Stereoselective O2-induced photoisomerization of all-trans-1,6-diphenyl-1,3,5-hexatriene

Canadian Journal of Chemistry

Volumn 81, Issue 6, 2003, Pages 673-679

  Saltiel, Jack ^a   Krishnamoorthy, Govindarajan ^a   Huang, Zhennian ^a   Ko, Dong Hoon ^a   Wang, Shujun ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Diphenylhexatrienes; Oxygen sensitization; Trans cis photoisomerization

Indexed keywords

CHEMICAL BONDS; DEGASSING; DEUTERIUM; IRRADIATION; ISOMERIZATION; MOLECULAR STRUCTURE; OXYGEN; PHOTOCHEMICAL REACTIONS; QUENCHING; STEREOCHEMISTRY;

PHOTOISOMERIZATIONS;

NITROGEN COMPOUNDS;

1,6 DIPHENYL 1,3,5 HEXATRIENE; ACETONITRILE; ALKENE; AMPHOLYTE; BENZYL DERIVATIVE; CYCLOHEXANE DERIVATIVE; DEUTERIUM; FURAN DERIVATIVE; NITRILE; OXYGEN;

AIR; ARTICLE; CHEMICAL BOND; CIS TRANS ISOMERISM; IRRADIATION; KINETICS; MOLECULAR INTERACTION; PHOTOSENSITIZATION; STEREOCHEMISTRY;

EID: 0042232835     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v03-082     Document Type: Article

References (58)

