Design, synthesis, and spectral luminescent properties of a novel polycarbocyanine series based on the 2,2-difluoro-1,3,2-dioxaborine nucleus

European Journal of Organic Chemistry

Volumn , Issue 9, 2008, Pages 1550-1558

  Zyabrev, Konstantin ^a   Doroshenko, Andrey ^b   Mikitenko, Elena ^a   Slominskii, Yurii ^a   Tolmachev, Alexei ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^b V N KARAZIN KHARKIV NATIONAL UNIVERSITY   (Ukraine)

Author keywords

Ab initio calculations; Absorption; Dioxaborine; Fluorescence; Polymethine dye

Indexed keywords

EID: 53849097347     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701012     Document Type: Article

References (34)

1. J. A. VanAllen, G. A. Reynolds, J. Heterocycl. Chem. 1969, 6, 29-35.
2. V. S. Markin, P. I. Abramenko, I. I. Boiko, Zh. Vses. Khim. Obshch. Im. D. I. Mendeleeva 1984, 29, 457-459 (in Russian).
3. D. S. Daniel, D. W. Heseltine (Eastman Kodak Company), US 3567439, 1971.
4. H. Depoorter, J. R. Schellekens (Agfa-Gevaert), UK 1353905, 1974.
5. S. Beckmann, R. Sens, G. Wagenblast, H. Hartmann, G. Goerlitz (BASF AG), DE 19532828, 1996.
6. M. Halik, H. Hartmann, Chem. Eur. J. 1999, 5, 2511-2517.
7. R. Kammler, G. Bourhill, Y. Jin, C. Brauchle, G. Gorlitz, H. Hartmann, J. Chem. Soc. Faraday Trans. 1996, 92, 945-947.
8. J. M. Hales, S. Zheng, S. Barlow, S. R. Marder, J. W. Perry, J. Am. Chem. Soc. 2006, 128, 11362-11363.
9. N. M. D. Brown, P. Blandon, J. Chem. Soc. A 1969, 527-532.
10. G. Gorlitz, H. Hartmann, J. Kossanyi, P. Valan, V. Wintgens, Ber. Bunsenges. Phys. Chem. 1998, 102, 1449-1458.
11. P. Czerney, C. Igney, G. Hauke, H. Hartmann, Z. Chem. 1988, 28, 23-24.
12. K. V. Zyabrev, A. Ya. Il'chenko, Yu. L. Slominskii, N. N. Romanov, A. I. Tolmachev, Dyes Pigm. 2006, 71, 199-206.
13. M. Halik, W. Wenseleers, C. Grasso, F. Stellacci, E. Zojer, S. Barlow, J. L. Brédas, J. W. Perry, S. R. Marder, Chem. Commun. 2003, 1490-1491.
14. J. Fabian, H. Hartmann, J. Phys. Org. Chem. 2004, 17, 359-369.
15. B. Domercq, C. Grasso, J.-L. Maldonado, M. Halik, S. Barlow, S. R. Marder, B. Kippelen, J. Phys. Chem. B 2004, 108, 8647-8651.
16. N. Tyutyulkov, J. Fabian, A. Mehlhorn, F. Dietz, A. Tadjer, Polymethine Dyes. Structure and Properties, St. Kliment Ohridski Univ. Press, Sofia, 1991, pp. 67-68.
17. K. V. Zyabrev, A. Ya. Il'chenko, Yu. L. Slominskii, A. I. Tolmachev, Ukr. Khim. Zh. 2006, 72, 56-63 (in Russian).
18. C. Risko, E. Zojer, P. Brocorens, S. R. Marder, J. L. Brédas, Chem. Phys. 2005, 313, 151-157.
19. a) Th. Forster, Z. Phys. Chem. 1940, 48, 12-31;
20. b) M. J. S. Dewar, J. Chem. Soc. 1950, 2329-2334;
21. c) E. B. Knott, J. Chem. Soc. 1951, 1024-1028.
22. G. Gorlitz, H. Hartmann, B. Nuber, J. J. Wolff, J. Prakt. Chem. 1999, 341, 167-172.
23. a) R. S. Lepkowicz, O. V. Przhonska, J. M. Hales, J. Fu, E. W. van Stryland, M. V. Bondar, Yu. L. Slominskii, A. D. Kachkovskii, Chem. Phys. 2004, 305, 259-270;
24. b) J. Fu, L. A. Padilha, E. W. van Stryland, O. V. Przhonska, M. V. Bondar, Yu. L. Slominskii, A. D. Kachkovskii, J. Opt. Soc. Am. B 2007, 24, 56-66;
25. c) J. Fabian, J. Mol. Struct.: THEOCHEM. 2006, 766, 49-60;
26. d) A. B. Ryabitsky, A. D. Kachkovskii, O. V. Przhonska, J. Mol. Struct: THEOCHEM. 2007, 802, 75-83.
27. A. A. Ishchenko, N. A. Derevyanko, V. A. Svidro, Opt. Spektrosk. 1992, 72, 110-114 (in Russian).
28. A. A. Ishchenko, Structure and Spectral Luminescent Properties of Polymethine Dyes, Naukova Dumka, Kiev, 1994, p. 46 (in Russian).
29. A. I. Tolmachev, Yu. L. Slominskii, A. A. Ishchenko in Near-Infrared Dyes for High Technology Applications, NATO ASI Series, 3. High Technology, vol. 52 (Eds.: S. Daehne, U. Resch-Genger, O. S. Wolfbeis), Kluwer Academic Publishers, Dordrecht, Boston, London, 1998, pp. 385-415.
30. S. Fery-Forgues, D. Lavabre, J. Chem. Educ. 1999, 76, 1260-1264.
31. R. F. Kubin, A. N. Fletcher, J. Lumin. 1982, 27, 455-462.
32. R. Sens, K. H. Drexhage, J. Lumin. 1981, 24, 709-712.
33. J. X. Duggan, J. DiGesare, J. F. Williams in New Directions in Molecular Luminescence, ASTM Special Technical Publication, vol. 822 (Ed.: D. Eastwood), Philadelphia, PA, 1983, pp. 112-126.
34. D. B. Benfey, D. C. Brown, S. J. Davis, L. G. Piper, R. F. Foutter, Appl. Opt. 1992, 31, 7034-7038.