B,B-diporphyrinbenzyloxy-BODIPY dyes: Synthesis and antenna effect

Journal of Organic Chemistry

Volumn 77, Issue 7, 2012, Pages 3646-3650

  Brizet, Bertrand ^a,b   Eggenspiller, Antoine ^a   Gros, Claude P ^a   Barbe, Jean Michel ^a   Goze, Christine ^a   Denat, Franck ^a   Harvey, Pierre D ^b  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTENNA EFFECTS; HIGH YIELD; PHOTOPHYSICAL PROPERTIES;

ENERGY TRANSFER;

PORPHYRINS;

PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENERGY TRANSFER; PHOTOCHEMISTRY; SYNTHESIS;

EID: 84859585028     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3000833     Document Type: Article

References (37)

1. Bozdemir, O. A.; Guliyev, R.; Buyukcakir, O.; Selcuk, S.; Kolemen, S.; Gulseren, G.; Nalbantoglu, T.; Boyaci, H.; Akkaya, E. U. J. Am. Chem. Soc. 2010, 132, 8029-8036
2. Barin, G.; Yilmaz, M. D.; Akkaya, E. U. Tetrahedron Lett. 2009, 50, 1738-1740
3. Benstead, M.; Mehl, G. H.; Boyle, R. W. Tetrahedron 2011, 67, 3573-3601
4. Coskun, A.; Akkaya, E. U. J. Am. Chem. Soc. 2005, 127, 10464-10465
5. Coskun, A.; Deniz, E.; Akkaya, E. U. Tetrahedron Lett. 2007, 48, 5359-5361
6. D'Souza, F.; Smith, P. M.; Zandler, M. E.; McCarty, A. L.; Itou, M.; Araki, Y.; Ito, O. J. Am. Chem. Soc. 2004, 126, 7898-7907
7. Dost, Z.; Atilgan, S.; Akkaya, E. U. Tetrahedron 2006, 62, 8484-8488
8. Gu, Z. Y.; Guo, D. S.; Sun, M.; Liu, Y. J. Org. Chem. 2010, 75, 3600-3607
9. Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57-69
10. Imahori, H.; Norieda, H.; Yamada, H.; Nishimura, Y.; Yamazaki, I.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 100-110
11. Koepf, M.; Trabolsi, A.; Elhabiri, M.; Wytko, J. A.; Paul, D.; Albrecht-Gary, A. M.; Weiss, J. Org. Lett. 2005, 7, 1279-1282
12. Kumaresan, D.; Agarwal, N.; Gupta, I.; Ravikanth, M. Tetrahedron 2002, 58, 5347-5356
13. Lee, C.-H.; Lindsey, J. S. Tetrahedron 1994, 50, 11427-11440
14. Lee, C. Y.; Hupp, J. T. Langmuir 2010, 26, 3760-3765
15. Lee, C. Y.; Jang, J. K.; Kim, C. H.; Jung, J.; Park, B. K.; Park, J.; Choi, W.; Han, Y.-K.; Joo, T.; Park, J. T. Chem.-Eur. J. 2010, 16, 5586-5599
16. Li, F.; Yang, S. I.; Ciringh, Y.; Seth, J.; Martin, C. H.; Singh, D. L.; Kim, D. H.; Birge, R. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Am. Chem. Soc. 1998, 120, 10001-10017
17. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891-4932
18. Maligaspe, E.; Tkachenko, N. V.; Subbaiyan, N. K.; Chitta, R.; Zandler, M. E.; Lemmetyinen, H.; D'Souza, F. J. Phys. Chem. A. 2009, 113, 8478-8489
19. Ulrich, G.; Ziessel, R.; Harriman, A. Angew. Chem., Int. Ed. 2008, 47, 1184-1201
20. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996-3997
21. Wijesinghe, C. A.; El-Khouly, M.; Subbaiyan, N. K.; Supur, M.; Zandler, M. E.; Ohkubo, K.; Fukuzumi, S.; D'Souza, F. Chem.-Eur. J. 2011, 17, 3147-3156
22. Wood, T. E.; Thompson, A. Chem. Rev. 2007, 107, 1831-1861
23. Zhang, X.; Xiao, Y.; Qian, X. H. Org. Lett. 2008, 10, 29-32
24. Bozdemir, O. A.; Erbas-Cakmak, S.; Ekiz, O. O.; Dana, A.; Akkaya, E. U. Angew. Chem., Int. Ed. 2011, 50, 10907-10912
25. Amin, A. N.; El-Khouly, M. E.; Subbaiyan, N. K.; Zandler, M. E.; Fukuzumi, S.; D'Souza, F. Chem. Commun. 2012, 48, 206-208
26. D'Souza, F.; Wijesinghe, C. A.; El-Khouly, M. E.; Hudson, J.; Niemi, M.; Lemmetyinen, H.; Tkachenko, N. V.; Zandlerb, M. E.; Fukuzumi, S. Phys. Chem. Chem. Phys. 2011, 13, 18168-18178
27. Gabe, Y.; Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. Anal. Bioanal. Chem. 2006, 386, 621-626
28. Tahtaoui, C.; Thomas, C.; Rohmer, F.; Klotz, P.; Duportail, G.; Mély, Y.; Bonnet, D.; Hibert, M. J. Org. Chem. 2007, 72, 269-272
29. Baumler, W.; Penzkofer, A. Chem. Phys. 1990, 140, 75-97
30. Schäfer, F. P. In Topics in Applied Physics: Structure and Properties of Laser Dyes; Springer-Verlag: Berlin, 1990; Vol. 1, Dye Lasers.
31. Harvey, P. D. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: Boston, 2003; Vol. 18, p 63.
32. Harvey, P. D.; Stern, C.; Guilard, R. In Handbook of Porphyrin Science With Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; World Scientific Publishing: Singapore, 2011; pp 1-179.
33. Förster, T. Naturwissenschaften 1946, 33, 166-175
34. Förster, T. Ann. Phys. 1948, 2, 55-73
35. Li, B.; Li, J.; Fu, Y.; Bo, Z. J. Am. Chem. Soc. 2004, 126, 3430-3431
36. Aly, S. M.; Ayed, C.; Stern, C.; Guilard, R.; Abd-El-Aziz, A. S.; Harvey, P. D. Inorg. Chem. 2008, 47, 9930-9940
37. Loutfy, R. O.; Law, K. Y. J. Phys. Chem. 1980, 84, 2803-2808