Novel fluorescent dyes by the extension of the core of perylenetetracarboxylic bisimides

European Journal of Organic Chemistry

Volumn , Issue 2, 2000, Pages 365-380

  Langhals, Heinz ^a   Kirner, Susanne ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Fluorescent dyes; Heterocycles; NIR dyes; Perylenes

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; FLUORESCENT DYE; IMIDE;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NITRATION; REDUCTION; SPECTRAL SENSITIVITY;

EID: 0033966961     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200001)2000:2<365::aid-ejoc365>3.0.co;2-r     Document Type: Article

References (34)

1. H. Langhals, Heterocycles 1995, 40, 477-500.
2. H. Langhals, D.O.S. 3016764 (April 30, 1980); Chem. Abstr. 1982, 96, P70417x.
3. H. Langhals, S. Demmig, T. Potrawa, J. Prakt. Chem. 1991, 333, 733-748.
4. U. Rohr, P. Schlichtling, A. Böhm, M. Groß, K. Merholz, C. Bräuchle, K. Müllen, Angew. Chem. 1998, 110, 1463-1467; Angew. Chem. Int. Ed. 1998, 37, 1434-1437.
5. U. Rohr, P. Schlichtling, A. Böhm, M. Groß, K. Merholz, C. Bräuchle, K. Müllen, Angew. Chem. 1998, 110, 1463-1467; Angew. Chem. Int. Ed. 1998, 37, 1434-1437.
6. H. Langhals, S. Grundner, Chem. Ber. 1986, 119, 2373-2376.
7. H. Langhals, L. Feiler, Liebigs Ann. 1996, 1587-1591.
8. E. Clar, M. Zander, J. Chem. Soc. 1957, 4616-4625.
9. H. Hopff, H. R. Schweizer, Helv. Chim. Acta 1959, 42, 2315-2333.
10. V. I. Rogovik, Zh. Org. Khim. 1974, 10, 1072-1075; J. Org. Chem. USSR (Engl. Transl.) 1974, 10, 1084-1087.
11. V. I. Rogovik, Zh. Org. Khim. 1974, 10, 1072-1075; J. Org. Chem. USSR (Engl. Transl.) 1974, 10, 1084-1087.
12. R. C. Cookson, S. S. H. Gilani, J. D. R. Stevens, J. Chem. Soc. C 1967, 1905-1909.
13. J. Sauer, B. Schröder, Chem. Ber. 1967, 100, 678-684.
14. M. Zander, Chem. Ber. 1974, 107, 1406-1408.
15. M. Zander, Chem.-Ztg. 1975, 99, 92-93.
16. W. Seidenfaden, D. Pawellek, D. Houben-Weyl, Methoden der Org. Chem. (Houben-Weyl) 4. Aufl. 1971, vol. 10/1, p. 488.
17. V. I. Rogovik, E. I. Shirokii, A. V. El'tsov, Zh. Org. Khim. 1980, 16, 867-872; J. Org. Chem. USSR (Enlg. Transl.) 1980, 16, 762-766.
18. V. I. Rogovik, E. I. Shirokii, A. V. El'tsov, Zh. Org. Khim. 1980, 16, 867-872; J. Org. Chem. USSR (Enlg. Transl.) 1980, 16, 762-766.
19. J. I. G. Cadogan, M. Cameron-Wood, Proc. Chem. Soc. 1962, 361.
20. L. Feiler, H. Langhals, K. Polborn, Liebigs Ann. 1995, 1229-1244.
21. I. D. Entwistle, A. E. Jackson, R. A. W. Johnstone, R. T. Telford, J. Chem. Soc., Perkin Trans. 1 1977, 443-444.
22. N. A. Cortese, R. F. Heck, J. Org. Chem. 1977, 42, 3491-3494.
23. H. Kaiser, J. Lindner, H. Langhals, Chem. Ber. 1991, 124, 529-535.
24. T. I. Solomentseva, V. I. Rogovik, T. A. Chibisova, V. F. Traven', B. I. Stepanov, Zh. Org. Khim. 1986, 22, 1050-1054; J. Org. Chem. USSR (Engl. Transl.) 1986, 22, 943-946.
25. T. I. Solomentseva, V. I. Rogovik, T. A. Chibisova, V. F. Traven', B. I. Stepanov, Zh. Org. Khim. 1986, 22, 1050-1054; J. Org. Chem. USSR (Engl. Transl.) 1986, 22, 943-946.
26. Free perylene-3,4:9,10-tetracarboxylic acid and its derivatives, have been reported for this synthesis. It is more probable that a ring closure to bis(anhydrides) proceeded under the reaction conditions because of the instability of the free acid; compare ref.[1]
27. H. Langhals, J. Karolin, L. B.-Å. Johansson, J. Chem. Soc., Faraday Trans. 1998, 94, 2919-2922.
28. J. Moser, M. Grätzel, J. Am. Chem. Soc. 1984, 106, 6557-6564.
29. O. Enea, J. Moser, M. Grätzel, J. Electroanal. Chem. 1989, 259, 59-65.
30. S. Ruile, Ph. D. Thesis, EPF Lausanne, 1997.
31. R. Borsdorf, H.-J. Hofmann, H.-J. Köhler, M. Scholz, J. Fabian, Tetrahedron 1970, 26, 3227-3231.
32. W. Schroth, H. Langguth, F. Billig, Z. Chem. 1965, 5, 353-354.
33. A. Y. Zheltov, V. Y. Rodinov, B. I. Stepanov, Zh. Org. Khim. 1975, 11, 1304-1311; J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 1288-1294.
34. A. Y. Zheltov, V. Y. Rodinov, B. I. Stepanov, Zh. Org. Khim. 1975, 11, 1304-1311; J. Org. Chem. USSR (Engl. Transl.) 1975, 11, 1288-1294.