 (6), 457 (9), 431 (5), 420 (3), 419 (13), 418 (27) [475-C ₄ H ₉ ], 417 (9), 393 (3), 392 ( 18), 391 (64), 390 (96) [474-C ₆ H ₁₂ ], 375 (4), 374 (11), 373 (30) [390-OH], 347 (4), 346 (13) , 345 (21) [373-CO], 320 (6), 302 (3), 289 (5), 275 (5), 274 (4), 178 (3), 69 (4), 41 (6) , 28 (9); C ₃₆ H ₃₄ N ₂ O ₄ (558.7): calc. C 77.40, H 6.13, N 5.01; gef. C 77.06, H 6.22, N 5.32.

N, N'-di- (L-1-methylpropyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (1a):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (8a, 600 mg, 1.53 mmol) and L - (-) - 2-aminobutane hydrobromide (500 mg, 3.25 mmol, [α] _D ²⁰ = -0.87 °, c = 2.0 in methanol) were reacted and worked up according to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide. Y. 370 mg (58%), mp> 330 ° C; R _f (silica gel, CHCl ₃ ): 0.16; IR (KBr): ν ~ = 2968 (w, CH ₂ / CH ₃ ), 2938 (w, CH ₂ / CH ₃ ), 2880 (w, CH ₂ / CH ₃ ), 1696 (s, C = O), 1658 (s, C = O), 1595 (s, aryl), 1579 (m, aryl), 1438 (w), 1405 (m, CH ₃ / CH _2), 1341 (s, CH _3), 1254 (m , CN), 1205 (w), 810 (m, aryl), 746 (m) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 457.0 (19360), 488.0 (51500), 524.5 nm (84980); Fluorescence (CHCl ₃ ): λ _max = 531.6, 570.5 nm; ¹ H NMR (CDCl ₃ ): δ = 0.95 (t, 6H, CH ₃ ), 1.63 (d, 6H, CH ₃ ), 1.99 (m, 2H, CH ₂ ), 2.25 (m, 2H, CH ₂ ), 5.22 (sec., 2H, N-CH), 8.50 (d, 4H, perylene), 8.60 (d, 4H, perylene); ¹³ C NMR (CDCl ₃ ): δ = 11.55 (2 C, CH ₃ ), 18.01 (2 C, CH ₃ ), 26.53 (2 C, CH ₃ ), 51.55 (2 C, N-CH), 122.91 (4 CH, perylene), 123.68 (4 C, perylene), 126.28 (2 C, perylene), 129.40 (2 C, perylene), 131.24 (4 CH, perylene), 134.32 (4 C, perylene), 163.82 (4 C = O, perylene); MS (70 eV): m / z (%) = 503 (13), 502 (37) [M ⁺ ], 473 (5) [M ⁺ -C ₂ H ₅ ], 447 (11), 446 (24) [M ⁺ -C ₄ H ₈ ], 417 (6) [473-C ₄ H ₈ ], 392 (6), 391 (37), 390 (100) [446-C ₄ H ₈ ], 375 (3) , 374 (10), 373 (17) [390-OH], 347 (4), 346 (15), 345 (16) [373-CO], 320 (5), 302 (6), 289 (8) , 275 (7), 274 (6), 273 (4), 264 (3), 263 (4), 262 (5), 249 (3), 248 (3), 178 (5), 167 (5) , 149 (8), 137 (4), 137 (4), 124 (8), 123 (6), 122 (8), 118 (4), 117 (6), 97 (4), 91 (3) , 83 (4), 81 (3), 71 (7), 69 (6), 67 (3), 57 (12), 56 (4), 55 (9), 44 (8), 43 (7) 41 (12), 39 (7), 32 (26), 29 (4); C ₃₂ H ₂₆ N ₂ O ₄ (502.6): calc. C 76.48, H 5.21, N 5.57; gef. C 76.57, H 5.10, N 5.54.

N, N'-di- (L-1,2-dimethylbutyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (1c):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (750 mg, 1.91 mmol) and L - (-) - 2-amino-3-methyl-pentane-hydrobromide (8b, 700 mg, 3.84 mmol, [α] _D ²⁰ = -0.74 °, c = 2.05 in methanol) were reacted and worked up corresponding to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide. Y. 850 mg (80%), mp> 330 ° C; R _f (silica gel, CHCl ₃ ): 0.34; IR (KBr): ν ~ = 2966 (m, CH ₂ / CH ₃ ), 2935 (w, CH ₂ / CH ₃ ), 2878 (w, CH ₂ / CH ₃ ), 1698 (s, C = O), 1658 (s, C = O), 1595 (s, aryl), 1579 (m, aryl), 1457 (w), 1437 (w), 1406 (m, CH ₂ / CH ₃ ), 1381 (w), 1339 (s, CH _3), 1252 (m, CN), 1212 (w), 1201 (w), 1084 (w), 852 (w, aryl), 810 (m, aryl), 748 (m, aryl) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 459.0 (19780), 490.5 (52290), 527.0 nm (86280); Fluorescence (CHCl ₃ ): λ _max = 532.0, 573.0 nm; ¹ H NMR (CDCl _3): δ = 0.82 (t, 6 H, _CH3), 1:01 to 1:12 (m, 2 H, CH _2), 1:07 (d, 6 H, _CH3), 1:31 to 1:41 (m , 2 H, CH _2), 1.63 (d, 6 H, CH _3), 2.49-2.60 (m, 2 H, CH), 4.97 (m, 2 H, N-CH), 8:54 (d, 4 H, Perylene), 8.63 (d, 4H, perylene); ¹³ C NMR (CDCl _3): δ = 10.86 (2 C, CH _3), 16:59 (2 C, CH _3), 17:00 (2 C, CH _3), 26.07 (2 C, CH _2), 36.25 (2 C , CH), 54.81 (2 C, N-CH), 122.97 (4 CH, perylene), 123.68 (4 C, perylene), 126.39 (2 C, perylene), 129.52 (2 C, perylene), 131.42 (4 CH , Perylene), 134.43 (4 C, perylene), 163.87 (4 C = O, perylene); MS (70 eV): m / z (%) = 559 (7), 558 (19) [M ⁺ ], 502 (3), 501 (12) [M ⁺ -C ₄ H ₉ ], 476 (8) , 475 (29), 474 (21) [m ⁺ -C ₆ H ₁₂ ], 457 (4), 418 (6), 417 (16) [501-C ₆ H ₁₂ ], 392 (14), 391 ( 55), 390 (86) [474-C ₆ H ₁₂ ], 374 (6), 373 (24) [390-OH], 346 (9), 345 (18) [373-CO], 320 (4) , 302 (3), 289 (6), 275 (5), 274 (5), 262 (4), 167 (4), 137 (3), 124 (5), 123 (6), 118 (4) , 92 (4), 91 (11), 87 (9), 85 (67), 83 (100), 69 (4), 55 (4), 49 (6), 48 (8), 47 (19) , 44 (21), 41 (7), 39 (4), 35 (5), 32 (15); C ₃₆ H ₃₄ N ₂ O ₄ (558.7): calc. C 77.40, H 6.13, N 5.01; gef. C 77.63, H 6.17, N 5.18.

N, N'-di- (3-pinylmethyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (1j):

Perylene-3,4: 9,10-tetracarboxylic bisanhydride (1.50 g, 3.82 mmol) and (+) - 3-aminomethyl-pinane hydrochloride (1.80 g, 8.83 mmol, [α] _D ²⁰ = + 39 °, c = 5.0 in water N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide were reacted and worked up accordingly. Y. 2.38 g (90%) of chloroform, mp> 300 ° C; R _f (silica gel, CHCl ₃ ): 0.32; IR (KBr): ν ~ = 2950 (m, CH ₂ / CH ₃ ), 2904 (m, CH ₂ / CH ₃ ), 1698 (s, C = O), 1658 (s, C = O), 1616 ( w), 1595 (s, aryl), 1579 (w, aryl), 1506 (w), 1473 (w), 1440 (m), 1404 (m, CH ₂ / CH ₃ ), 1366 (m), 1341 ( s, CH ₃ ), 1289 (w), 1250 (m, CN), 1177 (w), 1160 (w), 851 (w, aryl), 811 (m, aryl), 745 (w), 624 (w ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 458.8 (16160), 489.8 (44620), 526.8 nm (74780); Fluorescence (CHCl ₃ ): λ _max = 533.8, 574.5 nm; MS (70 eV): m / z (%) = 691 (12), 690 (22) [M ⁺ ], 673 (2) [M ⁺ -OH], 621 (5) [M ⁺ -C ₅ H ₉ ], 553 (4) [M ⁺ -C ₁₀ H ₁₇ ], 543 (13), 542 (50), 541 (100) [M ⁺ -C ₁₁ H ₁₇ ], 540 (9), 471 (2) [ 621-C ₁₁ H ₁₈ ], 418 (6), 406 (8), 405 (26), 404 (26) [541-C ₁₀ H ₁₇ ], 403 (6), 393 (16), 392 (54) , 391 (54) [541-C ₁₁ H ₁₈ ], 390 (32) [541-C ₁₁ H ₁₉ ], 387 (5), 376 (4), 373 (11) [390-OH], 359 (4 ), 346 (6), 345 (9) [373-CO], 150 (11), 149 (15) [C ₁₁ H ₁₇ ⁺ ], 137 (4), 124 (5), 123 (4), 121 (6), 107 (18), 105 (4), 95 (8), 93 (21), 91 (8), 83 (5), 81 (7), 79 (7), 69 (8), 67 (8), 57 (7), 55 (8), 43 (6), 41 (9); C ₄₆ H ₄₆ N ₂ O ₄ (690.9) C 79.97, H 6.71, N 4.05; gef. C 80.10, H 6.67, N 4.05.

N- (L-1-methyl-2-phenylethyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10g):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-anhydride-9,10-imide (500 mg, 0.870 mmol) and L - (-) - 2-amino-1 phenylpropane (150 mg, 1.10 mmol, [α] _D ²⁰ = -34.4 °, c = 1.5 in ethanol) was correspondingly N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: Reacted and worked up 9,10-tetracarboxylic bisimide. Y. 510 mg (85%), mp 213-214 ° C; R _f (silica gel, CHCl ₃ ): 0.54; IR (KBr): ν ~ = 2963 (m, CH ₃ ), 2930 (s, CH ₂ / CH ₃ ), 2860 (m, CH ₂ / CH ₃ ), 1698 (s, C = O), 1657 (s , C = O), 1598 (s, aryl), 1581 (m, aryl), 1438 (w, CH ₂ / CH ₃ ), 1408 (m, CH ₂ / CH ₃ ), 1342 (s, CH ₃ ), 1257 (m, CN), 1178 (m), 1128 (w), 854 (w), 815 (m, aryl), 751 (m, CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 459.5 (18020), 490.5 (51730), 526.5 nm (87070); Fluorescence (CHCl ₃ ): λ _max = 544.5, 573.5 nm; ¹ H NMR (CDCl _3): δ = 0.83 (t, 6 H, _CH3), 1:23 to 1:37 (m, 16 H, CH _2), 1.68 (d, 3 H, _CH3), 1.90 (m, 2 H, CH ₂ ), 2.26 (m, 2H, CH ₂ ), 3.33 (dd, 1H, CH ₂ ), 3.53 (dd, 1H, CH ₂ ), 5.19 (m, 1H, N-CH) , 5.63 (sec., 1H, N-CH), 7.11 (t, 1H, phenyl), 7.22 (t, 2H, phenyl, 7.30 (d, 2H, phenyl), 8.32 (d, 2H, . perylene), 8:37 (d, 2 H, perylene), 8:47 (d, 2 H, perylene), 8:56 (br, 2 H, perylene); ¹³ C NMR (CDCl _3): δ = 14.05 (2 C, CH ₃ ), 17.77 (1 C, CH ₃ ), 22.61 (2 C, CH ₂ ), 27.00 (2 C, CH ₂ ), 29.24 (2 C, CH ₂ ), 31.80 (2 C, CH ₂ ), 32.41 ( 2 C, CH ₂ ), 50.87 (1 C, NC), 54.83 (1 C, NC), 122.77 (2 CH, perylene), 122.81 (2 CH, perylene), 123.43 (4 C, perylene), 126.14 (1 C, perylene), 126.19 (1 C, perylene), 126.33 (1 C, phenyl), 128.35 (2 CH, phenyl), 129.15 (2 CH, Phe nyl), 129.19 (1 C, perylene), 129.42 (1 C, perylene), 131.11 (4 CH, perylene), 134.23 (4 C, perylene), 139.13 (1 C, phenyl), 163.65 (4 C = O, perylene). MS (70 eV): m / z (%) = 691 (11), 690 (23) [M ⁺ ], 600 (9), 599 (20) [M ⁺ -C ₆ H ₅ CH ₂ ], 574 (7), 573 (29), 572 (59) [M ⁺ -C ₆ H ₅ C ₃ H ₅ ], 555 (5) [572-OH], 509 (7) [M ⁺ -C ₁₃ H ₂₅ ] , 418 (5), 417 (13) [599-C ₁₃ H ₂₆ ], 392 (14), 391 (47), 390 (100) [572-C ₁₃ H ₂₆ ], 374 (5), 373 (17 ) [390-OH], 346 (5), 345 (9) [373-CO], 320 (2), 118 (4), 117 (4), 55 (3); C ₄₆ H ₄₆ N ₂ O ₂ (690.9): C79.97, H 6.71, N 4.05; gef. C 79.78, H 6.94, N 4.24.

