WO2001092420A2 - Perylene dyes with persistent fluorescence caused by steric inhibition of aggregation - Google Patents

Abstract

The invention relates to a series of novel perylene-based fluorescent dyes in which aggregation is suppressed by steric shielding so that a quenching of fluorescence at high concentrations does not take place. The novel substances can therefore also be used as fluorescent dyes in a concentrated solution.

Description

Perylene dyes with persistent fluorescence due to steric aggregation inhibition

description

The use of fluorescent dyes is generally limited to dilute solutions due to their tendency to aggregate. In more concentrated solutions, the fluorescence quenching (concentration quenching) becomes more and more important due to the interaction of the chromophores [1,2] and can lead to the complete absence of light emission. Even small amounts of aggregate formation can lead to considerable losses in the yield of fluorescent light. Even with easily soluble dyes, a considerable aggregation with optical densities of 2 / mm is often observed, whereas with poorly soluble dyes, quenching of fluorescence often comes to the fore even at extremely low concentrations. A solution to this problem would lead to significant progress, particularly in the practical use of the fluorescent dyes. We used perylene-3,4: 9,10-tetracarboxylic acid bis-imide (2, perylene dyes) [3] as the base fluorophore, because this class of substances is not only characterized by its high fluorescence quantum yields (see, for example, 2a [4]), but also has considerable thermal, photochemical and chemical resistance, which makes them ideal for fluorescence applications. We controlled the aggregation behavior through the substituents on the nitrogen atoms, since these positions can be economically provided with various residues. Orbital nodes on the nitrogen atoms [5] in HOMO and LUMO are particularly advantageous, so that the chromophore system at these positions is only slightly influenced by the substituents. We attached bulky residues to the nitrogen atoms to study the effect of such a substitution on the fluorescence behavior of the dyes in a concentrated solution. Based on this concept, we tried in a manner known per se to condense the anhydride 1 with the 2,4,6-triphenylaniline. Surprisingly, he does not get the condensation product 2b, but the decarboxylation product 3. This reaction finds its analogy in the preparative, partial decarboxylation [6] of 1 described earlier. Obviously the amino group in the triphenylaniline is too strongly shielded for conversion to 2b. The 4-tritylaniline is less shielded at the amino group, but takes up a similar amount of space as the 2,4,6-triphenylaniline. His condensation with 1 succeeds smoothly to 2c. The great steric nature of the end groups in 2c is evident from the fact

SPARE BLADE (RULE 26) that 2c cannot be saponified under the usual reaction conditions [7] for perylene bisimides. Bulky, purely aliphatic amines were obtained by the alkylation of acetonitrile with secondary alkyl halides and the subsequent reduction. Their condensation with 1 gave the highly branched aliphatic substituted dyes 2d to 2f. Partially shielded dyes were obtained from the anhydride imide 4 by condensation. The nitrogen atom in 4 was provided with the solubility-increasing sec-alkyl residues ("dovetail residues" [8]), which are of interest for the use of the dyes in homogeneous solution. The derivative 7 with the projecting purely aromatic residue was prepared from the amino derivative 5 and tetraphenylphthalic anhydride.

UV / Vis absorption of the new dyes

The UV / Vis spectra of 2 and 3 remain practically unaffected by the voluminous substituents: the spectra of 2d correspond to the spectra of 2a (1-hexylheptyl substituent) and that of 2c aromatically substituted perylene dyes. This also applies to 3. The fluorescence quantum yields of 2c, 2d, 2e and 2f are practically 100% in dilute solution and thus correspond to 2a [9]. The fluorescence quantum yield of 3 is lower (84% in chloroform), but corresponds to the values recently described for other derivatives of 3 [10]. However, completely different behavior is observed in concentrated solution, because the voluminous end groups of the dyes, in contrast to simple derivatives, prevent aggregation and the associated concentration-fluorescence quenching. Although the solubility of 2c is relatively low and the dye has a more pigment-like character, the fluorescence remains until solutions are saturated. In addition, 2c has a pronounced red solid fluorescence (see FIG. 5), while the solid fluorescence of the other perylene dyes generally. because of the stacking of the chromophores in the crystal is considerably weaker. The solubility of the dyes is increased considerably by replacing a nitrogen substituent with the solubility-increasing 1-hexylheptyl residue ("dovetail substituent" [8]) as in 6. With these dyes, strong fluorescence is also observed in concentrated solution, but not as a solid. The steric requirements of the N-terminus can be further increased by using the tetraphenylphthalimidyl residue, for example in 7. Highly branched, purely aliphatic residues, as in 2d, have an even greater aggregation-preventing effect. The effect of these "multiple dovetail residues" is so pronounced that strong fluorescence is observed even in highly concentrated solution. This then occurs essentially on the surface of the solutions because little light penetrates into the deeper layers of the dark solutions. The solid fluorescence of the dyes 2d to 2f is also very pronounced. Interestingly, the derivative 2d fluoresces brilliant orange with relatively short chains and therefore resembles the fluorescence of dye solutions, while the fluorescence of the longer-chain derivatives is shifted more towards red-orange for 2e and red for 2f. The longer, branched chains may cause an internal self-solvation and thus form a "closed cell", so that the shielding effect for the chromophore in the crystal is surprisingly not quite as great as with the shorter-chain derivatives.

conclusion

The effect of the bulky substituents on the perylene dyes shows that a sterically repulsive outer sphere can effectively prevent self-organization by aggregating dyes. In this way, fluorescent dyes can be developed for highly concentrated solutions. The principle of steric aggregation prevention was found in perylene dyes and perylenedicarboximides and was then systematically investigated. These classes of dyes were particularly suitable for the work because of the special properties of the chromophores. However, it can be assumed that the principle of steric aggregation prevention can generally be extended to fluorescent dyes. In difficult cases, the shielding sphere only has to be made sufficiently large.

Subject of the invention

1. A method for preventing aggregation of fluorescent dyes, characterized in that bulky groups are attached to the periphery of the dyes, which prevent the chromophores from accumulating and the resulting fluorescence quenching.

2. A method for preventing aggregation and preventing fluorescence quenching in fluorescent dyes by incorporating bulky aromatic groups according to 1.

3. A method for preventing aggregation and preventing fluorescence quenching in fluorescent dyes by incorporating voluminous heteroaromatic groups according to 1.

4. A method for preventing aggregation and preventing fluorescence quenching in fluorescent dyes by incorporating voluminous aliphatic groups according to 1.

5. The use of the substituted phenyl radical of the general formula I as a voluminous aromatic group corresponding to 2,

I in which R ¹ to R ^{5 can be the} same or different. R ¹ to R ⁵ represent hydrogen or one to five, preferably one to three, radicals, such as, for example, isocyanic aromatic radicals. R ¹ to R ⁵ then preferably each denotes a mono- to tetracyclic, in particular mono- or bicyclic radical, such as phenyl, diphenyl naphthyl or anthryl. R ¹ to R ^{5 are} heterocyclic aromatic radicals, then preferably mono- to tricyclic radicals. These radicals can be purely heterocyclic or contain a heterocyclic ring and one or more fused-on benzene rings. Examples of heterocyclic aromatic radicals are pyridyl, pyrimidyl, pyrazinyl, triazinyl, furanyl, pyrrolyl, thiophenyl, quinolyL isoquinolyl, coumarinyl, benzofuranyl, benzimidazolyl, benzoxazolyl, dibenzfuranyl, benzotbiophenyL dibenzothiophenyl, oxolylolylol indazolyl, benzothiazolyl, pyridazinyl, cinnolyl, quinazolinyl, quinoxalyl, phthalazinyl, phthalazine dionyl, phthalimidyl, chromonyl, Naphtholactamyl, Benzopyridonyl, ortho-Sulfobenz- imidyl, maleimidyl, Naphtharidinyl, benzimidazolonyl, benzoxazolonyl, Benzthiazolon- y L Benzthiazolinyl, quinazolonyl, pyrimidyl, Chinoxalonyl , Phthalazonyl, dioxapyrinidin-yl, pyridonyl, isoquinolonyL, isothiazolyl, benzisoxazolyl, benzisothiazolyl, indazolonyl, acridinyl, acridonyl, quinazolinedionyl, benzoxazinedionyl, benzoxazinonyl and phthalimidyl. Both the isocyclic and the heterocyclic aromatic radicals can have the following customary water-insolubilizing substituents, which can also mean R ¹ to R ⁵ , such as a) a halogen atom, for example chlorine, bromine, iodine or fluorine. b) Branched or unbranched alkyl groups or cycloalky groups with preferably 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4 carbon atoms. These alkyl groups can have non-water-solubilizing substituents, such as fluorine, hydroxy, cyano, -OCOR ⁶ , -OR ⁷ , -OCOOR ⁷ , - CON (R ⁹ ) (R ¹⁰ ) or -OCONHR ¹¹ , wherein R ⁶ to R ^u Aikyl, aryl such as naphthyl, or unsubstituted or substituted by halogen, alkyl, or -O-alkyl or a heterocyclic radical, hydrogen, unsubstituted or cyano or hydroxy-substituted alkyl, C3 to C24 cycloalkyl, preferably C5, Cg, Cj2, C15, C \, C20 and C24 cycloalkyl, aryl or heteroaryl, is especially unsubstituted or substituted by halogen, alkyl or -O-alkyl, or wherein R ⁶ to R ^π together with one of the other radicals R ⁷ to R ^{12 form} a 5-6 membered ring or hetero ring, such as a pyridine -, pyrrole, furan or pyran ring. Further possible substituents on the alkyl groups are mono- or dialkylated amino groups, aryl radicals, such as naphthyl or, in particular, phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, or furthermore heterocyclic aromatic radicals, such as, for example, the 2-thienyl 2-benzoxazolyl -, 2-benzothiazolyl-, 2-benzimidazolyl-, 6-benzimidazolonyl-, 2-, 3- or 4-pyridinyl-, 2-, 4-, or 6-quinolyl- or 1-, 3-, 4- , 6-, or 8-isoquinolyl residues. If the substituents mentioned under b) in turn contain alkyl, this alkyl can be branched, unbranched or cyclic and preferably contain 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4, carbon atoms.

Examples of unsubstituted alkyl groups are methyl, ethyl, w-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, tert-amyl, "-hexyl, 1,1,3,3, -tetramethylbutyl, w-heptyl, n-octyl, ra-nonyl, "-decyl," -undecyl, "-dodecyl," -octadecyl, 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl, 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetylymethyl or benzox or cycloalkyl with C ₃ to C ₂ o. c) The group -OR ¹² , in which R ^{12 is} hydrogen, alkyl aryl, for example naphthyl or in particular unsubstituted phenyl, C3 to C24-cycloalkyl, preferably C5-, C5-, Cj2 _>

^ 15 "'Cl6"_> C20 " ₅ and C24-cycloalkyl, aryl or heteroaryl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl. Alkyl which occurs in the definitions of R ¹³ can be, for example, number of carbon atoms indicated as preferred, examples of R ^{13 which} may be mentioned include: methyl, ethyl, rc-propyl, isopropyl, “-butyl, .see-butyl, tert-butyl, tert-amyl,“ -hexyl, 1 , 1,3,3, - tetramethylbutyl, "-heptyl, n-octyl," -nonyl, "-decyl," -undecyl, "-dodecyl, n-octadecyl, 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl, 1-pentyl-hexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1- Ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, benzyl, phenyl, o-, m- oάeτp- chlorophenyl, o-, m-, or -Methylphenyl, 1- or 2- Naphthyl, CyclopentyL Cyclohexyl, Cyclododecyl, Cyclopentadecyl, CyclohexadecyL Cycloeicosanyl, Cyclotetracosanyl, Thienyl or Pyranylmethyl. e) The cyano group. f) The group of the formula -N (R ¹³ ) (R ¹⁴ ), in which R ¹³ and R ^{14 have} the meaning given under b). Examples include: amino, methylamino, dimethylamino, ethylamino, diethylamino, w-propylamino, di - «- propylamino, isopropylamino,« -butylamino, di-w-butylamino, sec-butylamino, di-sec-butylamino, tert -Butylamino, tert-amylamino, w-hexylamino, di - «- hexylamino, 1,1,3,3, -Tetramethylbutylamino,« -heptylamino, di-H-heptylamino, w-octylamino, di-w-octylamino, "-Nonyl, Di -" - nonylamino, "-Decylamino, Di -" - decylamino, "-Undecylamino, Di -" - undecylamino, "-Dodecylamino, Oi-n-dodecylamino, w-octadecylamino, 1-Etylpropylamino, 1-propylbutylamino, 1-butylpentylaminino, 1-pentylhexylamino, 1-hexylheptylamino, 1-heptyloctylamino, 1-octylnonylamino, 1-nonyldecylamino, 1-decylimidecylamino, 1-ethylbutylamyl, amino-1-ethylamino, 1-ethylamino 1-Ethylnonylamino, Hydrox5τnethylamino, Dihydroxymethylamino, 2-Hydroxyethyl, N, N-Bis (2-hyc oxyethyl) amino, Trffluormethylamino, Trifluorethyla ino, Cyanomethylamino, Methoxycarbonylmethylamino, Acetoxymethylarnino, Benzyl arnino, dibenzyla ino, phenylamino, diphenylamino, o-, m- or chlorophenylamino, o-, m-, or methylphenylamino, 1- or 2-naphthylamino, cyclopentylamino, cyclohexylamino, cyclododecylamino, cyclopentadecylamino-cyclohexadylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino, cyclohexadecylamino , Thienyla ino or pyranylmethylamino, piperidyl or morpholyl. g) The group of the formula -COR ¹⁵ , in which R ^{15 has} the meaning given under a). Examples of R ¹⁵ are: methyl, ethyl, "-propyl, isopropyl," -butyl, sec-butyl, tert-butyl, tert-amyl, "-hexyl, 1,1,3,3, -tetramethylbutyl, n -Heptyl, w-octyl, «-Nonyl, n-decyl,« -Undecyl, «-Dodecyl, ra-Octadecyl, 1-Etylpropyl, 1-Propylbutyl, 1-Butylpentyl, 1-Pentylhexyl, 1-Hexylheptyl, 1-Heptyloctyl , 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, acetoxymethyl , o-, m- or ^ -Chlorphenyl, o-, m-, or j? -MethylphenyI, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL CycloeicosanyL Cyclotetracosanyl, Thienyl or Pyranylmethyl, Benzyl or Fiirfuryl. h) the group of the formula-N (R ¹⁶ ) COR ¹⁷ , in which R ^{16 has} the meaning given under b), R ^{17 is} hydrogen, alkyl, for example methyl, ethyl, w-propyl, isopropyl, w-butyl L-butyl, tert-butyl, tert-amyl, w-hexyl, 1,1,3,3, -tetramethylbutyl, w-heptyl, "-ctyl, n-nonyl, w-decyl," -undecyl, "-dodecyl," -ctadecyl , 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl, 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1 -EthylnonyL hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymefhyl, benzyl, phenyl, o-, m- or j9-chlorophenyl, o-, m-, or j? -Methylphenyl, 1- or 2-naphthyL cyclopentyl , Cyclohexyl, Cyclododecyl, Cyclopentadecyl, CyclohexadecyL Cycloeicosanyl, Cyclotetracosanyl, Thienyl or Pyranylmethyl or Fiirfuryl. Alkyl occurring in the definitions of R ¹⁶ can have, for example, one of the number of C atoms preferably given under b). Examples include: acetylamino, propionyl-arnino, butyrylamino, benzoylamino, j ^ -CUorbenzoylamino, -Methylbenzoylamino, N-methylacetamino, N-methylbenzoylamino, N-succinimido, N-phthalimido or N- (4-amino) phthalimido. i) The group of the formula -N (R ¹⁸ ) COOR ¹⁹ , in which R ¹⁸ and R ^{19 have} the meaning given under b) and c). Examples are the groups -NHCOOCH3, -

NHCOOC ₂ H ₅ , or -NHCOOC ₆ H ₅ called. j) The group of the formula -N (R ²⁰ ) CON (R ²¹ ) (R ²² ), in which R ²⁰ , R ²¹ and R ^{22 have} the meaning given under b) or c). Examples include: ureido, Ν-methylureido, N-phenylureido, or N, N'-2 ', 4'-dimethylphenylureido. k) The group of the formula -ΝΗSO2R ²³ , wherein R ^{23 has} the meaning given under b). Examples include: methylsulfonylamino, phenylsulfonylamino, p-

Tolylsulfonylamino or 2-naphthylsulfonylamino.

