Synthesis, Characterization and Photochromic Studies of Spirooxazine-Containing 2,2′-Bipyridine Ligands and Their Rhenium(I) Tricarbonyl Complexes

Chemistry - A European Journal

Volumn 10, Issue 3, 2004, Pages 766-776

  Ko, Chi Chiu ^a   Wu, Li Xin ^a   Wong, Keith Man Chung ^a   Zhu, Nianyong ^a   Yam, Vivian Wing Wah ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Luminescence; N ligands; Photochromism; Rhenium; Spirooxazine

Indexed keywords

COMPLEXATION; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

PHOTOCHROMIC REACTIONS; PHOTOPHYSICAL REACTIONS;

RHENIUM;

2,2' BIPYRIDINE; LIGAND; OXAZINE DERIVATIVE; RHENIUM COMPLEX; SPIROOXAZINE; TRICARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 1242353014     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305485     Document Type: Article

References (72)

1. a) S. Seikosha Co., Jap. Pat. 1984, 978(5), 721;
2. b) C. Salemi-Delvaux, B. Luccioni-Houze, G. Baillet, G. Giusti, R. Guglielmetti, J. Photochem. Photobiol. A 1995, 91, 223.
3. J. Malkin, A. S. Dvornikov, K. D. Straub, P. M. Rentzepis, Res. Chem. Intermed. 1993, 19, 159.
4. a) S. Yitzchaik, G. Berkovic, V. Krongauz, Chem. Mater. 1990, 2, 168;
5. b) N. Tamaoki, E. Van Keuren, H. Matsuda, K. Hasegawa, T. Yamaoka, Appl. Phys. Lett. 1996, 69, 1188.
6. a) I. Willner, S. Rubin, R. Shatzmiller, T. Zor, J. Am. Chem. Soc. 1993, 115, 8690;
7. b) M. L. Dagan, E. Katz, I. Willner, J. Chem. Soc. Chem. Commun. 1994, 2741;
8. c) I. Willner, B. Willner, Adv. Mater. 1995, 7, 587;
9. d) R. Blonder, E. Katz, I. Willner, V. Wray, A. F. Bückmann, J. Am. Chem. Soc. 1997, 119, 11747;
10. e) I. Willner, Acc. Chem. Res. 1997, 30, 347;
11. f) A. N. Shipway, I. Willner, Acc. Chem. Res. 2001, 34, 421.
12. a) H. Shinmori, M. Takeuchi, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1996, 1;
13. b) M. Inouye, M. Ueno, T. Kitao, J. Am. Chem. Soc. 1990, 112, 8977
14. c) M. Inouye, Y. Noguchi, K. Isagawa, Angew. Chem. 1994, 106, 1226; Angew. Chem. Int. Ed. Engl. 1994, 33, 1163;
15. c) M. Inouye, Y. Noguchi, K. Isagawa, Angew. Chem. 1994, 106, 1226; Angew. Chem. Int. Ed. Engl. 1994, 33, 1163;
16. c) M. Inouye, Coord. Chem. Rev. 1996, 148, 265;
17. d) M. Inouye, K. Akamatsu, H. Nakazumi, J. Am. Chem. Soc. 1997, 119, 9160;
18. e) M. Tanaka, M. Nakamura, M. A. A. Salhin, T. Ikeda, K. Kamada, H. Ando, Y. Shibutani, K. Kimura, J. Org. Chem. 2001, 66, 1534.
19. T. Inada, S. Uchida, Y. Yokoyama, Chem. Lett. 1997, 26, 321.
20. a) N. Y. C. Chu, Can. J. Chem. 1983, 61, 300;
21. b) N. Y. C. Chu, in Photochromism: Molecules and Systems (Eds.: H. Dürr, T. H. Bouas-Laurent), Elsevier, Amsterdam, 1990, p. 879.
22. a) J. C. Crano, R. Guglielmetti, Organic Photochromic and Thermochromic Compounds, Plenum Press, New York, vols. 1 and 2, 1999;
23. b) G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev. 2000, 100, 1741.
24. a) M. Querol, B. Bozic, N. Salluce, P. Belser, Polyhedron 2003, 22, 655;
25. b) J. L. Bahr, G. Kodis, L. Garza, S. Lin, A. L. Moore, T. A. Moore, D. Gust, J. Am. Chem. Soc. 2001, 123, 7124;
26. c) V. W. W. Yam, C. C. Ko, L. X. Wu, K. M. C. Wong, K. K. Cheung, Organometallics 2000, 19, 1820;
27. d) R. F. Khairutdinov, K. Giertz, J. K. Hurst, E. N. Voloshina, N. A. Voloshin, V. I. Minkin, J. Am. Chem. Soc. 1998, 120, 12707.
28. A. R. Oki, R. J. Morgan, Synth. Commun. 1995, 25, 4093.
29. D. G. McCafferty, B. M. Bishop, C. G. Wall, S. G. Hughes, Tetrahedron 1995, 51, 1093.
30. S. Gould, G. F. Strouse, T. J. Meyer, B. P. Sullivan, Inorg. Chem. 1991, 30, 2942.
31. a) E. Horn, M. R. Snow, Aust. J. Chem. 1980, 33, 2369;
32. b) P. Chen, M. Curry, T. J. Meyer, Inorg. Chem. 1989, 28, 2271;
33. c) V. W. W. Yam, V. C. Y. Lau, K. K. Cheung, J. Chem. Soc. Chem. Commun. 1995, 259;
