DE10026623A1 - Perylene dyes with persistent fluorescence due to steric aggregation inhibition - 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

The use of fluorescent dyes is generally indicated by their tendency to aggregate dilute solutions limited. The fluorescence quenching then occurs in more concentrated solutions (Concentration deletion) due to the interaction of the chromophores [1, 2] more and more in the Foreground and can lead to the complete absence of light emission. You can also small amounts of aggregate formation already lead to considerable losses in the yield of Lead fluorescent light. Even with easily soluble dyes, it is often a considerable one Observe aggregation at optical densities of 2 / mm, while with poorly soluble dyes often quenching fluorescence even at extremely low concentrations in the Foreground occurs. A solution to this problem would lead to significant progress, in particular in the practical use of fluorescent dyes.

We have the perylene-3,4: 9,10-tetracarboxylic acid bisimide (2, perylene dyes) as the basic fluorophore. [3], because this class of substances is not only yielded by its high fluorescence quantum yields distinguished (see e.g. 2a [4]), but also a considerable thermal, photochemical and chemical resistance, which makes them ideal for fluorescence applications. The We control the aggregation behavior through the substituents on the nitrogen atoms made because these positions are economically provided with various remnants can. Orbital nodes on the nitrogen atoms [5] in HOMO and LUMO, so the chromophore system at these positions has little of the substituent being affected. We have attached bulky residues to the nitrogen atoms in order to impact one to study such substitution on the fluorescence behavior of the dyes in concentrated solution. Based on this concept, we tried in a manner known per se, the anhydride 1 to condense with the 2,4,6-triphenylaniline. Surprisingly, you don't get that Condensation product 2b, but the decarboxylation product 3. This reaction takes place Analogy in the preparative, partial decarboxylation [6] of 1 described earlier. The amino group in the triphenylaniline is obviously too strongly shielded for conversion to 2b. The 4-tritylaniline is less shielded at the amino group, but has a similar size Space requirements like 2,4,6-triphenylaniline. His condensation with 1 succeeds smoothly to 2c. The great The steric claim of the end groups in 2c is evident from the fact that 2c is not among the usual reaction conditions [7] for perylene bisimides can be saponified.

Bulky, purely aliphatic amines were obtained by the alkylation of acetonitrile with secondary ones Amines and the subsequent reduction obtained. Their condensation with 1 gave the highly branched aliphatic substituted dyes 2d to 2f.  

Partially shielded dyes were made from the anhydride imide 4 by condensation receive. The nitrogen atom in 4 was combined with the solubility-increasing sec-alkyl residues ("Swallowtail remains" [8]) provided for the use of the dyes in a homogeneous Solution are of interest. The derivative 7 with the projecting purely aromatic residue were from the Amino derivative 5 and tetraphenylphthalic anhydride shown.

UV / Vis absorption of the new dyes

The UV / Vis spectra of 2 and 3 are practically unaffected by the bulky 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 is the same as for recently other derivatives of 3 values described [10].

In concentrated solution, however, a completely different behavior is observed, which 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. 1), 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 claim of the N-terminus can be reduced by using the tetraphenylphthalimidyl Residuals can be increased further, for example in 7.

Highly branched, purely aliphatic residues, as in 2d, act even more to prevent aggregation out. The effect of these "multiple dovetail remains" is so pronounced that even in highly concentrated solution strong fluorescence is observed. This essentially occurs the surface of the solutions because there is little light in the deeper layers of the dark solutions penetrates. The solid fluorescence of the dyes 2d to 2f is also very pronounced.

Interestingly, the derivative 2d fluoresces brilliantly orange and with relatively short chains therefore resembles the fluorescence of dye solutions, while the fluorescence of the longer chain Derivatives are shifted more towards red orange for 2e and red for 2f. Possibly effect the longer, branched chains reinforce an inner self-solvation and thus form one  "closed cell" so that the shielding effect for the chromophore in the crystal surprisingly not quite as large as the shorter-chain derivatives.

conclusion

The effect of the bulky substituents on the perylene dyes shows that one can sterically repulsive outer sphere effective self-assembly through aggregation of dyes can prevent. In this way, fluorescent dyes for highly concentrated solutions be developed.

The principle of steric aggregation prevention is with perylene dyes and Perylenedicarboximides were found and then systematically examined. This dye Classes were special because of the special properties of the chromophores for the work suitable. However, one can assume that the principle of steric aggregation prevention can generally be extended to fluorescent dyes. In difficult cases, the shielding Sphere can only be made big enough.