N- (R-1-cyclohexylethyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10e):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (500 mg, 0.870 mmol) and R - (-) - 1-cyclohexylethylamine (160 mg , 1.30 mmol, [α] ₅₄₆ ²⁰ = -4.7 ° in substance) were reacted according to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide and worked up , Y. 450 mg (76%), mp 220 ° C; R _f (silica gel, CHCl ₃ ): 0.70; IR (KBr): ν ~ = 3080 (w, aryl), 2927 (s, CH ₂ / CH ₃ ), 2854 (s, CH ₂ / CH ₃ ), 1698 (s, C = O), 1658 (s, C = O), 1595 (s, aryl), 1579 (s, aryl), 1448 (m), 1436 (m, CH ₂ / CH ₃ ), 1406 (s, CH ₂ / CH ₃ ), 1376 (w) , 1353 (m), 1340 (s, CH ₃ ), 1256 (s, CN), 1211 (m), 1176 (m), 1124 (w), 852 (m), 810 (s, aryl), 747 ( s, CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 458.0 (22980), 489.0 (57680), 526.5 nm (94500); Fluorescence (CHCl ₃ ): λ _max = 543.0, 573.0 nm; ¹ H NMR (CDCl _3): δ = 0.83 (t, 6 H, CH _3), 0.94-1.10 (m, 2 H, CH _2), 1:13 to 1:39 (m, 19 H, _CH2), 1:53 (m , 1 H, CH _2), 1.62 (d, 3 H, CH _3), 1.59-1.66 (m, 2 H, CH _2), 1.79-1.90 (m, 3 H, CH _2), 2:04 (m, 1 H, CH ₂ ), 2.21-2.29 (m, 2H, CH ₂ ), 2.32-2.42 (m, 1H, CH), 4.97 (m, 1H, N-CH), 5.19 (m, 1H, N-CH), 8.53 (d, 2H, perylene), 8.55 (d, 2H, perylene), 8.63 (d, 4H, perylene); ¹³ C NMR (CDCl _3): δ = 14.05 (2 C, CH _3), 16:50 (1 C, CH _3), 22.60 (2 C, CH _2), 25.84 (1C, CH _2), 26.01 (1 C , CH ₂ ), 26.27 (1 C, CH ₂ ), 26.96 (2 C, CH ₂ ), 29.24 (2 C, CH ₂ ), 30.05 (1 C, CH ₂ ), 31.13 (1 H, CH ₂ ), 31.78 (2 C, CH ₂ ), 32.41 (1 C, CH ₂ ), 39.34 (1 C, CH), 54.80 (1 C, N-CH), 54.90 (1 C, N-CH), 122.95 (2 CH , Perylene), 122.96 (2 CH, perylene), 123.61 (4 C, br., Perylene), 126.36 (1 C, perylene), 126.40 (1 C, perylene), 129.50 (1 C, perylene), 129.57 (1 C, perylene), 131.45 (4 CH, br., Perylene), 134.42 (4 C, perylene), 163.57 (4 C = O, perylene); MS (70 eV): m / z (%) = 683 (15), 682 (30) [M ⁺ ], 665 (5) [M ⁺ -OH], 599 (5) [ ^M -C ₆ H ₁₁ ] , 575 (4), 574 (20), 573 (58), 572 (44) [M ⁺ -C ₈ H ₁₄ ], 555 (4), 502 (3), 501 (9), 500 (4) [ M ⁺ -C ₁₃ H ₂₆ ], 418 (4), 417 (9) [599-C ₁₃ H ₂₆ ], 393 (6), 392 (25), 391 (70), 390 (100) [572-C ₁₃ H ₂₆ ], 374 (7), 373 (21) [390-OH], 346 (9), 345 (13) [373-CO], 320 (4), 289 (3), 167 (2), 124 (2), 81 (6), 69 (3), 67 (4), 55 (6), 41 (4); C ₄₅ H ₅₀ N ₂ O ₄ (682.9): calc. C 79.15, H 7.38, N 4.10; gef. C 78.61, H 7.28, N 4.16.

N- (S-1-cyclohexylethyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10f):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (1.00 g, 1.74 mmol) and S - (+) - 1-cyclohexylethylamine (250 mg , 2.00 mmol, [α] ₅₄₆ ²⁰ = + 4.7 °, in substance) were correspondingly reacted N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetra carboxylic acid bisimide and worked up. Y. 870 mg (73%), m.p. 220 ° C; R _f (silica gel, CHCl ₃ ): 0.72; IR (KBr): ν ~ = 2927 (s, CH ₂ / CH ₃ ), 2854 (m, CH ₂ / CH ₃ ), 1698 (s, C = O), 1658 (s, C = O), 1595 ( s, aryl), 1579 (m, aryl), 1449 (m), 1435 (m, CH ₂ / CH ₃ ), 1406 (s, CH ₂ / CH ₃ ), 1376 (w), 1353 (w), 1338 (s, CH _3), 1255 (s, CN), 1211 (w), 1196 (w), 1175 (w), 1124 (w), 1107 (w), 852 (m), 811 (s, aryl) , 747 (s, CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 457.5 (21950), 488.5 (54270), 525.5 nm (89330); Fluorescence (CHCl ₃ ): λ _max = 532.5, 572.0 nm; ¹ H NMR (CDCl _3): δ = 0.83 (t, 6 H, CH _3), 0.92-1.11 (m, 2 H, CH _2), 1:13 to 1:39 (m, 19 H, _CH2), 1:53 (m , 1 H, CH _2), 1.63 (d, 3 H, CH _3), 1.59-1.66 (m, 2 H, CH _2), 1.79-1.93 (m, 3 H, CH _2), 2:02 to 2:06 (m , 1 H, CH ₂ ), 2.21-2.30 (m, 2 H, CH ₂ ), 2.32-2.42 (m, 1 H, CH ₂ ), 4.97 (m, 1 H, N-CH), 5.19 (m, 1 H, N-CH), 8.49 (d, 2H, perylene), 8.51 (d, 2H, perylene), 8.59 (d, 4H, perylene); ¹³ C NMR (CDCl _3): δ = 14.05 (2 C, CH _3), 16:50 (1 C, CH _3), 22.61 (2 C, CH _2), 25.84 (1C, CH _2), 26.02 (1 C , CH ₂ ), 26.27 (1 C, CH ₂ ), 26.99 (2 C, CH ₂ ), 29.25 (2 C, CH ₂ ), 30.06 (1 C, CH ₂ ), 31.14 (1 C, CH ₂ ), 31.80 (2 C, CH ₂ ), 32.41 (2 C, CH ₂ ), 39.34 (1 C, CH), 54.82 (1 C, N-CH), 54.91 (1 C, N-CH), 122.89 (2 CH , Perylene), 122.90 (2 CH, perylene), 123.59 (4 C, br., Perylene), 126.28 (1 C, perylene), 126.33 (1 C, perylene), 129.44 (1 C, perylene), 129.52 (1 C, perylene), 131.38 (4 CH, br., Perylene), 134.34 (4 C, perylene), 163.50 (4 C = O, perylene); MS (70 eV): m / z (%) = 683 (15), 682 (32) [M ⁺ ], 665 (4) [M ⁺ -OH], 599 (3) [M ⁺ -C ₆ H ₁₁ ]), 575 (3), 574 (19), 573 (54), 572 (43) [M ⁺ -C ₈ H ₁₄ ], 555 (4) [572-OH], 502 (3), 501 (8 ), 500 (3) [M ⁺ -C ₁₃ H ₂₆ ], 417 (7) [599-C ₁₃ H ₂₆ ], 393 (5), 392 (25), 391 (72), 390 (100) [572 -C ₁₃ H ₂₆ ], 374 (7), 373 (23) [390-OH], 346 (9), 345 (15) [373-CO], 320 (4) 289 (3), 167 (5) , 149 (5), 137 (4), 124 (5), 123 (6), 83 (7), 81 (4), 69 (5), 67 (4), 57 (5), 55 (9) , 43 (4), 41 (6), 32 (5); C ₄₅ H ₅₀ N ₂ O ₄ (682.9): calc. C 79.15, H 7.38, N 4.10; gef. C 79.22, H 7.44, N 4.12.

N- (R- (1- (1-naphthyl) ethyl] -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10h):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (1.00 g, 1.74 mmol) and R - (+) - 1- (1-naphthyl ) ethylamine (310 mg, 1.80 mmol, [α] _D ²⁰ = + 54 °, c = 2 in ethanol) was correspondingly N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4 : 9,10-tetracarboxylic bisimide reacted and worked up. Y. 970 mg (77%), mp 259 ° C; R _f (silica gel, CHCl ₃ ): 0.64; IR (KBr): ν ~ = 3050 (w, aryl), 2955 (m, CH ₃ ), 2927 (s, CH ₂ / CH ₃ ), 2856 (m, CH ₂ ), 1698 (s, C = O), 1660 (s, C = O), 1594 (s, aryl), 1579 (m, aryl) , 1435 (w, CH ₂ / CH ₃ ), 1406 (m, CH ₂ / CH ₃ ), 1354 (w), 1337 (s, CH ₃ ), 1253 (m, CN), 1173 (w), 810 ( s, aryl), 778 (w), 748 (m, CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 459.0 (22295), 490.5 (57600), 527.5 nm (92200); Fluorescence (CHCl ₃ ): λ _max = 544.5, 572.0 nm; ¹ H NMR (CDCl _3): δ = 0.85 (t, 6 H, _CH3), 1:22 to 1:43 (m, 16 H, CH _2), 1.86-1.98 (m, 2 H, CH _2), 2.175 (d , 3 H, _CH3), 2:20 to 2:32 (m, 2 H, CH _2), 5:14 to 5:25 (m, 1 H, N-CH), 7:09 to 7:13 (quart, 1 H, N-CH), 7:42 (t, 1H, naph.), 7.59 (t, 1H, naph.), 7.63 (d, 2H, perylene), 7.71 (t, 1H, naph.), 7.74 (d, 2H, perylene , 7.90 (d, 1H, naph), 7.92 (d, 1H, naph), 8.01 (br., 2H, perylene), 8.19 (d, 1H, naph.), 8.21 (d, 1H, naph.), 8.30 (d, 2H, perylene); ¹³ C NMR (CDCl _3): δ = 14.08 (2 C, CH _3), 17.3 (1 C, CH _3), 22.64 (2 C, CH _2), 27.06 (2 C, CH _2), 29.28 (2 C , CH ₂ ), 31.82 (2 C, CH ₂ ), 32.38 (1 C, CH ₂ ), 32.46 (1 C, CH ₂ ), 48.03 (1 C, N-CH), 54.87 (1 C, N 122.16 (2 CH, perylene), 122.96 (2 CH, perylene), 122.95 (4 C, perylene), 123.31 (1 CH, naph.), 125.20 (1 CH, naph.), 125.35 (1C , Perylene), 125.39 (1 CH, naph), 125.70 (1 C, perylene), 126.55 (1 CH, naph), 128.48 (1 CH, naph), 128.50 (1 CH, naph), 128.65 ( 1 C, perylene), 129.04 (1 C, perylene), 129.24 (1 CH, naph), 130.76 (4 CH, perylene), 131.87 (1 C, naph), 133.55 (2 C, perylene), 133.69 ( 2 C, perylene), 133.74 (1 C, Naph.), 134.96 (1 C, Naph.), 162.89 (4 C = O, perylene); MS (70 eV): m / z (%) = 727 (18), 726 (32) [M ⁺ ], 709 (5) [M ⁺ -OH], 574 (8), 573 (21) [M ⁺ -C ₁₀ H ₇ C ₂ H ₂ ], 572 (5), 546 (7), 545 (17), 544 (22) [M ⁺ -C ₁₃ H ₂₆ ], 403 (4), 393 (11), 392 (46), 391 (100) [573-C ₁₃ H ₂₆ ], 390 (57) [544-C ₁₀ H ₇ C ₂ H ₃ ], 375 (5), 374 (13) [391-OH], 373 (23) [390-OH], 348 (4), 347 (6), 346 (19) [374-CO], 345 (18) [373-CO], 320 (5), 302 (5), 289 (5), 275 (5), 274 (5), 155 (20), 154 (87), 153 (96) [C ₁₀ H ₇ C ₂ H ₂ ⁺ ], 152 (46), 151 (17) , 150 (8), 137 (4), 128 (4), 127 (5), 126 (5), 124 (5), 123 (5), 87 (16), 85 (98), 84 (5) , 77 (6), 76 (15), 75 (5), 69 (7), 63 (9), 57 (5), 55 (12), 50 (5), 49 (8), 48 (13) , 47 (26), 44 (12), 43 (6), 41 (8), 36 (8), 35 (6), 32 (11); C ₄₉ H ₄₆ N ₂ O ₄ (726.9): calc. C 80.96, H 6.38, N 3.85; gef. C 80.95, H 6.47, N 3.87.

