Thiophene-fused phospholo[3,2-b]phospholes and their dichalcogenides: Synthesis and structure-photophysical properties relationships

Comptes Rendus Chimie

Volumn 13, Issue 8-9, 2010, Pages 1082-1090

  Fukazawa, Aiko ^a   Murai, Taka Aki ^a   Li, Liangchun ^a   Chen, Youming ^a   Yamaguchi, Shigehiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Chromophores; Conjugation; Cyclization; Fluorescence; Fused ring systems; Phosphorus

Indexed keywords

EID: 77956619174     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2010.04.021     Document Type: Article

References (59)

1. S. Yamaguchi, and K. Tamao Chem. Lett. 34 2005 2
2. M. Hissler, P. Dyer, and R. Réau Coord. Chem. Rev. 244 2003 1
3. A. Fukazawa, and S. Yamaguchi Chem. Asian J. 4 2009 1386
4. Recent reviews on phosphorus-containing π-conjugated materials:
5. T. Baumgartner, and R. Réau Chem. Rev. 106 2006 4681
6. F. Mathey Angew. Chem. Int. Ed. 42 2003 1578
7. Representative reviews on phospholes:
8. A.N. Hughes, C. Srivanavit, J. Heterocycl, and F. Mathey Chem. 7 1970 1
9. F. Mathey Chem. Rev. 88 1988 429
10. L.D. Quin, A.N. Huges, in: The Chemistry of Organophosphorus Compounds, ed. F.R. Hartley, Wiley, Chichester, 1990, vol. 1, pp. 295-384
11. L. Nyulászi Chem. Rev. 101 2001 1229
12. M. Hissler, C. Lescop, and R. Réau Pure Appl. Chem. 79 2007 201
13. Y. Matano, and H. Imahori Org. Biomol. Chem. 7 2009 1258
14. F. Mathey, F. Mercier, F. Nief, J. Fischer, and A. Mitschler J. Am. Chem. Soc. 104 1982 2077
15. M.-O. Bevierre, F. Mercier, L. Ricard, and F. Mathey Angew. Chem. Int. Ed. Engl. 29 1990 655
16. E. Deschamps, L. Ricard, and F. Mathey Angew. Chem. Int. Ed. Engl. 33 1994 1158
17. C. Hay, D.L. Vilain, V. Deborde, L. Toupet, and R. Réau Chem. Commun. 1999 345
18. C. Hay, C. Fischmeister, M. Hissler, L. Toupet, and R. Réau Angew. Chem. Int. Ed. 39 2000 1812
19. C. Hay, M. Hissler, C. Fischmeister, J. Rault-Berthelot, L. Toupet, L. Nyulászi, and R. Réau Chem. Eur. J. 7 2001 4222
20. C. Fave, T.-Y. Cho, M. Hissler, C.-W. Chen, T.-Y. Luh, C.-C. Wu, and R. Réau J. Am. Chem. Soc. 125 2003 9254
21. C. Hay, C. Fave, M. Hissler, J. Rault-Berthelot, and R. Réau Org. Lett. 5 2003 3467
22. C. Fave, M. Hissler, T. Kárpáti, J. Rault-Berthelot, V. Deborde, L. Toupet, L. Nyulászi, and R. Réau J. Am. Chem. Soc. 126 2004 6058
23. H.-C. Su, O. Fadhel, C.-J. Yang, T.-Y. Cho, C. Fave, M. Hissler, C.-C. Wu, and R. Réau J. Am. Chem. Soc. 128 2006 983
24. M. Sebastian, M. Hissler, C. Fave, J. Rault-Berthelot, C. Odin, and R. Réau Angew. Chem. Int. Ed. 45 2006 6152
25. S.S.H. Mao, and T.D. Tilley Macromolecules 30 1997 5566
26. Y. Morisaki, Y. Aiki, and Y. Chujo Macromolecules 36 2003 2594
27. Y. Matano, T. Nakabuchi, T. Miyajima, H. Imahori, and H. Nakano Org. Lett. 8 2006 5713
28. Y. Matano, T. Miyajima, T. Nakabuchi, H. Imahori, N. Ochi, and S. Sakaki J. Am. Chem. Soc. 128 2006 11760