Subject of the invention

• 1. A method for preventing aggregation of fluorescent dyes, characterized in that that bulky groups are attached to the periphery of the dyes, the one Prevent the chromophores from stacking and prevent the resulting quenching of fluorescence.
• 2. A method of preventing aggregation and preventing fluorescence quenching in Fluorescent dyes through the incorporation of voluminous aromatic groups after 1.
• 3. A method of preventing aggregation and preventing fluorescence quenching in Fluorescent dyes through the incorporation of bulky heteroaromatic groups after 1.
• 4. A method of preventing aggregation and preventing fluorescence quenching in Fluorescent dyes through the incorporation of voluminous aliphatic groups after 1.
• 5. The use of the substituted phenyl radical of the general formula I as a voluminous aromatic group corresponding to 2,
  in which R ¹ to R ^{5 may 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, isocyclic 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, isoquinolyl, benzimidazolyl, benzoxazolyl, dibenzfuranyl, benzothiophenyl, dibenzothiophenyl, oxolylol Thiazolyl, indazolyl, benzthiazolyl, pyridazinyl, cinnolyl, quinazolyl, quinoxalyl, phthalazinyl, phthalazinedionyl, phthalimidyl, chromonyl, naphtholactamyl, benzopyridonyl, ortho-sulfobenimidyl, benzimidazonyl, benzimidazonyl, benzimidazonylylbenzylidonylidonyl Dioxapyrinidinyl, 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 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, C ₃ - to C ₂₄ -cycloalkyl, preferably C ₅ - , C ₆ -, C ₁₂ -, C ₁₅ -, C ₁₆ -, C ₂₀ - and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, 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 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 further heterocyclic aromatic radicals, such as, for. B. 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, 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, n-propyl, isopropyl, n-butyl, sec-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 cyclyl with C ₃ to C ₂₀ .
  • c) The group -OR ¹² , in which R ^{12 is} hydrogen, alkyl, aryl, for example naphthyl or in particular unsubstituted phenyl, C ₃ to C ₂₄ -cycloalkyl, preferably C ₅ -, C ₆ -, C ₁₂ , C ₁₅ -, C ₁₆ -, C ₂₀ -, and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular unsubstituted or substituted by halogen, alkyl or -O-alkyl phenyl. In the definitions of occurring alkyl z. B. have one of the number b) given as preferred number of carbon atoms. Examples of R ¹³ are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, trifluorethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, benzyl -, m- or p-chlorophenyl, o-, m-, or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl.
  • d) The cyano group.
  • e) 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, n-propylamino, di-n-propylamino, isopropylamino, n-butylamino, di-n-butylamino, sec-butylamino, di-sec-butylamino, tert-butylamino , tert-amylamino, n-hexylamino, di-n-hexylamino, 1,1,3,3, -tetramethylbutylamino, n-heptylamino, di-n-heptylamino, n-octylamino, di-n-octylamino, n-nonyl, Di-n-nonylamino, n-decylamino, di-n-decylamino, n-undecylamino, di-n-undecylamino, n-dodecylamino, di-ndodecylamino, n-octadecylamino, 1-ethylpropylamino, 1-propylbutylamino, 1-butylpentylam 1-pentylhexylamino, 1-hexylheptylamino, 1-heptyloctylamino, 1-octylnonylamino, 1-nonyldecylamino, 1-decylundecylamino, 1-ethylbutylamino, 1-ethylpentylamino, 1-ethylheptylamino, 1-ethylnethylethylamino, hydroxymonylamino, hydroxymonylamino, hydroxymethyl N-bis (2-hydroxyethyl) amino, trifluoromethylamino, trifluoroethylamino, cyanomethylamino, methoxycarbonylmethylamino, acetoxymethylamino, benzylamino, dibenzylamino, Phe nylamino, diphenylamino, o-, m- or p-chlorophenylamino, o-, m- or p-methylphenylamino, 1- or 2-naphthylamino, cyclopentylamino, cyclohexylamino, cyclododecylamino, cyclopentadecylamino, cyclohexadecylamino, cycloeicotanyamylamino, cycloeicotanyl amyl Piperidyl or morpholyl.
  • f) The group of the formula -COR ¹⁵ , in which R ^{15 has} the meaning given under a). Examples of R ¹⁵ are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, trifluorethyl, cyanomethyl, methoxycarbonylmethyl, acetyl o-, m- or p-chlorophenyl, o-, m-, or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl, benzyl or furfuryl.
  • g) The group of the formula -N (R ¹⁶ ) COR ¹⁷ , where R ^{16 has} the meaning given under b), R ^{17 is} hydrogen, alkyl, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, benzyl, phenyl, o-, m- or p-chlorophenyl, o-, m-, or p-methylphenyl, 1- or 2- Naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl or furfuryl. In the definitions of R ¹⁶ occurring alkyl z. B. have one of the number of carbon atoms indicated preferably under b). Examples include: acetylamino, propionylamino, butyrylamino, benzoylamino, p-chlorobenzoylamino, p-methylbenzoylamino, N-methylacetamino, N-methylbenzoylamino, N-succinimido, N-phthalimido or N- (4-amino) phthalimido.
  • h) 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 include the groups -NHCOOCH ₃ , -NHCOOC ₂ H ₅ , or - NHCOOC ₆ H ₅ .
  • i) 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, N-phenylureido, or N, N'-2 ', 4'-dimethylphenylureido.
  • j) The group of the formula -NHSO ₂ R ²³ , in which R ^{23 has} the meaning given under b). Examples include: methylsulfonylamino, phenylsulfonylamino, p-tolylsulfonylamino or 2-naphthylsulfonylamino.
  • k) The groups of the formula -SO ₂ R ²⁴ or -SOR ²⁵ , wherein R ²⁴ or R ^{25 have} the meaning given under b). Examples include: methylsulfonyl, ethylsulfonyl, phenylsulfonyl, 2-naphthylsulfonyl, phenylsulfoxidyl.
  • l) The group of the formula -SO ₂ OR ²⁶ , wherein R ^{26 has} the meaning given under b). Examples of R ²⁷ are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl.
  • m) The group of the formula -CON (R ²⁷ ) (R ²⁸ ), in which R ²⁷ and R ^{28 have} the meaning given under b). Examples include: carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-phenylcarbamoyl, N, N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-1-naphthylcarbamoyl or N-piperdylcarbamoyl.
  • n) The group of the formula -SO ₂ N (R ²⁹ ) (R ³⁰ ), in which R ²⁹ and R ^{30 have} the meaning given under b). Examples include: sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsulfamoyl or N-morpholylsulfamoyl.
  • o) The group of the formula -N = NR ³¹ , in which R ^{31 is} the residue of a coupling component or a phenyl radical which is optionally substituted by halogen, alkyl or -O-alkyl. Alkyl occurring in the definitions of R ³¹ can e.g. B. have one of the number b) given as preferred number of carbon atoms. The following may be mentioned as examples of R ³¹ : the acetoacetarylide, pyrazolyl, pyridonyl, o-, p-hydroxyphenyl, o-hydroxynaphthyl, p-aminophenyl or p-N, N-dimethylaminophenyl radicals.
  • p) 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 p-chlorophenyl.
  • q) 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 p-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 , wherein 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, C ₃ - to C ₂₄ -cycloalkyl, preferably C ₅ -, C ₆ -, C ₁₂ -, C ₁₅ -, C ₁₆ -, C ₂₀ - and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, or wherein R ³⁷ and R ³⁸ together with one of the other radicals R ³⁴ to R ^{39 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. B. 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, n-propyl, isopropyl, n-butyl, sec-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 cyclyl 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, C ₃ to C ₂₄ -cycloalkyl, preferably C ₅ -, C ₆ -, C ₁₂ , C ₁₅ -, C ₁₆ -, C ₂₀ -, and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular unsubstituted or substituted by halogen, alkyl or -O-alkyl phenyl. In the definitions of R ₄₀ occurring alkyl z. B. have one of the number b) given as preferred number of carbon atoms. Examples of R ₄₀ include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl , Cycloeicosanyl, Cyclotetracosanyl, Thienyl or Pyranylmethyl.
    • d) The cyano group.
    • e) 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, n-propylamino, di-n-propylamino, isopropylamino, n-butylamino, di-n-butylamino, sec-butylamino, di-sec-butylamino, tert-butylamino , tert-amylamino, n-hexylamino, di-n-hexylamino, 1,1,3,3, -tetramethylbutylamino, n-heptylamino, di-n-heptylamino, n-octylamino, di-n-octylamino, n-nonyl, Di-n-nonylamino, n-decylamino, di-n-decylamino, n-undecylamino, di-n-undecylamino, n-dodecylamino, di-ndodecylamino, n-octadecylamino, 1-ethylpropylamino, 1-propylbutylamino, 1-butylpentylam 1-pentylhexylamino, 1-hexylheptylamino, 1-heptyloctylamino, 1-octylnonylamino, 1-nonyldecylamino, 1-decylundecylamino, 1-ethylbutylamino, 1-ethylpentylamino, 1-ethylheptylamino, 1-ethylnethylethylamino, hydroxymonylamino, hydroxymonylamino, hydroxymethyl N-bis (2-hydroxyethyl) amino, trifluoromethylamino, trifluoroethylamino, cyanomethylamino, methoxycarbonylmethylamino, acetoxymethylamino, benzylamino, dibenzylamino, Phe nylamino, diphenylamino, o-, m- or p-chlorophenylamino, o-, m- or p-methylphenylamino, 1- or 2-naphthylamino, cyclopentylamino, cyclohexylamino, cyclododecylamino, cyclopentadecylamino, cyclohexadecylamino, cycloeicotanyamylamino, cycloeicotanyl amyl Piperidyl or morpholyl
    • f) The group of the formula -COR ⁴³ , wherein R ^{43 has} the meaning given under a). Examples of R ⁴³ are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, Cycloeicosanyl, Cyclotetracosanyl, Thienyl, Pyranylmethyl, Benzyl or Furfuryl.
    • g) 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, n-propyl, isopropyl, n-butyl, sec-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 -Ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl with C ₃ to C ₂₀ , phenyl, especially unsubstituted or substituted by halogen, alkyl or -O-alkyl Phenyl, for example o-, m- or p-chlorophenyl, o-, m- or p-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 e.g. B. have one of the number of carbon atoms indicated preferably under b). Examples include: acetylamino, propionylamino, butyrylamino, benzoylamino, p-chlorobenzoylamino, p-methylbenzoylamino, N-methylacetamino, N-methylbenzoylamino, N-succinimido, N-phthalimido or N- (4-amino) phthalimido.
    • h) The group of the formula -N (R ⁴⁶ ) COOR ⁴⁷ , wherein R ⁴⁶ and R ^{47 have} the meaning given under b) and c). Examples include the groups -NHCOOCH ₃ , -NHCOOC ₂ H ₅ , or - NHCOOC ₆ H ₅ .
