Synthesis and photochromism of two new 1,2-bis(thiazolyl) perfluorocyclopentenes with chelating sites

New Journal of Chemistry

Volumn 29, Issue 3, 2005, Pages 439-446

  Giraud, Marion ^a   Léaustic, Anne ^a   Charlot, Marie France ^a   Yu, Pei ^a   Césario, Michèle ^b   Philouze, Christian ^c   Pansu, Robert ^d   Nakatani, Keitaro ^d   Ishow, Eléna ^d  

^a UNIVERSITÉ PARIS SUD   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

^c UNIVERSITÉ JOSEPH FOURIER   (France)

^d UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS(THIAZOLYL)PERFLUOROCYCLOPENTENE DERIVATIVE; 1,2 BIS[4' METHYL 2' (2'' PYRIDYL)THIAZOLYL]PERFLUOROCYCLOPENTENE; 1,2 BIS[5' METHYL 2' (2'' PYRIDYL)THIAZOLYL]PERFLUOROCYCLOPENTENE; CYCLOPENTENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHELATION; COLOR; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; FLUORESCENCE; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; ULTRAVIOLET IRRADIATION;

EID: 15244343153     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b409274k     Document Type: Article

References (69)

1. (a) J. C. Crano and R. J. Guglielmetti, Organic Photochromic and Thermochromic Compounds, Plenum, New York, 1999;
2. (b) ed. M. Irie, Chem. Rev., 2000, 100, special issue.
3. M. Irie, Chem. Rev., 2000, 100, 1685.
4. G. M. Tsivgoulis and J. M. Lehn, Angew. Chem., Int. Ed. Engl., 1995, 34, 1119.
5. (a) M. Takeshita and M. Irie, Chem. Lett., 1998, 1123;
6. (b) M.-S. Kim, T. Kawai and M. Irie, Chem. Lett., 2001, 702;
7. (c) T. Kawai, T. Sasaki and M. Irie, Chem. Commun, 2001, 711;
8. (d) A. Osuka, D. Fujikane, H. Shinmori, S. Kobatake and M. Irie, J. Org. Chem., 2001, 66, 3913;
9. (e) K. Yagi, C. F. Soong and M. Irie, J. Org. Chem., 2001, 66, 5419;
10. (f) K. Yagi and M. Irie, Bull. Chem. Soc. Jpn., 2003, 76, 1625;
11. (g) T. Fukaminato, T. Kawai, S. Kobatake and M. Irie, J. Phys. Chem. B, 2003, 107, 8372.
12. J. Ern, A. T. Bens, H.-D. Martin, S. Mukamel, S. Tretiak, K. Tsyganenko, K. Kuldova, H. P. Trommsdorff and C. Kryschi, J. Phys. Chem. A, 2001, 105, 1741.
13. T. B. Norsten and N. R. Branda, J. Am. Chem. Soc., 2001, 123, 1784.
14. (a) T. Yoshida, K. Arishima, F. Ebisawa, M. Hoshino, K. Sukegawa, A. Ishikawa, T. Kobayashi, M. Hanazawa and Y. Horikawa, J. Photochem. Photobiol., A, 1996, 95, 265;
15. (b) M. Hoshino, F. Ebisawa, T. Yoshida and K. Sukegawa, J. Photochem. Photobiol., A, 1997, 105, 75.
16. J. Biteau, F. Chaput, K. Lahlil and J. P. Boilot, Chem. Mater., 1998, 10, 1945.
17. M.-S. Kim, H. Maruyama, T. Kawai and M. Irie, Chem. Mater., 2003, 15, 4539.
18. S. Chen, H. P. Chen, Y. Geng, S. D. Jacobs and K. L. Marshall, Adv. Mater., 2003, 15, 1061.
19. C. Denekamp and B. L. Feringa, Adv. Mater., 1998, 10, 1080.
20. (a) K. Uchida, Y. Kawai, Y. Shimizu, V. Vill and M. Irie, Chem. Lett., 2000, 654;
21. (b) T. Yamaguchi, T. Inagawa, H. Nakazumi, S. Irie and M. Irie, J. Mater. Chem., 2001, 11, 2453.
22. K. E. Maly, M. D. Wand and R. P. Lemieux, J. Am. Chem. Soc., 2002, 124, 7898.
23. T. Saika, M. Irie and T. Shimidzu, Chem. Commun., 1994, 2123.
24. S. L. Gilat, S. H. Kawai and J. M. Lehn, Chem.-Eur. J., 1995, 1, 275.
25. S. H. Kawai, S. L. Gilat and J. M. Lehn, Eur. J. Org. Chem., 1999, 2359.
26. L. N. Lucas, J. V. Esch, R. M. Kellogg and B. L. Feringa, Chem. Commun., 2001, 759.
27. J. M. Endtner, F. Effenberger, A. Hartschuh and H. Port, J. Am. Chem. Soc., 2000, 122, 3037.