1) The groups of the formula -SO2R ²⁴ or -SOR ²⁵ , in which R ²⁴ or R ^{25 have} the meaning given under b). Examples include: methylsulfonyl, ethylsulfonyl,

Phenylsulfonyl, 2-naphthylsulfonyl, phenylsulfoxidyl. m) The group of the formula -SO2OR ²⁶ , in which R ^{26 has} the meaning given under b).

The following may be mentioned as examples of R ²⁷ : methyl, ethyl, phenyl O-, m-, or j? -Chlorophenyl, o-, m- or / 7-methylphenyl, 1- or 2-naphthyl. n) The group of the formula -CON (R ⁷ ) (R ^2S ), wherein R ²⁷ and R ^{28 are} those given under b) Have meaning. Examples include: carbamoyl, N-methylcarbamoyL N-ethylcarbamoyl, N-phenylcarbamoyL N, N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-1-naphthylcarbamoyl or N-piperdylcarbamoyl. o) The group of the formula -Sθ2N (R ²⁹ ) (R ³⁰ ), wherein R ²⁹ and R ^{30 are} those given under b)

Have meaning. Examples include: sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsuliamoyl or N-morpholylsuliamoyl. p) The group of the formula -N = NR ³¹ , in which R ^{31 is} the residue of a coupling component or a phenyl radical which may be substituted by halogen, alkyl or -O-alkyl. Alkyl occurring in the definitions of R ³¹ can have, for example, one of the number of C atoms given as preferred under b). The following may be mentioned as examples of R ³¹ : the acetoacetarylide, pyrazolyl, pyridonyl, o -, /> - hydroxyphenyl, o-hydroxynaphthyl, p-aminophenyl or? -N, N-dimethylarninophenyl radicals. q) The group of the formula -OCOR ³² wherein R ^{32 has} the meaning given under b). Examples of R ³² are: methyl, ethyl, phenyl, o-, m- or j ^ -chlorophenyl. r) The group of the formula -OCONHR ³³ , in which R ^{33 has} the meaning given under a). Examples of R ³³ include: methyl, ethyl, phenyl, o-, m- or chlorophenyl. R ¹ to R ⁵ can be hydrogen and one to four of the following radicals a) halogen atoms, for example chlorine, bromine, iodine or fluorine. b) Branched or unbranched alkyl groups with preferably 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4 carbon atoms. These alkyl groups can have non-water-solubilizing substituents, such as fluorine, hydroxy, cyano, -OCOR ³⁴ , -OR ³⁵ , -OCOOR ³⁶ , -CON (R ³⁷ ) (R ³⁸ ) or -OCONHR ³⁹ , where R ^{34 is} alkyl, Aryl such as naphthyL or unsubstituted or substituted by halogen, alkyl, or -O-alkyl, benzyl or a heterocyclic radical, R ³⁵ , R ³⁶ and R ³⁹ hydrogen, unsubstituted or substituted by cyano or hydroxy, C3- bis

C24- CycloalkyL preferably denotes C5-, Cg-, Ci2 "_> C15-, Cjg-, C20- and C24-cycloalkyl, aryl or heteroaryl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, or in which R ³⁷ and R ³⁸ together with one of the other radicals R ³⁴ to R ³⁹ each form a 5-6-membered ring or also hetero ring, such as a pyridine, pyrrole, furan or pyran ring, further possible substituents on the alkyl groups are mono- or dialkylated amino groups, aryl radicals, such as naphthyl or, in particular, unsubstituted or substituted by halogen, alkyl or -O-alkyl, or further heterocyclic aromatic radicals, such as, for example, the 2- Thienyl, 2-benzoxazolyl-, 2-benzthiazolyl-, 2-benzimidazolyl-, 6-benzimidazolonyl-, 2-, 3- or 4-pyridinyl-, 2-, 4-, or 6-quinolyl- or 1-, 3- , 4-, 6-, or 8-isoquinolyl residues. If the substituents mentioned under b) in turn contain alkyl, this alkyl can be branched or unbranched and preferably contain 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4 carbon atoms. Examples of unsubstituted alkyl groups are methyl, ethyl, w-propyl, isopropyl, 1-butyl, sec-butyl, tert-butyl, tert-amyl, w-hexyl, 1,1,3,3, -Tetramethylbutyl, w- Heptyl, w-octyl, n-nonyl, w-decyl, n-undecyl, n-dodecyl, «-octadecyl, 1-ethylpropyl, 1-propylbutyl 1-butylpentyl, 1-pentylhexyl, 1-hexylheptyl, 1-heptyl-octyl , 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or Benzyl or cycloalkyl with C ₃ to C ₂₀ . c) The group -OR ⁴⁰ , in which R ^{40 is} hydrogen, alkyl, aryl, for example naphthyl or in particular unsubstituted phenyl, C3 to C24-cycloalkyl, preferably C5-, Cg-, Cγχ,

^ 15 "'Cι6-> ^ 20" » ^{un (} ^ C24-CycloalkyL Aryl or HeteroaryL mean in particular unsubstituted or substituted by halogen, alkyl or -O-alkyl. Phenyl occurring in the definitions of R ⁴⁰ , for example, one of the under b ) have the number of carbon atoms indicated as preferred. Examples of R ⁴⁰ are: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert-amyl, hexyl, 1,1,3,3, tetramethylbutyl, w-heptyl , "-Octyl, w-nonyl," -decyl, w-undecyl, "-dodecyl, n-octadecyl, 1-ethylpropyl, 1-propylbutyl 1-butylpentyl 1-pentylhexyl 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl with C or ₃ to C _2o , phenyl, o-, m- or? -Chlorophenyl, o-, m-, or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL cycloeicosanyl, cyclotetracosanyl, or thienyl Pyranylmethyl. e) The cyano group. f) The group of the formula -N (R ⁴¹ ) (R ⁴² ), in which R ⁴¹ and R ^{42 have} the meaning given under b). Examples include: amino, methylamino, dimethylamino, ethylamino, diethylamino, "-propylamino, di -" - propylamino, isopropylamino, n-butylamino, di - "- butylamino, sec-butylarnino, di-5ec-butylamino, tert-butylamino , tert- Amylamino, n-hexylamino, di-n-hexylamino, 1,1,3,3, tetramethylbutylamino, "-heptylamino, di -" - heptylamino, n-octylamino, di-n-octylamino, w-nonyl, di -H-nonylamino, n-decylamino, di-w-decylamino, «-Undecylamino, Di -« - undecylamino, «-Dodecylarnino, Di -« - dodecylamino, «-Octadecylamino, 1-Etylpropylamino, 1-Propylbulylamino, 1-Butyl - pentylamino, 1-pentylhexylamino, 1-hexylheptylamino, 1-heptyloctylamino, 1-octylnon-ylamino, 1-nonyldecylamino, 1-decylundecylamino, 1-ethylbutylamino, 1-ethylpentylamino, 1-ethymeptylamino, 1-ethylamino methylamyl, 1 Dihydroxy methyl aminino, 2-hydroxyethyl, N, N-bis (2-hydroxyethyl) amino, trifluoromethylamino, trifluoroethylamino, cyanomethylamino, methoxycarbonylmethylamino, acetoxymethylamino, benzylarnino, dibenzylamino, phenyla ino, diphenylarnino or 7-, m- Chlorphenylamino, o-, m-, or methylphenylarnino, 1- or 2-naphthylamino, cyclopentylamino, cyclohexylamino, cyclododecylamino, cyclopentadecylamino, cyclohexadecylami no, Cycloeicosanylamino, Cyclotetracosanylamino, Thienylamino or Pyranylmethylarnino, Piperidyl or Morpholyl g) The group of the formula -COR ⁴³ , wherein R ^{43 has} the meaning given under a). Examples of R ⁴³ include: methyl, ethyl, w-propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert-amyl, hexyl, 1,1,3,3, tetramethylbutyl, Heptyl, n-octyl, "-nonyl, n-decyl," -undecyl, "-dodecyl," -octadecyL 1-ethylpropyl, 1-propylbutyl, 1-butylpentyL 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1- Octylnonyl, 1-nonyldecyl, 1 -decylundecyl 1-ethylbutyl 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl Cycloalkyl with C ₃ to C ₂ o, phenyl, o-, m- or βtp-chlorophenyl, o-, m- or? -Methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL cycloeicosanyl cyclotetracosanyl, Thienyl, pyranylmethyl, benzyl or furfuryl. h) The group of the formula-N (R ⁴⁴ ) COR ⁴⁵ , in which R ^{44 has} the meaning given under b), R ^{44 is} hydrogen, alkyl, for example methyl, ethyl, propyl, isopropyl, w-butyl, sec-butyl , tert-butyl, tert-amyl, "-hexyl, 1,1,3,3, -tetramethylbutyl, n-heptyl, w-octyl, n-NonyL ra-decyl, w-undecyl, n-dodecyl," -octadecyl , 1-Ethylpropyl, 1-Propylbutyl, 1-ButylpentyL 1-Pentylhexyl, 1-HexylheptyL 1-HeptyloctyL 1-Octylnonyl, 1-NonyldecyL 1-Decylundecyl 1-Ethylbutyl, 1-Ethylpentyl, 1-Ethylheptyl, 1-Ethylethylnon 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl with C ₃ to C ₂₀ , phenyl, in particular unsubstituted tuated or substituted by halogen, alkyl or -O-alkyl, for example o-, m- or ^ -chlorophenyl, o-, m-, or 7-methylphenyL 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL Cycloeicosanyl, Cyclotetracosanyl, Thienyl, Pyranylmethyl, Benzyl or Furfuryl. Alkyl occurring in the definitions of R ⁴⁵ can have, for example, one of the number of C atoms preferably given under b). Examples include: acetylamino, propionylamino, butyrylamino, benzoylamino, p-chlorobenzoylamino, p-methylbenzoylamino, N-methylacet-arnino, N-methylbenzoylamino, N-succinimido, N-phthalimido or N- (4-Arnmo) phthalirnido. i) The group of the formula -N (R ⁴⁶ ) COOR ⁴⁷ , in which R ⁴⁶ and R ^{47 have} the meaning given under b) and c). Examples are the groups -NHCOOCH3, -

NHCOOC2H5, or -NHCOOCgH5 called. j) The group of the formula -N (R ⁴⁸ ) CON (R ⁴⁹ ) (R ⁵⁰ ), in which R ⁴⁸ , R ⁴⁹ and R ^{50 have} the meaning given under b) or c). Examples include: ureido, N-methylureido, N-phenylureido, or NN ^ '^' - dimethylphenvlureido. k) The group of the formula -NHSO2R ⁵¹ , in which R ^{51 has} the meaning given under b). Examples include: methyteuffonylamino, phenylsulfonylamino, p-

Tolylsulfonylamino or 2-naphthylsulfonylamino

1) The groups of the formula -SO ₂ R ⁵² or -SOR ⁵³ , wherein R ⁵² or R ^{53 have} the meaning given under b). Examples include: MethylsulfonyL EthylsulfonyL

Phenylsulfonyl, 2-naphthylsulfonyl, phenylsulfoxidyl. m) The group of the formula -SO2OR ⁵⁴ , in which R ^{54 has} the meaning given under b).

Examples of R ⁵⁴ are: methyl, ethyl, phenyl, m-, or 7-chlorophenyl, o-, m- or 7-methylphenyl, 1- or 2-naphthyl. n) The group of the formula -CON (R ⁵⁵ ) (R ⁵⁶ ), wherein R ⁵⁵ and R ^{56 are} those given under b)

Have meaning. Examples include: carbamoyl, N-methylcarbamoyl, N-

Efhylcarbamoyl, N-phenylcarbamoyl, N, N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-1-naphthylcarbamoyl or N-piperdylcarbamoyl. o) The group of the formula -Sθ2N (R ⁵⁷ ) (R ⁵⁸ ), wherein R ⁵⁷ and R ^{58 are} those given under b)

Have meaning. Examples include: sulfamoyl, N-methylsulfamoyl, N-

Ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsultamoyl or N-

Morpholylsulfamoyl. p) The group of the formula -N = NR ⁵⁹ , wherein R ^{59 is} the remainder of a coupling component or a phenyl radical optionally substituted by halogen, alkyl or -O-alkyl. Alkyl occurring in the definitions of R ⁵⁹ can have, for example, one of the number of C atoms given as preferred under b). The following may be mentioned as examples of R ⁵⁹ : the acetoacetarylide, pyrazolyl, pyridonyl, o-, p-hydroxypheήyl, o-hydroxynaphthyl, p-aminophenyl or j9-N, N-dimethylaminophenyl radicals. q) The group of the formula -OCOR ⁶⁰ , in which R ^{60 has} the meaning given under b). Examples of R ⁶⁰ are: methyl, ethyl, phenyl, o-, m- or 7-chlorophenyl. r) The group of the formula -OCONHR ⁶¹ , wherein R ^{61 has} the meaning given under a). Examples of R ⁶¹ are: methyl, ethyl, phenyl, o-, m- or chlorophenyl.