    • i) 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 N, N'-2 ', 4'-dimethylphenylureido.
    • j) The group of the formula -NHSO ₂ R ⁵¹ , wherein R ^{51 has} the meaning given under b). Examples include: methylsulfonylamino, phenylsulfonylamino, p-tolylsulfonylamino or 2-naphthylsulfonylamino
    • k) 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.
    • l) The group of the formula -SO ₂ OR ⁵⁴ , wherein R ^{54 has} the meaning given under b). Examples of R ⁵⁴ are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl.
    • m) The group of the formula -CON (R ⁵⁷ ) (R ⁵⁶ ), in which R ⁵⁷ and R ^{56 have} the meaning given under b). Examples include: carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-phenylcarbamoyl, N, N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-1-naphthylcarbamoyl or N-piperdylcarbamoyl.
    • n) The group of the formula -SO ₂ N (R ⁵⁷ ) (R ⁵⁸ ), in which R ⁵⁷ and R ^{58 have} the meaning given under b). Examples include: sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsulfamoyl or N-morpholylsulfamoyl.
    • o) The group of the formula -N = NR ⁵⁹ , in which R ^{59 is} the radical of a coupling component or a phenyl radical which is optionally substituted by halogen, alkyl or -O-alkyl. Alkyl occurring in the definitions of R ⁵⁹ can e.g. B. have one of the number b) given as preferred number of carbon atoms. The following may be mentioned as examples of R59: the acetoacetarylide, pyrazolyl, pyridonyl, o-, p-hydroxyphenyl, o-hydroxynaphthyl, p-aminophenyl or p-N, N-dimethylaminophenyl radicals.
    • p) The group of the formula -OCOR ⁶⁰ , wherein R ^{60 has} the meaning given under b). Examples of R ⁶⁰ are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl.
    • q) 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 p-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 residue. An example of such a residue is the (3,4,5,6-tetraphenylphthalimidyl) residue.
• 8. Use of voluminous aliphatic radicals according to 4 with the general formula II,
  in which R ¹ to R ^{3 are} hydrogen or one to 3 of the radicals mentioned under 5.
• 9. Use of voluminous aliphatic radicals according to 4 with the general formula III,
  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,
  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 IV,
  in which x and y can be the same or different and are under 5 to 10 aggregation-preventing radicals or in x is one of the aggregation-preventing radicals mentioned under 5 to 10 and y is a solubility-increasing group, such as. B. 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.
  Preferred examples are x = y = p-triphenylmethyl, bis (2- (1-propylbutyl) -3-propyl-hexyl), N, N'-bis (-2- (1-butylpentyl) -3-butylheptyl) and bis (2- (1-pentyl) -3-pentyl-octyl) or x = p-triphenylmethyl, bis (2- (1-propylbutyl) -3-propyl-hexyl), N, N'-bis (-2- ( 1-butylpentyl) -3-butylheptyl) or bis (2- (1-pentylhexyl) -3-pentyloctyl) - 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
  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. Use 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 of 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 mentioned monomers.
• 16. Application of the dyes of 11 and 12 as vat dyes, e.g. B. 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 (e.g. horsehair) and their Conversion products such as B. the viscose fiber, nitrate silk or copper rayon (rayon).
• 17. Application of the dyes of 11 and 12 as stain dyes, for. B. 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 (e.g. horsehair) and their Conversion products such as B. the viscose fiber, nitrate silk or copper rayon (rayon). Preferred salts for pickling are aluminum, chromium and iron salts.
• 18. Application of the dyes of 11 and 12 as colorants, eg. B. for coloring colors, Varnishes and other paints, paper colors, printing inks, inks and other colors for Painting and writing purposes.  
• 19. Application of the dyes of 11 and 12 as pigment dyes, for. B. for coloring Paints, varnishes and other paints, paper paints, printing inks, inks and others Colors for painting and writing purposes.
• 20. Application of the dyes of 11 and 12 as pigments in electrophotography: z. B. for dry copy systems (Xerox process) and laser printers ("non-impact printing").
• 21. Application 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 matter. This is preferred for checks, check cards, banknotes Coupons, documents, identity documents and the like, for which a special, unmistakable color impression should be achieved.
• 22. application of the dyes of 11 and 12 to be used as an additive to other colors, in which a certain color shade is to be achieved, particularly bright ones are preferred Shades.
• 23. Use of the dyes of 11 and 12 for marking objects for machine detection of these objects over the fluorescence used, preferred is the automatic detection of objects for sorting, e.g. B. also for recycling of plastics.
• 24. Use of the dyes of 11 and 12 as fluorescent dyes for machine-readable Markings are used, preferably alphanumeric imprints or barcodes.
• 25. Application of the dyes of 11 and 12 used for frequency conversion of light be, e.g. B. 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, Notification and marking purposes, e.g. B. passive display elements, information and Traffic signs, such as traffic lights.
• 27. Application of the dyes of 11 and 12 in inkjet printers, preferably in 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. Application of the dyes of 11 and 12 for tracer purposes, e.g. B. in biochemistry, Medicine, technology and science. The dyes can be covalently bonded to substrates linked 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 method (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 Fluorescence 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 display of plastics.
• 39. Application of the dyes of 11 and 12 as dyes or fluorescent dyes for Material testing, e.g. B. in the manufacture of semiconductor circuits.
• 40. Application of the dyes of 11 and 12 as dyes or fluorescent dyes for 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 process.
• 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 by electrons, Ion or UV radiation takes place, e.g. B. 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 that uses dyes as such or in combination with other semiconductors e.g. B. in the form of an epitaxy.
• 45. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in Chemiluminescent systems, e.g. B. in chemiluminescent light sticks, in Lu minescence immunoassays or other luminescence detection methods.
• 46. Application 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 labeling signs and other objects, where a special optical color impression is to be achieved.  
• 47. Use 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. Application of the dyes of 11 and 12 as dyes in dye lasers as Q-switches Switch.
• 50. Application of the dyes of 11 and 12 as active substances for a non-linear Optics, e.g. B. 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'-tritylphenyl) perylene-3,4: 9,10-bis (dicarboximide) (2c): 4-tritylaniline ¹¹ (2.00 g, 5.96 mmol), perylene-3,4: 9,10-tetracarboxylic acid 3,4: 9,10-bisanhydride (1, 980 mg, 2.50 mmol) and imidazole (20 g) were heated at 140 ° C for 3 h. Water (10 ml) was added and, after cooling, 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 (silica gel, chloroform) and further purified by a second chromatography (silica gel, chloroform / ethanol 20: 1). Yield 2.14 g (85%) 2c as a bright red solid, mp. <360 ° C. - R _f (CHCl ₃ ): 0.22. - IR (KBr): = 3435 cm ^-1 (s br.), 2924 (w, CH aliphatic), 2853 (w), 1709 (s, C = O), 1671 (s), 1593 (m, CC arom.), 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 arom.), 745 (m), 702 (m). - UV (CHCl ₃ ): λ _max (ε) = 459.6 nm (14850), 490.9 (51 740), 527.8 (90 200). - Fluorescence (CHCl ₃ ): λ _max = 538 nm, 577. - Solid fluorescent fluorescence: λ _max = 593 nm. - MS (70 eV): m / z (%): 1027 (7) [M ⁺ ], 1026 (9 ), 952 (7), 951 (27), 950 (76) [M ⁺ - 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; found C 85.58, H 4.56, N 2.65. Reaction of 1 with 2,4,6-triphenylaniline: 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 (silica gel, chloroform) and a second column chromatography (silica gel, 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. - R _f (CHCl ₃ / ethanol 10: 1): 0.71. - R _f (CHCl ₃ ): 0.27. - IR (KBr): = 3436 cm ^-1 (s br.), 3057 (w, CH arom.), 1698 (s, C = O), 1656 (s), 1592 (m, CC arom.), 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). ¹ H NMR (CDCl ₃ ): δ = 7.01-7.05 (m, 1H, phenyl-H), 7.09-7.12 (m, 3H, phenyl-H), 7.30-7.34 (m, 2H, phenyl-H), 7.36-7.43 (m, 7H, phenyl-H), 7.52-7.54 (m, 2H, perylene-H), 7.63-7.66 (m, 6H, phenyl-H), 7.80 (d, J = 8.0 Hz, 2H, Perylene-H), 8.24 (d, J = 8.0 Hz, 2H, perylene-H), 8.32 (d, J = 7.4 Hz, 2H, perylene-H), 8.35 (d, J = 8.0 Hz, 2H, perylene- H). - UV / Vis (CHCl ₃ ): λ _max (ε) = 353.6 nm (4060), 450.5 (sh., 14 240), 485.5 (28 050), 510.1 (26 950). - Fluorescence (CHCl ₃ ): λ _max = 537 nm, 570. - MS (70 eV): m / z (%): 627 (11), 626 (47), 625 (100) [M ⁺ ], 608 ( 7), 581 (20), 580 (41), 312 (7), 304 (7), 276 (6). N, N'-bis (2- (1 propylbutyl) -3 propyl-hexyl) -perylene-3,4: 9,10-bis (dicarboximide) (2d): 1 (890 mg, 2.3 mmol) and 2- ( 1-Propylbutyl) -3-propyl-hexylamine (1.20 g, 4.97 mmol) was reacted and worked up analogously to 2c. Yield 1.46 g (77%) 2d as orange fluorescent crystal needles, mp. 335 ° C. - R _f (silica gel, chloroform): 0.80. - IR (KBr): = 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. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.78 (t, J = 7.2 Hz, 12H, 4CH ₃ ), 0.91 (t, J = 7.3 Hz, 12H, 4CH ₃ ), 1.20 (m _c , 16H , 8CH ₂ ), 1.33 (m _c , 16H, 8CH ₂ ), 1.66 (m _c , 4H, 4γ-CH), 2.21 (t, J 7.4 Hz, 2H, 2β-CH), 4.24 (d, J = 7.4 Hz, 4H, 2α-CH ₂ ), 8.60 (d, J = 8.0 Hz, 4H, perylene), 8.66, J = 8.0 Hz, 4H, perylene). - ¹³ C NMR (75 MHz, CDCl ₃ ): 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 (CHCl ₃ ): λ _max (ε) = 434.1 nm (7350), 458.5 (21 700), 488.9 (56 900), 525.9 (94 200). - Fluorescence (CHCl ₃ ): λ _max = 534 nm, 574, 621. - Fluorescence quantum yield (CHCl ₃ , reference N, N '- (1-hexylheptyl) perylene-3,4: 9,10- bis (dicarboximide) with Φ = 100%): 99%. - Solid-state fluorescence: λ _max = 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). - C ₅₆ H ₇₄ N ₂ O ₄ (839.2): calc. C 80.15, H 8.89, N 3.34; found C 80.33, H 8.79, N 3.57.