29. Y. Matano, T. Miyajima, N. Ochi, T. Nakabuchi, M. Shiro, Y. Nakao, S. Sakaki, H. Imahori, J. Am. Chem. Soc. 130 (2008) 130, 990;
30. Y. Matano, M. Nakashima, T. Nakabuchi, H. Imahori, S. Fujishige, and H. Nakano Org. Lett. 10 2008 553
31. Y. Matano, T. Nakabuchi, S. Fujishige, H. Nakano, and H. Imahori J. Am. Chem. Soc. 130 2008 16446
32. T. Sanji, K. Shiraishi, and M. Tanaka Org. Lett. 9 2007 3611
33. Y. Makioka, T. Hayashi, and M. Tanaka Chem. Lett. 33 2004 44
34. R.-F. Chen, R. Zhu, Q.-L. Fan, and W. Huang Org. Lett. 10 2008 2913
35. T. Baumgartner, T. Neumann, and B. Wirges Angew. Chem. Int. Ed. 43 2004 6197
36. T. Baumgartner, W. Bergmans, T. Kárpáti, T. Neumann, M. Nieger, and L. Nyuláski Chem. Eur. J. 11 2005 4867
37. T. Neumann, Y. Dienes, and T. Baumgartner Org. Lett. 8 2006 495
38. S. Durben, Y. Dienes, and T. Baumgartner Org. Lett. 8 2006 5893
39. Y. Dienes, S. Durben, T. Kárpáti, T. Neumann, U. Englert, L. Nyuláski, and T. Baumgartner Chem. Eur. J. 13 2007 7487
40. Y. Dienes, U. Englert, and T. Baumgartner Z. Anorg. Alleg. Chem. 635 2009 238
41. Y. Ren, Y. Dienes, S. Hettel, M. Parvez, B. Hoge, and T. Baumgartner Organometallics 28 2009 734
42. H. Tsuji, K. Sato, L. Ilies, Y. Itoh, Y. Sato, and E. Nakamura Org. Lett. 10 2008 2263
43. H. Tsuji, K. Sato, Y. Sato, and E. Nakamura J. Mater. Chem. 19 2009 3364
44. T. Sanji, K. Shiraishi, and M. Tanaka Org. Lett. 10 2008 2689
45. A. Fukazawa, Y. Ichihashi, Y. Kosaka, and S. Yamaguchi Chem. Asian J. 4 2009 1729
46. T. Miyajima, Y. Matano, and H. Imahori Eur. J. Org. Chem. 2008 255
47. Y. Matano, T. Miyajima, T. Fukushima, H. Kaji, Y. Kimura, and H. Imahori Chem. Eur. J. 14 2008 8102
48. A. Saito, T. Miyajima, T. Nakashima, T. Fukushima, H. Kaji, Y. Matano, and H. Imahori Chem. Eur. J. 15 2009 10000
49. A. Fukazawa, M. Hara, T. Okamoto, E.-C. Son, C. Xu, K. Tamao, and S. Yamaguchi Org. Lett. 10 2008 913
50. R.C. Smith, and J.D. Protasiewicz Dalton Trans. 2003 4738
51. S. Yamaguchi, S. Akiyama, and K. Tamao J. Organomet. Chem. 646 2002 277
52. K. Akasaka, T. Suzuki, H. Ohrui, and H. Meguro Anal. Lett. 20 1987 731
53. J. Bourson, and L. Oliveros Phosphorus Sulfur 26 1986 75
54. N.A. Rozenalskaya, A.I. Bakanov, B.M. Uzhinov, and B.I. Stepanov J. Gen. Chem. USSR 45 1975 263
55. M. Pañkowski, W. Chodkiewicz, and M.-P. Simonnin Inorg. Chem. 24 1985 533
56. A. Fukazawa, H. Yamada, and S. Yamaguchi Angew. Chem. Int. Ed. 47 2008 5582
57. A. Altomare, G. Cascarano, C. Giacovazzo, A. Gualiardi, A. G. G. Moliterni, M. C. Burla, G. Polidori, M. Camalli, R. Spagna, SIR 97, 1997.
58. G.M. Sheldrick SHELX-97, Program for the Refinement of Crystal Structures 1997 University of Gottingen Gottingen, Germany
59. Gaussian 03 (Revision C.02), M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Pittsburgh, PA (2004).