6. Use of polycyclic aromatics as voluminous aromatic groups according to 2. The polycyclic aromatics should in turn be provided with at least one, but at most five identical or different substituents R ¹ to R ⁵ , which have the meaning given under 5. Examples of this are the 1-naphthyl radical substituted in positions 2, 3, 4, 5, 6 and 7, 2-naphthyl radical substituted in positions 3, 4, 5, 6, 7 and 8, the 1-anthryl radical substituted in positions 2, 3, 4, 5,6,7,8 and 9, the 2-anthryl radical is substituted in positions 1, 3, 4, 5, 6, 7, 8, 9 and 10.

7. The use of heteroaromatic radicals as voluminous aromatic groups according to 3. The heterocaromatics should in turn be provided with at least one, but at most five identical or different substituents R ¹ to R ⁵ , which have the meaning given under 5. Examples are the 2-pyridyl radical, 3-pyridyl radical, 4-pyridyl radical, 2-thiophenyl radical, 3-tiophenyl radical, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-furoyl, 3 -Furoyl, 2-quinolyl, 3-quinolyl, 1-isoindolyl radical. An example of such a radical is the (3,4,5,6-tetraphenylphthalimidyl) radical.

8. Use of voluminous aliphatic radicals according to 4 with the general formula II,

H in which R ¹ to R ^{3 are} hydrogen or one to 3 of the radicals mentioned under 5. , Use of voluminous aliphatic radicals according to 4 with the general formula III,

IM in which R ¹ to R ^{3 are} hydrogen or one to 3 of the radicals mentioned under 5. 10. Use of the tetraphenylphthalimidyl radical of the general formula IV,

IV in which R ¹ to R ^{4 are} hydrogen or one to 4 of the radicals mentioned under 5. 11. perylene dyes of the general formula V,

V in which x and y can be the same or different and the residues mentioned under 5 to 10 are anti-aggregation residues or in which x is one of the anti-aggregation residues mentioned under 5 to 10 and y is a solubility-increasing group such as 1-ethylpropyl, 1- Propylbutyl, 1-butylpentyl 1-penthenxyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl or 2,5-di-tert-butylphenyl, 2,4-di-tert- butylphenyl, 2,6-di-isopropylphenyl or 2,4,6-triisopropylphenyl. Preferred examples are x = y

Bis (2- (l-propylbutyl) -3-propylhexyl), N, N'-bis (-2- (l-butylpentyl) -3-butylheptyl) and bis (2- (l-pentylhexyι) -3-pentyloctyι) or x —p- triphenylmethyl, bis (2- (l-propylbutyl) -3-propyihexyι), ΛζN'-bis (-2- (l-butylpentyl) -3-butylheptyl) or bis (2- (l-pentylhexyl) -3-pentyloctyι) - undy = 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl 1-pentylhexyl 1-hexylheptyl, 1-heptyl octyl 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl or 2,5-di-tert-butylphenyl , 2,4-di-ter / -butylphenyl, 2,6-diisopropylphenyl or 2,4,6-triisopropylphenyl. 12. Perylene-3,4-dicarboximides of the general formula VI

VI in which x is one of the aggregation-preventing residues mentioned under 5 to 10.

13. Use of the substances according to 11 and 12 as dyes.

14. Usage of the substances according to 11 and 12 as fluorescent dyes.

15. Application of dyes 11 and 12 for bulk dyeing of polymers. Examples are materials made from polyvinyl chloride, cellulose acetate, polycarbonates, polyamides, polyurethanes, polyimides, polybenzimidazoles, melamine resins, silicones, polyesters, polyethers, polystyrene, polymethyl methacrylate, polyethylene, polypropylene, polyvinyl acetate, polyacrylonitrile, polybutadiene, or polyenchlorophenadiene monomers or the polyenchloroputadiene monomers or the polyenchlorophenadiene monomers mentioned.

16. Application of the dyes of 11 and 12 as vat dyes, e.g. for coloring natural products. Examples are paper, wood, straw, leather, furs or natural fiber materials such as cotton, wool, silk, jute, sisal, hemp, flax or animal hair (e.g. horsehair) and their conversion products such as e.g. the viscose fiber, nitrate silk or copper rayon (rayon).

17. Application of the dyes of 11 and 12 as pickling dyes, for example for coloring natural products. Examples are paper, wood, straw, leather, skins or natural fiber materials such as cotton, wool, silk, jute, sisal, hemp, flax or animal hair (eg horsehair) and their conversion products such as viscose fiber, nitrate silk or copper rayon (Reyo). Preferred salts for pickling are aluminum, chromium and iron salts.

18. Use of the dyes of 11 and 12 as colorants, e.g. for coloring paints, varnishes and other paints, paper paints, printing inks, inks and other colors for painting and writing purposes.

19. Use of the dyes of 11 and 12 as pigment dyes, e.g. for coloring paints, varnishes and other paints, paper paints, printing inks, inks and other colors for painting and writing purposes.

20. Application of the dyes of 11 and 12 as pigments in electrophotography: e.g. for dry copy systems (Xerox process) and laser printer ("non-impact printing").

21. Use of the dyes of 11 and 12 for security marking purposes, the great chemical and photochemical resistance and possibly also the fluorescence of the substances being important. This is preferred for checks, check cards, bank notes, coupons, documents, identity papers and the like, in which a special, unmistakable color impression is to be achieved.

22. Application of the dyes of 11 and 12 can be used as an additive to other colors in which a certain color shade is to be achieved, particularly bright colors are preferred.

23. Use of the dyes of 11 and 12 to mark objects for machine recognition of these objects via fluorescence, preferably machine detection of objects for sorting, e.g. also for recycling plastics.

24. Use of the dyes of 11 and 12 can be used as fluorescent dyes for machine-readable markings, preferably alphanumeric prints or barcodes.

25. Application of the dyes of 11 and 12 can be used for frequency conversion of light, e.g. to make longer-wave, visible light from short-wave light.

26. Application of the dyes of 11 and 12 in display elements for various display, information and marking purposes, for example passive display elements, information and traffic signs, such as traffic lights. 27. Application of the dyes of 11 and 12 in ink jet printers, preferably in a homogeneous solution as fluorescent ink.

28. Application of the dyes of 11 and 12 as a starting material for superconducting organic materials.

29. Use of the dyes of 11 and 12 for solid fluorescent labels.

30. Application of dyes from 11 and 12 for decorative purposes.

31. Application of dyes from 11 and 12 for artistic purposes.

32. Use of dyes from 11 and 12 for tracer purposes, e.g. in biochemistry, medicine, technology and science. The dyes can be covalently linked to substrates or via secondary valences such as hydrogen bonds or hydrophobic interactions (adsorption).

33. Use of the dyes of 11 and 12 as fluorescent dyes in highly sensitive detection methods (see C. Aubert, J. Fünfschilling, I. Zschokke-Gränacher and H. Langhals, Z.Analyt.Chem. 1985, 320, 361).

34. Application of the dyes of 11 and 12 as fluorescent dyes in scintillators.

35. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in optical light collection systems.

36. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in fluorescent solar collectors (see H. Langhals, Nachr. Chem. Tech. Lab. 1980, 28, 716).

37. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in fluorescence-activated displays (see W. Greubel and G. Baur, Elektronik 1977, 26, 6).

38. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in cold light sources for light-induced polymerization for the preparation of plastics.

39. Use of the dyes of 11 and 12 as dyes or fluorescent dyes for material testing, e.g. in the manufacture of semiconductor circuits.

40. Application of the dyes of 11 and 12 as dyes or fluorescent dyes for the investigation of MiloEst structures of integrated semiconductor components.

41. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in photoconductors. 42. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in photographic processes.

43. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in display, lighting or image converter systems in which the excitation is carried out by electrons, ions or UV radiation, e.g. in fluorescent displays, Braun tubes or in fluorescent tubes.

44. Application of the dyes of 11 and 12 as dyes or fluorescent dyes as part of an integrated semiconductor circuit, the dyes as such or in connection with other semiconductors e.g. in the form of an epitaxy.

45. Use of the dyes of 11 and 12 as dyes or fluorescent dyes in chemiluminescent systems, e.g. in chemiminescent light sticks, in luminescent immunoassays or other luminescence detection methods.

46. Use of the dyes of 11 and 12 as dyes or fluorescent dyes as signal colors, preferably for optically highlighting lettering and drawings or other graphic products, for marking signs and other objects in which a special visual color impression is to be achieved.

47. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in dye lasers, preferably as fluorescent dyes for generating laser beams.

48. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in dye lasers.

49. Use of the dyes of 11 and 12 as dyes in dye lasers as Q-switch switches.

50. Use of the dyes of 11 and 12 as active substances for non-linear optics, e.g. for frequency doubling and frequency tripling of laser light.

51. Use of the dyes of 11 and 12 as rheology improvers.

Experimental part

N, N'-bis (4'-tritylpheτψl) perylene-3,4: 9,10-bis (dicarboximide) (2c): 4-tritylaniline ¹¹ (2.00 g,

5.96 mmoi), perylene-3,4: 9,10-tefracarbonsäιιre-3,4: 9,10-bisanhydride (1, 980 mg, 2.50 mmol) and

Imidazole (20 g) was heated to 140 ° C for 3 h. Water (10 ml) was added and after the Cooling off 2N hydrochloric acid (70 ml) with stirring. After stirring for 12 h, the precipitate was filtered off with suction, washed with distilled water (100 ml), dried, chromatographed (KieselgeL chloroform) and further purified by a second chromatography (KieselgeL chloroform ethanol 20: 1).

Yield 2.14 g (85%) 2c as a bright red solid, mp> 360 ° C. - R _{ (CHC1 ₃ ): 0.22. - IR (KBr): v = 3435 cm ¹ (s br.), 2924 (w, CH aliphatic), 2853 (w), 1709 (s, CO), 1671 (s), 1593 (m, CC aro) , 1579 (w), 1493 (w), 1432 (w), 1404 (w, CC arom), 1356 (s), 1256 (m), 1177 (w), 1122 (w), 1035 (w), 958 (w), 834 (w), 810 (m, CH aroma), 745 (m), 702 (m). - UV (CHC1 ₃ ): n _a x (ε) = 459.6 nm (14850), 490.9 (51740), 527.8 (90200). - Fluorescence (CHC1 ₃ ): nax = 538 nm, 577. - Solid fluorescence: = 593 nm - MS (70 eV): m / z (%): 1027 (7) pVl], 1026 (9), 952 (7) , 951 (27), 950 (76) pvf - Ph], 949 (100), 691 (9), 437 (10), 436 (15), 243 (27), 241 (17), 165 (18). - C ₇₄ H ₄₆ N ₂ O ₄ (1027.2): calc. C 86.52, H 4.51, N 2.73; gef. C 85.58, H 4.56, N 2.65. Reaction of 1 with 2,4,6-tripheηylaniline: 2,4,6-triphenylaniline (230 mg, 0.72 mmol), zinc acetate dihydrate (160 mg, 0.73 mmol), 1 (140 mg, 0.36 mmol) and imidazole (15 g) were reacted analogously to 2c (autoclave, 24 h, 175 ° C.) and worked up by column chromatography (KieselgeL chloroform) and a second column chromatography (KieselgeL chloroform / ethanol 20: 1) was purified. No 2b, but small amounts of 3 could be isolated. Yield 1 mg (0.3%) 3 as a red powder, mp> 360 ° C. - i? _f (CHCl ₃ / ethanol 10: 1): 0.71. - R _f (CHCl ₃ ): 0.27. - IR (KBr): v = 3436 cm ¹ (s br.), 3057 (w, CH aroma), 1698 (s, C = O), 1656 (s), 1592 (m, CC aroma), 1577 (m ), 1494 (w), 1458 (w), 1434 (w), 1408 (w), 1362 (s), 1293 (w), 1248 (w), 1199 (w), 1178 (w), 1137 (w ), 1032 (w), 921 (w), 890 (w), 812 (m), 758 (w), 701 (w). - ^X H NMR (CDC1 ₃ ): δ = 7.01 - 7.05 (m, 1 H, phenyl-H), 7.09 - 7.12 (m, 3 H, phenyl-H), 7.30 - 7.34 (m, 2 H, phenyl- H), 7.36 - 7.43 (m, 7 H, phenyl-H), 7.52 - 7.54 (, 2 H, perylene-H), 7.63 - 7.66 (m, 6 H, phenyl-H), 7.80 (d, J = 8.0 Hz, 2 H, perylene-H), 8.24 (d, J = 8.0 Hz, 2H, perylene-H), 8.32 (d, J = 7.4 Hz, 2 H, perylene-H), 8.35 (d, J = 8.0 Hz, 2H, perylene-H). - UV / Vis (CHC1 ₃ ): / (ε) = 353.6 nm (4060), 450.5 (sh, 14240), 485.5 (28050), 510.1 (26950). - Fluorescence (CHC1 ₃ ): nax = 537 nm, 570. - MS (70 eV): m / z (%): 627 (11), 626 (47), 625 (100) [ ⁴ ], 608 (7) , 581 (20), 580 (41), 312 (7), 304 (7), 276 (6). N, N-bis (2- (l-propylbutyl) -3-propyl-hexyl) -perylene-3,4: 9,10-bis (dicarhoximide) (2d): 1 (890 mg, 2.3 mmol) and 2- (l-Propylbutyl) -3-propyl-hexylamine (1.20 g, 4.97 mmol) were reacted and worked up analogously to 2c. Yield 1.46 g (77%) 2d as orange fluorescent crystal needles,

Mp 335 ° C. - Rf (KieselgeL chloroform): 0.80. - IR (KBr): v = 3436 cm ^-1 m, 2957 s, 2929

s, 2871 m, 1698 s, 1659 s, 1595 s, 1580 w, 1443 w, 1404 w, 1335 m, 1249 w, 1176 w, 1107 w,

853 w, 811 m, 784 w. - * HNMR (300 MHz, CDC1 ₃ ): δ = 0.78 (t, J = 7.2 Hz, 12 H, 4 CH3), 0.91

(t, J = 7.3 Hz, 12 H, 4 CH3), 1.20 (1, 16 H, 8 CH ₂ ), 1.33 (mc, 16 H, 8 CH ₂ ), 1.66 (4 H, 4

γ-CΗ, 2.21 (t, J = 7.4 Hz, 2 H, 2 ß-OX), 4.24 (d, J = 7.4 Hz, 4 H, 2 α-CH ₂ ), 8.60 (d, J = 8.0

