Claims
- 1. A perylene-3,4:9,10-tetracarboxylic diirnide of the formula I whereR1, R2, R3 and R4 are independently hydrogen, chlorine, bromine or substituted or unsubstituted aryloxy, arylthio, arylamino, heteraryloxy or hetarylthio; R5, R6, R7 R8, R9 and R10 are independently hydrogen, or C8-20-alkyl, C8-C20-alkoxy or C8-C20-alkylthio whose carbon chain may in each case contain up to four double bonds, with the proviso that at least four of these radicals are not hydrogen.
- 2. The perylene-3,4:9,10-tetracarboxylic diimide as claimed in claim 1 of formula I whereR1, R2, R3 and R4 are independently hydrogen, chlorine, bromine or phenoxy which may be substituted by up to three of the following substituents: C1-C20-alkyl whose carbon chain may be interrupted by one or more moieties selected from the group consisting of —O—, —S—, —NR11—, —CO— and —SO2— and/or which may be substituted by one or more substituents selected from the group consisting of —COOR11, —SO3R11, hydroxyl, cyano, C1-C6-alkoxy, C5-C8-cycloalkyl and a 5- to 7-membered, nitrogen containing heterocyclic radical which is attached by a nitrogen atom and which may contain another heteroatom; C1-C6-alkoxy; cyano; hydroxyl; halogen; nitro, —COOR11 or —SO3R11; R5, R6, R7 R8, R9 and R10 are independently C8-C20-alkyl, C8-C20-alkoxy or C8-C20-alkylthio whose carbon chain may in each case contain up to four double bonds; and R11 is hydrogen or C1-C6-alkyl.
- 3. The perylene-3,4:9,10-tetracarboxylic diimide as claimed in claim 1 of formula I whereR1, R2, R3 and R4 are independently hydrogen or phenoxy which may be monosubstituted by C1-C8-alkyl; and R5, R6, R7 R8, R9 and R10 are each C10-C14-alkyl.
- 4. A process for preparing a perylene-3,4:9,10-tetracarboxylic diimide of the formula I as set forth in claim 1, which comprises reacting a perylene-3,4:9,10-tetracarboxylic dianhydride of formula II with identical or different primary amines of formulae III wherein R1-R10 are as defined in claim 1 in the presence of a polar aprotic solvent and of an imidation catalyst.
- 5. A process for preparing a perylene-3,4:9,10-tetracarboxylic diimide of claim 1 having the structure ot formula Ia where Ar is substituted or unsubstituted atyloxy, arylthio, heteraryloxy or hetarylthio and R5-R6 are as defined in claim 1, which comprises:reacting 1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic dianhydride (IIa) with identical or different primary amines of formulae III in the presence of a polar aprotic solvent and of an imidation catalyst; andreacting the resultant 1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic diimide of formula I′with an aromatic alcohol or thioalcohol of formula IVH—Ar in the presence of an inert aprotic solvent and of a non-nucleophilic or only minimally nucleophilic base.
- 6. A process for preparing a perylene-3,4:9,10-tetracarboxylic diimide of claim 1 having the structure ot formula Ib where Ar is substituted or unsubstituted aryloxy, arylthio, heteraryloxy or hetarylthio and R5-R6 are as defined in claim 1, which comprises:reacting 1,7-dibromoperylene-3,4:9,10-tetracarboxylic dianhydride (IIb) with identical or different primary amines of formulae III in the presence of a polar aprotic solvent and of an imidation catalyst; andreacting the resultant 1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide of formula I′, with an aromatic alcohol or thioalcohol of formula IVH—Ar in the presence of an inert aprotic solvent and of a non-nucleophilic or only minimally nucleophilic base.
- 7. The perylene-3,4:9,10-tetracarboxylic diimide as claimed in claim 2 of formula I wherein said 5- to 7-membered nitrogen containing heterocyclic radical is morpholinyl, pyrrolidinyl or piperidyl.
- 8. The perylene-3,4:9,10-tetracarboxylic diimide as claimed in claim 2 wherein for groups R1, R2, R3 and R4; said aryloxy is phenoxy or 2-naphthyloxy, said arylthio is phenylthio or 2-naphthylthio, said arylamino is phenylamino, said hetaryloxy is 2-, 3- or 4-pyridyloxy or 2-, 4-, or 5-pyrimidyloxy and said hetarylthio is 2-, 3- or 4-pyridylthio or 2-, 4-, or 5-pyrimidylthio.
- 9. The process according to claim 4, wherein the primary amine III is reacted with said perylene-3,4:9,10-tetracarboxylic dianhydride in a molar ratio of 2:1 to 4:1.
- 10. The process according to claim 5, wherein the primary amine III is reacted with said perylene-3,4:9,10-tetracarboxylic dianhydride in a molar ratio of 2:1 to 4:1.
- 11. The process according to claim 6, wherein the primary amine III is reacted with said perylene-3,4:9,10-tetracarboxylic dianhydride in a molar ratio of 2:1 to 4:1.
- 12. The process according to claim 4, wherein the imidation catalyst is a Lewis acid salt of an organic or inorganic acid with a metal selected from the group consisting of zinc, iron, copper and magnesium or is an oxide of one of these metals.
- 13. The process according to claim 5, wherein the imidation catalyst is a Lewis acid salt of an organic or inorganic acid with a metal selected from the group consisting of zinc, iron, copper and magnesium or is an oxide of one of these metals.
- 14. The process according to claim 6, wherein the imidation catalyst is a Lewis acid salt of an organic or inorganic acid with a metal selected from the group consisting of zinc, iron, copper and magnesium or is an oxide of one of these metals.
Priority Claims (1)
Number |
Date |
Country |
Kind |
100 39 232 |
Aug 2000 |
DE |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a 371 of PCT/EP01/08524 filed Jul. 24, 2001 which is based on German priority application Serial No. 10039232.6 filed Aug. 11, 2000.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
PCT/EP01/08524 |
|
WO |
00 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO02/14318 |
2/21/2002 |
WO |
A |
US Referenced Citations (6)
Number |
Name |
Date |
Kind |
3294778 |
Randall et al. |
Dec 1966 |
A |
3554776 |
Gerson |
Jan 1971 |
A |
4378302 |
Aftergut et al. |
Mar 1983 |
A |
5151516 |
Beck et al. |
Sep 1992 |
A |
5677417 |
Muellen et al. |
Oct 1997 |
A |
6143905 |
Boehm et al. |
Nov 2000 |
A |
Foreign Referenced Citations (3)
Number |
Date |
Country |
3016764 |
Nov 1981 |
DE |
31 10 955 |
Sep 1982 |
DE |
196 20 746 |
Nov 1997 |
DE |
Non-Patent Literature Citations (3)
Entry |
F. Wuerthner et al.: “Fluorescent J-type aggregates and thermotropic columnar mesophases of perylene bisimide dyes” Chem. Eur. J., vol. 7, No. 10, pp. 2245-2253 May 10, 2001. |
R.A. Cormier et al.: “Synthesis and characterization of liquid crystalline perylene diimides” Chem. Mater., vol. 10, pp. 1309-1319 1998. |
Ulrike Rohr et al.: “Fluessigkristalline coronenderivate mit aussergewoehnlichen fluoreszenziegenschaften” Angew. Chem., vol. 110, No. 10, pp. 1463-1467 1998. |