34. d) V. W. W. Yam, K. M. C. Wong, V. W. M. Lee, K. K. W. Lo, K. K. Cheung, Organometallics 1995, 14, 4034;
35. e) V. W. W. Yam, V. C. Y. Lau, K. K. Cheung, Organometallics 1996, 15, 1740;
36. f) V. W. W. Yam, K. Z. Wang, C. R. Wang, Y. Yang, K. K. Cheung, Organometallics 1998, 17, 2440;
37. h) V. W. W. Yam, S. H. F. Chong, K. K. Cheung, Chem. Commun. 1998, 2121;
38. i) V. W. W. Yam, S. H. F. Chong, C. C. Ko, K. K. Cheung, Organometallics 2000, 19, 5092.
39. a) E. Miler-Srenger, R. Guglielmetti, Acta Crystallogr. Sect. C 1984, 40, 2050;
40. b) J. C. A. Boeyens, J. Cryst. Mol. Struct. 1978, 8, 317;
41. c) R. Millini, G. D. Piero, P. Allegrini, L. Crisci, V. Malatesta, Acta Crystallogr. Sect. C 1991, 47, 2567;
42. d) W. Clegg, N.C. Norman, J. G. Lasch, W. S. Kwak, Acta Crystallogr. Sect. C 1987, 43, 1222;
43. e) J. Crano, D. Knowles, P. Kwiatkowski, T. Flood, R. Ross, L. Chiang, J. Lasch, R. Chadha, C. Siuzdak, Acta Crystallogr. Sect. B 1994, 50, 772;
44. f) K. Chamontin, V. Lokshin, R. Guglielmetti, A. Samat, G. Pèpe, Acta Crystallogr. Sect. C 1998, 54, 670.
45. G. Favaro, F. Masetti, U. Mazzucato, G. Ottavi, P. Allegrini, V. Malatesta, J. Chem. Soc. Faraday Trans. 1994, 90, 333.
46. a) M. S. Wrighton, D. L. Morse, J. Am. Chem. Soc. 1974, 96, 998;
47. b) J. C. Luong, H. Faltynak, M.S. Wrighton, J. Am. Chem. Soc. 1979, 101, 1597;
48. c) S. M. Fredericks, J. C. Luong, M. S. Wrighton, J. Am. Chem. Soc. 1979, 101, 7415;
49. d) P. J. Giordano, M. S. Wrighton, J. Am. Chem. Soc. 1979, 101, 2888;
50. e) J. V. Caspar, T. J. Meyer, J. Phys. Chem. 1983, 87, 952.
51. a) H. Görner, A. K. Chibisov, J. Chem. Soc. Faraday Trans. 1998, 94, 2557;
52. b) J.-L. Pozzo, A. Samat, R. Guglielmetti, D. Keukeleire, J. Chem. Soc. Perkin Trans. 2 1993, 1327.
53. a) D. Eloy, P. Escaffre, R. Gautron, P. Jardon, J. Chim. Phys. 1992, 89, 897;
54. b) G. Favaro, V. Malatesta, C. Miliani, A. Romani, J. Photochem. Photobiol. A 1996, 97, 45;
55. c) J. Hobley, F. Wilkinson, J. Chem. Soc. Faraday Trans. 1996, 92, 1323.
56. a) A. K. Chibisov, H. Görner, J. Phys. Chem. A 1999, 103, 5211;
57. b) A. K. Chibisov, H. Görner, Phys. Chem. Chem. Phys. 2001, 3, 424.
58. M. Campredon, G. Giusti, R. Guglielmetti A. Samat, G. Gronchi, A. Alberti, M. Benaglia, J. Chem. Soc. Perkin Trans. 2 1993, 2089.
59. A. Alberti, C. Barberis, M. Campredon, G. Gronchi, M. Guerra, J. Phys. Chem. 1995, 99, 15779.
60. a) J. C. Luong, L. Nadjo, M. S. Wrighton, J. Am. Chem. Soc. 1978, 100, 5790;
61. b) C. Kutal, M. A. Weber, G. Ferraudi, D. Geiger, Organometallics 1985, 4, 2161;
62. c) J. Hawecker, J. M. Lehn, R. Ziessel, Helv. Chim. Acta 1986, 69, 1990;
63. d) K. Kalyanasundaram, J. Chem. Soc. Faraday Trans. 2 1986, 82, 2401;
64. e) B. J. Yoblinski, M. Stathis, T. F. Guarr, Inorg. Chem. 1992, 31, 5.
65. a) M. Hosoda, Eur. Pat. Appl. EP 186364 A2, July 2, 1986.
66. b) B. Osterby, R. D. McKelvey, L. Hill, J. Chem. Educ. 1991, 68, 424.
67. a) J. V. Caspar, B. P. Sullivan, T. J. Meyer, Inorg. Chem. 1984, 23, 2104;
68. b) B. P. Sullivan, T. J. Meyer, J. Chem. Soc. Chem. Commun. 1984, 403.
69. Derivation of Equation 3, please refer to Supporting Information.
70. DENZO (version 1.3.0): "The HKL Manual - A description of programs DENZO, XDISPLAYF, and SCALEPACK" written by D. Gewirth, with the co-operation of the program authors Z. Otwinowski, W. Minor, (1995), Yale University, New Haven, U.S.A.
71. Sir97: a new tool for crystal structure determination and refinement, A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst., 1998, 32, 115.
72. SHELXS-97, G. M. Sheldrick, (1997). SHELX-97: Programs for Crystal Structure Analysis (Release 97-2). University of Göttingen, Germany.