N- [S-1- (1-naphthyl) ethyl] -N '- (1-hexylheptyl) -perylene-3,4: 9,10-tetracarbonsäurebisimid (10i):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (1.00 g, 1.74 mmol) and S - (-) - 1- (1-naphthyl ) ethylamine (310 mg, 1.80 mmol, [α] _D ²⁰ = -54 °, c = 2.0 in ethanol) was correspondingly N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4 : 9,10-tetracarboxylic bisimide reacted and worked up. Y. 980 mg (78%), mp 259 ° C; R _f (silica gel, CHCl ₃ ): 0.62; IR (KBr): ν ~ = 3055 (w, aryl), 2954 (m, CH ₃ ), 2927 (s, CH ₂ / CH ₃ ), 2857 (m, CH ₂ ), 1698 (s, C = O) , 1658 (s, C = O), 1594 (s, aryl), 1579 (m, aryl), 1435 (w), 1406 (m, CH ₂ / CH ₃ ), 1376 (w), 1354 (w), 1338 (s, CH ₃ ), 1253 (m, CN), 1209 (w), 1174 (w), 855 (w), 810 (s, aryl), 797 (w), 778 (w), 748 (m , CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 459.5 (20540), 491.0 (50945), 527.5 nm (81750); Fluorescence (CHCl ₃ ): λ _max = 543.5, 572.5 nm; ¹ H NMR (CDCl _3): δ = 0.84 (t, 6 H, _CH3), 1:21 to 1:43 (m, 16 H, CH _2), 1.86-1.97 (m, 2 H, CH _2), 2.175 (d , 3 H, _CH3), 2:20 to 2:31 (m, 2 H, CH _2), 5:14 to 5:22 (m, 1 H, N-CH), 7:07 to 7:14 (quart, 1 H, N-CH), 7:44 (t, 1H, naph), 7.58 (t, 1H, naph), 7.70 (t, 1H, naph), 7.71 (d, 2H, perylene), 7.81 (d, 2H, perylene ), 7.89 (d, 1H, naph.), 7.91 (d, 1H, naph.), 8.07 (d, 2H, perylene), 8.19 (d, 1H, naph.), 8.20 (d, 1 H, Naph.), 8.34 (d, 2H, perylene); ¹³ C NMR (CDCl _3): δ = 14.07 (2 C, CH _3), 17.4 (1 C, CH _3), 22.63 (2 C, CH _2), 27.05 (2 C, CH _2), 29.27 (2 C , CH ₂ ), 31.80 (1 C, CH ₂ ), 31.81 (1 C, CH ₂ ), 32.38 (1 C, CH ₂ ), 32.45 (1 C, CH ₂ ), 48.06 (1 C, N-CH) , 54.86 (1 C, N-CH), 122.22 (2 CH, perylene), 122.52 (2 CH, perylene), 123.01 (4 C, perylene), 123.29 (1 CH, naph.), 125.18 (1 CH, naph 125.38 (1 CH, naph), 125.46 (1 C, perylene), 125.78 (1 C, perylene), 126.54 (1 CH, naph), 128.41 (1 CH, naph), 128.49 (1 CH , Naph.), 128.73 (1 C, perylene), 129.09 (1 C, perylene), 129.22 (1 CH, naph.), 130.85 (4 CH, perylene), 131.86 (1 C, naph.), 133.63 (2 C, perylene), 133.74 (1 C, Naph.), 133.78 (2 C, perylene), 134.97 (1 C, Naph.), 162.95 (4 C = O, perylene); MS (70 eV): m / z (%) = 727 (9), 726 (16) [M ⁺ ], 709 (2) [M ⁺ -OH], 574 (4), 573 (9) [M ⁺ -C ₁₀ H ₇ C ₂ H ₂ ], 545 (8), 544 (9) [M ⁺ -C ₁₃ H ₂₆ ], 393 (5), 392 (18), 391 (42) [573-C ₁₃ H _26], 390 (25) [544 C ₁₀ H ₇ C ₂ H _3], 374 (5) [391-OH], 373 (9) [390-OH], 346 (8) [374-CO] 345 (7) [373-CO], 289 (2), 155 (12), 154 (74), 153 (100) [C ₁₀ H ₇ C ₂ H ₂ ⁺ ], 152 (52), 151 (18) , 150 (9), 128 (3), 127 (4), 126 (5), 85 (5), 83 (8), 77 (6), 76 (18), 75 (6), 74 (3) , 69 (4), 63 (8), 57 (4), 55 (6), 51 (4), 44 (3), 43 (3), 41 (4), 32 (13); C ₄₉ H ₄₆ N ₂ O ₄ (726.9): calc. C 80.96, H 6.38, N 3.85; gef. C 80.68, H 6.33, N 3.78.

N-dehydroabietyl-N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10k):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-anhydride-9,10-imide (500 mg, 0.870 mmol) and (+) - dehydroabietylamine (300 mg, 1.00 mmol, [α] _D ²⁰ = + 41.0 °, c = 1.0 in ethanol) were reacted and worked up corresponding to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide , Y. 590 mg (81%), mp 162 ° C; R _f (silica gel, CHCl ₃ ): 0.72; IR (KBr): ν ~ = 3070 (w, aryl), 2955 (s, CH ₃ ), 2927 (s, CH ₂ / CH ₃ ), 2857 (m, CH ₂ ), 1698 (s, C = O) , 1660 (s, C = O), 1595 (s, aryl), 1579 (m, aryl), 1455 (w), 1436 (m, CH ₂ / CH ₃ ), 1379 (w), 1336 (s, CH ₃ ), 1252 (m, CN), 1213 (w), 1174 (w), 1124 (w), 1107 (w), 852 (m), 811 (s, aryl), 750 (s, CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 458.2 (16180), 489.8 (49000), 526.2 nm (83440); Fluorescence (CHCl ₃ ): λ _max = 535.2, 573.5 nm; ¹ H NMR (CDCl _3): δ = 0.84 (t, 6 H, CH ₃₎ 1.08 (s, 3 H, _CH3), 1.21 (s, 3 H, CH _3), 1.235 (d, 6 H, CH ₃ ), 1.22-1.42 (m, 18 H, CH ₂ ), 1.49-1.72 (m, 4 H, CH ₂ ), 1.81-1.97 (m, 3 H, CH ₂ ), 2.19-2.38 (m, 4 H, CH / CH ₂ ), 2.82 (sept, 1H, CH), 2.98-3.13 (m, 2H, CH ₂ ), 4.18 (d, 1H, N-CH ₂ ), 4.22 (d, 1H , N-CH ₂ ), 5.19 (m, 1H, N-CH), 6.94 (d, 2H, perylene), 6.95 (s, 2H, aryl), 7.11 (d, 2H, aryl), 8.30 (d, 2H, perylene ), 8.38 (dd, 4H, perylene), 8.57 (br., 2H, perylene); ¹³ C NMR (CDCl _3): δ = 14.06 (2 C, CH _3), 18.62 (1C, CH _2), 19:31 (1 C, CH _3), 19.89 (1C, CH _2), 22.63 (1 C , CH ₂ ), 22.64 (1 C, CH ₂ ), 23.99 (1 C, CH ₃ ), 26.07 (1 C, CH ₃ ), 27.04 (2 C, CH ₂ ), 29.30 (2 C, CH ₂ ), 30.53 (1 C, CH ₂ ), 31.82 (2 C, CH ₂ ), 32.44 (2 C, CH ₂ ), 33.47 (1 C, CH), 37.44 (1 C, CH ₂ ), 37.84 (1 C, C 38.19 (1 C, CH ₂ ), 40.05 (1 C, C), 46.36 (1 C, CH), 49.86 (1 C, N-CH ₂ ), 54.88 (1 C, N-CH), 122.76 ( 2 CH, perylene), 122.81 (2 CH, perylene), 123.14 (4 C, perylene), 123.70 (1 CH, aryl), 123.86 (1 CH, aryl), 126.00 (1 C, perylene), 126.12 (1C , Perylene), 127.01 (1 CH, aryl), 128.95 (1 C, perylene), 129.45 (1 C, perylene), 131.24 (4 CH, perylene), 134.04 (2 C, perylene), 134.18 (2 C, perylene ), 135.10 (1 C, aryl), 145.53 (1 C, aryl), 147.50 (1 C, aryl), 164.13 (4 C = O, perylene); MS (70 eV): m / z (%) = 843.5 (3), 842.5 (14), 841.5 (42) [M ⁺ , 840.5 (68) [M ⁺ ] 825.5 (3) [M ⁺ -CH ₃ ] , 659 (3) [M ⁺ -C ₁₃ H ₂₆ ], 587 (11), 586 (26) [M ⁺ -C ₁₉ H ₂₇ ], 574 (8), 573 (8) [M ⁺ -C ₂₀ H _28], 569 (5), 406 (14), 405 (51), 404 (100) [586 C ₁₃ H _26], 403 (6), 392 (10), 391 (15) [573-C ₁₃ H ₂₆ ], 390 (8), 387 (4), 376 (6), 373 (9) [390-OH], 345 (5) [373-CO], 255 (4) [C ₁₉ H ₂₇ ⁺ ] , 253 (4), 239 (9), 237 (4), 197 (5), 185 (13), 174 (5), 173 (40), 171 (5), 159 (6), 157 (5) , 155 (4), 143 (6), 131 (8), 129 (5), 95 (7), 69 (5), 55 (8); C ₅₇ H ₆₄ N ₂ O ₄ (841.2): calc. C 81.39, H 7.67, N 3.33; gef. C 81.32, H 7.64, N 3.10.

N- (L-1,2-dimethylpropyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10b):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-anhydride-9,10-imide (500 mg, 0.870 mmol) and L - (+) - 2-amino-3- Methylbutane hydrobromide (8c, 200 mg, 1.20 mmol, [α] _D ²⁰ = = + 0.96 °, c = 1.95 in methanol) was correspondingly N, N'-di- (L-1-methyl-2-phenylethyl) perylene -3,4: 9,10-tetracarboxylic bisimide reacted and worked up. Y. 420 mg (75%), mp 246 ° C; R _f (silica gel, CHCl ₃ ): 0.63; IR (KBr): ν ~ = 2959 (m, CH ₃ ), 2928 (m, CH ₂ / CH ₃ ), 2857 (w, CH ₂ ), 1700 (s, C = O), 1658 (C = O) , 1595 (s, aryl), 1579 (m, aryl), 1465 (w), 1457 (w), 1406 (m, CH ₂ / CH ₃ ), 1353 (w), 1339 (s, CH ₃ ), 1254 (m, CN), 1175 (w), 810 (m, aryl), 747 (m) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 457.5 nm (19800), 488.5 (52550), 524.5 nm (87650); Fluorescence (CHCl ₃ ): λ _max = 532.0, 571.0 nm; ¹ H NMR (CDCl ₃ ): δ = 0.83 (t, 6H, CH ₃ ), 0.85 (d, 3H, CH ₃ ), 1.12 (d, 3H, CH ₃ ), 1.18-1.40 (m, 16 H, CH ₂ ), 1.64 (d, 3H, CH ₃ ), 1.84-1.93 (m, 2H, CH ₂ ), 2.21-2.31 (m, 2H, CH ₂ ), 2.68-2.77 (m , 1H, CH), 4.90 (m, 1H, N-CH), 5.19 (m, 1H, N-CH), 8.50 (d, 2H, perylene), 8.51 (d, 2H, perylene). , 8.60 (d, 4H, perylene); ¹³ C NMR (CDCl _3): δ = 14.05 (2 C, CH _3), 16.87 (1 C, CH _3), 20:16 (1 C, CH _3), 20.83 (1 C, CH _3), 22.61 (2 C , CH ₂ ), 26.99 (2 C, CH ₂ ), 29.25 (2 C, CH ₂ ), 30.38 (1 C, CH), 31.79 (2 C, CH ₂ ), 32.41 (2 C, CH ₂ ), 54.82 (1 C, N-CH), 56.26 (1 C, N-CH), 122.91 (4 CH, perylene), 123.59 (4 C, perylene), 126.31 (1 C, perylene), 126.34 (1 C, perylene). , 129.45 (1 C, perylene), 129.53 (1 C, perylene), 131.35 (4 CH, perylene), 134.37 (4 C, perylene), 163.82 (4 C = O, perylene); MS (70 eV): m / z (%) = 643 (19), 642 (39) [M ⁺ ], 625 (4), 599 (6) [M ⁺ -C ₃ H ₇ ], 574 (6) , 573 (21), 572 (28) [M ⁺ -C ₅ H ₁₀ ], 555 (3) [572-OH], 462 (5), 461 (15), 460 (11) [M ⁺ -C ₁₃ H ₂₆ ], 418 (4), 417 (10) [599-C ₁₃ H ₂₆ ], 392 (16), 391 (57), 390 (100) [572-C ₁₃ H ₂₆ ], 374 (5), 373 (17) [390-OH], 346 (7), 345 (11) [373-CO], 320 (3), 289 (1), 167 (2), 69 (2), 55 (5), 41 (3), 28 (4); C ₄₂ H ₄₆ N ₂ O ₄ (642.8): calc. C 78.47, H 7.21, N 4.36; gef. C 78.81, H 7.37, N 4.30.

