Temperature dependence of the photoisomerization of cis-1-(2-antrhyl)-2-phenylethene. Conformer-specificity, torsional energetics and mechanism

Journal of the American Chemical Society

Volumn 119, Issue 46, 1997, Pages 11202-11210

  Saltiel, Jack ^a   Zhang, Yuxin ^a   Sears Jr , Donald F ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; ENERGY TRANSFER; ENTHALPY; MOLECULAR DYNAMICS; PHOTOCHEMISTRY; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

EID: 0030664510     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972293a     Document Type: Article

References (52)

1. (a) Olson, A. R. Trans. Faraday Soc. 1931, 27, 69-76.
2. (b) Olson, A. R.; Hudson, F. L. J. Am. Chem. Soc. 1933, 55, 1410-1424.
3. (c) Olson A. R.; Maroney, W. J. Am. Chem. Soc. 1934, 56, 1320-1322.
4. Mulliken, R. S. Phys. Rev. 1932, 41, 751.
5. Hückel, E. Z. Phys. 1930, 60, 423.
6. Lewis, G. N.; Magel, T. T.; Lipkin, D. J. Am. Chem. Soc. 1940, 62, 2973-2980.
7. (a) Arai, T.; Karatsu, T.; Sakuragi, H.; Tokumaru, K. Tetrahedron Lett. 1983, 24, 2873-2876.
8. (b) Karatsu, T.; Aral, T.; Sakuragi, H.; Tokumaru, K. Chem. Phys. Lett. 1985, 115, 9-15.
9. (c) Arai, T.; Karatsu, T.; Misawa, H.; Kuriyama, Y.; Okamoto, H.; Hiresaki, T.; Furuuchi, H.; Zeng, H.; Sakuragi, H.; Tokumaru, K. Pure Appl. Chem. 1988, 60, 989-998.
10. (d) Tokumaru, K.; Arai, T. J. Photochem. Photobiol. A 1992, 65, 1-13.
11. (e) Arai, T.; Tokumaru, K. Chem. Rev. 1993, 93, 23-39.
12. (f) Tokumaru, K.; Arai, T. Bull. Chem. Soc. Jpn. 1995, 68, 1065-1087.
13. (a) Sandros, K.; Becker, H.-D. J. Photochem. 1987, 39, 301-315.
14. (b) Görner, H. J. Photochem. Photobiol. A 1988, 43, 263-288.
15. (c) Sandros, K.; Becker, H.-D. J. Photochem. Photobiol. A 1988, 43, 291-292.
16. (a) Sandros, K.; Sundahl, M.; Wennerström, O.; Norinder, U. J. Am. Chem. Soc. 1990, 112, 3082-3086.
17. (b) Sandros, K.; Sundahl, M.; Wennerström J. Phys. Chem. 1993, 97, 5291-5294.
18. (c) Sandros, K;, Sundahl, M. J. Phvs. Chem. 1994, 98, 5705-5708.
19. (a) Saltiel, J.; Waller, A.; Sun, Y.-P.; Sears, D. F., Jr. J. Am. Chem. Soc. 1990, 112, 4580-4581.
20. (b) Saltiel, J.; Waller, A. S.; Sears, D. F., Jr. J. Photochem. Photobiol. A 1992, 65, 29-40.
21. (c) Saltiel, J.; Waller, A. S.; Sears, D. F., Jr. J. Am. Chem. Soc. 1993, 115, 2453-2465.
22. (d) Saltiel, J.; Tarkalanov, N.; Sears, D. F., Jr. J. Am. Chem. Soc. 1995, 117, 5586-5587.
23. (e) Saltiel, J.; Zhang, Y.; Sears, D. F., Jr. J. Am. Chem. Soc. 1996, 118, 2811-2817.
24. (a) Spalletti, A.; Bartocci, G.; Mazzucato, U.; Galiazzo, G. Chem. Phys. Lett. 1991, 186, 297-302.