N, N'-Bis (2- (1-butylpentyl) -3-butylheptyl) perylene-3,4: 9,10-bis (dicarboximide) (2e): 1 (300 mg, 0.8 mmol), 3-butyl -2- (1-butylpentyl) heptylamine (600 mg, 2.0 mmol) and imidazole (900 mg) were reacted analogously to 2c (160 ° C., 3 h) and purified by column chromatography (silica gel, chloroform). Yield 600 mg (81%) of 2e, mp. 238 ° C. - R _f (silica gel / CHCl ₃ ): 0.81. - IR (KBr): = 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. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.82 (t, J 7.1 Hz, 12H, 4CH ₃ ), 0.88 (t, J 7.2 Hz, 12H, 4CH ₃ ), 1.20-1.55 (m, 34H, 17 CH ₂ ), 1.65 (m _c , 18H, 8CH ₂ + 2γ-CH), 2.14 (m _c , 2H, 2β-CH), 4.22 (d, J = 7.2 Hz, 4H, 2α-CH ₂ ), 8.56 (d, J = 8.1 Hz, 4H, perylene), 8.63 (d, J = 8.1 Hz, 4H, perylene). ¹³ C NMR (75 MHz, CDCl ₃ ): δ = 14.06 (CH ₃ ), 14.21 (CH ₃ ), 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 (γ-CH), 39.37 (β-CH), 39.68 (α-CH ₂ ), 122.98 (perylene), 123.34 (perylene), 131.33 (perylene), 134.50 (perylene), 163.67 (NC = O). - UV / Vis (CHCl ₃ ): λ _max (ε) = 458.2 nm (18700), 488.2 (51 500), 525.1 (84 800). - Fluorescence (CHCl ₃ ): λ _max = 534 nm, 574, 621. - Fluorescence quantum yield (CHCl ₃ , reference N, N '- (1-hexylheptyl) perylene-3,4: 9,10- bis (dicarboximide) with Φ = 100%): 97%. - Solid-state fluorescence: λ _max = 587.9 nm. - MS (70 eV): m / z (%): 951 (70) [M ⁺ + 1], 950 (100) [M ⁺ ], 824 (3) [M ⁺ + 1 - C ₉ H ₁₉ ], 823 (5) [M ⁺ - C ₉ H ₁₉ ], 684 (5) [M ⁺ + 1 - C ₁₉ H ₃₉ ], 683 (7) [M ⁺ - C ₁₉ H ₃₉ ], 673 (24), 672 (70), 671 (88), 544 (2) [671 - C ₉ H ₁₉ ], 541 (3), 418 (4), 417 (5) [544 - C ₉ H ₁₉ ], 405 (26), 404 (35) [671 - C ₁₉ H ₃₉ ], 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 ₆₄ H ₉₀ N ₂ O ₄ (951.4): calc. C 80.80, H 9.53, N 2.94; found C 81.10, H 9.65, N 3.18.