Hz, 4 H, perylene), 8.66, J = 8.0 Hz, 4 H, perylene). - ¹³ C NMR (75 MHz, CDCI3): δ = 14.41, 14.55, 21.18, 21.47, 33.43, 34.53, 37.56, 39.38, 39.71, 123.07, 123.40, 126.50, 129.35, 131.41, 134.61, 163.74. - UV / Vis (CHCI3): nax O) = 434.1 nm (7350), 458.5 (21700), 488.9 (56900),

525.9 (94200). - Fluorescence (CHCI3): rjax ⁼ 534 nm, 574, 621. - Fluorescence quantum yield

(CHCI3, reference N, N- (l-hexylheptyl) perylene-3,4: 9,10-bis (dicarboximide) with Φ = 100%):

99%. - Solid-state fluorescence: nax = 596 nm. - MS (70 eV): m / z (%): 840 (11), 839 (36), 838

(58) [M ⁺ ], 783 (26), 782 (44), 740 (11), 627 (9), 617 (12), 616 (39), 615 (63), 614 (12), 560

(26), 559 (45), 558 (12), 517 (14), 418 (10), 417 (9), 406 (12), 405 (44), 404 (67), 403 (20), 393 (17), 392 (68), 391 (100), 390 (87), 373 (16), 345 (9), 199 (16), 111 (9), 97 (15), 91 (14), 83

(24), 71 (11), 69 (41), 57 (58), 55 (32). - C56H7 N2O4 (839.2): calc. C 80.15, H 8.89, N 3.34; gef. C 80.33, H 8.79, N 3.57. N, N-bis (-2- (l-butylpentyl) -3-butylheptyl) perylene-3,4: 9,10-bis (dicarboximide) (2e); 1 (300 mg, 0.8 mmol), 3-Bu1yl-2- (l-bu1ylpentyl) -heptylarnine (600 mg, 2.0 mmol) and imidazole (900 mg) were reacted analogously to 2c (160 ° C, 3 h) and through Column chromatography cleaned

(Silica gel, chloroform). Yield 600 mg (81%) of 2e, mp. 238 ° C. - R _f (silica gel / CHC1 ₃ ):

0.81. - IR (KBr): v = 2923 cm ^-1 s, 2857 s, 1691 s, 1651 s, 1594 s, 1579 s, 1508 w, 1467 m,

1446 m, 1404 s, 1372 s, 1338 s, 1247 m, 1177 m, 1130 w, 1110 w, 1016 w, 871 w, 816 s, 796 w, 749 m. - ^ NMR (300 MHz, CDC1 ₃ ): δ = 0.82 (t, J = 7.1 Hz, 12 H, 4 CH ₃ ), 0.88 (t, J = 7.2 Hz,

12 H, 4 CH3), 1.20-1.55 (m, 34 H, 17 CH ₂ ), 1.65 (mc, 18 H, 8 CH ₂ + 2 ^ CH), 2.14 (mc, 2 H, 2

ß-C), 4.22 (d, J = 7.2 Hz, 4 H, 2 α-CH ₂ ), 8.56 (d, J = 8.1 Hz, 4 H, perylene), 8.63 (d, J = 8.1

Hz, 4H, perylene). ¹³ C NMR (75 MHz, CDCI3): δ = 14.06 (CH3), 14.21 (CH3), 22.97 (CH ₂ ),

23.13 (CH ₂ ), 29:60 (CH ₂ ), 30.39 (CH ₂ ), 30.63 (CH ₂ ), 30.78 (CH ₂ ), 31.91 (CH ₂ ), 38.13

(y-CK), 39.37 (ß-CH, 39.68 (α-CH ₂ ), 122.98 (perylene), 123.34 (perylene), 131.33 (perylene),

134.50 (perylene), 163.67 (Ν-C = O). - UV / Vis (CHCI3):; i _max (ε) = 458.2 nm (18700), 488.2

(51500), 525.1 (84800). - Fluorescence (CHCI3): na = 534 nm, 574, 621. -

Fluorescence quantum yield (CHCI3, reference N, N '- (l-hexylheptyι) -perylene-3,4: 9,10-

bis (dicarboximide) with Φ = 100%): 97%. - Solid-state fluorescence: i _max = 587.9 nm. - MS (70 eV):

m / z (%): 951 (70) [M ⁺ + 1], 950 (100) M ⁺ ], 824 (3) M ⁺ + 1 - C9H19], 823 (5) [M ⁺ - C9H19],

684 (5) [M ⁺ + 1 - C19H39], 683 (7) M ⁺ - C ₁₉ H ₃₉ ], 673 (24), 672 (70), 671 (88), 544 (2) [671

- C9H19], 541 (3), 418 (4), 417 (5) [544 - C9H19], 405 (26), 404 (35) [671 - C19H39], 403 (10), 393 (19), 392 (63), 391 (68), 390 (52), 373 (13), 346 (6), 345 (7), 111 (8), 97 (18), 71 (12), 69 (20), 57 (18), 55 (20). - C ₆ 4H9oN ₂ O ₄ (951.4): calc. C 80.80, H 9.53, N 2.94; gef. C

81.10, H 9.65. Ν 3.18.

N, N ^f -Bis (2- (l-pentylhexyl) -3-pentyl-octyl) perylene-3,4: 9,10-bis (dicarboximide) (ϊi): 1 (200 mg, 0.51 mmol) and the Crude amine mixture containing l-amino-2- (l-penty] hexyl) -3-pentyl-octane (400 mg) was reacted and worked up analogously to 2c. Yield 300 mg (55%) 2f as red fluorescent crystal needles, mp 195-196 ° C. - Rf (silica gel, chloroform): 0.83. - Rf

(Silica gel, toluene): 0.65. - IR (KBr): v = 3441 cm ^"1 w, 2958 s, 2928 s, 2857 s, 1693 s, 1658 s,

1594 s, 1583 w, 1467 m, 1406 m, 1332 m, 1247 m, 1110 w, 871 w, 813 s, 796 w, 751 m. - *H

NMR (300 MHz, CDC1 ₃ ): δ = 0.74 (t, J = 6.9 Hz, 12 H, 4 CH ₃ ), 0.88 (t, J = 6.4 Hz, 12 H, 4

CH ₃ ), 1.00-1.18 (m, 16 H, 8 CH ₂ ), 1.20-1.35 (m, 32 H, 16 CH ₂ ), 1.66 (mc, 4 H, 4 r-CH), 2.14

(t, J = 7.1 Hz, 2 H, 2 ß-CH), 4.22 (d, J = 7.2 Hz, 4 H, 2 α-CH ₂ ), 8.53 (d, J = 8.13 Hz, 4 H,

Perylene), 8.62 (d, J = 8.0 Hz, 4H, perylene). - ¹³ C-DEPT-NMR (75 MHz, CDCI ₃ ): δ = 14.41, 14.58, 23.01, 23.18, 28.21, 28.37, 30.10, 31.39, 32.53, 32.74, 38.43 (γ-CH), 39.69 (ß-C) , 40.03 (-CH ₂ ), 123.35, 131.71. - ¹³ C NMR (75 MHz, CDCI3): δ = 14.41, 14.58, 23.01, 23.18, 28.21, 28.37, 30.10, 31.39, 32.53, 32.74, 38.43, 39.69, 40.03, 123.35, 123.77, 126.76, 129.67, 131.71, 134.85 , 164.02. - UV / Vis (CHCI ₃ ): nax O) = 434.1 nm (4750), 458.5 (17800), 489.1

(50500), 525.9 (85400). - Fluorescence (CHCI ₃ ):; t _max = 534 nm, 574, 621. -

Fluorescence quantum yield (CHCI3, reference N, N "- (l-hexylheptyl) perylene-3,4: 9,10-

bis (dicarboximide) with Φ = 100%): 97%. - Solid-state fluorescence:; i _max = 624 nm. - MS (70 eV):

m / z (%): 1066 (8), 1065 (30), 1064 (77), 1063 (100) [M ⁺ ], 908 (5) [M ⁺ - C _π H ₂₃ ], 881 (8), 729 (18), 728 (49), 727 (57), 726 (12), 545 (7), 521 (6), 450 (6), 405 (15), 404 (21), 393 (7), 392

(34), 391 (41), 390 (34), 368 (21), 367 (79), 366 (9), 365 (7), 297 (12), 296 (73), 268 (10), 213

(10), 142 (7), 125 (6), 111 (7), 100 (29), 97 (12), 85 (11), 83 (13), 71 (16), 69 (18), 57 (26), 55

(19). - C ₇ 2H ₁₀ 6N ₂ O ₄ (1063.6): calc. C 81.30, H 10.04, N 2.63; gef. C 81.24, H 9.46, N 2.75.

N- (l-hexylheptyl) -N '- (4'-tritylphenyl) perylene-3,4: 9,10-bis (dicarboximide) (6): ^ - (l-hexylheptyl) - perylene-3,4: 9,10-tefracarboxylic acid-3,4-anhyατid-9,10-carboximide ⁷ (4,270 mg, 0.45 mmol), 4-tritylaniline (600 mg, 1.79 mmol) and imidazole (15 g) were reacted analogously to 2c and worked up. The precipitate was purified by column chromatography twice (KieselgeL chloroform ethanol 20: 1 and KieselgeL chloroform). Yield 230 mg (56%) 6 as a dark red solid, mp. 292-293 ° C. - R _f (CHC1 ₃ ): 0.24. - TR (KBr): v = 3435 cm ¹ (s br.), 3056 (w), 3030 (w), 2953 (w, CH aliphatic), 2926 (w), 2856 (w), 1698 (s, C = O), 1660 (s), 1594 (m, CC arom), 1579 (w), 1507 (w), 1493 (w), 1433 (w), 1343 (s), 1254 (m), 1175 (w ), 1137 (w), 1124 (w), 1107 (w), 1035 (w), 966 (w), 853 (w), 811 (w), 747 (), 702 (w). - 1HNMR (CDC1 ₃ ): δ = 0.83 (t, J = 6.7 Hz, 3 H, CH ₃ ), 1.23-1.32 (m, 16 H, 8 CH ₂ ), 1.83-1.90 (m, 2 H, CH ₂ ), 2.22-2.30 (m, 2 H, CH ₂ ), 5.16-5.19 (m, 2 H, CH), 7.21-7.30 (m, 19 H, phenyl-H), 8.60-8.73 (m, 8 H, perylene-H). - ¹³ C NMR (CDC1 ₃ ): δ = 14.06, 22.59, 26.94, 29.22, 31.76, 32.36, 54.83, 64.91, 123.10, 123.30, 126.08, 126.41, 126.65, 127.34, 127.53, 127.60, 129.54, 129.81, 131.23, 131.78 , 132.10, 132.72, 134.28, 135.10, 146.46, 147.36, 163.59. - UV (CHC1 ₃ ): λ ^ (ε) = 366.7 nm (4650), 430.0 (sh., 6560), 458.8 (21150), 490.6 (56350), 527.0 (93430). - Fluorescence (CHC1 ₃ ): ^ = 535 nm, 575. - MS (70 eV): m / z (%): 892 (12), 891 (35) Pvl ⁴ ], 890 (51), 815 (9) , 814 (19), 813 (47) [M "- CeHe], 711 (8), 710 (26), 709 (51) M" - C ₁₃ H ₂₆ ], 633 (15), 632 (54) U - C ₁₃ H ₂₆ - Ph], 631 (100) [Nf - d ₃ H ₂₆ - Ä], 541 (7), 374 (14), 373 (51), 346 (17), 345 (25), 319 (7), 317 (8), 316 (26), 243 (28), 241 (27), 239 (9), 165 (26), 69 (7), 55 (11). - C ₆₂ H ₅₄ N ₂ O (891.1): calc. C 83.57, H 6.11, N 3.14; gef. C 83.41, H 6.07, N 3.17. N- (l-Hexylheptyl) -N '- (3, 4, 5, 6-tetraphenylphthalimidyl) perylene-3, 4: 9, 10-bis (dicarboximide) (7):

4 (160 mg, 0.272 mmol), 3,4,5,6-tetraphenylphthalic anhydride (346 mg, 0.765 mmol) and

Imidazole (2 g) were reacted analogously to 2c (130 ° C., 3 h) and worked up and through

Column chromatography purified (silica gel, chloroform / acetone 15: 1). Yield 210 mg (75%)

5b as a dark red powder, mp. 312 ° C. - Rf (silica gel, chloroform / acetone 15: 1): 0.19. - IR

(KBr): v = 3436 cm ^-1 s, 2927 m, 2856 w, 1749 s, 1726 m, 1700 s, 1660 s, 1594 s, 1579 m,

1444 w, 1405 m, 1337 s, 1325 s, 1281 w, 1251 w, 1211 w, 1174 w, 1128 w, 1029 w, 965 w, 942 w, 856 w, 810 m, 780 w, 768 w, 756 w , 739 m, 654 w, 641 w, 562 w, 496 w. - * H NMR (300

MHz, CDC1 ₃ ): δ = 0.82 (t, J = 6.8 Hz, 6 H, 2 CH ₃ ), 1.16-1.4 (m, 16 H, 8 CH ₃ ), 1.87 (mc, 2 H,? -CH ₂ ), 2.26 (mc, 2 H, / ^ CH ₂ ), 5.19 (mc, 1 H, a-CH), 6.80 - 6.84 (m, 4 H, phenyl), 6.91 - 6.97 (m, 6 H, phenyl) , 71.3 - 7.23 (m, 10 H, phenyl), 8.52 (d, J = 8.3 Hz, 2 H, perylene), 8.58 (d, J = 8.1 Hz, 2 H, perylene), 8.59 (d, J = 8.2 Hz, 2H, perylene), 8.67 (n, 2H, perylene). - ¹³ C NMR

(75 MHz, CDCI ₃ ): δ = 14.5, 23.0, 27.3, 29.6, 30.1, 32.1, 32.8, 55.3, 122.5, 123.3, 124.1, 124.7, 126.6, 126.9, 127.1, 127.5, 127.8, 127.9, 129.8, 129.9, 130.2, 130.4, 131.1, 132.7, 134.3, 135.6, 136.2, 138.2, 140.9, 149.2, 160.6, 163.2. - UV / Vis (CHCI3): Ä ^ (ε) = 352.8 n (8800), 368.0

(7100), 434 (6000), 459.6 (19100), 491.1 (51100), 527.4 (84100). - Fluorescence (CHCI3): nax

= 539 nm, 577, 631 sh. - Solid-state fluorescence:; i _max = 628 nm - MS (70 eV): m / z (%): 1023 (5),

1022 (13), 1021 (16) [M ⁺ ], 1005 (3), 937 (1), 936 (1), 900 (3), 842 (6), 841 (20), 840 (40), 839

(37) [M ⁺ - Cι ₃ H ₂₆ ], 838 (8), 822 (2), 762 (1) [M ⁺ - C ₁₃ H ₂₆ - C ₆ H ₅ ], 453 (6), 452 (34 ), 451

(100) [(C ₆ H ₅ ) 4C6C ₂ O ₂ NH ⁺ = R ⁺ ], 450 (28), 449 (5), 448 (7), 434 (4), 433 (6), 432 (9) , 422 (4), 420 (4), 408 (5), 407 (13), 406 (5), 405 (7), 404 (7), 403 (5), 402 (7), 401 (3), 392 (4), 391

(9), 390 (15) M ⁺ + 2 H - Cι ₃ H ₂₆ -R], 389 (5), 388 (4), 379 (7), 378 (8), 377 (11), 376 (13 ), 375 (5), 374 (11) [R ⁺ - C ₆ H ₅ ], 373 (6), 372 (5), 364 (6), 363 (8), 328 (4), 327 (5) , 303 (4), 302

(8), 301 (4), 194 (4), 188 (6), 187 (5), 181 (5), 180 (4), 174 (3), 55 (4). - C ₆ 9H55N ₃ O ₆ (1022.2): calc. C 81.07, H 5.43, N 4.11; gef. C 81.13, H 5.83, N 3.81.