N- (L-1,3-dimethylbutyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10d):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-anhydride-9,10-imide (500 mg, 0.870 mmol) and L - (+) - 2-amino-4- Methylpentane hydrobromide (8d, 200 mg, 1.10 mmol, [α] _D ²⁰ = + 5.68 °, c = 2.05 in methanol) was correspondingly N, N'-di- (L-1-methyl-2-phenylethyl) perylene Reacted and worked up 3,4: 9,10-tetracarboxylic bisimide. Y. 450 mg (79%), mp 237 ° C; R _f (silica gel, CHCl ₃ ): 0.69; IR (KBr): ν ~ = 2957 (m, CH ₃ ), 2927 (s, CH ₂ / CH ₃ ), 2857 (m, CH ₂ ), 1700 (s, C = O), 1658 (s, C = O), 1595 (s, aryl), 1577 (m, aryl), 1457 (w), 1437 (w), 1406 (m, CH ₂ / CH ₃ ), 1339 (s, CH ₃ ), 1253 (w, CN), 810 (s, aryl), 746 (m) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 457.5 (23310), 488.5 (54890), 525.0 nm (89100); Fluorescence (CHCl ₃ ): λ _max = 533.0, 571.5 nm; ¹ H NMR (CDCl _3): δ = 0.83 (t, 6 H, _CH3), 0.95 (d, 3 H, _CH3), 0.97 (d, 3 H, _CH3), 1:18 to 1:40 (m, 16 H, CH ₂ ), 1.52-1.61 (m, 1 H, CH), 1.62 (d, 3 H, CH ₃ ), 1.72-1.77 (m, 1 H, CH), 1.83-1.91 (m, 2 H, CH ₂ ), 2.19 (m, 1H, CH ₂ ), 2.21-2.31 (m, 2H, CH ₂ ), 5.19 (m, 1H, N-CH), 5.40 (m, 1H, N-CH ), 8.52 (d, 2H, perylene), 8.54 (d, 2H, perylene), 8.61 (d, 4H, perylene); ¹³ C NMR (CDCl _3): δ = 14.05 (2 C, CH _3), 18.63 (1 C, CH _3), 22.60 (2 C, CH _2), 22.63 (1 C, CH _3), 22.94 (1 C , CH ₃ ), 25.83 (1 C, CH ₂ ), 26.97 (2 C, CH ₂ ), 29.24 (2 C, CH ₂ ), 31.78 (2 C, CH ₂ ), 32.41 (2 C, CH ₂ ), 42.74 (1 C, CH), 48.18 (1 C, N-CH), 54.82 (1 C, N-CH), 122.93 (4 CH, perylene), 123.75 (4 C, perylene), 126.33 (1 C, perylene ), 126.37 (1 C, perylene), 129.42 (1 C, perylene), 129.55 (1 C, perylene), 131.28 (4 CH, perylene), 134.37 (4 C, perylene), 163.80 (4 C = O, perylene ); MS (70 eV): m / z (%) = 658 (12), 657 (48), 656 (100) [M ⁺ ], 640 (5), 639 (11) [M ⁺ -OH], 574 ( 4), 573 (12), 572 (9) [M ⁺ -C ₆ H ₁₂ ], 487 (3) [572-C ₆ H ₁₃ ], 476 (14), 475 (41), 474 (53) [ M ⁺ -C ₁₃ H ₂₆ ], 457 (4), 431 (3), 419 (6), 418 (15) [475-C ₄ H ₉ ], 417 (5), 393 (5), 392 (23 391 (73), 390 (95) [474-C ₆ H ₁₂ ], 374 (8), 373 (25) [390-OH], 346 (10), 345 (14) [373-CO], 320 (4), 124 (3), 111 (4), 97 (5), 95 (4), 83 (6), 71 (5), 69 (9), 57 (8), 55 (10), 41 (7), 28 (17); C ₄₃ H ₄₈ 2 _Z O ₄ (656.9): comp. C 78.63, H 7.37, N 4.26; gef. C 78.75, H 7.43, N 4.06.

N- (L-1-methylpropyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10a):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-anhydride-9,10-imide (500 mg, 0.870 mmol) and L - (-) - 2-aminobutane hydrobromide ( 8a, 150 mg, 0.970 mmol, [α] _D ²⁰ = -0.87 °, c = 2.0 in methanol) were corresponding to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: Reacted and worked up 9,10-tetracarboxylic bisimide. Y. 420 mg (77%), mp 270 ° C; R _f (silica gel, CHCl ₃ ): 0.52; IR (KBr): ν ~ = 2958 (m, CH ₃ ), 2928 (s, CH ₂ / CH ₃ ), 2858 (m, CH ₂ ), 1698 (s, C = O), 1658 (s, C = O), 1595 (s, aryl), 1579 (m, aryl), 1461 (w), 1435 (w), 1406 (m, CH ₂ / CH ₃ ), 1339 (s, CH ₃ ), 1254 (m, CN), 1211 (w), 1176 (w), 852 (w), 810 (s, aryl), 746 (s) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 457.5 (19290), 488.5 (52380), 525.0 nm (86690); Fluorescence (CHCl ₃ ): λ _max = 532.0, 573.0 nm; ¹ H NMR (CDCl _3): δ = 0.83 (t, 6 H, _CH3), 0.95 (t, 3 H, _CH3), 1:19 to 1:40 (m, 16 H, CH _2), 1.63 (d, 3 H, CH _3), 1.83-1.93 (m, 2 H, CH _2), 1.94-2.05 (m, 1 H, CH _2), 2:18 to 2:31 (m, 3 H, CH _2), 5.17 (m, 1 H, N-CH), 5.21 (m, 1H, N-CH), 8.48 (d, 2H, perylene), 8.50 (d, 2H, perylene), 8.58 (d, 2H, perylene), 8.62 (br., 2H, perylene); ¹³ C NMR (CDCl _3): δ = 11:55 (1 C, CH _3), 14.5 (2 C, CH _3), 18.2 (1 C, CH _3), 22.61 (2 C, CH _2), 26.54 (1 C , CH ₂ ), 26.99 (2 C, CH ₂ ), 29.25 (2 C, CH ₂ ), 31.80 (2 C, CH ₂ ), 32.42 (2 C, CH ₂ ), 51.55 (1 C, N-CH) , 54.83 (1 C, N-CH), 122.89 (4 CH, perylene), 123.67 (4 C, perylene), 126.28 (1 C, perylene), 126.33 (1 C, perylene), 129.40 (1 C, perylene). , 129.53 (1 C, perylene), 131.23 (4 CH, perylene), 134.32 (4 C, perylene), 163.80 (4 C = O, perylene); MS (70 eV): m / z (%) = 629 (13), 628 (30) [M ⁺ ], 611 (5) [M ⁺ -OH], 543 (1) [M ⁺ -C ₆ H ₁₃ ], 448 (9), 447 (28), 446 (46) [M ⁺ -C ₁₃ H ₂₆ ], 417 (5) [446-C ₂ H ₅ ], 392 (12), 391 (51), 390 (100) [446-C ₄ H _8], 374 (8), 373 (20) [390-OH], 346 (12), 345 (19) [373-CO], 320 (4), 302 (7 ), 131 (7), 124 (8), 123 (8), 97 (10), 95 (8), 91 (8), 83 (11), 71 (11), 69 (37), 67 (11 ), 57 (24), 55 (34), 44 (23) 43 (23), 41 (39), 39 (24), 32 (87), 29 (17); C ₄₁ H ₄₄ N ₂ O ₄ (628.8): calc. C 78.31, H 7.05, N 4.46; gef. C 78.09, H 6.99, N 4.33.

N- (L-1,2-dimethylbutyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10c):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (400 mg, 0.700 mmol) and L - (-) - 2-amino-3- Methylpentane hydrobromide (8b, 140 mg, 0.770 mmol, [α] _D ²⁰ = -0.74 °, c = 2.05 in methanol) was prepared corresponding to N, N'-di- (L-1-methyl-2-phenylethyl) perylene Reacted and worked up 3,4: 9,10-tetracarboxylic bisimide. Y. 350 mg (76%), mp 213 ° C; R _f (silica gel, CHCl ₃ ): 0.61; IR (KBr): ν ~ = 2958 (s, CH ₃ ), 2927 (s, CH ₂ / CH ₃ ), 2857 (m, CH ₂ ), 1698 (s, C = O), 1658 (s, C = O), 1594 (s, aryl), 1579 (m, aryl), 1457 (w), 1435 (w), 1406 (s, CH ₂ / CH ₃ ), 1381 (w), 1339 (s, CH ₃ ) , 1252 (m, CN), 1210 (w), 1175 (w), 1124 (w), 852 (m), 810 (s, aryl), 747 (s) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 458.5 (22040), 489.5 (55210), 526.0 nm (89580); Fluorescence (CHCl ₃ ): λ _max = 543.5, 573.5 nm; ¹ H NMR (CDCl _3): δ = 0.83 (dt, 9 H, _CH3), 1:01 to 1:12 (m, 1 H, CH _2), 1:07 (d, 3 H, _CH3), 1:21 to 1:41 (m , 17 H, CH _2), 1.65 (d, 3 H, CH _3), 1.84-1.95 (m, 2 H, CH _2), 2:21 to 2:31 (m, 2 H, CH _2), 2:48 to 2:59 (m , 1H, CH), 4.93-5.01 (m, 1H, N-CH), 5.15-5.23 (m, 1H, N-CH), 8.42 (d, 2H, perylene), 8.44 (d, 2 H, perylene), 8.55 (d, 2H, perylene), 8.58 (br., 2H, perylene); ¹³ C NMR (CDCl _3): δ = 10.86 (1 C, CH _3), 14.5 (2 C, CH _3), 16:57 (1 C, CH _3), 16.98 (1 C, CH _3), 22.61 (2 C , CH ₂ ), 26.06 (1 C, CH ₂ ), 27.00 (2 C, CH ₂ ), 29.25 (2 C, CH ₂ ), 31.80 (2 C, CH ₂ ), 32.41 (2 C, CH ₂ ), 36.21 (1 C, CH), 54.81 (1 C, N-CH), 54.82 (1 C, N-CH), 122.81 (4 CH, perylene), 123.57 (4 C, perylene), 126.17 (1 C, perylene ), 126.22 (1 C, perylene), 129.34 (1 C, perylene), 129.45 (1 C, perylene), 131.23 (4 CH, perylene), 134.22 (4 C, perylene), 163.73 (4 C = O, perylene ); MS (70 eV): m / z (%) = 657 (19), 656 (38) [M ⁺ ], 639 (6) [M ⁺ -OH], 599 (8) [M ⁺ -C ₄ H ₉ ], 574 (12), 573 (38), 572 (42) [M ⁺ -C ₆ H ₁₂ ], 555 (4) [572-OH], 476 (4), 475 (11), 474 (6) [M ⁺ -C ₁₃ H ₂₆ ], 417 (10) [599-C ₁₃ H ₂₆ ], 392 (18), 391 (63), 390 (100) [572-C ₁₃ H ₂₆ ], 374 (5) , 373 (17) [390-OH], 346 (6), 345 (10) [373-CO], 320 (2), 69 (3), 55 (5), 41 (3); C ₄₃ H ₄₈ N ₂ O ₄ (656.9): calc. C 78.63, H 7.37, N 4.26; gef. C 78.75, H 7.28, N 4.06.