N, N'-bis (2- (1 pentylhexyl) -3 pentyl-octyl) perylene-3,4: 9,10-bis (dicarboximide) (2f): 1 (200 mg, 0.51 mmol) and the crude amine Mixture containing 1-amino-2- (1-pentylhexyl) -3-pentyl-octane (400 mg) were reacted and worked up analogously to 2c. Yield 300 mg (55%) 2f as red fluorescent crystal needles, mp 195-196 ° C. - R _f (silica gel, chloroform): 0.83. - R _f (silica gel, toluene): 0.65.- IR (KBr): = 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. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.74 (t, J 6.9 Hz, 12H, 4CH ₃ ), 0.88 (t, J = 6.4 Hz, 12H, 4CH ₃ ), 1.00-1.18 (m, 16H , 8CH ₂ ), 1.20-1.35 (m, 32 H, 16CH ₂ ), 1.66 (m _c , 4H, 4γ-CH), 2.14 (t, J 7.1 Hz, 2H, 2β-CH), 4.22 (d, J = 7.2 Hz, 4H, 2 α-CH ₂ ), 8.53 (d, J = 8.13 Hz, 4H, perylene), 8.62 (d, J = 8.0 Hz, 4H, perylene). - ¹³ C-DEPT-NMR (75 MHz, CDCl 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 (β-CH) , 40.03 (α-CH ₂ ), 123.35, 131.71. - ¹³ C NMR (75 MHz, CDCl ₃ ): 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 (CHCl ₃ ): λ _max (ε) = 434.1 nm (4750), 458.5 (17800), 489.1 (50 500), 525.9 (85 400). - Fluorescence (CHCl ₃ ): λ _max = 534 nm, 574, 621. - Fluorescence quantum yield (CHCl ₃ , reference N, N '- (1-hexylheptyl) perylene-3,4: 9,10-bis (dicarboximide) with Φ = 100%): 97%. - Solid state fluorescence: λ _max = 624 nm. - MS (70 eV): m / z (%): 1066 (8), 1065 (30), 1064 (77), 1063 (100) [M ⁺ ], 908 (5 ) [M ⁺ - C ₁₁ 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 ₇₂ H ₁₀₆ N ₂ O ₄ (1063.6): calc. C 81.30, H 10.04, N 2.63; found C 81.24, H 9.46, N 2.75.

N- (1-Hexylheptyl) -N '- (4'-tritylphenyl) perylene-3,4: 9,10-bis (dicarboximide) (6): N (1-hexylheptyl) perylene-3,4: 9 , 10-tetracarboxylic acid-3,4-anhydride-9,10-carboximide ⁷ (4,270 mg, 0.45 mmol), 4-tritylaniline (600 mg, 1.79 mmol) and imidazole (15 g) were reacted and worked up analogously to 2c . The precipitate was purified by column chromatography twice (silica gel, chloroform / ethanol 20: 1 and silica gel, chloroform). Yield 230 mg (56%) 6 as a dark red solid, mp. 292-293 ° C. - R _f (CHCl ₃ ): 0.24. - IR (KBr): = 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 (m), 702 (w). - ¹ H NMR (CDCl ₃ ): δ = 0.83 (t, J = 6.7 Hz, 3H, CH ₃ ), 1.23-1.32 (m, 16H, 8CH ₂ ), 1.83-1.90 (m, 2H, CH ₂ ), 2.22-2.30 (m, 2H, CH ₂ ), 5.16-5.19 (m, 2H, CH), 7.21-7.30 (m, 19H, phenyl-H), 8.60-8.73 (m, 8H, perylene-H). - ¹³ C NMR (CDCl 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 (CHCl ₃ ): λ _max (ε) = 366.7 nm (4650), 430.0 (sh., 6560), 458.8 (21150), 490.6 (56 350), 527.0 (93 430). - Fluorescence (CHCl ₃ ): λ _max = 535 nm, 575. - MS (70 eV): m / z (%): 892 (12), 891 (35) [M ⁺ ], 890 (51), 815 ( 9), 814 (19), 813 (47) [M ⁺ - C ₆ H ₆ ], 711 (8), 710 (26), 709 (51) [M ⁺ - C ₁₃ H ₂₆ ], 633 (15) , 632 (54) [M ⁺ - C ₁₃ H ₂₆ - Ph], 631 (100) [M ⁺ - C ₁₃ H ₂₆ - C ₆ H ₆ ], 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 ₄ (891.1): calc. C 83.57, H 6.11, N 3.14; found C 83.41, H 6.07, N 3.17.

N- (1-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 purified by column chromatography (silica gel, chloroform / acetone 15: 1 ). Yield 210 mg (75%) 5b as a dark red powder, mp. 312 ° C. - R _f (silica gel, chloroform / acetone 15: 1): 0.19. - IR (KBr): = 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. - NMR (300 MHz, CDCl ₃ ): δ = 0.82 (t, J = 6.8 Hz, 6H, 2CH ₃ ), 1.16-1.4 (m, 16H, 8CH ₃ ), 1.87 (m _c , 2H, β-CH ₂ ), 2.26 (m _c , 2H, β-CH ₂ ), 5.19 (m _c , 1H, α-CH), 6.80-6.84 (m, 4H, phenyl), 6.91-6.97 (m, 6H, phenyl), 71.3 -7.23 (m, 10H, phenyl), 8.52 (d, J = 8.3 Hz, 2H, perylene), 8.58 (d, J = 8.1 Hz, 2H, perylene), 8.59 (d, J = 8.2 Hz, 2H, perylene ), 8.67 (m _c , 2H, perylene). - ¹³ C NMR (75 MHz, CDCl 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 (CHCl ₃ ): λ _max (ε) = 352.8 nm (8800), 368.0 (7100), 434 (6000), 459.6 (19 100), 491.1 (51 100), 527.4 (84 100). - Fluorescence (CHCl ₃ ): λ _max = 539 nm, 577, 631 sh. - Solid-state fluorescence: λ _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 ⁺ - C ₁₃ 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 ) ₄ C ₆ C 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 ⁺ + 2H - C ₁₃ 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 ₆₉ H ₅₅ N ₃₀₆ (1022.2): calc. C 81.07, H 5.43, N 4.11; found C 81.13, H 5.83, N 3.81.