N- (l-Hexylheptyl) -N ^r - (2- (l-propylbutyl) -3-propyl-hexyl) -perylene-3, 4: 9,10-bis (dicarboximide): 4 (1.27 g, 2.20 mmol) , 2- (l-Propylbutyl) -3-propyl-hexylamine (900 mg, 3.7 mmol) were analogous to

2c implemented and processed. Yield 980 mg (50%; mp. 148 ° C. - Rf (KieselgeL toluene):

00:41. - IR (KBr): v = 2957 cm ^-1 s, 2930 s, 2860 m, 1697 s, 1653 s, 1595 s, 1580 m, 1457 w,

1405 m, 1338 s, 1251 m, 1177 w, 855 w, 810 m, 747 m. - UV / Vis (CHC1 ₃ ): (ε) = 434.1 nm

(4730), 458.5 (18000), 489.1 (50500), 526.0 (85200). Fluorescence (CHCI3): nax = 534 nm,

574, 621. Fluorescence quantum yield (CHCI3, reference N, N - (l-hexylheptyι) -perylene-

3,4: 9,10-bis (dicarboximide) with Φ = 100%): 99%. - * H NMR (300 MHz, CDCI3): δ = 0.80 (mc,

18 H, 6 CH3), 1.16-1.57 (m, 34 H, 2 7-CH + 16 CH ₂ ), 1.89 (1 ^, 2 H, jö-CH ₂ ), 2.24 (c, 3 H, ß-

CH + _J Ö-CH2), 4.22 (d, J = 7.1 Hz, 2 H, α CH ₂ ), 5.18 (quint, J = 7.0 Hz, 1 H, -C), 8.53 (d, J = 8.1 Hz, 2 H, perylene), 8.58 (d, J = 8.3 Hz, 2 H, perylene), 8.61 (d, J = 8.0 Hz, 4 H, perylene). - ¹³ C NMR (75 MHz, CDCI3): δ = 14.44, 14.76, 14.90, 21.51, 21.81, 22.99, 27.37, 29.63, 32.17, 32.79, 33.75, 34.85, 37.86, 39.67, 40.00, 55.20, 123.36, 123.68, 126.73 , 129.66, 129.94, 131.27, 131.70, 134.87, 164.02. - MS (70 eV): m / z (%): 798 (55) M ⁺ + 1], 797 (100) [M ⁺ ], 615 (5)

[M ⁺ + 1 - C ₁₃ H ₂₇ ], 573 (78) [M ⁺ + 1 - C16H ₃₃ ], 572 (26) [M ⁺ - C ₁₆ H ₃₃ ], 574 (38), 405 (13), 404 (27), 403 (13), 392 (35), 391 (85), 390 (97), 374 (3), 373 (10), 345 (3), 379 (6), 167 (8),

150 (3), 149 (24), 111 (3), 104 (3), 97 (5), 85 (15), 83 (23), 71 (7), 70 (8), 69 (18), 67 (3), 57 (32), 56 (6), 55 (18), 48 (3), 47 (7). - C ₅ 3H ₆₈ N ₂ O ₄ : calc. 796.5179; gef. 796.5161 (MS).

N- (2- (l-butylpentyl) -3-butyl-heptyl) -N ^f - (l-hexylheptyl) perylene-3,4: 9,10-bis (dicarboximide) (8): 4 (440 mg, 0.76 mmol), 2- (l-butylpentyl) -3-butyl-heptylamine (250 mg, 0.84 mmol) were reacted and worked up analogously to 2c. Yield 490 mg (76%) 8 as a red, fluorescent

Needles, mp. 131 ° C. - R _f (KieselgeL chloroform): 0.61. - R _f (silica gel, toluene): 0.55. - IR

(KBr): v = 3442 cm ^-1 , 2957 s, 2928 s, 2857 s, 1699 s, 1660 s, 1597 s, 1580 s, 1507 w, 1467

m, 1447 m, 1406 s, 1339 s, 1254 m, 1176 m, 1131 w, 1112 w, 1017 w, 853 m, 810 s, 799 w, 748 m. - * H NMR (300 MHz, CDC1 ₃ ): δ = 0.78 (t, J = 6.7, 12 H, 4 CH ₃ ), 0.88 (t, J = 7 Hz, 6 H, 2

CH ₃ ), 1.17-1.35 (m, 40 H, 20 CH ₂ ), 1.66 (mc, 2 H, ^ CH), 1.85 (mc, 2 H, ß-CH ₂ ), 2.16-2.24

(m, 3 H, y # -CH ₂ + yÖ-CH), 4.22 (d, J = 7.3 Hz, 2 H, a-CH ₂ ), 5.16 (quint, J = 7.6, 1 H, a-CH) , 8.57 (d, J = 8.1 Hz, 2 H, perylene), 8.58 (d, J = 8.1 Hz, 2 H, perylene), 8.65 (d, J = 8.0 Hz, 4 H, perylene). - ¹³ C NMR (75 MHz, CDCI3): 5 = 14.44, 14.48, 14.63, 22.99, 23.54, 17.35, 29.62,

30.80, 31.19, 32.33, 32.78, 38.53, 39.78, 40.08, 55.18, 123.42, 123.79, 126.91, 129.75, 129.99, 131.79, 134.96, 164.10. - UV / Vis (CHCI3): ^^ (ε) = 433.0 nm (6430), 458.1 (19800), 488.9

(53300), 525.9 (88900). - Fluorescence (CHCI3):; i _max = 534 nm, 574, 621. -

Fluorescence quantum yield (CHCI3, reference N, N - (l-hexylheptyl) perylene-3,4: 9,10-

bis (dicaroximide) with Φ = 100%): 100%. Solid fluorescence:; i _max = 605 nm. - MS (70 eV):

m / z (%): 855 (7), 854 (20), 853 (31) [M ⁺ , 586 (5), 585 (7), 575 (12), 574 (40), 573 (77), 572 (19), 405 (14), 404 (29), 403 (14), 393 (10), 392 (41), 391 (95), 390 (100), 373 (16), 345 (8), 279 (10), 250 (9), 167 (13), 149 (26), 126 (19), 111 (14), 97 (16), 85 (23), 71 (37), 70 (12), 69

(23), 57 (40), 55 (35). - C ₅ 7H ₇₆ N ₂ θ4 (853.3): calc. C 80.24, H 8.98, N 3.28; gef. C 80.44, H

8.96, N3.40.

N- (2- (l-pentylhexyl) -3-pentyloctyl) -N '- (l-octylnonyl) perylene-3,4: 9,10-bis (dicarboximide) (9): N- (l-octylnonyl) -perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (4,300 mg, 0.48 mmol) and the crude l-amino-2- (l-pentylhexyl) -3- Pentyl octane (300 mg) was reacted and worked up analogously to 2c. First fraction: lane N- (2-bis (l-pentylhexyl) -3-pentyl-octyl) -N- (l-octymonyl) perylene-3,4: 9,10-bis (dicarboximide). - Rf (silica gel, chloroform): 0.98. - Rf

(Silica gel, toluene): 0.86. - UV / Vis (CHC1 ₃ ): na = 434.1 nm, 458.5, 489.1, 526.0. -

Fluorescence (CHCI3): na = 534 nm, 574, 621. - MS (70 eV): m / z (%): 1120.8 (1), 1119.8 (3)

[M ⁺ ], 1118.8 (3), 1117.8 (1), 1077.7 (1), 1077.6 (1), 1036.8 (1), 1035.7 (3), 1034.7 (3), 1022.7

(1), 1021.7 (3) [M ⁺ - C ₈ H ₁₆ ], 1020.7 (1), 1007.7 (1), 1006.6 (1), 963.6 (1) \ M ⁺ - C _π H ₂₄ ],

937.5 (1), 936.6 (1), 882.5 (1) M ⁺ - C17H34], 810.4 (1) [M ⁺ - 2 x CnH ₂₄ ], 783.4 (2), 699.4

(2), 685.3 (1), 667.6 (1), 654.4 (1) [M ⁺ - 3 x CιιH ₂₄ ], 639.6 (1), 628.6 (1) [M ⁺ -

CH ₂ -C (CnH ₂₄ ) ₃ ], 628.5 (1), 627.6 (2), 626.6 (5), 624.5 (2), 623.5 (2), 622.6 (1), 528.5 (9),

472.4 (20), 471.4 (11), 401.3 (13), 374.3 (14), 373.3 (9), 360.3 (17), 359.3 (10), 331.2 (9), 318.2 (17), 359.3 (9), 331.2 (9), 318.2 (17), 317.2 (14), 303.2 (12), 295.2 (18), 278.2 (37), 251.2 (8), 247.2 (19), 220.2 (13). 213.2 (10), 206.1 (12), 183.1 (10), 177.1 (11), 155.1 (9), 154.1 (27), 141.1 (16), 125.1 (11), 124.1 (28), 112.1 (10), 111.1 (18), 109.1 (10), 99.1 (11), 98.1 (13), 97.1 (35), 96.1 (21), 95.1 (19), 85.1 (34), 84.1 (18), 83.1 (37), 82.0 (18), 71.1 (51), 70.0 (35), 69.0 (64), 68.0 (13), 67.0 (28), 57.1 (100), 56.1 (47), 55.1 (93), 54.0 (13), 53.0 (10).

Second fraction: Yield 250 mg (54%) 9 as red, fluorescent needles, mp. 108 ° C. - Rf (Silica gel, chloroform): 0.70. - R _f (silica gel, toluene): 0.60. - IR (KBr): v = 3440 cm ^-1 m, 2958

s, 2926 s, 2855 s, 1698 s, 1658 s, 1595 s, 1579 s, 1508 w, 1467 m, 1446 m, 1405 s, 1339 s, 1253 m, 1174 m, 1130 w, 1112 w, 1016 w, 851 m, 810 s, 799 w, 747 m. - * H NMR (300 MHz,

CDC1 ₃ ): δ = 0.72 (t, J = 7.2 Hz, 6 H, 2 CH3), 0.80 (t, J = 6.9 Hz, 6 H, 2 CH3), 0.89 (t, J- 7.0

Hz, 6 H, 2 CH ₃ ), 1.17-1.48 (m, 60 H, 30 CH ₂ ), 1.64 (mc, 2H, 2 ^ CH), 1.90 (never, 2 H, ^ -CH ₂ ),

2.15-2.27 (m, 3 H,? -CH ₂ + ß-C), 4.22 (d, J = 7.3 Hz, 2 H, α-CH ₂ ), 5.15 (quint, J = 7.5 Hz,

1 H, aC), 8.59 (d, J = 8.3 Hz, 4 H, perylene), 8.66 (d, J = 8.2 Hz, 4 H, perylene). - ¹³ C NMR

(75 MHz, CDCI3): δ = 14.07, 14.18, 22.62, 22.77, 26.97, 27.80, 27.98, 29.24, 29.50, 29.55, 31.00, 31.83, 32.13, 32.38, 39.68, 54.77, 123.04, 123.31, 131.42, 134.54, 164.23 , - UV / Vis (CHCI3): max (ε) = 534.1 nm (5230), 458.9 (18700), 489.9 (52100), 526.0 (87700). -

Fluorescence (CHCI3): Ima = 534 nm, 574, 621. - Fluorescence quantum yield (CHCI3 reference

N; N- (l-hexylheptyl) perylene-3,4: 9,10-bis (dicarboximide) with Φ = 100%): 98%. - Solid-state fluorescence: _max = 610 nm. - MS (70 eV): m / z (%): 968 (7), 967 (25), 966 (69), 965

(100) [M ⁺ ], 869 (9), 868 (28), 867 (42), 727 (5), 642 (6), 641 (7), 631 (14), 630 (50), 629 ( 90)

628 (40), 405 (10), 404 (17), 403 (9), 392 (9), 391 (30), 390 (92), 373 (6), 281 (16), 126 (8), 97

(15), 83 (17), 72 (44), 69 (20), 59 (88), 57 (26). - C ₆ 5H ₉₂ N ₂ O ₄ (965.4): calcd. C 80.87, H 9.60,

N 2.90; found C 80.89, H 9.57, N 3.06. l-Cyano-l- (l-propylbutyl) -2-propylpentane: 1.6 M tert-butyllithium solution in pentane (40 ml, 0.064 mol) was evaporated to dryness under argon below 50 ° C. Anhydrous ether (13 ml, -78 ° C) and a solution of acetonitrile (700 mg, 17 mmol) in anhydrous ether (13 ml) were added. The mixture was warmed to -40 ° C (development of gaseous 2-methylpropane) and a solution of bromheptane (16 g, 89 mmol) in anhydrous tetrahydrofuran (18 ml) was added dropwise with stirring. The mixture was stirred at this temperature for 6 h, warmed to room temperature, mixed with water (17 ml), extracted with ether, dried (magnesium sulfate) and distilled in vacuo. Yield 4.15 g (20%) l-cyano-l- (l-propylbutyl) -2-propylpentane, bp 97 ° C / 2 mbar. - IR

(Film): v = 2978 s, 2935 s, 2868 s, 2222 w (CN), 1742 s, 1387 m, 737 w. - ¹ H NMR (300 MHz,

CDC1 ₃ ): δ = 0.83 (t, J = 6.9 Hz, 6 H, 2 CH ₃ ), 0.90 (t, J = 7.1 Hz, 6 H, 2 CH3), 1.2-1.4 (m, 18 H,