N- (3-Pinylmethyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-tetracarbonsäurebisimid (10j):

N- (1-Hexylheptyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (800 mg, 1.9 = mmol) and (+) - 3-aminomethyl-pinane hydrochloride (300 mg, 1.50 mmol, [α] _D ²⁰ = + 39 °, c = 5 in water) were corresponding N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10 Tetracarbonsäurebisimid reacted and worked up. Y. 770 mg (77%), m.p. 268 ° C; R _f (silica gel, CHCl ₃ ): 0.63; IR (KBr): ν ~ = 2954 (s, CH ₃ ), 2928 (s, CH ₂ / CH ₃ ), 2858 (m, CH ₂ ), 1697 (s, C = O), 1658 (s, C = O), 1595 (s, aryl), 1579 (m, aryl), 1456 (w), 1437 (m), 1405 (m, CH ₂ / CH ₃ ), 1340 (s, CH ₃ ), 1252 (m, CN), 1215 (w), 1175 (w), 852 (w), 811 (s, aryl), 745 (m) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 458.0 (20370), 489.0 (53760), 525.5 nm (88650); Fluorescence (CHCl ₃ ): λ _max = 533.0, 574.5 nm; ¹ H NMR (CDCl _3): δ = 0.81 (t, 6 H, _CH3), 0.95 (s, 3 H, _CH3), 0.96 (d, 1 H, CH), 1:04 (d, 3 H, CH _3), 1.16 (s, 3 H, _CH3), 1:19 to 1:39 (m, 16 H, CH _2), 1.68-1.79 (m, 2 H, CH _2), 1.83-1.97 (m, 4 H, CH _2), 2:00 to 2:09 (m, 1 H, CH), 2:19 to 2:29 (m, 2 H, CH _2), 2:30 to 2:38 (m, 1 H, CH), 2:37 to 2:47 (m, 1 H, CH ), 4:10 to 4:21 (m, 2 H, N-CH _2), 5:12 to 5:21 (m, 1 H, N-CH), 8:37 (d, 2 H, perylene), 8:42 (d, 2 H, perylene) , 8.47 (d, 2H, perylene), 8.57 (br., 2H, perylene); ¹³ C NMR (CDCl _3): δ = 05.14 (2 C, CH _3), 21.92 (1 C, CH _3), 22.62 (2 C, CH _2), 23.07 (1 C, CH _3), 27.02 (1 C , CH ₂ ), 27.03 (1 C, CH ₂ ), 28.00 (1 C, CH ₃ ), 29.27 (2 C, CH ₂ ), 31.62 (1 C, CH ₂ ), 31.80 (2 C, CH ₂ ), 32.42 (2 C, CH ₂ ), 33.96 (1 C, CH ₂ ), 34.57 (1 C, CH), 38.63 (1 C, N-CH ₂ ), 41.10 (1 C, CH), 41.64 (1 C, CH), 48.15 (1 C, CH), 48.62 (1 C, C), 54.88 (1 C, N-CH), 122.84 (2 CH, perylene), 122.91 (2 CH, perylene), 123.03 (4 C, perylene), 126.14 (1 C, Perylene), 126.20 (1 C, perylene), 129.23 (1 C, perylene), 129.45 (1 C, perylene), 131.24 (4 CH, perylene), 134.10 (2 C, perylene), 134.40 (2 C, perylene). , 163.69 (4 C = O, perylene); MS (70 eV): m / z (%) = 723 (14), 722 (25) [M ⁺ ], 653 (5) [M ⁺ -C ₅ H ₉ ], 575 (11), 574 (46) , 573 (100) [M ⁺ -C ₁₁ H ₁₇ ], 572 (35) [M ⁺ -C ₁₁ H ₁₈ ], 555 (4) [572-OH], 541 (6) [M ⁺ -C ₁₃ H ₂₅ ], 405 (14), 404 (26) [541-C ₁₀ H ₁₇ ], 403 (8), 393 (8), 392 (31), 391 (61), 390 (71) [572-C ₁₃ H ₂₆ ], 374 (4), 373 (16) [390-OH], 346 (6), 345 (10) [373-CO], 320 (3), 150 (6), 149 (8) [C ₁₁ H ₁₇ ⁺ ], 107 (7), 95 (4), 93 (8), 69 (6), 57 (4), 55 (9), 43 (4), 41 (6); C ₄₈ H ₅₄ N ₂ O ₄ (723.0): C79.74, H 7.53, N 3.88; gef. C 79.62, H 7.25, N 3.97.

N- (S-1-cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide and N- (S-1-cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-imide-9,10-lactam:

N, N'-di- (S-1-cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide (1f, 3.00 g, 4.91 mmol), KOH powder (85%, 1.00 g, 15.0 mmol) and tert. Butyl alcohol (100 mL) was refluxed with stirring for 20 min, cooled with ice, acidified with glacial acetic acid (50 mL) and 2N HCl (200 mL), allowed to stand for 16 h, filtered with suction (D4 glass filter), washed with distilled water, three times with hot, aqueous K ₂ CO ₃ (10%), acidified with 2N HCl, dried in air at 120 ° C and purified by column chromatography (silica gel, chloroform) to separate the starting material as a first fraction. The violet main fraction was eluted with chloroform / glacial acetic acid 10: 1. 1. violet fraction: N (S-1-cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-imide-9,10-lactam. M.p. 186 ° C; R _F (silica gel, CHCl ₃ ): 0.13; IR (KBr): ν ~ = 2929 (s, CH ₂ / CH ₃ ), 2853 (m, CH ₂ ), 1695 (s, C = O), 1655 s, C = O), 1624 (w), 1583 (s, aryl), 1492 (s, aryl), 1462 (w, CH ₂ / CH ₃ ), 1397 (m), 1354 (s, CH ₃ ), 1287 (w), 1252 (w, CN), 807 (m, aryl [2H]), 742 (w, CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 329.5 (5100), 362.7 (4590), 397.4 (6400), 412.1 (7340), 544.9 nm (21020); Fluorescence (CHCl ₃ ): λ _max = 530.0, 575.0, 618.5 nm; ¹ H NMR (CDCl _3): δ = 0.80-1.45 (m, 12 H, CH _2), 1.48-1.69 (m, 4 H, CH _2), 1.57 (d, 3 H, _CH3), 1.59 (d, 3 H, CH _3), 1.54-1.86 (m, 2 H, CH _2), 1.93-2.07 (m, 3 H, CH / CH _2), 2:29 to 2:42 (m, 1 H, CH), 4.30-4.39 (m, 1H, N-CH), 4.91-5.00 (m, 1H, N-CH), 7.12 (d, 1H, aryl), 8.10 (d, 1H, aryl), 8.18 ( d, 1H, aryl), 8.26 (d, 1H, aryl), 8.40 (2d, 2H, aryl), 8.53 (d, 1H, aryl), 8.56 (d, 1H, aryl); ¹³ C NMR (CDCl _3): δ = 16:49 (1 C, CH _3), 16.96 (1 C, CH _3), 25.77 (1C, CH _2), 25.82 (1C, CH _2), 25.96 (1 C , CH ₂ ), 26.00 (1 C, CH ₂ ), 26.09 (1 C, CH ₂ ), 26.26 (1 C, CH ₂ ), 30.01 (1 C, CH ₂ ), 30.08 (1 C, CH ₂ ), 30.64 (1 C, CH ₂ ), 31.12 (1 C, CH ₂ ), 39.34 (1 C, CH), 41.30 (1 C, CH), 53.37 (1 C, N-CH), 54.63 (1 C , N-CH), 108.39 (CH, aryl), 120.07 (CH, aryl), 121.96 (CH, aryl), 123.56 (2 C, aryl), 123.76 (CH, aryl), 124.40 (C, aryl), 124.68 (CH, aryl), 125.49 (CH, aryl), 125.86 (C, aryl), 125.49 (CH, aryl), 125.86 (C, aryl), 126.32 (C, aryl), 126.37 (C, aryl), 130.06 ( C, aryl), 131.38 (2CH, aryl), 133.73 (2C, aryl), 134.64 (C, aryl), 135.72 (2C, aryl), 140.04 (1C, C = O), 167.39 (2C , C = O); MS (70 eV): m / z (%) = 584 (9), 583 (41), 582 (95) [M ⁺ ], 565 (7) [M ⁺ -OH], 500 (12), 499 ( 32) [M ⁺ -C ₆ H ₁₁ ], 474 (10), 473 (41), 472 (73) [M ⁺ -C ₈ H ₁₄ ], 455 (6) [472-OH], 391 (6) , 390 (32), 389 (100) [472-C ₆ H ₁₁ ], 364 (5), 363 (24), 362 (46) [472-C ₈ H ₁₄ ], 361 (12), 345 (9 ) [362-OH], 320 (5), 318 (5), 317 (9) [345-CO], 263 (4), 149 (7), 111 (6), 109 (4), 97 (9 ), 95 (6), 85 (8), 83 (9), 81 (8), 71 (11), 70 (5), 69 (11), 67 (7), 57 (16), 56 (5 ), 55 (15); C ₃₉ H ₃₈ N ₂ O ₄ : calc. 582.2882, ref. 582.2830 (MS); C ₃₉ H ₃₈ N ₂ O ₄ (582.7): calc. C 80.38, H 6.57, N 4.81; gef. C 78.76, H 7.16, N 4.59. 2nd fraction: N- (S-1-cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic acid 3,4-anhydride-9,10-imide. Y. 1.22 g (50%), mp> 350 ° C; R _f (silica gel, CHCl ₃ ): 0.08; IR (KBr): ν ~ = 2930 (m, CH ₂ / CH ₃ ), 2857 (w, CH ₂ / CH ₃ ), 1770 (s, C = O), 1732 ((m, C = O), 1702 (m, C = O), 1658 (m, C = O), 1634 (w), 1618 (w), 1596 (s, aryl), 1581 (w, aryl), 1406 (m, CH ₂ / CH ₃ ), 1358 (w), 1321 (s), 1254 (m, CN), 1126 (w), 1023 (w), 810 (m, aryl [2H]), 739 (m, CH ₂ ) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 456.9 (17820), 486.2 (46460), 522.5 nm (74250), fluorescence (CHCl ₃ ): λ _max = 534.5, 568.0 nm, ¹ H NMR (CDCl ₃ ): δ = 0.91-1.36 (m, 5 H, CH _2), 1:50 (d, 1 H, CH _2), 1:58 (d, 3 H, _CH3), 1.63 (d, 1 H, CH _2), 1.79 (d, 1 H, CH _2), 2.01, (d, 1 H, CH _2), 2:35 (m, 1 H, CH), 4.95 (m, 1 H, N-CH), 8.66 (d, 4 H , aryl), 8.69 (d, 2H, aryl), 8.70 (d, 2H, aryl); ¹³ C NMR (CDCl _3): δ = 16:46 (1 C, CH _3), 25.79 (1 C, CH ₂ ), 25.95 (1C, CH ₂ ), 26.20 (1C, CH ₂ ), 30.01 (1C, CH ₂ ), 31.07 (1C, CH ₂ ), 39.30 (1C, CH), 55.01 (1C , N-CH), 113.34 (2 C, perylene), 119.05 (2 C, perylene), 123.17 (2 CH, perylene), 123.90 (2 CH, perylene), 126.56 (1 C, perylene), 129.47 (1C . Perylene), 131.90 (1 C, perylene), 132.24 (1 C, perylene), 133.50 (4 CH, perylene), 133.67 (2 C, perylene), 136.44 (2 C, perylene), 159.96 (4 C, C = O); MS (70 eV): m / z (%) = 501 (12) [M ⁺ ], 484 (4) [M ⁺ -OH], 419 (6), 418 (17) [M ⁺ -C ₆ H ₁₁ 394 (13), 393 (40), 392 (100) [M ⁺ -C ₈ H ₁₄ ], 391 (77), 375 (5), 374 (21) [391-OH], 348 (6) , 347 (13) [392-CHO ₂ ], 346 (8), 320 (5), 319 (11) [347-CO], 302 (4) [319-OH], 275 (7), 274 (10 ) [302-CO], 249 (4), 248 (6), 129 (3), 109 (3), 97 (3), 85 (4), 83 (5), 81 (7), 73 (4 ), 71 (4), 69 (4), 67 (6), 60 (4), 57 (10), 55 (12); C ₃₂ H ₂₃ O ₅ N (501.5): calc. C 76.64, H 4.62, N 2.79; gef. C 76.65, H 4.64, N 3.00.