25. (b) Mazzucato, U.; Spalletti, A.; Bartocci, G. Coord. Chem. Rev. 1993, 125, 251-260.
26. (c) Kikuchi, Y.; Okamoto, H.; Arai, T.; Tokumaru, K. Chem. Phys. Lett. 1994, 229, 564-570.
27. Saltiel, J.; Sears, D. F., Jr.; Choi, J.-O.; Sun, Y.-P.; Eaker, D. W. J. Phys. Chem. 1994, 98, 35-46, 8260.
28. Saltiel, J.; Zhang, Y.; Sears, D. F., Jr. J. Phys. Chem. 1997, 101A, 7053-7060.
29. Meech, S. R.; Phillips, D. J. Photochem. 1983, 23, 193-217.
30. Caldwell, R. A.; Gajewski, R. P. J. Am. Chem. Soc. 1971, 93, 532.
31. Valentine, D., Jr.; Hammond, G. S. J. Am. Chem. Soc. 1972, 94, 3449.
32. Satiel, F.; Dabestani, R.; Schanze, K. S.; Trojan, D.; Townsend, D. E.; Goedken, V. L. J. Am. Chem. Soc. 1986, 108, 2674-2687.
33. Lamola, A. A.; Hammond, G. S. J. Chem. Phys. 1965, 43, 2129.
34. (a) Green, B. S.; Rejtö, M.; Johnson, D. E.; Hoyle, C. E.; Simpson, J. T.; Correa, P. E.; Ho, T.-I.; McCoy, F.; Lewis, F. D. J. Am. Chem. Soc. 1979, 101, 3325-3331.
35. (b) Lewis, F. D.; Simpson, J. T. J. Phys. Chem. 1979, 83, 2015-2019.
36. (c) Hub, W.; Klüter, U.; Schneider, S.; Dörr, F.; Oxman, J. D.; Lewis, F. D. J. Phys. Chem. 1984, 88, 2308-2315.
37. Aloisi, G. G.; Elisei, F.; Mazzucato, U.; Prats, M. J. Photochem. Photobiol. A Chem. 1991, 62, 217-228.
38. Saltiel, J.; Zhang, Y.; Sears, D. F., Jr.; Choi, J.-O. Res. Chem. Intermed. 1995, 21, 899-921.
39. (a) Bartocci, G.; Masetti, F.; Mazzucato, U.; Spalletti, A.; Orlandi, G.; Poggi, G. J. Chem. Soc., Faraday Trans 2 1988, 84, 385-399.
40. (b) Bartocci, G.; Masetti, F.; Mazzucato, U.; Baraldi, L; Fischer, E. J. Mol. Struct. 1989, 193, 173-183.
41. (a) Weller, A. Z. Phys. Chem. NF 1957, 13, 335-352.
42. (b) Hui, M.-H.; Ware, W. R. J. Am. Chem. Soc. 1976, 98, 4718-4727.
43. Arai, T.; Karatsu, T.; Tsuchiya, M.; Sakuragi, H.; Tokumaru, K. Chem Phys. Lett. 1988, 149, 161-166.
44. Karatsu, T.; Tsuchiya, M.; Arai, T.; Sakuragi, H.; Tokumaru, K. Bull. Chem. Soc. Jpn. 1994, 67, 3030-3039.
45. Wismontski-Knittel, T.; Das, P. K. J. Phys. Chem. 1984, 88, 1168-1173.
46. Laarhoven, W. H.; Cuppen, Th. J. H. M.; Nivard, R. J. F. Tetrahedron 1970, 4865-4881.
47. -1 as the temperature is raised from 4.3 to 59. 3 °C.
48. (a) Bartocci, G.; Mazzucato, U.; Spalletti, A.; Elisei, F. Spectrochim. Acta, A 1990, 46, 413-418.
49. (b) Spalletti, A.; Bartocci, G.; Masetti, F.; Mazzucato, U.; Cruciani, G. Chem. Phys. 1992, 160, 131-144.
50. Saltiel, J.; Ganapathy, S.; Werking, C. J. Phys. Chem. 1987, 91, 2755-2758.
51. For a review see: Jacobs, H. J.; Havinga, E. Adv. Photochem. 1979, 11, 305-373.
52. For a review see: Birge, R. R. Biochim. Biophys. Acta 1990, 1016, 293-327.