CH, CH ₂ ), 2.49 (t, J = 7.0 Hz, 1 H, HC-CN). - ¹³ C NMR (75 MHz, CDCI3): δ = 13.8, 14.9,

19.5, 35.5, 36.5, 43.5, 121.4. - MS (70 eV): m / z (%): 238 (5) [M ⁺ + 1], 194 (49) [M ⁺ - C3H7],

96 (100) M ⁺ - C3H7 - C7H14], 57 (17). l-Cyano-l- (l-butylpentyl) -2-propylpentane: sodium (1.5 g, 65 mmol) was dissolved in liquid ammonia (20 ml, -78 ° C) and with iron (UI) nitrae (200 mg, 0.83 mmol) was added. After stirring for 2 h, a solution of anhydrous acetonitrile (600 mg, 15 mmol) and 5-bromundecane (12 g, 58 mmol) in anhydrous ether (12 ml) was added dropwise with stirring. The ammonia was evaporated (3 h) anhydrous ether (20 ml) was added and then after 16 h stirring carefully anhydrous ethanol and 2N sulfuric acid (50 ml). The reaction product was obtained by extraction with ether, drying (magnesium sulfate) and vacuum fractionation over a Vigreux column (20 cm). Yield 200 mg (5%) 1-cyano-l- (l-butylpentyl) -2-propylpentane as a viscous oil, b.p. 113 ° C / 0.3 mbar. - IR (film / KBr): v = 2978 s, 2935 s, 2868 s, 2223 w (CN), 1387 m, 737 w. - * H NMR (300 MHz, CDCI3): δ =

0.905 (t, J = 7 Hz, 6 H, 2 CH ₃ ), 0.915 (t, J = 7 Hz, 6 H, 2 CH3), 1.42-1.08 (m, 24 H, 12 CH ₂ ),

1.61 (mc, 2 H, β-CH), 2.52 (t, J = 7 Hz, 1 H, HC-CN). - ¹³ C NMR (75 MHz, CDCI3): δ = 13.97 (CH ₃ ), 14.01 (CH ₃ ), 14.14 (CH ₃ ), 22.85 (CH ₂ ), 22.90 (CH ₂ ), 23.12 (CH ₂ ), 28.10 (CH ₂ ),

28.87 (CH ₂ ), 30.39 (CH ₂ ), 30.45 (CH ₂ ), 30.55 (CH ₂ ), 30.81 (CH ₂ ), 36.51 ((HQ ₂ CH-CN),

39.55 (HC-CN), 120.95 (CN). - MS (70 eV): m / z (%): 293 (2) [M ⁺ ], 264 (5) [M ⁺ - C ₂ H ₅ ], 250

(7) [M ⁺ - C3H7], 237 (17), 236 (89) [M ⁺ - C4H9], 194 (9), 166 (8) [M ⁺ - C9H19], 110 (100)

[M ⁺ + 1 - C4H9 - C9H ₁₉ ], 82 (8), 71 (13), 57 (12), 55 (12). - C ₂₀ H ₃₉ N (293.6): calc. C 81.84,

H 13.39, N 4.77; gef. C 81.91, H 13.52, N 4.63. l-Cyano-l- (l-pentylhexyl) -2-pentylheptane: acetonitrile (1.5 g, 37 mmol) and 6-bromundecane (35.0 g, 149 mmol) were prepared analogously to l-cyano-l- (l-butylpentyl) - 2-propylpentane implemented and worked up. Yield 1.8 g (25%) 1 -Cyano- l- (l-pentylhexyι) -2-pentylheptane as a viscous oil

Bp 148 ° C / 1.5 mbar. - IR (film / KBr): v = 2972 cm ^-1 s, 2924 s, 2853 s, 2223 w, 1465 s, 1379

m, 728 w. - ^ NMR (300 MHz, CDCI ₃ ): δ = 0.88 (t, J = 8 Hz, 6 H, CH ₃ ), 1.34-1.18 (m, 16 H,

CH ₂ ), 1.68 (quint, J = 4 Hz, 1 H, β-H), 2.32 (d, J = 8 Hz, 2 H, H ₂ C-CN). - ¹³ C NMR (75

MHz, CDCI3): δ = 14.09 (CH3), 22.68 (CH ₂ ), 27.81 (CH ₂ ), 30.64 (CH ₂ ), 32.34 (CH ₂ ), 35.11

0 # -CH), 39.57 (H ₂ C-CN), 118.92 (CN). l-Amino-3-propyl-2- (l-propylbutyl) hexane: Litumumaluininiumhydrid (410 mg, 11 mmol) was dissolved in anhydrous ether (30 ml) and with a solution of 1-cyano-1- (1-propylbutyl ) -2-propylpentane (1.66 g, 7.00 mmol) in anhydrous ether (12 ml) was added dropwise, the mixture was heated to boiling for 3 hours with stirring and reflux, cooled with ice, added dropwise with aqueous sodium hydroxide solution (2 ml, 20%), extracted with ether, dried (magnesium sulfate) and distilled in vacuo. Yield 1.8 g (56%) of l-amino-3-propyl-2- (l-ρropylbutyl) hexane, b.p. 102

° C / 2 mbar. - IR (film): v = 3380 cm ^"1 w (ΝH ₂ ), 2956 s (CH3), 2928 s (CH ₂ ), 2872 s (CH ₃ ), 2859 s (CH ₂ ), 1667 w (NH ₂ ), 1064 w (CN), 790 w (NH ₂ ), 730 w (ΝH ₂ ). - ¹ H NMR (300

MHz, CDC1 ₃ ): <? = 0.80 (t, J = 8.0 Hz, 6 H, 2 CH3), 0.83 (t, J8.0 Hz, 6 H, 2 CH ₃ ), 1.1-1.4 (m,

16 H, CH ₂ ), 1.4-1.5 (m, 3 H, CH), 2.60 (d, J = 6.9 Hz, α-CH ₂ ). - ¹³ C NMR (75 MHz, CDCI3):

δ = 14.9 (CH ₃ ), 19.9-37 (CH ₂ ), 38.0 (ß-CH), 40.8 (α-CH ₂ ). l-Amino-3-butyl-2- (l-butylpentyl) heptylamine: 1-cyano-l- (l-pentylhexyl) -2-pentylheptane (1.0 g, 3.4 mmol) and Lit un aluminum hydride (200 mg, 5.3 mmol ) were reacted and worked up analogously to l-amino-3-propyl-2- (l-propylbutyl) -hexane. Yield 830 mg (82%) of oily 1-amino-3-butyl-2- (l-butylpentyl) heptylamine, b.p. 150 ° C / (1 - 2) mbar. - IR (film / KBr): v =

3380 cm ^-1 w (NH ₂ ), 2956 s (CH ₃ ), 2928 s (CH ₂ ), 2872 s (CH ₃ ), 2859 (CH ₂ ), 1667 w (NH ₂ ),

1466 m (CH ₂ ), 1446 m (CH ₂ ), 1380 m (CH ₃ ), 1064 w (CN), 790 w (ΝH ₂ ), 730 w (ΝH ₂ ). - ^λ

NMR (300 MHz, CDCI ₃ ): δ = 0.89 (t, J = 8 Hz, 6 H, 2 CH ₃ ), 0.90 (t, J = 8 Hz, 6H, 2 CH3), 1.1-

1.4 (m, 24 H, 12 CH ₂ ), 1.42-1.5 (m, 3 H, 3 CH), 2.66 (d, J = 4 Hz, 2 H, a-CH ₂ ). - ¹³ C NMR

(75 MHz, CDCI3): δ = 14.10 (CH ₃ ), 14.12 (CH ₃ ), 22.68 (CH ₂ ), 22.84 (CH ₂ ), 23.12 (CH ₂ ),

23.15 (CH ₂ ), 28.05 (CH ₂ ), 29.80 (CH ₂ ), 29.99 (CH ₂ ), 30.20 (CH ₂ ), 30.38 (CH ₂ ), 30.45 (CH ₂ ),

30.51 (CH2), 30.78 (CH ₂ ), 31.73 (CH ₂ ), 34.80 (α-CH ₂ ), 36.50 (f-CH), 36.67 (r-CH), 38.04

(.Beta.-CH). - MS (70 eV): m / z (%): 297 (5) \ M ⁺ ], 280 (39) M ⁺ - NH3], 236 (100) [M ⁺ - 1 - NH ₃

- C ₃ H ₇ ], 223 (22) [M ⁺ - NH3 - C4H9], 209 (64) [M ⁺ - NH3 - C5H11], 170 (23) [M ⁺ -

C9H19], 168 (22), 154 (24) M ⁺ -NH3 + 1 - C9H19], 153 (20) M ⁺ -NH3 - C9H19], 141 (31),

140 (62) [M ⁺ - C9H1 ₉ -H ₂ C = NH ₂ ], 126 (17), 112 (31), 111 (23), 110 (95) [M ⁺ -NH ₃ - C ₃ H7 - C9H19], 98 (35), 97 (37) [M ⁺ - NH3 - C9H19 - C4H9], 85 (35), 83 (39) M ⁺ - C9H19 -

H ₂ C = NH ₂ - C4H9], 71 (54), 70 (35), 69 (38), 57 (58), 56 (26), 55 (54). l-Amino-2- (l-pentylhexyl) -3-pentyl-octane: 1-cyano-l- (l-penty] hexyl) -2-pentylheptane (1.0 g) analogous to to l-cyano-l- (l -propylbutyl) -2-propylpentane and mixed with 1-cyano-l, l-bis- (l-pentylhexyl) -2-pentylheptane was analogous to l-amino-3-propyl-2- (l-propylbutyl) hexane reacted with LitMiunaluminiumhydride (410 mg, 11 mmol). Yield 760 mg of a viscous, oily mixture of l-arnino-3-pentyl-2- (l-pentylhexyl) octane and minor proportions of l-amino-2,2-b / ^ - (l-pentylhexyl) -3-pentyl octane. The mixture was used for further syntheses without further purification.

1. T. Förster, Natural Sciences. 1946, 166-175.

2. T. Förster, Fluorescence of Organic Compounds, Vandenhoec & Ruprecht, Göttingen 1951 and references cited therein.

3. H. Langhals, Heterocycles 1995, 40, MI-500.

4. H. Langhals, J. Karolin, L. B.-Ä. Johansson, J. Chem. Soc, Faraday Trans. 1998, 94, 2919-2922.

5 H. Langhals, S. Demmig, H. Huber, Spectrochim. Acta 1988, 44A, 1189-1193.

6. L. Feiler, H. Langhals, K. Polborn, Liebigs Ann. Chem. 1995, 1229-1244.

7. H. Kaiser, J. Lindner, H. Langhals, Chem. Ber. 1991, 124, 529-535.

8. H. Langhals, S. Demmig, T. Potrawa, J. Prakt. Chem. 1991, 333, 733-748.

9. H. Langhals, J. Karolin, L. B.-Ä. Johansson, J. Chem. Soc, Faraday Trans. 1998, 94, 2919-2922.

10. H. Langhals, W. Jona, F r. J. Org. Chem. 1998, 847-851.

11. F. Ullmann, A. Münzhuber, Ber. German chem. Ges. 1903, 36, 404-410. LIST OF REFERENCE NUMBERS

Fig. 1: Structural formula of dye 2a.

Fig. 2: Synthesis of fluorescent dyes with sterically shielding substituents.

Fig. 3: Structures of perylene dyes with shielding, aliphatic groups.

Fig. 4: Unsymmetrically substituted perylene dyes with sterically shielding groups.

Fig. 5: UV / Vis absorption and quantum corrected fluorescence spectra of

Perylenetetracarboxylic acid bisimides. From left to right: absorption and fluorescence spectra of 2d in chloroform and solid fluorescence spectra of 2d, 2e and 2f.

Claims

claims

1. A method for preventing aggregation of fluorescent dyes, characterized in that bulky groups are attached to the periphery of the dyes, which prevent the chromophores from accumulating and the resulting fluorescence quenching.

2. A method for preventing aggregation and preventing fluorescence quenching in fluorescent dyes by incorporating bulky aromatic groups according to 1.

3. A method for preventing aggregation and preventing fluorescence quenching in fluorescent dyes by incorporating voluminous heteroaromatic groups according to 1.

4. A method for preventing aggregation and preventing fluorescence quenching in fluorescent dyes by incorporating voluminous aliphatic groups according to 1.

5. The use of the substituted phenyl radical of the general formula I as a completely aromatic group corresponding to 2,

I in which R ¹ to R ^{5 can be the} same or different. R ¹ to R ⁵ represent hydrogen or one to five, preferably one to three, radicals, such as, for example, isocyanic aromatic radicals. R ¹ to R ⁵ then preferably each denotes a mono- to tetracyclic, in particular mono- or bicyclic radical, such as phenyl, diphenyl naphthyl or anthryl. R ¹ to R ^{5 are} heterocyclic aromatic radicals, then preferably mono- to tricyclic radicals. These radicals can be purely heterocyclic or contain a heterocyclic ring and one or more fused-on benzene rings. Examples of heterocyclic aromatic radicals are pyridyl, pyrimidyl, triazinyl, furanyl, pyrrolyL thiophenyl, quinolyl, benzimidazolyl, benzoxazolyl, dibenzfuranyl, benzothiophenyl, dibenzo hiophenyl, oxolyl Thiazolyl, indazolyl, benzthiazolyl, Pyridazinyl, cinnolyl, quinazolinyl, quinoxalyl, phthalazinyl, PhthalazindionyL phthalimidyl chromonyl, Naphtholactamyl, Benzopyridonyl, ortho-Sulfobenzimidyl, maleimidyl, Naphtharidinyl, benzimidazolonyl, benzoxazolonyl, Benzthiazolonyl, Benzthiazolinyl, quinazolonyl, pyrimidyl, Chinoxalonyl, Phthalazonyl, Dioxapyrinidinyl, pyridonyl, IsochinolonyL isothiazolyl, benzisoxazolyl , Benzisothiazolyl, Indazolonyl, Acridinyl, Acridonyl, Quinazolindionyl, Benzoxazindionyl, Benzoxazinonyl and PhthalimidyL Both the isocyclic and the heterocyclic aromatic radicals can have the following customary non-water-soluble substituents, which can also mean R ¹ to R ⁵ , such as a) a halogen atom, for example chlorine, bromine, iodine or fluorine. b) Branched or unbranched alkyl groups or cycloalky groups with preferably 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4 carbon atoms. These alkyl groups can have non-water-solubilizing substituents, such as fluorine, hydroxy, cyano, -OCOR ⁶ , -OR ⁷ , -OCOOR ⁷ , - CON (R ⁹ ) (R ¹⁰ ) or -OCONHR ¹¹ , where R ⁶ to R ¹¹ alkyl, aryl such as naphthyl, or unsubstituted or substituted by halogen, alkyl, or -O-alkyl, benzyl or a heterocyclic radical, hydrogen, unsubstituted or substituted by cyano or hydroxyalkyl, C3- to C24-cycloalkyl, preferably C5-, C -, Cχ2- _> C15-, C \ -, C20- and C24-cycloalkyl, aryl or heteroaryl, in particular unsubstituted or by

Halogen, alkyl or -O-alkyl are substituted phenyl, or in which R ⁶ to R ¹¹ together with one of the other radicals R ⁷ to R ¹² each form a 5-6-membered ring or hetero ring, such as, for example, a pyridine or pyrrole ring. , Furan or pyran ring. Further possible substituents on the alkyl groups are mono- or dialkylated amino groups, aryl radicals, such as naphthyl or, in particular, phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, or furthermore heterocyclic aromatic radicals, such as, for example, the 2-thienyl, 2- Benzoxazolyl-, 2-benzothiazolyl-, 2-benzimidazolyl-, 6-benzimidazolonyl-, 2-, 3- or 4-pyridinyl-, 2-, 4-, or 6-quinolyl- or 1-, 3-, 4-, 6-, or 8-isoquinolyl residues. If the substituents mentioned under b) in turn contain alkyl, this alkyl can be branched, unbranched or cyclic and preferably contain 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4, carbon atoms.