N-Dehydroabietylperylen-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide:

N, N '- (di-dehydroabietyl) perylene-3,4: 9,10-tetracarboxylic bisimide (1k, 1.35g, 1.46mmol), KOH powder (85%, 280mg, 4.20mmol) and tert-butyl alcohol (28mL ) were reacted correspondingly N- (S-1-cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic 3,4-anhydride-9,10-imide and worked up (25 min). Y. 120 mg (13%), mp 264 ° C; R _f (silica gel, CHCl ₃ / glacial acetic acid 10: 1): 0.61; IR (KBr): ν ~ = 2958 (m, CH ₃ ), 2931 (m, CH ₂ / CH ₃ ), 2868 (w, CH ₂ ), 1700 (s, C = O), 1662 (s, C = O), 1616 (w), 1595 (s, aryl), 1580 (m, aryl), 1507 (w), 1498 (w), 1438 (m), 1405 (m, CH ₂ / CH ₃ ), 1378 ( w), 1334 (s, CH ₃ ), 1252 (m, CN), 1161 (w), 1108 (w), 811 (s, aryl [2H]), 754 (m) cm ^-1 ; MS (70 eV): m / z (%) = 686 (4), 674 (4), 673 (8), 672 (14), 671 (10), 660 (8), 659 (11) [M ⁺ ], 432 (5), 420 (5), 419 (23), 418 (83), 417 (33), 405 (44) [M ⁺ -C ₁₉ H ₂₆ ], 404 (60) [M ⁺ -C ₁₉ H ₂₇ ], 391 (17) [M ⁺ -C ₂₀ H ₂₈ ], 387 (15), 373 (11), 285 (10), 273 (42), 239 (47), 185 (47), 173 (100), 131 (35), 109 (36), 95 (39), 91 (49), 81 (41), 69 (36), 55 (64).

N- (S-1-cyclohexylethyl) -N '- (9-acridinyl) perylene-3,4: 9,10-tetracarbonsäurebisimid:

N- (S-1-Cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (200 mg, 0.400 mmol), 9-aminoacridine (120 mg, 0.480 mmol) and imidazole (2.00 g) were reacted and worked up corresponding to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide. Y. 190 mg (70%); M.p. 227 ° C; R _f (silica gel, CHCl ₃ / glacial acetic acid 20: 1): 0.42; IR (KBr): ν ~ = 3068 (w, aryl), 2927 (s, CH ₂ / CH ₃ ), 2850 (m, CH ₂ ), 1710 (s, C = O), 1698 (s, C = O ), 1675 (s, C = O), 1660 (s, C = O), 1594 (s, aryl), 1579 (s, aryl), 1518 (w), 1437 (m), 1404 (s, CH ₂ / CH _3), 1357 (m), 1334 (s, CH _3), 1255 (s, CN), 1196 (m), 1177 (m), 965 (w), 857 (m), 810 (s, aryl [2H]), 746 (CH ₂ / aryl [4H]), 733 (m), 633 (s), 612 (w) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 258.6 (116110), 346.1 (8900), 364.1 (17750), 464.8 (14870), 496.1 (41310), 532.0 nm (67950); Fluorescence (CHCl ₃ ): λ _max = 542.0, 582.0 nm; ¹ H NMR (CDCl ₃ ): δ = 0.88-1.38 (m, 5 H, CH ₂ ), 1.52 (d, br., 1 H, CH ₂ ), 1.61 (d, 3 H, CH ₃ ), 1.57- 1.67 (br., 2 H, CH _2), 1.80 (m, 1 H, CH _2), 2:03 (m, 1 H, CH _2), 2:36 (m, 1 H, CH _2), 4.97 (m, 1 H, N-CH), 7.51 (dd, 2H, acr.), 7.78 (dd, 1H, acr.), 7.85 (d, 2H, acr.), 8.33 (d, 2H, acr.). , 8.63-8.71 (m, 6H, perylene), 8.76 (d, 2H, perylene); ¹³ C NMR (CDCl _3): δ = 16:53 (1 C, CH _3), 25.84 (1C, CH _2), 26.00 (1C, CH _2), 26.25 (1C, CH _2), 30.08 (1 C , CH ₂ ), 31.12 (1 C, CH ₂ ), 39.35 (1 C, CH ₂ ), 55.01 (1 C, N-CH), 122.33 (2 CH, perylene), 122.69 (2 C, Acr.), 123.17 (2 CH, perylene), 123.61 (4 C, perylene), 123.70 (2 CH, acr.), 126.42 (1 C, perylene), 127.00 (1 C, perylene), 127.44 (2 CH, acr.), 129.50 (1 C, perylene), 130.29 (2 CH, acr.), 130.42 (2 CH, perylene), 130.51 (1 C, perylene), 131.58 (2 CH, perylene), 132.44 (2 CH, acr.), 134.07 (2C, perylene), 135.88 (2C, perylene), 138.04 (1CN, acr.), 149.74 (2C = N, acr.), 163.17 (4C, C = O); MS (70 eV): m / z (%) = 678 (7), 677 (14) [M ⁺ ], 669 (6), 595 (7), 594 (15) [M ⁺ -C ₆ H ₁₁ ] , 570 (10), 569 (40), 568 (100), 567 (99) [M ⁺ -C ₈ H ₁₄ ], 551 (4), 550 (10) [567-OH], 522 (6) [ 550-CO], 375 (3), 374 (23), 373 (83) [550 C ₁₃ H ₇ N], 346 (10), 345 (24) [373-CO], 329 (5), 328 (21) [345-OH], 303 (4), 301 (3), 300 (9) [328-CO], 289 (5), 283 (4), 275 (7), 274 (5), 195 (6), 179 (5), 178 (4), 167 (3), 149 (4), 81 (6), 69 (3), 67 (5), 60 (4), 57 (4), 55 (5); C ₄₅ H ₃₁ N ₃ O ₄ : calc. 677.2314, ref. 677.2317 (MS); Ca ₅ H ₃₁ N ₃ O ₄ (677.8): calc. C 79.75, H 4.61, N 6.20; gef. C 79.26, H 4.87, N 6.01.

N- (S-1-cyclohexylethyl) -N '- (9-anthracenyl) perylene-3,4: 9,10-tetracarbonsäurebisimid:

N- (S-1-Cyclohexylethyl) perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (200 mg, 0.400 mmol), 9-aminoanthracene (100 mg, 0.450 mmol) and imidazole (2.00 g) were reacted and worked up corresponding to N, N'-di- (L-1-methyl-2-phenylethyl) perylene-3,4: 9,10-tetracarboxylic bisimide. Y. 90 mg (33%), mp> 300 ° C; R _f (silica gel, CHCl _3): 0.09; IR (KBr): ν ~ = 2927 (m, CH ₂ / CH ₃ ), 2853 (w, CH ₂ / CH ₃ ), 1697 (s, C = O), 1658 (s, C = O), 1596 ( s, aryl), 1578 (m, aryl), 1433 (w), 1404 (m, CH ₂ / CH ₃ ), 1357 (m), 1336 (s, CH ₃ ), 1256 (m, CN), 1177 ( w), 862 (w), 811 (m, aryl [2H]), 748 (m, aryl [4H], 736 (w), 635 (w) cm ^-1 , UV / Vis (CHCl ₃ ): λ _max (ε) = 348.0 (8140) 365.8 (11150), 385.1 (8370) 459.9 (18510), 490.8 (50440), 527.9 nm (82140); fluorescence (CHCl _3): λ _max = 540.0, 574.5 nm; ¹ H NMR (CDCl _3): δ = 0.82-1.40 (m, 6 H, CH _2), 1:59 (d, 1 H, CH _2), 1.62 (d, 3 H, _CH3), 1.66 (d, 1 H , CH ₂ ), 1.82 (d, 1H, CH ₂ ), 2.05 (d, 1H, CH ₂ ), 2.34-2.44 (m, 1H, CH), 5.00 (m, 1H, N-CH) , 7.44-7.51 (m, 4H, anthr.), 7.80 (d, 2H, anthr.), 8.14 (d, 2H, anthr.), 8.67 (s, 1H, anthr.), 8.71-8.74 (m, 4 H, perylene), 8.75 (d, 2 H, perylene), 8.81 (d, 2 H, perylene); ¹³ C NMR (CDCl _3): δ = 16:53 (1 C, CH _3), 25.85 ( 1 C, CH ₂ ), 26.27 (1 C, CH ₂ ), 30.06 (1 C, CH ₂ ), 31.14 (1 C, CH ₂ ), 39.36 (1 C, CH ₂ ), 41.06 (1 C, CH) , 54.9 5 (1 C, N-CH), 121.99 (2 CH, anthr.), 123.23 (2 CH, perylene), 123.28 (4 C, perylene), 123.50 (2 CH, perylene), 125.46 (2 CH, anthr. ), 126.57 (1 C, perylene), 127.29 (1 C, perylene), 127.37 (2 CH, anthr.), 128.54 (2 C, anthr.), 128.78 (1 CH, anthr), 129.15 (2 CH, perylene ), 129.61 (1 C, perylene), 130.50 (1 C, perylene), 131.53 (2 CH, perylene), 131.94 (2 C, anthr.), 132.33 (2 CH, anthr.), 133.46 (1 C, anthr ), 134.39 (2 C, perylene), 135.53 (2 C, perylene), 163.69 (4 C, C = O); MS (70 eV): m / z (%) = 678 (6), 677 (24), 676 (50) [M ⁺ ], 660 (3), 659 (6) [M ⁺ -OH], 599 ( 2), 594 (7), 593 (14) [M ⁺ -C ₆ H _11], 569 (6), 568 (32), 567 (86), 566 (99) [M ⁺ -C ₈ H _14] , 549 (2) [566-OH], 522 (4), 521 (10) [549-CO], 483 (3) [659-C ₁₄ H ₈ ], 450 (3), 401 (4), 390 (3) [566-C ₁₄ H _8], 375 (4), 374 (26), 373 (100) [483-C ₈ H _14], 372 (7), 347 (4), 346 (21) 345 (39) [373-CO], 329 (5), 328 (14) [345-OH], 303 (4), 300 (9) [328-CO], 289 (8), 275 (8), 274 (7), 262 (3), 193 (3), 97 (3) 81 (6), 57 (5), 55 (7); C ₄₆ H ₃₂ N ₂ O ₄ : calc. 676.2362, ref. 676.2290 (MS); C ₄₆ H ₃₂ N ₂ O ₄ (676.8): calc. C 81.64, H 4.77, N 4.14; gef. C 79.70, H 4.94, N 4.21.

2,7-bis - ((R) -1-naphthalen-1-yl-ethyl) benzo [lmn] [3,8] phenanthroline-1,3,6,8-tetraone (12h):

Excluded from air and moisture (Ar shielding gas) were (R) - (+) - 1- (1-naphthyl) ethylamine (502 mg, 2.93 mmol) and isochromeno [6,5,4-def] isochromene-1,3 , 6,8-tetraone (262 mg, 977 .mu.mol) in N, N-dimethylformamide (15 mL) heated to 170 ° C for six hours, stirred after cooling in ice-cold 2 M hydrochloric acid (13 mL), stirred for 1 h at room temperature , filtered off, dried in a drying oven (16 h, 110 ° C) and chromatographed (silica gel, dichloromethane). Y. 432 mg (77%), mp> 300 ° C; R _f (silica gel, CH ₂ Cl _2): 0.61; ¹ H-NMR (600 MHz, CDCl _3, 25 ° C): δ = 2.12 (d, ³ J (H, H) = 7.0 Hz, 6 H, _CH3), 7:03 (q, ³ J (H, H ) = 6.9 Hz, 2 H, N-CH), 7:31 to 7:35 (m, 4 H, Naph. H ^2, H ^3), 7:58 (t, ³ J (H, H) = 7.8 Hz, 2 H, Naph H ⁶ ), 7.79-7.82 (m, 4 H, naph, H ⁴ , H ⁷ ), 7.88-7.89 (m, 2 H, naph, H ⁵ ), 8.06 (d, ³ J (H, H) 7.3 Hz, 2H, naph, H ⁸ ), 8.62 (s, 4H, arom. CH); ¹³ C-NMR (151 MHz, CDCl _3, 25 ° C): δ = 17.1, 48.7, 122.6, 124.9, 125.2, 126.5, 126.7, 127.7, 128.6, 129.1, 131.0, 131.5, 133.6, 134.4, 162.8 ppm; IR (KBr): ν ~ = 1700.4 (m), 1658.0 (s), 1579.1 (w), 1511.0 (w), 1450.5 (w), 1317.1 (m), 1245.4 (m), 1208.6 (w), 1196.4 ( w), 1171.3 w, 1093.5 w, 1065.1 w, 1030.0 w, 967.6 w, 878.3 w, 800.5 w, 768.8 m, 750.4 w) cm ^-1 ; UV / Vis (CHCl ₃ ): λ _max (ε) = 286 (16,800), 297 (14,200), 344 (12,900), 361 (21,400), 382 nm (25,200 L · mol ^-1 · cm ^-1 ); MS (DEI ⁺ / 70 eV): m / z (%): 574 (100) [M ⁺ ], 421 (11) [M ⁺ -C ₁₂ H ₁₁ + H], 268 (33) [M ⁺ -2 × C ₁₂ H ₁₁ + 2 H), 267 (18), 249 (15), 154 (78); C, H, N analysis for C ₃₈ H ₂₆ N ₂ O ₄ (574.6): calcd C 79.43, H 4.56 N 4.87;. gef. C 79.15, H 4.75, N 4.78.