N- (1-Hexylheptyl) -N '- (2- (1 propylbutyl) -3 propylhexyl) perylene-3,4: 9,10-bis (dicarboximide): 4 (1.27 g, 2.20 mmol), 2 - (1-Propylbutyl) -3-propyl-hexylamine (900 mg, 3.7 mmol) were reacted and worked up analogously to 2c. Yield 980 mg (50%; mp 148 ° C. - R _f (silica gel, toluene): 0.41. - IR (KBr): = 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 (CHCl ₃ ): λ _max (ε) = 434.1 nm (4730), 458.5 (18,000), 489.1 (50,500), 526.0 (85,200) - Fluorescence (CHCl ₃ ): λ _max = 534 nm, 574, 621. - Fluorescence quantum yield (CHCl ₃ , reference N, N '- (1-hexylheptyl ) -perylene-3,4: 9,10-bis (dicarboximide) with Φ = 100%): 99%. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.80 (m _c , 18H, 6CH ₃ ) , 1.16-1.57 (m, 34H, 2γ-CH + 16CH ₂ ), 1.89 (m _c , 2H, β-CH ₂ ), 2.24 (m _c , 3H, β-CH + β-CH ₂ ), 4.2 (i.e. , J = 7.1 Hz, 2H, α-CH ₂ ), 5.18 (quint, J = 7.0 Hz, 1H, α-CH), 8.53 (d, J = 8.1 Hz, 2H, -perylene), 8.58 (d, J = 8.3 Hz, 2H, perylene), 8.61 (d, J = 8.0 Hz, 4H, perylene) - ¹³ C NMR (75 MHz, CDCl ₃ ): 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 - C ₁₆ H 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 ₅₃ H ₆₈ N ₂ O ₄ : calc. 796.5179; found 796.5161 (MS).

N- (2- (1-Butylpentyl) -3-butyl-heptyl) -N '- (1-hexylheptyl) perylene-3,4: 9,10-bis (dicarboximide) (8): 4 (440 mg, 0.76 mmol), 2- (1-butylpentyl) -3-butyl-heptylamine (250 mg, 0.84 mmol) were reacted and worked up analogously to 2c. Yield 490 mg (76%) 8 as red, fluorescent needles, mp. 131 ° C. - R _f (silica gel, chloroform): 0.61. - R _f (silica gel, toluene): 0.55. - IR (KBr): = 3442 cm ^-1 m, 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. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.78 (t, J 6.7, 12H, 4CH ₃ ), 0.88 (t, J = 7 Hz, 6H, 2CH ₃ ), 1.17-1.35 (m, 40H, 20CH ₂ ), 1.66 (m _c , 2 H, γ-CH), 1.85 (m _c , 2H, β-CH ₂ ), 2.16-2.24 (m, 3H, β-CH ₂ + β-CH), 4.22 ( d, J 7.3 Hz, 2H, α-CH ₂ ), 5.16 (quint, J = 7.6, 1H, α-CH), 8.57 (d, J 8.1 Hz, 2H, perylene), 8.58 (d, J = 8.1 Hz , 2H, perylene), 8.65 (d, J = 8.0 Hz, 4H, perylene). - ¹³ C NMR (75 MHz, CDCl ₃ ): δ = 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 (CHCl ₃ ): λ _max (ε) = 433.0 nm (6430), 458.1 (19800), 488.9 (53 300), 525.9 (88 900). - Fluorescence (CHCl ₃ ): λ _max = 534 nm, 574, 621. - Fluorescence quantum yield (CHCl ₃ , reference N, N '- (1-hexylheptyl) perylene-3,4: 9,10-bis (dicaroximide) with 45 = 100%): 100%. - Solid-state fluorescence: λ _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 ₅₇ H ₇₆ N ₂ O ₄ (853.3): calc. C 80.24, H 8.98, N 3.28; found C 80.44, H 8.96, N 3.40.

N- (2- (1-pentylhexyl) -3 pentyloctyl) -N '- (1-octylnonyl) perylene-3,4: 9,10-bis (dicarboximide) (9): N- (1-octylnonyl) - perylene-3,4: 9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (4,300 mg, 0.48 mmol) and the crude 1-amino-2- (1-pentylhexyl) -3-pentyl octane (300 mg) were reacted and worked up analogously to 2c. First faction. Lane N- (2-bis (1-pentylhexyl) -3-pentyl-octyl) -N '- (1-octylnonyl) perylene-3,4: 9,10-bis (dicarboximide). - R _f (silica gel, chloroform): 0.98. - R _f (silica gel, toluene): 0.86. - UV / Vis (CHCl ₃ ): 14117 00070 552 001000280000000200012000285911400600040 0002010026623 00004 13998λ _max = 434.1 nm, 458.5, 489.1, 526.0. - Fluorescence (CHCl ₃ ): λ _max = 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 ₉ H ₁₆ ], 1020.7 (1), 1007.7 (1), 1006.6 (1), 963.6 (1) [M ⁺ - C ₁₁ H ₂₄ ], 937.5 (1), 936.6 (1), 882.5 (1) [M ⁺ - C ₁₇ H ₃₄ ], 810.4 (1) [M ⁺ - 2 × C ₁₁ H ₂₄ ], 783.4 (2), 699.4 (2), 685.3 (1), 667.6 (1), 654.4 (1) [M ⁺ - 3 × C ₁₁ H ₂₄ ], 639.6 (1), 628.6 (1) [M ⁺ - CH ₂ -C (C ₁₁ H ₂₄ ) ₃ ], 628.5 (1), 627.6 (2), 626.6 (5), 624.5 (2), 623.5 (2), 6226 (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. - R _f (silica gel, chloroform): 0.70. - R _f (silica gel, toluene): 0.60. - IR (KBr): = 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. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.72 (t, J = 7.2 Hz, 6H, 2CH ₃ ), 0.80 (t, J = 6.9 Hz, 6H, 2CH ₃ ), 0.89 (t, J = 7.0 Hz, 6H, 2 CH ₃ ), 1.17-1.48 (m, 60H, 30CH ₂ ), 1.64 (m _c , 2H, 2γ-CH), 1.90 (m _c , 2H, β-CH ₂ ), 2.15-2.27 (m, 3H, β-CH ₂ + β-CH), 4.22 (d, J = 7.3 Hz, 2H, α-CH ₂ ), 5.15 (quint, J = 7.5 Hz, 1H, α-CH), 8.59 ( d, J = 8.3 Hz, 4H, perylene), 8.66 (d, J = 8.2 Hz, 4H, perylene). - ¹³ C NMR (75 MHz, CDCl ₃ ): 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 (CHCl ₃ ): λ _max (ε) = 534.1 nm (5230), 458.9 (18 700), 489.9 (52 100), 526.0 (87 700). - Fluorescence (CHCl ₃ ): λ _max = 534 nm, 574, 621. - Fluorescence quantum yield (CHCl ₃ reference N, N '- (1-hexylheptyl) perylene-3,4: 9,10- bis (dicarboximide) with Φ = 100%): 98%. - Solid fluorescence: λ _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 ₆₅ H 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.

1-Cyano-1- (1 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 (evolution 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%) of 1-cyano-1- (1-propylbutyl) -2-propylpentane, bp 97 ° C / 2 mbar. - IR (film): = 2978 s, 2935 s, 2868 s, 2222 w (CN), 1742 s, 1387 m, 737 w. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.83 (t, J = 6.9 Hz, 6H, 2CH ₃ ), 0.90 (t, J = 7.1 Hz, 6H, 2 CH ₃ ), 1.2-1.4 (m , 18H, CH, CH ₂ ), 2.49 (t, J = 7.0 Hz, 1H, HC-CN). - ¹³ C NMR (75 MHz, CDCl ₃ ): 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 ⁺ - C ₃ H ₇ ], 96 (100) [M ⁺ - C ₃ H ₇ - C ₇ H ₁₄ ], 57 (17).