28. P. A. Liddell, G. Kodis, A. L. Moore, T. A. Moore and D. Gust, J. Am. Chem. Soc., 2002, 124, 7668.
29. (a) K. Matsuda and M. Irie, J. Am. Chem. Soc., 2000, 122, 7195;
30. (b) K. Matsuda and M. Irie, Chem.-Eur. J., 2001, 7, 3466;
31. (c) K. Matsuda, M. Matsuo, S. Mizoguti, K. Higashiguchi and M. Irie, J. Phys. Chem. B., 2002, 106, 11218.
32. M. Munakata, L. P. Wu, T. Kuroda-Sowa, M. Maekawa, Y. Suenaga and K. Furuichi, J. Am. Chem. Soc., 1996, 118, 3305.
33. (a) A. Fernandez-Acebes and J. M. Lehn, Adv. Mater., 1998, 10, 1519;
34. (b) A. Fernandez-Acebes and J. M. Lehn, Chem.-Eur. J., 1999, 5, 3285.
35. S. Fraysse, C. Coudret and J. P. Launay, Eur. J. Inorg. Chem., 2000, 1581.
36. (a) K. Matsuda, K. Takayama and M. Irie, Chem. Commun., 2001, 363;
37. (b) K. Yakayama, K. Matsuda and M. Irie, Chem.-Eur. J., 2003, 9, 5605;
38. (c) K. Matsuda, K. Takayama and M. Irie, Inorg. Chem., 2004, 43, 482.
39. (a) T. B. Norsten and N. R. Branda, Adv. Mater., 2001, 13, 347;
40. (b) E. Murguly, T. B. Norsten and N. R. Branda, Angew. Chem., Int. Ed., 2001, 40, 1752.
41. (a) B. Chen, M. Wang, Y. Wu and H. Tian, Chem. Commun., 2002, 1060;
42. (b) H. Tian, B. Chen, H. Tu and K. Müllen, Adv. Mater., 2002, 14, 918.
43. H. Konaka, L. P. Wu, M. Munakata, T. Kuroda-Sowa, M. Maekawa and Y. Suenaga, Inorg. Chem., 2003, 42, 1928.
44. K. Uchida, T. Matsuoka, K. Sayo, M. Iwamoto, S. Hayashi and M. Irie, Chem. Lett., 1999, 835.
45. A. Heynderickx, A. M. Kaou, C. Moustrou, A. Samat and R. Guglielmetti, New J. Chem., 2003, 27, 1425.
46. S. Iwata, Y. Ishihara, C. Qian and K. Tanaka, J. Org. Chem., 1992, 57, 3726.
47. (a) K. Uchida, T. Ishihawa, M. Takeshita and M. Irie, Tetrahedron, 1998, 54, 6627;
48. (b) S. Takami, T. Kawai and M. Irie, Eur. J. Org. Chem., 2002, 3796.
49. A. T. Baker, H. A. Goodwin and A. D. Rae, Inorg. Chem., 1987, 26, 3513.
50. E. C. Taylor and J. A. Zoltewicz, J. Am. Chem. Soc., 1960, 82, 2656.
51. F. Bellesia, M. Boni, F. Ghelfi and U. M. Pagnoni, Gazz. Chim. Ital., 1993, 123, 629.
52. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
53. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988, 37, 785.
54. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98 (Revision A.6), Gaussian, Inc., Pittsburgh, PA, 1998.
55. A. Schaefer, H. Horn and R. Ahlrichs, J. Chem. Phys., 1992, 97, 2571.
56. M. E. Casida, C. Jamorski, K. C. Casida and D. R. Salahub, J. Chem. Phys., 1998, 108, 4439.
57. P. Karrer and J. Schukri, Helv. Chim. Acta, 1945, 28, 820.
58. Kappa-CCD Software, Enraf-Nonius, Delft, The Netherlands, 1997.
59. Z. Otwinovski and W. Minor, Methods Enzymol., 1997, 276, 307.
60. G. M. Sheldrick, Acta Crystallogr., Sect A, 1990, 46, 467.
61. G. M. Sheldrick, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen, Germany, 1993.
62. CAD-4 Software, Enraf-Nonius, Delft, The Netherlands, 1989.
63. TeXsan. (version 1.7.), Molecular Structure Corporation, The Woodlands, TX, USA, 1992-1997.
64. A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Crystallogr., 1993, 26, 343.
65. H. Rau, G. Greiner, G. Gauglitz and H. Meier, J. Phys. Chem, 1990, 94, 6523.
66. M. Irie, S. Kobatake and M. Horichi, Science, 2001, 291, 1769.
67. S. Kobatake, K. Uchida, E. Tsuchida and M. Irie, Chem. Commun., 2002, 2804.
68. F. Sun, F. Zhang, H. Guo, X. Zhou, R. Wang and F. Zhao, Tetrahedron, 2003, 59, 7615.
69. K. Morimitsu, S. Kobatake and M. Irie, Tetrahedron Lett., 2004, 45, 1155.