Synthesis and photochromism of crowned spirobenzothiapyran: Facilitated photoisomerization by cooperative complexation of crown ether and thiophenolate moieties with metal ions

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4342-4347

  Tanaka, Mutsuo ^a   Kamada, Kenji ^a   Ando, Hisanori ^a   Kitagaki, Takashi ^b   Shibutani, Yasuhiko ^b   Kimura, Keiichi ^a,c  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b OSAKA INSTITUTE OF TECHNOLOGY   (Japan)

^c WAKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CROWN ETHER; METAL ION; PYRAN DERIVATIVE; THIOPHENOL DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; COMPLEX FORMATION; ISOMERISM; MOLECULAR INTERACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034647546     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000175r     Document Type: Article

References (37)

1. (a) Bertelson, R. C. Photometric Process Involving Hetercyclic Cleavage. In Photochromism; Brown, G. H., Ed.; Wiley-Interscience: New York, 1971; Chapter 3.
2. (b) Crano, J. C.; Guglielmetti, R. J. Organic Photochromic and Thermochromic Compounds; Plenum: New York, 1999.
3. (a) Taylor, L. D.; Nicholson, J.; Davis, R. B. Tetrahedron Lett. 1967, 1585.
4. (b) Sunamoto, J.; Iwamoto, K.; Mohri, Y.; Kominato, T. J. Am. Chem. Soc. 1982, 104, 5502.
5. (c) Anzai, J.; Ueno, A.; Osa, T. J. Chem. Soc., Chem. Commun. 1984, 688.
6. (d) Irie, M.; Iwayanagi, T.; Taniguchi, Y. Macromolecules 1985, 18, 2418.
7. (e) Winkler, J. D.; Deshayes, K.; Shao, B. J. Am. Chem. Soc. 1989, 111, 769.
8. (f) Ciardelli, F.; Fabbri, D.; Pieroni, O.; Fissi, A. J. Am. Chem. Soc. 1989, 111, 3470.
9. (g) Winkler, J. D.; Bowen, C. M.; Michelet, V. J. Am. Chem. Soc. 1998, 120, 3237.
10. (h) Willner, I.; Rubin, S.; Shatzmiller, R.; Zor, T. J. Am. Chem. Soc. 1993, 115, 8690.
11. (i) Willner, I.; Blonder, R.; Dagan, A. J. Am. Chem. Soc. 1994, 116, 9365.
12. (j) Willner, I.; Blonder, R.; Dagan, A. J. Am. Chem. Soc. 1994, 116, 3121.
13. (k) Lion-Dagan, M.; Katz, E.; Willner, I. J. Am. Chem. Soc. 1994, 116, 7913.
14. (l) Willner, I.; Rubin, S.; Cohen, Y. J. Am. Chem. Soc. 1993, 115, 4937.
15. (m) Willner, I.; Lion-Dagan, M.; Marx-Tibbon, S.; Katz, E. J. Am. Chem. Soc. 1995, 117, 6581.
16. (n) Sunamoto, J.; Iwamoto, K.; Akutagawa, M.; Nagase, M.; Kondo, H. J. Am. Chem. Soc. 1982, 104, 4904.
17. (o) Inouye, M.; Kim, K.; Kitao, T. J. Am. Chem. Soc. 1992, 114, 778.
18. (p) Lion-Dagan, M.; Marx-Tibbon, S.; Katz, E.; Willner, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 1604.
19. (q) Pieroni, D.; Fissi, A.; Viegi, A.; Fabbri, D.; Ciardelli, F. J. Am. Chem. Soc. 1992, 114, 2734.
20. (r) Lion-Dagan, M.; Katz, E.; Willner, I. J. Chem. Soc., Chem. Commun. 1994, 2741.
21. (s) Hachisako, H.; Ihara, H.; Kamiya, T.; Hirayama, C.; Yamada, K. J. Chem. Soc., Chem. Commmun. 1997, 19.
22. (a) Becker, R. S.; Kolc, J. J. Phys. Chem. 1968, 72, 997.
23. (b) Arakawa, S.; Kondo, H.; Seto, J. Chem. Lett. 1985, 1805.
24. (c) Tamura, S.; Asai, N.; Seto, J. Bull. Chem. Soc. Jpn. 1989, 62, 358.
25. Hirano, M.; Miyashita, A.; Nohira, H. Chem. Lett. 1991, 209.
26. (a) Sasaki, H.; Ueno, A.; Anzai, J.; Osa, T. Bull. Chem. Soc. Jpn. 1986, 59, 1953.
27. (b) Inouye, M.; Ueno, M.; Kitao, T.; Tsuchiya, K. J. Am. Chem. Soc. 1990, 112, 8977.
28. (c) Kimura, K.; Yamashita, T.; Yokoyama, M. Chem. Lett. 1991, 965.
29. (d) Kimura, K.; Yammashita, T.; Yokoyama, M. J. Phys. Chem. 1992, 96, 5614.
30. (e) Kimura, K.; Teranishi, T.; Yokoyama, M.; Yajima, S.; Miyake, S.; Sakamoto, H.; Tanaka, M. J. Chem. Soc., Perkin Trans. 2 1999, 199.
31. (a) Kimura, K.; Yamashita, T.; Yokoyama, M. J. Chem. Soc., Chem. Commun. 1991, 147.
32. (b) Kimura, K.; Yamashita, T.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 2 1992, 613.
33. (a) Inouye, M.; Akamatsu, K.; Nakazumi, H. J. Am. Chem. Soc. 1997, 119, 9160.
34. (b) Inouye, M.; Noguchi, Y.; Isagawa, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1163.
35. (c) Inouye, M.; Ueno, M.; Kitao, T. J. Org. Chem. 1992, 57, 1639.
36. (d) Inouye, M.; Ueno, M.; Tsuchiya, K.; Nakayama, N.; Konishi, T.; Kitao, T. J. Org. Chem. 1992, 57, 5377.
37. Tanaka, M.; Kamada, K.; Ando, H.; Kitagaki, K.; Shibutani, Y.; Yajima, S.; Sakamoto, H.; Kimura, K. Chem. Commun. 1999, 1453.