1-Cyano-1- (1-butylpentyl) -2 propylpentane: Sodium (1.5 g, 65 mmol) was dissolved in liquid ammonia (20 ml, -78 ° C) and with iron (III) nitrae (200 mg, 0.83 mmol ) offset. 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 stirring for 16 h, 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%) of 1-cyano-1- (71-butylpentyl) -2-propylpentane as a viscous oil, b.p. 113 ° C / 0.3 mbar. - IR (film / KBr): = 2978 s, 2935 s, 2868 s, 2223 w (CN), 1387 m, 737 w. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.905 (t, J = 7 Hz, 6H, 2CH ₃ ), 0.915 (t, J = 7 Hz, 6H, 2CH ₃ ), 1.42-1.08 (m, 24H, 12 CH ₂ ), 1.61 (m _c , 2H, β-CH), 2.52 (t, J = 7 Hz, 1H, HC-CN). ¹³ C NMR (75 MHz, CDCl ₃ ): 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 ((HC) 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 ⁺ - C ₃ H ₇ ] , 237 (17), 236 (89) [M ⁺ - C ₄ H ₉ ], 194 (9), 166 (8) [M ⁺ - C ₉ H ₁₉ ], 110 (100) [M ⁺ + 1 - C ₄ H ₉ - C ₉ H 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; found C 81.91, H 13.52, N 4.63.

1-Cyano-1- (1 pentylhexyl) -2 pentylheptane: acetonitrile (1.5 g, 37 mmol) and 6-bromundecane (35.0 g, 149 mmol) were analogous to 1-cyano-1- (1-butylpentyl) -2- implemented and processed propylpentane. Yield 1.8 g (25%) of 1-cyano-1- (1-pentylhexyl) -2-pentylheptane as a viscous oil, bp 148 ° C / 1.5 mbar. - IR (film / KBr): = 2972 cm ^-1 s, 2924 s, 2853 s, 2223 w, 1465 s, 1379 m, 728 w. - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.88 (t, J = 8 Hz, 6H, CH ₃ ), 1.34-1.18 (m, 16H, CH ₂ ), 1.68 (quint, J = 4 Hz, 1 H, β-CH), 2.32 (d, J = 8 Hz, 2H, H ₂ C-CN). - ¹³ C NMR (75 MHz, CDCl ₃ ): δ = 14.09 (CH ₃ ), 22.68 (CH ₂ ), 27.81 (CH ₂ ), 30.64 (CH ₂ ), 32.34 (CH ₂ ), 35.11 (β-CH) , 39.57 (H ₂ C-CN), 118.92 (CN).

1-Amino-3 propyl-2- (1 propylbutyl) hexane: lithium aluminum hydride (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) added dropwise, heated to boiling with stirring and reflux for 3 h, cooled with ice, added dropwise with aqueous sodium hydroxide solution (2 ml, 20%), with Extracted ether, dried (magnesium sulfate) and distilled in vacuo. Yield 1.8 g (56%) of 1-amino-3-propyl-2- (1-propylbutyl) -hexane, b.p. 102 ° C / 2 mbar. - IR (film): = 3380 cm ^-1 w (NH ₂ ), 2956 s (CH ₃ ), 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 (NH ₂ ). - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.80 (t, J = 8.0 Hz, 6H, 2CH ₃ ), 0.83 (t, J8.0 Hz, 6H, 2CH ₃ ), 1.1-1.4 (m, 16H, CH ₂ ), 1.4-1.5 (m, 3H, CH), 2.60 (d, J = 6.9 Hz, α-CH ₂ ). - ¹³ C NMR (75 MHz, CDCl ₃ ): δ = 14.9 (CH ₃ ), 19.9-37 (CH ₂ ), 38.0 (β-CH), 40.8 (α-CH ₂ ).

1-Amino-3-butyl-2- (1-butylpentyl) heptylamine: 1-cyano-1- (1-pentylhexyl) -2-pentylheptane (1.0 g, 3.4 mmol) and lithium aluminum hydride (200 mg, 5.3 mmol) were added analogously to 1-amino-3-propyl-2- (1-propylbutyl) -hexane implemented and worked up. Yield 830 mg (82%) of oily 1-amino-3-butyl-2- (1-butylpentyl) heptylamine, b.p. 150 ° C / (1-2) mbar. - IR (film / K / Br): = 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 (NH ₂ ), 730 w (NH ₂ ). - ¹ H NMR (300 MHz, CDCl ₃ ): δ = 0.89 (t, J = 8 Hz, 6H, 2CH ₃ ), 0.90 (t, J = 8 Hz, 6H, 2CH ₃ ), 1.1-1.4 (m, 24H, 12CH ₂ ), 1.42-1.5 (m, 3H, 3CH), 2.66 (d, J = 4 Hz, 2H, α-CH ₂ ). ¹³ C NMR (75 MHz, CDCl ₃ ): 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 (CH ₂ ), 30.78 (CH ₂ ), 31.73 ( CH ₂ ), 34.80 (α-CH ₂ ), 36.50 (γ-CH), 36.67 (γ-CH), 38.04 (β-CH). - MS (70 eV): m / z (%): 297 (5) [M ⁺ ], 280 (39) [M ⁺ - NH ₃ ], 236 (100) [M ⁺ - 1 - NH ₃ - C ₃ H ₇ ], 223 (22) [M ⁺ - NH ₃ - C ₄ H ₉ ], 209 (64) [M ⁺ - NH ₃ - C ₅ H ₁₁ ], 170 (23) [M ⁺ - C ₉ H ₁₉ ], 168 (22), 154 (24) [M ⁺ - NH ₃ + 1 - C ₉ H ₁₉ ], 153 (20) [M ⁺ - NH ₃ - C ₉ H ₁₉ ], 141 (31), 140 ( 62) [M ⁺ - C ₉ H ₁₉ - H ₂ C = NH ₂ ], 126 (17), 112 (31), 111 (23), 110 (95) [M ⁺ - NH ₃ - C ₃ H ₇ - C ₉ H ₁₉ ], 98 (35), 97 (37) [M ⁺ - NH ₃ - C ₉ H ₁₉ - C ₄ H ₉ ], 85 (35), 83 (39) [M ⁺ - C ₉ H ₁₉ - H ₂ C = NH ₂ - C ₄ H ₉ ], 71 (54), 70 (35), 69 (38), 57 (58), 56 (26), 55 (54).

1-amino-2- (1-pentylhexyl) -3-pentyl-octane: 1-cyano-1- (1-pentylhexyl) -2-pentylheptane (1.0 g) analogous to to 1-cyano-1- (1-propylbutyl) -2-propylpentane and mixed with 1-cyano-1,1-bis- (1-pentylhexyl) -2-pentylheptane was analogous to 1-amino-3-propyl-2- (1-propylbutyl) hexane with lithium aluminum hydrides ( 410 mg, 11 mmol). Yield 760 mg of a viscous oily mixture of 1-amino-3-pentyl-2- (1-pentylhexyl) octane and smaller proportions of 1-amino-2,2-bis- (1-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, Vandenhoeck & Ruprecht, Göttingen 1951 and references cited therein.
3. H. Langhals, Heterocycles 1995, 40, 477-500.
4. H. Langhals, J. Karolin, LB-Å. 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, LB-Å. Johansson, J. Chem. Soc., Faraday Trans. 1998, 94, 2919-2922.
10. H. Langhals, W. Jona, Eur. J. Org. Chem. 1998, 847-851,
11. F. Ullmann, A. Münzhuber, Ber. German chem. Ges. 1903, 36, 404-410.