Examples of unsubstituted alkyl groups are methyl, ethyl, w-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, tert-amyl, w-hexyl 1,1,3,3, tetramethyl butyl, «-heptyl L n- Octyl, n-NonyL R-decyl, «-undecyl, w-dodecyl, w-octadecyl, 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1- nonyldecyl, 1 -Decylundecyl 1-ethylbutyl 1-ethylpentyl, 1-ethylheptyl, 1-Ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl with C ₃ to C ₂₀ , c) The group -OR ¹² , where R ^{12 is} hydrogen, alkyl, aryl, for example naphthyl or in particular unsubstituted phenyl, C3 to C24-cycloalkyl, preferably C5-, C-, Cγ, ^ 15 "'^ 16"' C20 " ₃ and C24-cycloalkyl, aryl or heteroaryl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl. Alkyl which occurs in the definitions of R ¹³ can have, for example, one of the number of C atoms indicated as preferred under b). Examples of R ¹³ are: methyl, ethyl, "-propyl, isopropyl," -butyl, sec-butyl, tert-butyl, tert-amyl, n-hexyl, 1,1,3,3, - tetramethylbutyl, " -Heptyl, 77-OctyL R-Nonyl, n-Decyl, w-Undecyl, «-DodecyL w-Octa-decyl, 1-Etylpropyl, 1-Propylbutyl, 1-ButylpentyL 1-Pentylhexyl, 1-Hexylheptyl, 1-Heptyl- octyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethyl-heptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetyl l, benzyl, phenyl, o-, m- or JP-chlorophenyl, o-, m-, or 7-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl , e) The cyano group. f) The group of the formula -N (R ¹³ ) (R ¹⁴ ), in which R ¹³ and R ^{14 have} the meaning given under b). Examples include: amino, methylamino, dimethylamino, ethylamino, diethylamino, "-propylamino, di -" - propylamino, isopropylamino, "-butylamino, di -" - butylamino, aec-butylamino, di-aec-butylamino, tert -Butylamino, tert-amylamino, "-hexylamino, di -" - hexylamino, 1,1,3,3, -tetramethylbutylamino, w-heptylamino, di - "- heptylamino," -octylamino, di - "- octylamino, "-Nonyl, Di -" - nonylamino, w-decylamino, Di-K-decylamino, "-undecylamino, Di-π-undecylamino, w-dodecylamino, Di-" dodecyla ino, 77-octadecylamino, l-elylpropylamino, 1-propylbutylamino, 1-butylpentylamino, 1-pentylhexylamino, 1-hexylheptylamino, 1-heptyloctylamino, 1-octyl nonylamino, 1-nonyldecylamino, 1-decylundecylamino, 1-ethylbutylamino, 1-ethylamino, 1-ethylamino, 1-ethylamino 1-ethylnonylamino, hydroxymethylamino, dihydroxymethylamino, 2-hydroxyethylN, N-bis (2-hydroxyethyl) amino, trifluoromethylamino, Trifluoroethylamino, cyanomethylamino, methoxycarbonylmethylamino, acetoxymetbylamino, benzylamino, dibenzylamino, phenylamino, diphenyla ino, o-, m- or p-chlorophenylamino, o-, m-, or /? - methylphenylamino, 1- or 2-naphthylamino , Cyclohexylamino, Cyclododecylamino, Cyclopentadecylamino, Cyclohexadecylamino, Cycloeicosanylamino, Cyclotetracosanylamino, Ttaenylamino or Pyranylmethylamino, Piperidyl or Morpholyl. g) The group of the formula -COR ¹⁵ , in which R ^{15 has} the meaning given under a). Examples of R ¹⁵ include: methyl, ethyl, "-propyl, isopropyl," -butyl, sec-butyl, tert-butyl, tert-amyl, "-hexyl, 1,1,3,3, -tetramethylbutyl," Heptyl, octyl, nonyl, n-decyl, undecyl, n-dodecyl, n-octadecyl, 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, acetoxymethyl, o-, m- or -Chlorphenyl, o-, m-, or j? -methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl, benzyl or furfuryl. h) The group of the formula-N (R ¹⁶ ) COR ¹⁷ , in which R ^{16 has} the meaning given under b), R ^{17 is} hydrogen, alkyl, for example methyl, ethyl, rc-propyl, isopropyl, κ-butyl, sec-butyi , tert-butyl, tert-amyl, w-hexyl, 1,1,3,3, -tetramethylbutyl, "-heptyl, n-octyl, n-nonyl," -decyl, "-undecy" -dodecyl, "-octadecyl , 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl, 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl, 1-ethylbutyl, 1-ethylpentyL 1-ethylheptyl, 1- Ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, benzyl, phenyl, o-, m- or p-chlorophenyl, o-, -, or j> -methylphenyl, 1- or 2-naphthyl, cyclopentyl , Cyclohexyl, Cyclododecyl, Cyclopentadecyl, CyclohexadecyL Cycloeicosanyl, Cyclotetracosanyl, Thienyl or Pyranylmethyl or Furfuryl. Alkyl occurring in the definitions of R ¹⁶ can have, for example, one of the number of C atoms preferably given under b). Examples include: acetylamino, propionylamino, butyrylarnino, benzoylamino, chlorobenzoylamino, /? - methylbenzoylamino, N-methylacetamino, N-methylbenzoylamino, N-succinimido, N-phthalimido or N- (4-Arnmo) phthalimido. i) The group of the formula -N (R ¹⁸ ) COOR ¹⁹ , wherein R ¹⁸ and R ^{19 have} the meaning given under b) and c). Examples are the groups -NHCOOCH3, - NHCOOC ₂ H ₅ , or -NHCOOC ₆ H ₅ called. j) The group of the formula -N (R ²⁰ ) CON (R ²¹ ) (R ²² ), in which R ²⁰ , R ²¹ and R ^{22 have} the meaning given under b) or c). Examples include: ureido, N-methylureido, Ν-phenylureido, or N, N'-2 ', 4'-dimethylphenylureido. k) The group of the formula -NHSO2R ²³ , in which R ^{23 has} the meaning given under b). Examples include: methylsulfonylamino, phenylsuffonylamino, p-tolylsuffonylamino or 2-naphthyls tonylamino.

1) The groups of the formula -SO2R ²⁴ or -SOR ²⁵ , in which R ²⁴ or R ^{25 have} the meaning given under b). Examples include: MethylsulfonyL EthylsulfonyL

PhenylsulfonyL 2-naphthylsulfonyl, phenylsulfoxidyl. m) The group of the formula -SO2OR ²⁶ , in which R ^{26 has} the meaning given under b).

The following may be mentioned as examples of R ²⁷ : methyl, ethyl, phenyl, o-, m- or chlorophenyl, o-, m- or methylphenyl, 1- or 2-naphthyl. n) The group of the formula -CON (R) (R), in which R and R are those given under b)

Have meaning. Examples include: carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-phenylcarbamoyl, 7Y, 7V-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl,

N-1-naphthylcarbamoyl or N-piperdylcarbamoyl. o) The group of the formula -Sθ2N (R) (R), where R and R are those given under b)

Have meaning. Examples include: sulfamoyl, N-methylsuliamoyl, N-ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsulfamoyl or 7V-morpholylsulfamoyl. p) The group of the formula -N = NR ³¹ , in which R ^{31 is} the residue of a coupling component or a phenyl radical which may be substituted by halogen, alkyl or -O-alkyl. Alkyl occurring in the definitions of R ³¹ can have, for example, one of the number of C atoms given as preferred under b). The following may be mentioned as examples of R ³¹ : the acetoacetarylide, pyrazolyl, pyridonyl, o-, »-hydroxyphenyl, tf-hydroxynaphfhyl,> - aminophenyl or j9-N, N-dimethylaminophenyl radicals. q) The group of the formula -OCOR ³² wherein R ^{32 has} the meaning given under b). Examples of R ³² are: methyl, ethyl, phenyl, o-, m- or chlorophenyl. r) The group of the formula -OCONHR ³³ , in which R ^{33 has} the meaning given under a). Examples of R ³³ include: methyl, ethyl, phenyl, o-, m- or j? -Chlorophenyl. R ¹ to R ⁵ can be hydrogen and one to four of the following radicals a) halogen atoms, for example chlorine, bromine, iodine or fluorine. b) branched or unbranched alkyl groups having preferably 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4, carbon atoms. These alkyl groups can have non-water-solubilizing substituents, such as fluorine, hydroxy, cyano, -OCOR ³⁴ , -OR ³⁵ , -OCOOR ³⁶ , -CON (R ³⁷ ) (R ³⁸ ) or -OCONHR ³⁹ , where R ^{34 is} alkyl, Aryl such as naphthyl, or unsubstituted or substituted by halogen, alkyl, or -O-alkyl or a heterocyclic radical, R ³⁵ , R ³⁶ and R ^{39 are} hydrogen, unsubstituted or substituted by cyano or hydroxy, C3- bis

C24- cycloalkyl, preferably C5-, Cg-, Cχ2 ^_ ₅ 15-, Cjg-, C20- and C24-cycloalkyl, aryl or heteroaryl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, or in which R. ³⁷ and R ³⁸ together with one of the other radicals R ³⁴ to R ³⁹ each form a 5-6-membered ring or hetero ring, such as a pyridine, pyrrole, furan or pyran ring. Further possible substituents on the alkyl groups are mono- or dialkylated amino groups, aryl radicals, such as naphthyl or, in particular, phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, or furthermore heterocyclic aromatic radicals, such as, for example, the 2-thienyl, 2-benzoxazolyl , 2-benzothiazolyl-, 2-benzimidazolyl-, 6-benzimidazolonyl-, 2-, 3- or 4-pyridinyl-, 2-, 4-, or 6-quinoly- or 1-, 3-, 4-, 6- , or 8-isoquinolyl residues. If the substituents mentioned under b) in turn contain alkyl, this alkyl can be branched or unbranched and preferably contain 1 to 21, in particular 1 to 12, especially 1 to 8 and particularly preferably 1 to 4 carbon atoms. Examples of unsubstituted alkyl groups are methyl, ethyl, "-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, tert-amyl, w-hexyl, 1,1,3,3, -tetramethylbutyl," -heptyl, n-octyl, n-nonyl, "-decyl," -undecyl, "-dodecyl, K-octadecyl, 1-ethylpropyl, 1-propylbutyl, 1-butylpentyL 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl , 1-Nonyldecyl, 1 -decylundecyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl C ₃ to C ₂₀ . c) The group -OR ⁴⁰ , in which R ^{40 is} hydrogen, alkyl, aryl, for example naphthyl or in particular unsubstituted phenyl, C3 to C24-cycloalkyl, preferably C5-, Cg-, Cχ2 _?

