Synthesis and photochromism of 1,2-dicyano[2.n]metacyclophan-1-enes

Journal of Physical Organic Chemistry

Volumn 20, Issue 11, 2007, Pages 830-837

  Takeshita, Michinori ^a   Inoue, Masako ^a   Hisasue, Hideki ^a   Maekawa, Syun ^a   Nakamura, Takeshi ^a  

^a SAGA UNIVERSITY   (Japan)

Author keywords

Absorption spectrum; Cyclophane; Molecular switch; Photochromism; Photocyclization; Quantum yield

Indexed keywords

ABSORPTION SPECTRA; CATALYST ACTIVITY; PHASE TRANSITIONS; PHOTOCHROMISM; QUANTUM YIELD; ULTRAVIOLET RADIATION;

CYCLOPHANES; INTRAMOLECULAR COUPLING REACTION; MOLECULAR SWITCHES; PHOTOCYCLIZATION REACTIONS;

OLEFINS;

EID: 36348992592     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1174     Document Type: Conference Paper

References (37)

1. (a) In Photochromism, Molecules and Systems, Dürr H, Bouas-Laurent H (eds). Elsevier: Amsterdam, 1990;
2. (b) Irie M. Chem. Rev. 2000; 100: 1685-1716;
3. (c) Yokoyama Y. Chem. Rev. 2000; 100:1717-1740;
4. (d) Berkovic G, Krongauz V, Weiss V Chem. Rev. 2000; 100: 1741-1754;
5. (e) In Molecular Switches, Feringa BL (eds). Wiley-VCH: Weinheim, 2001.
6. (a) Irie M, Uchida K. Bull. Chem. Soc. Jpn. 1998; 71: 985-986;
7. (b) Myles AJ, Branda NR. Adv. Funct. Mat. 2002; 12: 167-173;
8. (c) Irie M. In Molecular Switches, Feringa BL (eds). Wiley-VCH: Weinheim, 2001.
9. In Cyclophanes, Keehn PM, Rosenfeld SM (eds). Academic Press: New York, 1983.
10. (a) Ramey CE, Boekelheide V. J. Am. Chem. Soc. 1970; 92: 3675-3681;
11. (b) Naef R, Fischer E. Helv. Chim. Acta 1974; 57: 2224-2233;
12. (c) Tashiro M, Yamato T. J. Am Chem. Soc. 1982; 104:3701-3707;
13. (d) Murakami S, Tsutsui T, Saito S, Miyazawa A, Yamato T, Tashiro M. Chem. Lett. 1988; 5-8;
14. (e) Grützmacher H-F, Neumann E. Chem Ber. 1993; 126: 1495-1497;
15. (f) Mitchell RH, Zhang L. J. Org. Chem 1999; 64: 7140-7152;
16. (g) Takeshita M, Yamato T. Tetrahedron Lett. 2001; 42: 4345-4357.
17. Tashiro M, Fukata G, Yamato T. Org. Prep. Proc. Int. 1976; 8: 263-266.
18. Tashiro M, Yamato T. J. Org. Chem. 1981; 46: 1543-1552.
19. Yamato T, Sakamoto H, Kobayashi K, Tashiro M. J. Chem. Res. Synopses 1986; 352.
20. (a) Horiuchi J, Polanyi M. Trans. Faraday Soc. 1934; 30: 1164-1172;
21. (b) Evans MG, Polanyi M. Trans. Faraday Soc. 1938; 34: 11-24.
22. Irie M, Mohri M. J. Org. Chem. 1988; 53: 803-808.
23. (a) For example, Takeshita M, Tashiro M. J. Org. Chem. 1991; 56: 2837-2845;
24. (b) Takeshita M, Tashiro M, Tsuge A, Chem. Ber. 1991; 124: 1403-1409.
25. (a) Takeshita M, Yamato T. Angew. Chem Int. Ed. 2002; 41: 2156-2157;
26. (b) Takeshita M, Yamato T. Angew. Chem. 2002; 114: 2260-2261.
27. Morimitsu K, Shibata K, Kobatake S, Irie M. J. Org. Chem. 2002; 67: 4574-4578.
28. The quantum yields for the photochromic reactions were obtained relatively in comparison to the initial rates for photoisomerizations of 6 with those of bis(2-methyl-1-benzothien-3-yl)hexafluorocy clo-pentene; Uchida K, Tsuchida E, Aoi Y, Nakamura S, Irie M, Chem. Lett. 1999; 63.
29. (a) Nakayama Y, Hayashi K, Irie M. J. Org. Chem. 1990; 55: 2592-2596;
30. (b) Uchida K, Nakayama Y, Irie M. Bull. Chem. Soc. Jpn. 1990; 63: 1311-1315.
31. (a) Ramamurthy V, Venkatesan K. Chem. Rev. 1987; 87: 433-481;
32. (b) Morimoto M, Kobatake S, Irie M. Chem. Eur. J. 2003; 9: 621-627.
33. Takeshita M, Yamato T. Chem. Lett. 2004; 33: 844-845.
34. Takeshita M, Tanaka A, Hatanaka T. Opt. Mat. 2007; 29:499-502.
35. (a) Takeshita M, Nagai M, Yamato T. Chem. Commun. 2003; 1496-1497;
36. (b) Hossain MK, Takeshita M, Yamato T. Tetrahedron Lett. 2005; 46: 431-433;
37. (c) Hossain MK, Takeshita M, Yamato T. Eur. J. Org. Chem. 2005; 2771-2776.