Reference list formula 1

Structural formula of dye 2a

Scheme 1

Synthesis of fluorescent dyes with sterically shielding substituents

Formula 2

Structures of perylene dyes with shielding aliphatic groups

Formula 3

Unsymmetrically substituted perylene dyes with sterically shielding groups

Fig. 1

UV / Vis absorption and quantum corrected fluorescence spectra of perylene tetracarboxylic acid bisimides. From left to right: absorption and fluorescence spectra of 2d in chloroform and solid fluorescence spectra of 2d, 2e and 2f

Claims (51)

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 of preventing aggregation and preventing fluorescence quenching in Fluorescent dyes through the incorporation of voluminous aromatic groups after 1. 3. A method of preventing aggregation and preventing fluorescence quenching in Fluorescent dyes through the incorporation of voluminous heteroaromatic groups according to I. 4. A method of preventing aggregation and preventing fluorescence quenching in Fluorescent dyes through the incorporation of voluminous aliphatic groups after 1. 5. The use of the substituted phenyl radical of the general formula I as a voluminous aromatic group corresponding to 2,
in which R ¹ to R ^{5 may 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, isocyclic 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, isoquinolyl, benzimidazolyl, benzoxazolyl, dibenzfuranyl, benzothiophenyl, dibenzothiophenyl, oxolylol Thiazolyl, indazolyl, benzthiazolyl, pyridazinyl, cinnolyl, quinazolyl, quinoxalyl, phthalazinyl, phthalazinedionyl, phthalimidyl, chromonyl, naphtholactamyl, benzopyridonyl, ortho-sulfobenimidyl, benzimidazonyl, benzimidazonyl, benzimidazonylylbenzylidonylidonyl Dioxapyrinidinyl, pyridonyl, isoquinolonyl, isothiazolyl, benzisoxazolyl, benzisothiazolyl, indazolonyl, acridinyl, acridonyl, quinazolinedionyl, benzoxazinedionyl, benzoxazinonyl and phthalimidyl. Both the isocyclic and the heterocyclic aerodynamic 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 , wherein R ⁶ to R ^{11 are} 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, C ₃ - to C ₂₄ -cycloalkyl, preferably C ₅ -, C ₆ -, C ₁₂ -, C ₁₅ -, C ₁₆ -, C ₂₀ - and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular phenyl which is unsubstituted or substituted by halogen, alkyl or -O-alkyl, or in which R ¹⁶ 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 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. B. 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, 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, n-propyl, isopropyl, n-butyl, sec-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 cyclyl with C ₃ to C ₂₀ .
• c) The group -OR ¹² , in which R ^{12 is} hydrogen, alkyl, aryl, for example naphthyl or in particular unsubstituted phenyl, C ₃ to C ₂₄ -cycloalkyl, preferably C ₅ -, C ₆ -, C ₁₂ , C ₁₅ -, C ₁₆ -, C ₂₀ -, and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular unsubstituted or substituted by halogen, alkyl or -O-alkyl phenyl. In the definitions R ¹³ occurring alkyl z. B. have one of the number b) given as preferred number of carbon atoms. Examples of R ¹³ are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, trifluorethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, benzyl -, m- or p-chlorophenyl, o-, m-, or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl.
• d) The cyano group.
• e) 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, n-propylamino, di-n-propylamino, isopropylamino, n-butylamino, di-n-butylamino, sec-butylamino, di-sec-butylamino, tert- Butylamino, tert-amylamino, n-hexylamino, di-n-hexylamino, 1,1,3,3, -tetramethylbutylamino, n-heptylamino, di-n-heptylamino, n-octylamino, di-n-octylamino, n-nonyl , Di-n-nonylamino, n-decylamino, di-n-decylamino, n-undecylamino, di-n-undecylamino, n-dodecylamino, di-ndodecylamino, n-octadecylamino, 1-ethylpropylamino, 1-propylbutylamino, 1-butylpentyl , 1-pentylhexylamino, 1-hexylheptylamino, 1-heptyloctylamino, 1-octylnonylamino, 1-nonyldecylamino, 1-decylundecylamino, 1-ethylbutylamino, 1-ethylpentylamino, 1-ethylheptylamino, 1-ethylymethylethylamino, 2-hydroxymononethylamino, 1-hydroxymethylethyl, amino , N-bis (2-hydroxyethyl) amino, trifluoromethylamino, trifluoroethylamino, cyanomethylamino, methoxycarbonylmethylamino, acetoxymethylamino, benzylamino, dibenzylamino, Ph enylamino, diphenylamino, o-, m- or p-chlorophenylamino, o-, m- or p-methylphenylamino, 1- or 2-naphthylamino, cyclopentylamino, cyclohexylamino, cyclododecylamino, cyclopentadecylamino, cyclohexadecylamino, cycloeicotanyamylamino, cycloeicotanyamylamino Piperidyl or morpholyl.
• f) The group of the formula -COR ¹⁵ , in which R ^{15 has} the meaning given under a). Examples of R ¹⁵ are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, trifluoroethyl, cyanomethyl, methoxycarbonymmethyl, acetyl Benzyl phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl, benzyl or furfuryl.
• g) 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, n-propyl, isopropyl, n-butyl, sec-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, trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl, benzyl, phenyl, o-, m- or p-chlorophenyl, o-, m-, or p-methylphenyl, 1- or 2- Naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, cycloeicosanyl, cyclotetracosanyl, thienyl or pyranylmethyl or furftryl. In the definitions of R ¹⁶ occurring alkyl z. B. have one of the number of carbon atoms indicated preferably under b). Examples include: acetylamino, propionylamino, butyrylamino, benzoylamino, p-chlorobenzoylamino, p-methylbenzoylamino, N-methylacetamino, N-methylbenzoylamino, N-succinimido, N-phthalimido or N- (4-amino) phthalimido.
• h) 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 include the groups -NHCOOCH ₃ , -NHCOOC ₂ H ₅ , or - NHCOOC ₆ H ₅ .
• i) 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, N-phenylureido, or N, N'-2 ', 4'-dimethylphenylureido.
• j) The group of the formula -NHSO ₂ R ²³ , in which R ^{23 has} the meaning given under b). Examples include: methylsulfonylamino, phenylsulfonylamino, p-tolylsulfonylamino or 2-naphthylsulfonylamino.
• k) The groups of the formula -SO ₂ R ²⁴ or -SOR ²⁵ , wherein R ²⁴ or R ^{25 have} the meaning given under b). Examples include: methylsulfonyl, ethylsulfonyl, phenylsulfonyl, 2-naphthylsulfonyl, phenylsulfoxidyl.
• l) The group of the formula -SO ₂₀ R ²⁶ , wherein R ^{26 has} the meaning given under b). Examples of R ²⁷ are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl.
• m) The group of the formula -CON (R ²⁷ ) (R ²⁸ ), in which R ²⁷ and R ^{28 have} the meaning given under b). Examples include: carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-phenylcarbamoyl, N, N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-1-naphthylcarbamoyl or N-piperdylcarbamoyl.
• n) The group of the formula -SO ₂ N (R ²⁹ ) (R ³⁰ ), in which R ²⁹ and R ^{30 have} the meaning given under b). Examples include: sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsulfamoyl or N-morpholylsulfamoyl.
• o) The group of the formula -N = NR ³¹ , in which R ^{31 is} the residue of a coupling component or a phenyl radical which is optionally substituted by halogen, alkyl or -O-alkyl. Alkyl occurring in the definitions of R31 can e.g. B. have one of the number b) given as preferred number of carbon atoms. The following may be mentioned as examples of R ³¹ : the acetoacetarylide, pyrazolyl, pyridonyl, o-, p-hydroxyphenyl, o-hydroxynaphthyl, p-aminophenyl or p-N, N-dimethylaminophenyl radicals.
• p) 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 p-chlorophenyl.
• q) 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 p-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 , wherein 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, C ₃ - to C ₂₄ -cycloalkyl , preferably C ₅ -, C ₆ -, C ₁₂ -, C ₁₅ -, C ₁₆ -, C ₂₀ - and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular unsubstituted or substituted by halogen, alkyl or -O-alkyl phenyl , or wherein R ³⁷ and R ³⁸ together with one of the other radicals R ³⁴ to R ^{39 form} a 5-6 member 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. B. 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, n-propyl, isopropyl, n-butyl, sec-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 cyclyl 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, C ₃ to C ₂₄ -cycloalkyl, preferably C ₅ -, C ₆ -, C ₁₂ , C ₁₅ - C ₁₆ - , C ₂₀ -, and C ₂₄ -cycloalkyl, aryl or heteroaryl, in particular unsubstituted or substituted by halogen, alkyl or -O-alkyl phenyl. In the definitions of R ⁴⁰ occurring alkyl z. B. have one of the number b) given as preferred number of carbon atoms. Examples of R ⁴⁰ include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, Cycloeicosanyl, Cyclotetracosanyl, Thienyl or Pyranylmethyl.
  • d) The cyano group.
  • e) 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, n-propylamino, di-n-propylamino, isopropylamino, n-butylamino, di-n-butylamino, sec-butylamino, di-sec-butylamino, tert-butylamino , tert-amylamino, n-hexylamino, di-n-hexylamino, 1,1,3,3, -tetramethylbutylamino, n-heptylamino, di-n-heptylamino, n-octylamino, di-n-octylamino, n-nonyl, Di-n-nonylamino, n-decylamino, di-n-decylamino, n-undecylamino, di-n-undecylamino, n-dodecylamino, di-ndodecylamino, n-octadecylamino, 1-ethylpropylamino, 1-propylbutylamino, 1-butylpentylam 1-pentylhexylamino, 1-hexylheptylamino, 1-heptyloctylamino, 1-octylnonylamino, 1-nonyldecylamino, 1-decylundecylamino, 1-ethylbutylamino, 1-ethylpentylamino, 1-ethylheptylamino, 1-ethylnethylethylamino, hydroxymonylamino, hydroxymonylamino, hydroxymethyl N-bis (2-hydroxyethyl) amino, trifluoromethylamino, trifluoroethylamino, cyanomethylamino, methoxycarbonylmethylamino, acetoxymethylamino, benzylamino, dibenzylamino, Phe nylamino, diphenylamino, o-, m- or p-chlorophenylamino, o-, m- or p-methylphenylamino, 1- or 2-naphthylamino, cyclopentylamino, cyclohexylamino, cyclododecylamino, cyclopentadecylamino, cyclohexadecylamino, cycloeicotanyamylamino, cycloeicotanyl amyl Piperidyl or morpholyl
  • f) The group of the formula -COR ⁴³ , wherein R ^{43 has} the meaning given under a). Examples of R ⁴³ are: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-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, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl, cyclopentyl, cyclohexyl, cyclododecyl, cyclopentadecyl, cyclohexadecyl, Cycloeicosanyl, Cyclotetracosanyl, Thienyl, Pyranylmethyl, Benzyl or Furfuryl.
  • g) 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, n-propyl, isopropyl, n-butyl, sec-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 -Ethylnonyl, hydroxymethyl, 2-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, cyanomethyl, methoxycarbonylmethyl, acetoxymethyl or benzyl or cycloalkyl with C ₃ to C ₂₀ , phenyl, especially unsubstituted or substituted by halogen, alkyl or -O-alkyl Phenyl, for example o-, m- or p-chlorophenyl, o-, m- or p-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 e.g. B. have one of the preferred number given under b) number of carbon atoms. Examples include: acetylamino, propionylamino, butyrylamino, benzoylamino, p-chlorobenzoylamino, p-methylbenzoylamino, N-methylacetamino, N-methylbenzoylamino, N-succinimido, N-phthalimido or N- (4-amino) phthalimido.
  • h) The group of the formula -N (R ⁴⁶ ) COOR ⁴⁷ , wherein R ⁴⁶ and R ^{47 have} the meaning given under b) and c). Examples include the groups -NHCOOCH ₃ , -NHCOOC ₂ H ₅ , or - NHCOOC ₆ H ₅ .
  • i) The group of the formula -N (R ⁴⁸ ) CON (R ⁴⁹ ) (R ⁵⁰ ) wherein R ⁴⁸ , R ⁴⁹ and R ^{50 have} the meaning given under b) or c). Examples include: ureido, N-methylureido, N-phenylureido, or N, N'-2 ', 4'-dimethylphenylureido.
  • j) The group of the formula -NHSO ₂ R ⁵¹ , wherein R ^{51 has} the meaning given under b). Examples include: methylsulfonylamino, phenylsulfonylamino, p-tolylsulfonylamino or 2-naphthylsulfonylamino
  • k) 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.
  • l) The group of the formula -SO ₂ OR ⁵⁴ , wherein R ^{54 has} the meaning given under b). Examples of R ⁵⁴ are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl, o-, m- or p-methylphenyl, 1- or 2-naphthyl.
  • m) The group of the formula -CON (R ⁵⁵ ) (R ⁵⁶ ), wherein R ⁵⁵ and R ^{56 have} the meaning given under b). Examples include: carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl, N-phenylcarbamoyl, N, N-dimethylcarbamoyl, N-methyl-N-phenylcarbamoyl, N-1-naphthylcarbamoyl or N-piperdylcarbamoyl.
  • n) The group of the formula -SO ₂ N (R ⁵⁷ ) (R ⁵⁸ ), in which R ⁵⁷ and R ^{58 have} the meaning given under b). Examples include: sulfamoyl, N-methylsulfamoyl, N-ethylsulfamoyl, N-phenylsulfamoyl, N-methyl-N-phenylsulfamoyl or N-morpholylsulfamoyl.
  • o) The group of the formula -N = NR ⁵⁹ , in which R ^{59 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 ⁵⁹ can e.g. B. have one of the number b) given as preferred number of carbon atoms. The following may be mentioned as examples of R ⁵⁹ : the acetoacetarylide, pyrazolyl, pyridonyl, o-, p-hydroxyphenyl, o-hydroxynaphthyl, p-aminophenyl or p-N, N-dimethylaminophenyl radicals.
  • p) The group of the formula -OCOR ⁶⁰ , wherein R ^{60 has} the meaning given under b). Examples of R ⁶⁰ are: methyl, ethyl, phenyl, o-, m- or p-chlorophenyl.
  • q) 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 p-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 residue is the (3,4,5,6-tetraphenylphthalimidyl) residue. 8. Use of voluminous aliphatic radicals according to 4 with the general formula II,
in which R ¹ to R ^{3 are} hydrogen or one to 3 of the radicals mentioned under 5. 9. Use of voluminous aliphatic radicals according to 4 with the general formula III,
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,
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 IV,
in which x and y can be the same or different and are under 5 to 10 aggregation-preventing radicals or in x is one of the aggregation-preventing radicals mentioned under 5 to 10 and y is a solubility-increasing group, such as. B. 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.
Preferred examples are x = y = p-triphenylmethyl, bis (2- (1-propylbutyl) -3-propyl-hexyl), N, N'-bis (-2- (1-butylpentyl) -3-butylheptyl) and bis (2- (1-pentylhexyl) -3-pentyl-octyl) or x = p-triphenylmethyl, bis (2- (1-propylbutyl) -3-propyl-hexyl), N, N'-bis (-2- ( 1-butylpentyl) -3 - butylheptyl) or bis (2- (1-pentylhexyl) -3-pentyloctyl) - 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
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. Use 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 of 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 mentioned monomers. 16. Application of the dyes of 11 and 12 as vat dyes, e.g. B. 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 (e.g. horsehair) and their Conversion products such as B. the viscose fiber, nitrate silk or copper rayon (rayon). 17. Application of the dyes of 11 and 12 as stain dyes, for. B. 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 (e.g. horsehair) and their Conversion products such as B. the viscose fiber, nitrate silk or copper rayon (rayon). Preferred salts for pickling are aluminum, chromium and iron salts. 18. Application of the dyes of 11 and 12 as colorants, eg. B. for coloring colors, Varnishes and other paints, paper colors, printing inks, inks and other colors for Painting and writing purposes. 19. Application of the dyes of 11 and 12 as pigment dyes, for. B. for coloring Paints, varnishes and other paints, paper paints, printing inks, inks and others Colors for painting and writing purposes. 20. Application of the dyes of 11 and 12 as pigments in electrophotography: z. B. for dry copy systems (Xerox process) and laser printers ("non-impact printing"). 21. Application 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 matter. This is preferred for checks, check cards, banknotes Coupons, documents, identity documents and the like, for which a special, unmistakable color impression should be achieved. 22. application of the dyes of 11 and 12 to be used as an additive to other colors, in which a certain color shade is to be achieved, particularly bright ones are preferred Shades. 23. Use of the dyes of 11 and 12 for marking objects for machine detection of these objects over the fluorescence used, preferred is the automatic detection of objects for sorting, e.g. B. also for recycling of plastics. 24. Use of the dyes of 11 and 12 as fluorescent dyes for machine-readable Markings are used, preferably alphanumeric imprints or barcodes. 25. Application of the dyes of 11 and 12 used for frequency conversion of light be, e.g. B. 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, Notification and marking purposes, e.g. B. passive display elements, information and Traffic signs, such as traffic lights. 27. Application of the dyes of 11 and 12 in inkjet printers, preferably in 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. Application of the dyes of 11 and 12 for tracer purposes, e.g. B. in biochemistry, Medicine, technology and science. The dyes can be covalently bonded to substrates linked 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 method (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 Fluorescence 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 display of plastics. 39. Application of the dyes of 11 and 12 as dyes or fluorescent dyes for Material testing, e.g. B. in the manufacture of semiconductor circuits. 40. Application of the dyes of 11 and 12 as dyes or fluorescent dyes for 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 1 I and 12 as dyes or fluorescent dyes in photographic process. 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 by electrons, Ion or UV radiation takes place, e.g. B. 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 that uses dyes as such or in combination with other semiconductors e.g. B. in the form of an epitaxy. 45. Application of the dyes of 11 and 12 as dyes or fluorescent dyes in Chemiluminescent systems, e.g. B. in chemiluminescent light sticks, in Lu minescence immunoassays or other luminescence detection methods. 46. Application 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 labeling signs and other objects, where a special optical 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. Application of the dyes of 11 and 12 as dyes in dye lasers as Q-switches Switch.   50. Use of the dyes of 11 and 12 as active substances for a nonlinear Optics, e.g. B. for frequency doubling and frequency tripling of laser light. 51. Use of the dyes of 11 and 12 as rheology improvers.