^ 15 "» ^ 16 "'C2O" »and C24-CycloalkyL aryl or heteroaryl, in particular unsubstituted or substituted by halogen, alkyl or -O-alkyl. In the definitions of R ⁴⁰ alkyl, for example, one of the under b) as preferred have the specified number of carbon atoms. Examples of R ⁴⁰ include: methyl, ethyl, "-propyl, isopropyl," -butyl sec-butyl, tert-butyl, tert-amyl n-hexyl, 1,1,3,3, - tetramethylbutyl, "-heptyl , «-Octyl,« -Nonyl, n-decyl, w-undecyl, n-dodecyl, n-octadecyl, 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl, 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1 -Octylnonyl, 1-nonyldecyL 1 -decylundecyl 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoromethyl, cyanomethyl, methoxycarbonylmethyl or benzyl or cycloalkyl with C ₃ to C ₂₀ , phenyl, o-, m- or? -chlorophenyl, o-, m-, orjσ-methylphenyl, 1- or 2-naphthyL cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL cycloeicosanyl, cyclotetracosanyL thienyl or pyranylmethyl. e) The Cyanograppe. f) The group of the formula -N (R ⁴¹ ) (R ⁴² ), in which R ⁴¹ and R ^{42 have} the meaning given under b). Examples include: amino, methylamino, dimethylamino, ethylamino, diethylamino, propylamino, di-w-propylamino, isopropylamino, n-butylamino, di-K-butylarnino, sec-butylamino, di-sec-butylamino, tert -Butylamino, tert- amylamino, «-hexylamino, di -« - hexylamino, 1,1,3,3, -Tetramethylbutylamino, n- heptylarnino, di - «- heptylamino, n-octylamino, di-R-octylamino, w- Nonyl, di - "- nonylamino," -decylamino, di-w-decylamino, n-undecylamino, di- / ϊ-undecylamino, n-dodecylamino, di- "dodecylamino, n-octadecylamino, 1-ethylpropylamino, 1-propylbutyl- amino, 1-butylpentylamino, 1-pentylhexylamino, 1-hexymeptylamino, 1-heptyloctylamino, 1-octymonylamino, 1-nonyldecylamino, 1-decylundecylamino, 1-ethylbutylamino, 1-ethylpentylamino, 1-ethylheptylam Hydroxymethylamino, dihydroxymethylamino, 2-hydroxyethyl, N, N-bis (2-hydroxyethyl) amino, trffluoromethylamino, trifluoroethylamino, cyanomethylamino, methoxycarbonylmethylamino, acetoxvmethylamino, benzylamino, di benzylamino, phenylamino, diphenylamino, o-, m- or j3-chlorophenylamino, o-, m-, or j? -methylphenylamino, 1- or 2-naphthylamino, cyclopentylamino, cyclohexylamino, cyclododecylamino, cyclopentadecylylino, cyclohexadecotanyamino, cyclohexadecotanyamino, , T enylamino or pyranylmethylamino, piperidyl or morpholyl g) The group of the formula -COR ⁴³ , wherein R ^{43 has} the meaning given under a). Examples of R ⁴³ are: methyl, ethyl, propyl, isopropyl, H-butyl, sec-butyl, tert-butyl, tert-amyl, n-ex l, 1,1,3,3, tetramethylbutyl, w-heptyl, n-octyl, "-NonyL n-decyl," -undecyl, w-dodecyl, ra-octadecyl, 1-ethylpropyl, 1-propylbutyl, 1-butylpentyL 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1-ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2 , 2,2-trifluorefhyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl with C ₃ to C ₂₀ , phenyl, o-, m- or p-chlorophenyl, o-, m- or j? -Methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyL cyclohexadecyL cycloeicosanyL cyclotetracosanyl, thienyl, pyranylmethyl, benzyl or furfuryl. h) The group of the formula-N (R ⁴⁴ ) COR ⁴⁵ , in which R ^{44 has} the meaning given under b), R ^{44 is} hydrogen, alkyl, for example methyl, ethyl, w-propyl, isopropyl, w-butyl, scc-butyl , tert-butyl, tert-AmyL n-hexyl, 1,1,3,3, -tetramethylbutyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-octadecyl , 1-ethylpropyl, 1-propylbutyl, 1-butylpentyl, 1-pentylhexyl, 1-hexylheptyl, 1-heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1-decylundecyl 1-ethylbutyl, 1-ethylpentyl, 1-ethylheptyl, 1- Ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl with C ₃ to C ₂₀ , phenyl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl , for example o-, m- or 7-chlorophenyl, o-, m- or /? - methylphenyL 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyL cycloeicosanyl, cyclotetracosanyl, thienyl, pyranylmethyl, B enzyl or furfuryl. Alkyl occurring in the definitions of R ⁴⁵ can have, for example, one of the number of C atoms preferably given under b). Examples include: acetylamino, propionylamino, butyrylamino, benzoyl-arino, p-chlorobenzoylamino, p-methylbenzoylamino, N-methylacetamino, N-methyl-benzoylamino, N-succinimido, N-phthalimido or N- (4-aιnino) phthalirnido. i) The Grappe of the formula -N (R ⁴⁶ ) COOR ⁴⁷ , wherein R ⁴⁶ and R ^{47 have} the meaning given under b) and c). Examples are the groups -NHCOOCH3, -

NHCOOC ₂ H ₅ , or -NHCOOC ₆ H ₅ called. j) The group of the formula -N (R ⁴⁸ ) CON (R ⁴⁹ ) (R ⁵⁰ ), in which R ⁴⁸ , R ⁴⁹ and R ^{50 have} the meaning given under b) or c). Examples include: ureido, N-methylureido, N-phenylureido, or NN'-T ^ '- dimethylphenylureido. k) The group of the formula -NHSO2R ⁵¹ , in which R ^{51 has} the meaning given under b). Examples include: methylsulfonylamino, phenylsulfonylamino, p-tolylsulfonylamino or 2-naphthylsulfonylamino 1) The Grappen of the formula -SO2R ⁵² or -SOR ⁵³ , wherein R ⁵² or R ^{53 have} the meaning given under b). Examples include: MethylsulfonyL EthylsulfonyL

Phenylsulfonyl, 2-naphthylsulfonyl, phenylsulfoxidyl. m) The group of the formula -SO2OR ⁵⁴ , in which R ^{54 has} the meaning given under b).

The following may be mentioned as examples of R ⁵⁴ : methyl, ethyl, phenyl, o-, m-, or »-chlorophenyl, o-, m- or? -Methylphenyl, 1- or 2-naphthyl. n) The group of the formula -CON (R ⁵⁵ ) (R ⁵⁶ ), wherein R ⁵⁵ and R ^{56 are} those given under b)

Have meaning. Examples include: carbamoyl, N-methylcarbamoyl, N-

Ethylcarbamoyl, N-phenylcarbamoyl, N, N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-1-naphthylcarbamoyl or N-piperdylcarbamoyl. o) The group of the formula -Sθ2N (R ⁵⁷ ) (R ⁵⁸ ), wherein R ⁵⁷ and R ^{58 are} those given under b)

Have meaning. Examples include: sulfamoyl, N-methylsulfamoyl, Ν-ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsulfamoyl or N-morpholylsulfamoyl. p) The group of the formula -N = NR ⁵⁹ , in which R ^{59 is} the radical of a coupling component or a phenyl radical which may be substituted by halogen, alkyl or -O-alkyl. Alkyl occurring in the definitions of R ⁵⁹ can have, for example, one of the number of C atoms given as preferred under b). The following may be mentioned as examples of R ⁵⁹ : the acetoacetarylide, pyrazolyl, pyridonyl, o-,? -Hydroxyphenyl, o-hydroxynaphthyl -, ^ - aminophenyl or /> - N ^ -dimethylaminophenyl residues. q) The group of the formula -OCOR ⁶⁰ , in which R ^{60 has} the meaning given under b). Examples of R ⁶⁰ are: methyl, ethyl, phenyl, o-, m- or chlorophenyl. r) The group of the formula -OCONHR ⁶¹ , wherein R ^{61 has} the meaning given under a). Examples of R ⁶¹ include: methyl, ethyl phenyl, o-, m- or? -Chlorophenyl.

6. Use of polycychic aromatics as voluminous aromatic groups according to 2. The polycyclic aromatics should in turn be provided with at least one but at most five identical or different substituents R ¹ to R ⁵ , which have the meaning given under 5. Examples are the 1-naphthyl radical substituted in positions 2, 3, 4, 5, 6 and 7, 2-naphthyl radical substituted in positions 3, 4, 5, 6, 7 and 8, the 1-anthryl radical substituted in positions 2, 3, 4, 5,6,7,8 and 9,, the 2-anthryl radical is substituted in positions 1, 3, 4, 5, 6, 7, 8, 9 and 10.

7. The use of heteroaromatic residues as voluminous aromatic groups according to 3. The heterocaromatics should in turn have at least one but no more than five of the same or various substituents R ¹ to R ⁵ which have the meaning given under 5. Examples are the 2-pyridyl radical, 3-pyridyl radical, 4-pyridyl radical, 2-thiophenyl radical, 3-tiophenyl radical, 1-PyrrolyL 2-pyrrolyl, 3-pyrrolyl, 2-FuroyL 3-furoyl , 2-quinolyl, 3-quinolyl, 1-isoindolyl radical. An example of such a radical is the (3,4,5,6-tetraphenylphthalimidyl) radical. 8. Use of voluminous aliphatic radicals according to 4 with the general formula II,

π in which R ¹ to R ^{3 are} hydrogen or one to 3 of the radicals mentioned under 5. 9. Use of voluminous aphatic residues according to 4 with the general formula ITI,

πi in which R ¹ to R ^{3 are} hydrogen or one to 3 of the radicals mentioned under 5. 10. Use of the tetraphenylphthalimidyl radical of the general formula IV,

IV in the R ι lx bi: s R is hydrogen or one to 4 of the radicals mentioned under 5.

1. perylene dyes of the general formula V,

V in which x and y can be the same or different and the residues mentioned under 5 to 10 are anti-aggregation radicals or in which x is one of the anti-aggregation radicals mentioned under 5 to 10 and y is a solubility-increasing group, e.g. 1- ethyl propyl, 1-propyl butyl, 1-butyl pentyl 1-pentyl hexyl, 1-hexyl heptyl, 1-heptyl octyl, 1-octyl nonyl, 1-nonyl decyl, 1-decyl undecyl or 2,5-di-tert-butylphenyl, 2,4-di tert-butylphenyl, 2,6-di-isopropylphenyl or 2,4,6-triisopropylphenyl. Preferred examples are x = y = /? - triphenylmethyl, bis (2- (l-propylbutyl) -3-propyl-hexyl), N, N'-bis (-2- (l-butylpentyl) -3-butylheptyl) and Bis (2- (l-pentylhexyl) -3-pentyloctyl) or x = /? - triphenylmethyl, bis (2- (l-propylbutyl) -3-propyl-hexyl), N, iV-bis (-2- (l-butylpentyl) -3-butylheptyι) or bis (2- (l-pentylhexyl) -3-pentyl-octyl) - and y = 1 -ethylpropyL 1-propylbutyl, 1-butylpentyL 1-pentylhexyl, 1-hexylheptyl, 1 -Heptyloctyl, 1-octylnonyl, 1-nonyldecyl, 1 -decylundecyl or 2,5-di-tert-butylphenyl, 2,4-di-tert-butylphenyl, 2,6-di-isopropylphenyl or 2,4,6-triisopropylphenyl , 12. Perylene-3,4-dicarboximides of the general formula VI

VI in which x is one of the aggregation-preventing residues mentioned under 5 to 10.

13. Use of the substances according to 11 and 12 as dyes.

14. Usage of the substances according to 11 and 12 as fluorescent dyes.

15. Application of the dyes of 11 and 12 for bulk dyeing of polymers. Examples are materials made from polyvinyl chloride, cellulose acetate, polycarbonates, polyamides, polyurethanes, polyimides, polybenzimidazoles, melamine resins, silicones, Polyesters, polyethers, polystyrene, polymethyl methacrylate, polyethylene, polypropylene, polyvinyl acetate, polyacrylonitrile, polybutadiene, polychlorobutadiene or polyisoprene or the copolymers of the monomers mentioned.

16. Use of the dyes of 11 and 12 as vat dyes, e.g. for coloring natural products. Examples are paper, wood, straw, leather, furs or natural fiber materials such as cotton, wool, silk, jute, sisal, hemp, flax or animal hair (e.g. horsehair) and their conversion products such as e.g. the viscose fiber, nitrate silk or copper rayon (rayon).

17. Use of the dyes of 11 and 12 as mordant dyes, e.g. for coloring natural products. Examples are paper, wood, straw, leather, furs or natural fiber materials such as cotton, wool, silk, jute, sisal, hemp, flax or animal hair (e.g. horsehair) and their conversion products such as e.g. the viscose fiber, nitrate silk or copper rayon (rayon). Preferred salts for pickling are aluminum, chromium and iron salts.

18. Use of the dyes of 11 and 12 as colorants, e.g. for coloring paints, varnishes and other paints, paper paints, printing inks, inks and other colors for painting and writing purposes.

19. Use of the dyes of 11 and 12 as pigment dyes, e.g. for coloring paints, varnishes and other paints, paper paints, printing inks, inks and other colors for painting and writing purposes.

20. Application of the dyes of 11 and 12 as pigments in electrophotography: e.g. for dry copy systems (Xerox process) and laser printer ("non-impact printing").

21. Use of the dyes of 11 and 12 for security marking purposes, the great chemical and photochemical resistance and possibly also the fluorescence of the substances being important. This is preferred for checks, check cards, bank notes, coupons, documents, identity papers and the like, in which a special, unmistakable color impression is to be achieved.

22. Application of the dyes of 11 and 12 can be used as an additive to other colors in which a certain color shade is to be achieved, particularly bright colors are preferred.

23. application of the dyes of 11 and 12 to marking objects are used for machine detection of these objects via fluorescence, The mechanical detection of objects for sorting, for example also for recycling plastics, is preferred.

24. Use of the dyes of 11 and 12 can be used as fluorescent dyes for machine-readable markings, preferably alphanumeric prints or barcodes.

25. Application of the dyes of 11 and 12 can be used for frequency conversion of light, e.g. to make longer-wave, visible light from short-wave light.

26. Use of the dyes of 11 and 12 in display elements for a variety of display, information and marking purposes, e.g. passive display elements, signs and traffic signs, such as traffic lights.

27. Application of the dyes of 11 and 12 in inkjet printers, preferably in a homogeneous solution as fluorescent ink.

28. Application of the dyes of 11 and 12 as a starting material for superconducting organic materials.

29. Use of the dyes of 11 and 12 for solid fluorescent labels.

30. Application of dyes from 11 and 12 for decorative purposes.

31. Application of dyes from 11 and 12 for artistic purposes.

32. Use of dyes from 11 and 12 for tracer purposes, e.g. in biochemistry, medicine, technology and science. The dyes can be covalently linked to substrates or via secondary valences such as hydrogen bonds or hydrophobic interactions (adsorption).

33. Application of the dyes of 11 and 12 as fluorescent dyes in highly sensitive detection methods (see C. Aubert, J. Fünfschüling, I. Zschokke-Gränacher and H. Langhals, Z.Analyt.Chem. 1985, 320, 361).

34. Application of the dyes of 11 and 12 as fluorescent dyes in scintillators.

35. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in optical light collection systems.

36. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in fluorescent solar collectors (see H. Langhals, Nachr. Chem. Tech. Lab. 1980, 28, 716).

37. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in fluorescence-activated displays (see W. Greubel and G. Baur, Elektronik 1977, 26,

6).

38. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in cold light sources for highly-induced polymerization to produce plastics.

39. Use of the dyes of 11 and 12 as dyes or fluorescent dyes for material testing, e.g. in the manufacture of semiconductor circuits.

40. Application of the dyes of 11 and 12 as dyes or fluorescent dyes for the investigation of microstructures of integrated semiconductor components.

41. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in photoconductors.

42. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in photographic processes.

43. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in display, lighting or image converter systems in which the excitation is carried out by electrons, ions or UV radiation, e.g. in fluorescent displays, Braun tubes or in fluorescent tubes.

44. Application of the dyes of 11 and 12 as dyes or fluorescent dyes as part of an integrated semiconductor circuit, the dyes as such or in connection with other semiconductors e.g. in the form of an epitaxy.

45. Use of the dyes of 11 and 12 as dyes or fluorescent dyes in chemiluminescent systems, e.g. in chemical luminescent sticks, in luminescence immunoassays or other luminescence detection methods.

46. Use of the dyes of 11 and 12 as dyes or fluorescent dyes as signal colors, preferably for optically highlighting lettering and drawings or other graphic products, for marking signs and other objects in which a special visual color impression is to be achieved.

47. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in dye lasers, preferably as fluorescent dyes for generating laser beams.

48. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in dye lasers.

49. Use of the dyes of 11 and 12 as dyes in dye lasers as Q-switch switches.

50. Use of the dyes of 11 and 12 as active substances for non-linear optics, e.g. for frequency doubling and frequency tripling of laser light.

51. Use of the dyes of 11 and 12 as rheology improvers.