Application of 2-pyridyl-substituted hemithioindigo as a molecular switch in hydrogen-bonded porphyrins

Journal of Organic Chemistry

Volumn 73, Issue 10, 2008, Pages 3768-3774

  Tanaka, Kiyoshi ^a   Kohayakawa, Kiyoshi ^a   Iwata, Satoru ^a   Irie, Takayuki ^a  

^a SEIKEI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; ISOMERIZATION; PHOTOCHROMISM; RATE CONSTANTS; THERMODYNAMIC STABILITY;

ASSOCIATION CONSTANTS; BINDING ABILITY; HEMITHIOINDIGO SHUTTLE; MOLECULAR SWITCH; PHOTOIRRADIATION;

PORPHYRINS;

2 (3' PYRIDYLMETHYLENE) 7 ETHYLBENZO[B]THIOPHEN 3(2H) ONE; HEMITHIOINDIGO; PENTAFLUOROBENZAMIDOPORPHYRIN; PORPHYRIN; PYRIDINE DERIVATIVE; QUINONE DERIVATIVE; UREIDOPORPHYRIN;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; ISOMERIZATION; LIGHT IRRADIANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; THERMOSTABILITY;

EID: 43449136993     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800091d     Document Type: Article

References (30)

1. (a) Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72.
2. (b) Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines; Wiley-VCH: Weinheim, Germany, 2003; Chapter 7.
3. (c) Feringa, B. L., Ed. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001; Chapters 6 and 9.
4. (d) Willner, I.; Rubin, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 367.
5. (a) Shinkai, S.; Nakaji, T.; Ogawa, T.; Shigematsu, K.; Manabe, O. J. Am. Chem. Soc. 1981, 103, 111.
6. (b) Shinkai, S.; Ishihara, M.; Ueda, K.; Manabe, O. J. Chem. Soc., Perkin Trans. 2 1985, 511.
7. (c) Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashima, N. J. Am. Chem. Soc. 1997, 119, 7605.
8. (d) Murakami, H.; Kawabuchi, A.; Matsumoto, R.; Ido, T.; Nakashima, N. J. Am. Chem. Soc. 2005, 127, 15891.
9. (e) Stanier, C. A.; Alderman, S. J.; Claridge, T. D. W.; Anderson, H. L. Angew. Chem., Int. Ed. 2002, 41, 1769.
10. (f) Qu, D.-H.; Wang, Q.-C.; Tian, H. Angew. Chem., Int. Ed. 2005, 44, 5296.
11. (g) Sugimoto, H.; Kuramoto, K.; Inoue, S. J. Chem. Soc., Perkin Trans. 1 2002, 1826.
12. (h) Alfimov, M. V.; Gromov, S. P.; Fedorov, Yu, V.; Fedorova, O. A.; Vedernikov, A. I.; Charakov, A. V.; Kuz'mina, L. G.; Howard, J. A. K.; Bossmann, S.; Braun, A.; Woerner, M.; Sears, D. F., Jr.; Saltiel, J. J. Am. Chem. Soc. 1999, 121, 4992.
13. (i) Lednev, I. K.; Hester, R. E.; Moore, J. N. J. Am. Chem. Soc. 1997, 119, 3456.
14. (j) Irie, M.; Kato, M. J. Am. Chem. Soc. 1985, 107, 1024.
15. (k) Rahman, S. M. F.; Fukunishi, K. J. Chem. Soc., Chem. Commun. 1994, 917.
16. (a) Hayashi, T.; Miyahara, T.; Koide, N.; Kato, Y.; Masuda, H.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 7281.
17. (b) Hayashi, T.; Asai, T.; Hokazono, H.; Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 12210.
18. (c) Aoyama, Y.; Asakawa, M.; Matsui, Y.; Ogoshi, H. J. Am. Chem. Soc. 1991, 113, 6233.
19. (d) D'Souza, F. J. Am. Chem. Soc. 1996, 118, 923.
20. (e) D'Souza, F.; Deviprasad, G. R.; Hsieh, Y.-Y. Chem. Commun. 1997, 533.
21. (f) D'Souza, F.; Deviprasad, G. R. J. Org. Chem. 2001, 66, 4601.
22. (a) Tanaka, K.; Yamamoto, Y.; Machida, I.; Iwata, S. J. Chem. Soc., Perkin Trans. 2 1999, 285.
23. (b) Tanaka, K.; Yamamoto, Y.; Obara, H.; Iwata, S. Supramol. Chem. 2002, 14, 347.
24. (c) Tanaka, K.; Taguchi, K; Iwata, S.; Obara, H. J. Porphyrins Phthalocyanines 2005, 9, 262.
25. (a) Tanaka, K.; Taguchi, K; Iwata, S.; Irie, T. Chem. Lett. 2004, 33, 848.
26. (b) Tanaka, K.; Taguchi, K; Iwata, S.; Irie, T. Supramol. Chem. 2005, 17, 637.
27. (a) Mostoslavskii, M. A.; Izmail'skii, V. A. J. Gen. Chem. USSR 1965, 35, 519.
28. (b) Seki, T.; Tamaki, T.; Yamaguchi, T.; Ichimura, K. Bull. Chem. Soc. Jpn. 1992, 65, 657.
29. (c) Eggers, K.; Fyles, T. M.; Montoya-Pelaez, P. J. J. Org. Chem. 2001, 66, 2966.
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