2,7-bis - ((S) -1-naphthalen-1-yl-ethyl) benzo [lmn) [3,8] phenanthroline-1,3,6,8-tetraone (12i):

(S) - (-) - 1- (1-naphthyl) ethylamine (507mg, 2.96mmol) and isochromeno [6,5,4-def] isochromene-1,3,6,8-tetraone (265mg, 987 1 μmol) in N, N-dimethylformamide (15 ml) were correspondingly converted into 2,7-bis - ((R) -1-naphthalen-1-yl-ethyl) benzo [lmn] [3,8] phenanthroline-1,3, 6,8-tetraone (12h) reacted and worked up. Y. 397 mg (70%), mp> 300 ° C; R _f (silica gel, CH ₂ Cl _2): 0:57; ¹ H-NMR (600 MHz, CDCl _3, 25 ° C): δ = 2.13 (d, ³ J (H, H) = 7.0 Hz, 6 H, _CH3), 7:02 (q, ³ J (H, H ) = 6.9 Hz, 2 H, N-CH), 7:31 to 7:34 (m, 4 H, Naph. H ^2, H ^3), 7:58 (t, ³ J (H, H) = 7.8 Hz, 2 H, Naph H ⁶ ), 7.79-7.81 (m, 4 H, naph, H ⁴ , H ⁷ ), 7.88-7.89 (m, 2 H, naph, H ⁵ ), 8.06 (d, ³ J (H, H) 7.3 Hz, 2H, naph, H ⁸ ), 8.61 (s, 4H, arom. CH); ¹³ C-NMR (151 MHz, CDCl _3, 25 ° C): δ = 17.1, 48.7, 122.6, 124.9, 125.2, 126.5, 126.6, 127.7, 128.5, 129.0, 131.0, 131.5, 133.6, 134.4, 162.8; IR (KBr): ν ~ = 1699.9 (m), 1657.2 (s), 1598.1 (w), 1578.2 (m), 1510.8 (w), 1450.1 (w), 1397.9 (w), 1372.9 (w), 1356.0 ( w), 1316.3 (m), 1244.7 (m), 1207.9 (w), 1195.9 (w), 1170.5 (w), 1144.1 (w), 1092.9 (w), 1054.2 (w), 1029.8 (w), 966.9 ( w), 895.0 (w), 876.8 (w), 838.1 (w), 800.1 (w), 778.1 (w), 768.0 (m), 750.1 (w), 734.8 (w), 703.8 (w) cm ^-1 ; UV / Vis (CHCl ₃₎ λ _max (ε) = 286 (17400), 297 (14700), 344 (13100), 361 (21900), 381 nm (25100 L · mol ^-1 · cm ^-1); MS (DEI ⁺ / 70 eV): m / z (%): 574 (100) [M ⁺ ], 421 (10) [M ⁺ -C ₁₂ H ₁₁ + H], 268 (33) [M ⁺ - 2 × C ₁₂ H ₁₁ + 2 H), 267 (21), 249 (19), 154 (49); C ₃₈ H ₂₆ N ₂ O ₄ (574.64): calcd C 79.43, H 4.56 N 4.87;. gef. C 79.06, H 4.63, N 4.86.

Subject of the invention

• 1. chiral perylene dyes of general formula 13,
  
  in which the radicals R ¹ to R ^{8 may be} identical or different, in particular at least the radicals R ¹ and R ^{2 must be} different and may not be hydrogen, and independently of one another hydrogen or linear alkyl radicals having at least one and at most 37 C atoms mean, in which one to 10 CH ₂ -Enheiten may be replaced independently of one another in each case by carbonyl groups, oxygen atoms, sulfur atoms, selenium atoms, tellurium atoms, cis- or in which a CH unit is replaced by a nitrogen atom, trans-CH = CH-groups, acetylenic C≡C groups can be 1,2-, 1,3- or 1,4-substituted phenyl radicals, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine radicals, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene radicals, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene radicals in which one or two CH groups can be replaced by nitrogen atoms, 1,2- , 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1, 9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene residues in which one or two CH groups are represented by nitrogen atoms can be replaced. Up to 12 individual hydrogen atoms of the CH ₂ groups can each be replaced independently of each other on the same carbon atoms by the halogens fluorine, chlorine, bromine or iodine or the cyano group or a linear alkyl chain having up to 18 C atoms, in which one to 6 CH ₂ units can be replaced independently by carbonyl groups, oxygen atoms, sulfur atoms, selenium atoms, tellurium atoms, cis or trans-CH = CH groups in which a CH unit may also be replaced by a nitrogen atom, acetylenic C≡C groups, 1,2-, 1,3- or 1,4-substituted phenyl radicals, 2 , 3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-disubstituted pyridine, 2,3- 2,4-, 2,5- or 3,4-disubstituted Thiophene residues, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7 disubstituted naphthalene radicals in which one or two carbon atoms may be replaced by nitrogen atoms, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8- , 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted Anthracenreste in which one or two carbon atoms Nitrogen atoms can be replaced. Up to 12 individual hydrogen atoms of the CH ₂ groups of the alkyl radicals can each be replaced independently of the same C atoms by the halogens fluorine, chlorine, bromine or iodine or or cyano groups or linear alkyl chains having up to 18 carbon atoms, in which one to 6 CH ₂ units can be replaced independently by carbonyl groups, oxygen atoms, sulfur atoms, selenium atoms, tellurium atoms, cis or trans-CH = CH groups in which a CH unit can also be replaced by a nitrogen atom, acetylenic C ≡C groups 1,2-, 1,3- or 1,4-substituted phenyl radicals, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5- disubstituted pyridine radicals, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene radicals, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene radicals in which one or two carbon atoms may be replaced by nitrogen atoms, 1,2-, 1,3-, 1 , 4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2 , 9, 2, 10-od he 9,10-disubstituted Anthracenreste in which one or two carbon atoms may be replaced by nitrogen atoms. Instead of carrying substituents, the free valencies of the methine groups or of the quaternary C atoms can be linked in pairs to form rings, such as cyclohexane rings. The radicals R ¹ to R ⁸ can also independently of one another denote the halogen atoms F, Cl, Br or I.
• 2. chiral perylene dyes of general formula 14,
  
  in which the radicals R ¹ to R ^{6 have} the meaning given under 1.
• 3. Chiral Perylenanhydridimide of the general formula 15,
  
  in which the radicals R ¹ to R ^{6 have} the meaning given under 1.
• 4. chiral perylene lactamimides of general formula 16,
  
  in which the radicals R ¹ to R ^{8 have} the meaning given under 1.
• 5. chiral naphthalene bisimides of general formula 17,
  
  in which the radicals R ¹ to R ^{8 have} the meaning given under 1.
• 6. Application of the dyes according to 1 to 5 as vat dyes, e.g. for coloring of textiles, preferably textiles of plant origin such as cotton or else preferably synthetic fibers such as polyester or nylon.
• 7. Use of the substances according to 1 to 5 as pigments.
• 8. Use of the substances according to 1 to 5 as pigments for glues and related colors such as watercolor paints and watercolors and colors for inkjet printers Paper colors, printing inks, inks and inks and other colors for painting and writing purposes and in paints.
• 9. Use of the substances according to 1 to 5 as pigments in paints. Preferred paints are synthetic resin paints such as acrylic or vinyl resins, Polyester lacquers, novolaks, nitrocellulose lacquers (nitro lacquers) or also natural substances such as Zaponlack, shellac or Qi-Lack (Japanlack or Chinese lacquer or East Asian lacquer).
• 10. Use of the dyes according to 1 to 5 in data memories, preferably in optical memories. Examples are systems like the CD or DVD disc.
• 11. Use of the substances according to 1 to 5 as fluorescent dyes.
• 12. Application of the dyes of 1 to 5 for mass-staining of Polymers. Examples are materials of polyvinyl chloride, cellulose acetate, Polycarbonates, polyamides, polyurethanes, polyimides, polybenzimidazoles, Melamine resins, silicones, polyesters, polyethers, polystyrene polymethylmethacrylate, Polyethylene, polypropylene, polyvinyl acetate, polyacrylonitrile, polybutadiene, Polychlorobutadiene or polyisoprene or the copolymers of the mentioned Monomers, as well as alkyd resin and acrylic paints.
• 13. Application of the dyes according to 1 to 5 as vat dyes, e.g. for coloring of natural substances. Examples are paper, wood, straw, leather, skins or natural Fiber materials such as cotton, wool, silk, jute, sisal, hemp, Flax or animal hair (for example horsehair) and their conversion products such as e.g. the viscose fiber, nitrate silk or copper rayon (Reyon).
• 14. Application of the dyes according to 1 to 5 as mordant dyes, e.g. for coloring of natural substances. Examples are paper, wood, straw, leather, skins or natural Fiber materials such as cotton, wool, silk, jute, sisal, hemp, Flax and its conversion products such as e.g. the viscose fiber, Nitrate silk or copper rayon (Reyon). Preferred salts for pickling are aluminum, chromium and iron salts.
• 15. Application of the dyes of 1 to 5 as colorants, e.g. for coloring of paints, varnishes and other paints, paper inks, inks, Inks and other colors for Painting, writing and coloring purposes all kinds.
• 16. Application of the dyes according to 1 to 5 as pigments in the Electrophotography: e.g. For Dry copier systems (Xerox process) and laser printers ("non-impact printing").
• 17. Application of the dyes according to 1 to 5 for security marking purposes, wherein the size chemical and photochemical resistance and possibly also the Fluorescence of the substances is important. This is preferred for checks, Check cards, banknotes coupons, documents, identity documents and the like, in which a special, unmistakable color impression should be achieved.
• 18. Application of the dyes of 1 to 5 as an additive to other colors that achieve a certain shade of color should, are particularly bright shades.
• 19. Application of the dyes of 1 to 5 for marking of objects for machine recognition of these objects via fluorescence is the machine detection of articles for sorting, e.g. also for the Recycling of plastics.
• 20. Application of the dyes of 1 to 5 as fluorescent dyes for machine readable Markings, preferred are alphanumeric imprints or barcodes.
• 21. Application of the dyes according to 1 to 5 for frequency conversion of light, e.g. from short-wave light, wavelength-wave, visible light close.
• 22. Application of the dyes of 1 to 5 in display elements for many things Display, hint and marking purposes, e.g. passive display elements, Signs and traffic signs, such as traffic lights.
• 23. Application of the dyes according to 1 to 5 in inkjet printers in homogeneous solution as an ink or as a fluorescent ink.
• 24. Application of the dyes according to 1 to 5 as starting material for superconducting organic materials.
• 25. Application of the dyes according to 1 to 5 for solid fluorescence labels.
• 26. Application of dyes from 1 to 5 for decorative Purposes.
• 27. Application of the dyes according to 1 to 5 for artistic purposes.
• 28. Use of the dyes according to 1 to 5 for tracer purposes, e.g. in biochemistry, medicine, engineering and science. in this connection can the dyes are covalently linked to substrates or via minor valences like hydrogen linkages or hydrophobic interactions (adsorption).
• 29. Application of the dyes according to 1 to 5 as fluorescent dyes in highly sensitive detection methods.
• 30. Application of the dyes according to 1 to 5 as fluorescent dyes in scintillators.
• 31. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in optical light harvesting systems.
• 32. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in fluorescence solar collectors.
• 33. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in fluorescence-activated displays.
• 34. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in cold light sources for light-induced polymerization for the representation of plastics.
• 35. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes for material testing, e.g. in the preparation of of semiconductor circuits.
• 36. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes for the study of integrated microstructures Semiconductor devices.
• 37. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in photoconductors.
• 38. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in photographic processes.
• 39. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in display, illumination or image converter systems, where the excitation by electrons, ions or UV radiation takes place, e.g. in fluorescent displays, Braun tubes or in fluorescent tubes.
• 40. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes as part of a semiconductor integrated circuit, the dyes as such or in conjunction with other semiconductors e.g. in the form of an epitaxy.
• 41. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in chemiluminescent systems, e.g. in chemiluminescent light rods, in Luminescence immunoassays or other luminescence detection method.
• 42. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes as signal colors, preferably for optical Highlighting lettering and drawings or other graphic products, for marking of signs and other objects, where a special one optical color impression is to be achieved.
• 43. Application of the dyes according to 1 to 5 as dyes or Fluorescent dyes in dye lasers, preferably as fluorescent dyes for generating laser beams.
• 44. Application of the dyes according to 1 to 5 as dyes in Dye lasers as a Q-switch switch.
• 45. Application of the dyes according to 1 to 5 as active substances for one non-linear optics, e.g. For the frequency doubling and frequency tripling of laser light.
• 46. Application of the dyes according to 1 to 55 for leak testing closed Systems.
• 47. Application of the dyes according to 1 to 5 as Rheologieverbesserer.

