Photoinduced hinge-like molecular motion: Studies on xanthene-based cyclic azobenzene dimers

Journal of Organic Chemistry

Volumn 70, Issue 23, 2005, Pages 9304-9313

  Nagamani, S Anitha ^a   Norikane, Yasuo ^a   Tamaoki, Nobuyuki ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; MOLECULAR DYNAMICS; PHOTOCHEMICAL REACTIONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

AZOBENZE DIMERS; MOLECULAR MOTIONS; SMART SYSTEMS; XANTHENE;

DIMERS;

AZOBENZENE DERIVATIVE; DIMER; XANTHENE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; IRRADIATION; ISOMER; MATHEMATICAL ANALYSIS; MOLECULAR DYNAMICS; MOLECULAR STABILITY; MOTION; PHOTOCHEMISTRY; PHOTOREACTIVITY; STRUCTURE ANALYSIS; THERMAL ANALYSIS; X RAY ANALYSIS;

EID: 27744519604     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0513616     Document Type: Article

References (36)

1. Balzani, V.; Credit, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
2. Balzani, V.; Gomez, L. M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414.
3. (a) Sauvage, J. P. Acc. Chem. Res. 1998, 31, 611-619.
4. (b) Mao, C. D.; Sun, W. Q.; Shen, Z. Y.; Seeman, N. C. Nature 1999, 397, 144-146.
5. (a) Dobson, C. M. Nature 1990, 348, 198-199.
6. (b) Cordes, F. S.; Bright, J. N.; Samson, M. S. P. J. Mol. Biol. 2002, 323, 951-960.
7. (c) Schwarzinger, S.; Wright, P. E.; Dyson, H. J. Biochemistry 2002, 41, 12681-12686.
8. (a) Ashton, P. R.; Brown, G. R.; Isaacs, N. S.; Giuffrida, D.; Kohneke, F. H.; Mathias, J. P.; Slawin, A. M.; Smith, Z. D. R.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 6330-6353.
9. (b) Mataka, S.; Mitoma, Y.; Sawada, T.; Thiemann, T.; Taniguchi, M.; Tashiro, M. Tetrahedron 1998, 54, 5171-5186.
10. (c) Warrener, R. N.; Butler, D. N.; Liu, L.; Margetic, D.; Russell, R. A. Chem.-Eur. J. 2001, 15, 3406-3414.
11. (a) Rau, H. Studies in organic chemistry: Photochromism, molecules, and systems; Durr, H., Bonas-Laurent, H. Eds.; 1990.
12. (b) Feringa, B. L. Molecular Switches; Wiley VCH GmBH: Weinheim, Germany, 2001.
13. Norikane, Y.; Tamoaki, N. Org. Lett. 2004, 6, 2595-2598.
14. (a) Kelly, C.; Mark, V.; Vanessa, Y.; Simon, C.; Alan, F. Biorg. Med. Chem. Lett. 2000, 10, 1147-1151.
15. (b) Dunayevskiy, Y. M.; Vouros, P.; Wintner, E. A.; Shipps, G. W.; Carell, T.; Rebek, J. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 6152-6157.
16. (c) Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647-1654.
17. Bouwstra, J. A.; Schouten, A.; Kroon, J. Acta Crystallogr. 1983, C39, 1121-1123.
18. Mostad, A.; Romming, C. Acta Chem. Scand. 1971, 25, 3561-3568.
19. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991. The H-bonds have been identified based on the distance between the proton and the acceptor (i.e.,d(H⋯O) and the angle made between the donor-proton-acceptor atoms (i.e., θ(N-H⋯O)). H-bonds are present between a H (H3 and H4) of the free amine and the O (O1 and O2) of the xanthene unit, and the distance d(H⋯O) is 2.33 Å and the angle θ(N-H⋯O) is 103° in both 2(t) and 2(c). The additional H-bond in 2(c) has d(H⋯O) of 2.45 Å and an angle θ(N-H⋯O) of 136°.
20. Tait, K. M.; Parkinson, J. A.; Bates, S. P.; Ebenezer, W. J.; Jones, A. C. J. Photochem. Photobiol., A 2003, 154, 179-188.
21. Forber, C. L.; Kelusky, E. C.; Bunce, N. J.; Zerner, M. C. J. Am. Chem. Soc 1985, 107, 5884-5890.
22. Rottger, D.; Rau, H. J. Photochem. Photobiol, A 1996, 101, 205-214.
23. (a) Norikane, Y.; Kitamoto, K.; Tamaoki, N. J. Org. Chem. 2003, 68, 8291-8304.
24. (b) Tamaoki, N.; Koseki, K.; Yamaoka, T. Angew. Chem., Int. Ed. Eng. 1990, 29, 105-106.
25. (c) Tamaoki, N.; Ogata, K.; Koseki, K.; Yamaoka, T. Tetrahedron 1990, 46, 5931-5942.
26. (d) Tamaoki, N.; Yamaoka, T. J. Chem. Soc., Perkin. Trans. 1991, 873-878.
27. (e) Tamaoki, N.; Yoshimura, S.; Yamaoka, T. Thin Solid Films 1992, 221, 132-139.
28. (f) Rau, H.; Rottger, D. Mol. Cryst. Liq. Cryst. 1994, 246, 143-146.
29. (g) Tauer, E.; Machinek, R. Liebigs Ann. 1996, 1213-1216.
30. (h) Luboch, E.; Wagner-Wysiecka, V. C.; Kravtsov; Kessler, V. Pol. J. Chem. 2003, 77, 189-196.
31. Gore, P. H.; Wheeler, O. H. J. Am. Chem. Soc. 1961, 26, 3295-3298.
32. Morris, R. J.; Brode, W. R. J. Am. Chem. Soc. 1948, 70, 2485-2488.
33. Nishimura, N.; Sueyoshi, T.; Yamanaka, H.; Imai, E.; Yamamoto, S.; Hasegawa, S. Bull. Chem. Soc. Jpn. 1976, 49, 1381-1387.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J.; Dapprich, S. C.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y. C.; Morokuma, K. Q.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B. C.; Wong, M. W.; Andres, J. L. W.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.9; Gaussian, Inc: Pittsburgh, PA 1998.
35. Corruccini, R. J.; Gilbert, E. C. J. Am. Chem. Soc. 1939, 61, 2925-2927.
36. Asano, T.; Okada, T.; Shinkai, S.; Shigematsu, K.; Kusano, Y.; Manabe, O. J. Am. Chem. Soc. 1981, 103, 5161-5165.