3,5-diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes: Synthesis, spectroscopic, electrochemical, and structural properties

Journal of Organic Chemistry

Volumn 64, Issue 21, 1999, Pages 7813-7819

  Burghart, Armin ^a   Kim, Heejin ^a   Welch, Mike B ^a   Thoresen, Lars H ^a   Reibenspies, Joe ^a   Burgess, Kevin ^a   Bergström, Fredrik ^b   Johansson, Lennart B Å ^b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b UMEÅ UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

DYE; INDACENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; FLUORESCENCE; QUANTUM MECHANICS; SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032740860     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990796o     Document Type: Article

References (30)

1. Treibs, A.; Kreuzer, F.-H. Liebigs Ann. Chem. 1968, 718, 208-23.
2. Karolin, J.; Johansson, L. B.-A.; Strandberg, L.; Ny, T. J. Am. Chem. Soc. 1994, 116, 7801-6.
3. Wagner, R. W.; Lindsey, J. S. Pure Appl. Chem. 1996, 68, 1373-80.
4. Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 6th ed.; Molecular Probes: Eugene, OR, 1996.
5. Thoresen, L. H.; Kim, H.; Welch, M. B.; Burghart, A.; Burgess, K. Synlett 1998, 1276-8.
6. Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 211, 314-21.
7. Sato, M.; Miyaura, N.; Suzuki, A. Chem. Lett. 1989, 1405-8.
8. Chen, W.; Cava, M. P. Tetrahedron Lett. 1987, 28, 6025-6026.
9. Chen, W.; Stephenson, E. K.; Cava, M. P.; Jackson, Y. A. Org. Synth. 1991, 70, 151-156.
10. Martina, S.; Schluter, A. D. Macromolecules 1992, 25, 3607-3608.
11. Hasan, I.; Marinelli, E. R.; Lin, L. C. C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157-164.
12. Trofimov, B. A. Adv. Heterocycl. Chem 1990, 51, 177-301.
13. Boukou-Poba, J. P.; Farnier, M.; Guilard, R. Tetrahedron Lett. 1979, 19, 1717-1720.
14. Katrizky, A. R.; Li, J.; Gordeev, M. F. Synthesis 1994, 93-96.
15. Thoresen, L. H.; Kim, H.; Burghart, A.; Gibbs, R. A.; Burgess, K. Unpublished results.
16. Birks, J. B. Photophysics in aromatic molecules; Wiley: New York, 1970.
17. Förster, T. Ann. Physik 1948, 2, 55-75.
18. Kollmannsberger, M.; Gareis, T.; Heinl, S.; Breu, J.; Daub, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1333-5.
19. Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2551-89.
20. Diaz, A. F. In Organic Electrochemistry; Lund, H., Baizer, M. M., Eds.; Marcel Dekker: New York, 1991.
21. Isgor, Y. G.; Akkaya, E. U. Tetrahedron Lett. 1997, 38, 7417-20.
22. Gust, D. Nature 1987, 386, 21-2.
23. Wagner, R. W.; Seth, J.; Yang, S. I.; Kim, D.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Org. Chem. 1998, 63, 5042-9.
24. Lipset, F. R. Prog. Dielectr. 1967, 7, 217.
25. Melhuish, W. H. J. Phys. Chem, 1960, 64, 762-4.
26. Weber, G.; Teale, F. W. J. Trans. Faraday Soc. 1968, 54, 640-8.
27. Drexhage, K. H. In Topics in Applied Physics; Schäfer, F. P., Ed., 1977; Vol. 1, pp 147-52, 171-2.
28. Langhals, H.; Karolin, J.; Johansson, L. B.-A. J. Chem. Soc., Faraday Trans. 1998, 94, 2919-22.
29. Sheldrick, G. M. In SHELX86 Program for Crystal Structure Determination; University of Gottingen, Federal Republic of Germany, 1986.
30. Sheldrick, G. M. University of Gottingen, Federal Republic of Germany, 1993.