• [1] H. Langhals, Helv. Chim. Acta. 2005, 88, 1309-1343.
• [2] H. Langhals, Heterocycles 1995, 40, 477-500.
• [3] L. B.-Å. Johansson, H. Langhals, Spectrochim. Acta 1991, 47A, 857-861.
• [4] H. Langhals, S. Demmig, H. Huber, Spectrochim. Acta 1988, 44A, 1189-1193.
• [5] H. Langhals, P. v. Unold, Angew. Chem. 1995, 107, 2936-2439; Angew. Chem., Int. Ed. Engl. 1995, 34, 2234-2236.
• [6] S. Nakamura, A. Murakami, M. Adachi, M. Irie, Pure Appl. Chem. 1996, 68, 1441-1442.
• [7] G. Snatzke, Angew. Chem. 1979, 91, 180-393; Angew. Chem. Int. Ed. Engl. 1979, 18, 363-377.
• [8] H. Langhals, J.Gold, Liebigs Ann./Recueil 1997, 1151-1153.
• [9] W. Kuhn, Z. Phys. Chem. 1929, B4, 14-36.
• [10] W. Kuhn, Trans. Faraday Soc. 1930, 26, 293-308.
• [11] J.G. Kirkwood, J. Chem. Phys. 1937, 5, 479-421.
• [12] H. Langhals, H. Jaschke, Chem. Eur. J. 2006, 12, 2815-2824.
• [13] O. Vogl, M. Pöhm, Monatsh. Chem. 1952, 83, 541.
• [14] O. Vogl, M. Pöhm, Monatsh. Chem. 1953, 84, 1097.
• [15] P. Karrer, P. Dinkel, Helv. Chim. Acta. 1953, 36, 122.
• [16] W. Kern, H. Willersinn, Angew. Chem. 1955, 67, 573-581.
• [17] H. Langhals, Chem. Ber. 1985, 118, 4641-4645.

LIST OF REFERENCE NUMBERS

• 1 , Synthesis of Perylene Dyes 1 and Anhydride Imides 3.
• 2 , Synthesis of chiral amines 8 from amino acids 4.
• 3 , Synthesis of Unsymmetrically Substituted Perylene Dyes 10.
• 4 , Synthesis of naphthalene bisimides 12.
• 5 , UV / Vis spectra of 1h, 1l, 8f, 10h, 12a and 12h in chloroform.
• 6 , CD spectra of 1h, 1i, 8f, 8g, 10h, 10i, 12h and 12i in chloroform.

Claims (47)

Chiral perylene dyes of general formula 13,

in which the radicals R ¹ to R ^{8 may be} identical or different, in particular at least the radicals R ¹ and R ^{2 must be} different and may not be hydrogen, and independently of one another hydrogen or linear alkyl radicals having at least one and at most 37 C atoms mean, in which one to 10 CH ₂ -Enheiten may be replaced independently of one another in each case by carbonyl groups, oxygen atoms, sulfur atoms, selenium atoms, tellurium atoms, cis- or in which a CH unit is replaced by a nitrogen atom, trans-CH = CH-groups, acetylenic C≡C groups can be 1,2-, 1,3- or 1,4-substituted phenyl radicals, 2,3-, 2,4-, 2,5-2,6-, 3,4- or 3,5-disubstituted pyridine radicals, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene radicals, 1,2-, 1,3-, 1,4-, 1,5-, 1 , 6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene radicals in which one or two CH groups may be replaced by nitrogen atoms, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9 , 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene residues in which one or two CH groups are replaced by nitrogen atoms could be. Up to 12 individual hydrogen atoms of the CH ₂ groups can each independently be replaced on the same C atoms by the halogens fluorine, chlorine, bromine or iodine or the cyano group or a linear alkyl chain with up to 18 C atoms, in which a to 6 CH ₂ units can be replaced independently by carbonyl groups, oxygen atoms, sulfur atoms, selenium atoms, tellurium atoms, cis or trans-CH = CH groups in which a CH unit may also be replaced by a nitrogen atom, acetylenic C≡ C groups, 1,2-, 1,3- or 1,4-substituted phenyl radicals, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5- disubstituted pyridine radicals, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene radicals, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene radicals in which one or two carbon atoms may be replaced by nitrogen atoms, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2,9-, 2,10- or 9,10-disubstituted anthracene residues in which one or two carbon atoms may be replaced by nitrogen atoms. Up to 12 individual hydrogen atoms of the CH ₂ groups of the alkyl radicals can each be replaced independently of the same C atoms by the halogens fluorine, chlorine, bromine or iodine or or cyano groups or linear alkyl chains having up to 18 carbon atoms, in which one to 6 CH ₂ units can be replaced independently by carbonyl groups, oxygen atoms, sulfur atoms, selenium atoms, tellurium atoms, cis or trans-CH = CH groups in which a CH unit can also be replaced by a nitrogen atom, acetylenic C ≡C groups 1,2-, 1,3- or 1,4-substituted phenyl radicals, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5- disubstituted pyridine radicals, 2,3-, 2,4-, 2,5- or 3,4-disubstituted thiophene radicals, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6- or 2,7-disubstituted naphthalene radicals in which one or two carbon atoms may be replaced by nitrogen atoms, 1,2-, 1,3-, 1 , 4-, 1,5-, 1,6-, 1,7-, 1,8-, 1,9-, 1,10-, 2,3-, 2,6-, 2,7-, 2 , 9, 2, 10-od he 9,10-disubstituted Anthracenreste in which one or two carbon atoms may be replaced by nitrogen atoms. Instead of carrying substituents, the free valencies of the methine groups or of the quaternary C atoms can be linked in pairs to form rings, such as cyclohexane rings. The radicals R ¹ to R ⁸ can also independently of one another denote the halogen atoms F, Cl, Br or I. Chiral perylene dyes of general formula 14,

in which the radicals R ¹ to R ^{6 have} the meaning given under 1. Chiral Perylenanhydridimide of general formula 15,

in which the radicals R ¹ to R ^{6 have} the meaning given under 1. Chiral perylene lactamimides of general formula 16,

in which the radicals R ¹ to R ^{8 have} the meaning given under 1. Chiral naphthalene bisimides of general formula 17,

in which the radicals R ¹ to R ^{8 have} the meaning given under 1. Application of the dyes according to 1 to 5 as vat dyes, e.g. for coloring of textiles, preferably textiles of plant origin such as cotton or else preferably synthetic fibers such as polyester or nylon. Use of the substances according to 1 to 5 as pigments. Use of the substances according to 1 to 5 as pigments for glue colors and related colors such as watercolor paints and watercolors and colors for inkjet printers Paper colors, printing inks, inks and inks and other colors for painting and writing purposes and in paints. Use of the substances according to 1 to 5 as pigments in paints. Preferred paints are synthetic resin paints such as acrylic or Vinyl resins, polyester paints, novolaks, nitrocellulose paints (nitro paints) or natural substances such as zapon varnish, shellac or Qi varnish (Japanese varnish or Chinese lacquer or East Asian lacquer). Use of dyes from 1 to 5 in data memories, preferably in optical memories. Examples are systems like the CD or DVD disc. Use of the substances according to 1 to 5 as fluorescent dyes. Application of dyes from 1 to 5 for mass staining of Polymers. Examples are materials of polyvinyl chloride, cellulose acetate, Polycarbonates, polyamides, polyurethanes, polyimides, polybenzimidazoles, Melamine resins, silicones, polyesters, polyethers, polystyrene polymethylmethacrylate, Polyethylene, polypropylene, polyvinyl acetate, polyacrylonitrile, polybutadiene, Polychlorobutadiene or polyisoprene or the copolymers of the mentioned Monomers, as well as alkyd resin and acrylic paints. Application of the dyes according to 1 to 5 as vat dyes, e.g. for coloring of natural substances. Examples are paper, wood, straw, leather, skins or natural Fiber materials such as cotton, wool, silk, jute, sisal, hemp, Flax or animal hair (for example horsehair) and their conversion products such as e.g. the viscose fiber, nitrate silk or copper rayon (Reyon). Application of the dyes according to 1 to 5 as mordant dyes, e.g. for coloring of natural substances. Examples are paper, wood, straw, leather, skins or natural Fiber materials such as cotton, wool, silk, jute, sisal, hemp, Flax and its conversion products such as e.g. the viscose fiber, Nitrate silk or copper rayon (Reyon). Preferred salts for pickling are aluminum, chromium and iron salts. Use of the dyes according to 1 to 5 as colorants, e.g. for coloring paints, varnishes and other paints, paper inks, printing inks, Inks and other colors for Painting, writing and coloring purposes all kinds. Application of the dyes according to 1 to 5 as pigments in electrophotography: e.g. for dry copying systems (Xerox process) and laser printers (non-impact printing). Application of the dyes according to 1 to 5 for security marking purposes, being the big one chemical and photochemical resistance and possibly also the Fluorescence of the substances is important. This is preferred for checks, Check cards, banknotes coupons, documents, identity documents and the like, in which a special, unmistakable color impression should be achieved. Application of the dyes of 1 to 5 as an additive to other colors where a certain shade of color is achieved should, are particularly bright shades. Application of the dyes from 1 to 5 for marking of objects for machine recognition of these objects via fluorescence is the machine detection of articles for sorting, e.g. also for the Recycling of plastics. Application of the dyes from 1 to 5 as fluorescent dyes for machine readable Markings, preferred are alphanumeric imprints or barcodes. Application of the dyes according to 1 to 5 for frequency conversion of light, e.g. from short-wave light, longer-wave, visible light close. Application of the dyes from 1 to 5 in display elements for many things Display, hint and marking purposes, e.g. passive display elements, Information and traffic signs, like traffic lights. Application of Dyes 1 to 5 in Inkjet Printers in homogeneous solution as an ink or as a fluorescent ink. Application of the dyes according to 1 to 5 as starting material for superconducting organic materials. Application of the dyes according to 1 to 5 for solid fluorescence labels. Application of dyes from 1 to 5 for decorative Purposes. Application of dyes from 1 to 5 for artistic Purposes. Application of the dyes according to 1 to 5 for tracer purposes, e.g. in biochemistry, medicine, engineering and science. in this connection can the dyes are covalently linked to substrates or via minor valences like hydrogen bonds or hydrophobic interactions (adsorption). Application of the dyes according to 1 to 5 as fluorescent dyes in highly sensitive detection methods. Application of the dyes according to 1 to 5 as fluorescent dyes in scintillators. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in optical light harvesting systems. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in fluorescence solar collectors. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in fluorescence-activated displays. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in cold light sources for light-induced Polymerization for the preparation of plastics. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes for material testing, e.g. in the preparation of of semiconductor circuits. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes for the study of microstructures of integrated semiconductor devices. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in photoconductors. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in photographic processes. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in display, illumination or image converter systems, where the excitation by electrons, ions or UV radiation takes place, e.g. in fluorescent displays, Braun tubes or in fluorescent tubes. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes as part of a semiconductor integrated circuit, the dyes as such or in conjunction with other semiconductors e.g. in the form of an epitaxy. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in chemiluminescent systems, e.g. in Chemiluminescent light sticks, in luminescence immunoassays or other luminescence detection methods. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes as signal colors, preferably for optical Highlighting lettering and drawings or other graphic products, for marking of signs and other objects, where a special one optical color impression is to be achieved. Application of the dyes according to 1 to 5 as dyes or fluorescent dyes in dye lasers, preferably as fluorescent dyes for generating laser beams. Application of the dyes according to 1 to 5 as dyes in dye lasers as a Q-switch Switch. Application of the dyes according to 1 to 5 as active Substances for a non-linear optics, e.g. For the frequency doubling and frequency tripling of laser light. Application of the dyes according to 1 to 55 for leak testing closed Systems. Application of the dyes according to 1 to 5 as Rheologieverbesserer.