1. B.S. Hudson and B.E. Kohler. Annu. Rev. Phys. Chem. 25, 437 (1974).
2. B.S. Hudson, B.E. Kohler, and K. Schulten. In Excited states. Vol. 6. Edited by E.C. Lim. Academic Press, New York. 1982. pp. 1-95.
3. J. Saltiel and Y.-P. Sun. In Photochromism, molecules and systems. Edited by H. Dürr and H. Bouas-Laurent. Elsevier, Amsterdam. 1990. pp. 64-164.
4. W. Fuß, S. Lochbrunner, W.E. Schmid, and K.L. Kompa. J. Phys. Chem. A, 102, 9334 (1998).
5. W. Fuß, W. E. Schmid, and S.A. Trushin. J. Chem. Phys. 112, 8347 (2000).
6. For a recent review of polyene photophysics, see: W. Fuß, Y. Haas, and S. Zilberg. Chem. Phys. 259, 273 (2000).
7. (a) S.H. Pullen, N.A. Anderson, L.A. Walker, II, and R.J. Sension. J. Chem. Phys. 108, 556 (1998);
8. (b) N.A. Anderson, J.J. Shiang, and R.J. Sension. J. Phys. Chem. A, 103, 10 730 (1999).
9. J. Saltiel, S. Wang, L.P. Watkins, and D.-H. Ko. J. Phys. Chem. A, 104, 11 443 (2000).
10. (a) J. Saltiel, S. Wang, D.-H. Ko, and D.A. Gormin. J. Phys. Chem. A, 102, 5383, (1998);
11. (b) J. Saltiel, J.M. Crowder, and S. Wang. J. Am. Chem. Soc. 121, 895 (1999).
12. J. Saltiel, G. Krishnamoorthy, Z. Huang, D.-H. Ko, and S. Wang. J. Phys. Chem. A, 107, 3178 (2003).
13. E.D. Cehelnik, R.B. Cundall, J.R. Lockwood, and T.J. Palmer. J. Phys. Chem. 79, 1369 (1975).
14. S.K. Chattopadhyay, P.K. Das, and G.L. Hug. J. Am. Chem. Soc. 104, 4507 (1982).
15. F.W. Schael. Ph.D. Dissertation, Technische Universität, Carlo-Wilhelmina zu Braunschweig, Germany, 1995.
16. (a) F.W. Schael and H.-G. Löhmannsröben. Chem. Phys. 206, 193 (1996);
17. (b) F.W. Schael, J. Kühster, and H.-G. Löhmannsröben. Chem. Phys. 218, 175 (1997).
18. (c) F.W. Schael and H.-G. Löhmannsröben. J. Photochem. Photobiol. A, 105, 317 (1997).
19. J.F. O'Donnel, J.T. Ayres, and C.K. Mann. Anal. Chem. 37, 1161 (1965).
20. F.G. Moses, R.S.H. Liu, and B.M. Monroe. Mol. Photochem. 1, 245 (1969).
21. H.A. Hammond, D.E. DeMeyer, and J.L.R. Williams. J. Am. Chem. Soc. 91, 5180 (1969).
22. D. Valentine, Jr. and G.S. Hammond. J. Am. Chem. Soc. 94, 3449 (1972).
23. J. Saltiel, D.F. Sears, Jr., J.-O. Choi, Y.-P. Sun, and D.W. Eaker. J. Phys. Chem. 98, 35 (1994); 98, 8260 (1994).
24. J. Saltiel, D.F. Sears, Jr., J.-O. Choi, Y.-P. Sun, and D.W. Eaker. J. Phys. Chem. 98, 35 (1994); 98, 8260 (1994).
25. (a) I.B. Berlman. Handbook. of fluorescence spectra of aromatic molecules. 2nd ed. Academic Press, New York. 1971;
26. (b) J. Saltiel and B.W. Atwater. Adv. Photochem. 14, 1 (1988);
27. (c) F. Wilkinson, W.P. Helman, and A.B. Ross. J. Phys. Chem. Ref. Data, 22, 113 (1993).
28. (a) G. Porter and M.R. Wright. Discuss. Faraday Soc. 27, 18 (1959);
29. (b) B. Stevens and B.E. Algar. Ann. N. Y. Acad. Sci. 171, 50 (1970).
30. O.L.J. Gijzeman, F. Kaufman, and G. Porter. J. Chem. Soc., Faraday Trans. 2, 69, 708 (1973).
31. R. Potashnik, C.R. Goldschmidt, and M. Ottolenghi. Chem. Phys. Lett. 9, 424 (1971).
32. (a) F. Wilkinson, D.J. McGarvey, and A.F. Olea. J. Am. Chem. Soc. 115, 12 144 (1993);
33. (b) A.F. Olea and F. Wilkinson. J. Phys. Chem. 99, 4518 (1995).
34. C. Sato, K. Kikuchi, C. Sato, Y. Takahashi, and T. Miyashi. J. Phys. Chem. 99, 161925 (1995).
35. K. Kikuchi, K. Okamura, M. Watabe, H. Ikeda, Y. Takahashi, and T. Miyashi. J. Am. Chem. Soc. 115, 5180 (1993).
36. A.A. Abdel-Shafi and F. Wilkinson. J. Phys. Chem. A, 104, 5747 (2000).
37. K.C. Wu and A.M. Trozzolo. J. Phys. Chem. 83, 3180 (1979).
38. S.K. Chattopadhyay, C.V. Kumar, and P.K. Das. J. Phys. Chem. 89, 670 (1985).
39. M. Almgren and J.K. Thomas. Photochem. Photobiol. 31, 329 (1980).
40. (a) Z. Wang and W.G. McGimpsey. J. Phys. Chem. 97, 3324 (1993);
41. (b) Z. Wang and W.G. McGimpsey. J. Phys. Chem. 97, 5054 (1993).
42. H. Görner. J. Photochem. 19, 343 (1982).
43. W.D.K. Clark and C. Steel. J. Am. Chem. Soc. 93, 6347 (1971).
44. S. Wang. Ph.D. Dissertation, Florida State University, Tallahassee, Florida, 1998.
45. P. Bortolus and G. Galiazzo. J. Photochem. 2, 361 (1974).
46. G. Fischer and E. Fischer. Mol. Photochem. 6, 463 (1974).
47. G.G. Aloisi, U. Mazzucato, J.B. Birks, and L. Minuti. J. Am. Chem. Soc. 99, 6340 (1977).
48. For a review see: J. Saltiel, J.L. Charlton. In Rearrangements in ground and excited states. Vol. 3. Edited by P. de Mayo. Academic Press, New York. 1980. Essay 14.
49. G.O. Schenck and R. Steinmetz. Bull. Soc. Chim. Belg. 71, 781 (1962).
50. D.-H. Ko. Ph.D. Dissertation, Florida State University, Tallahassee, Florida, 1997.
51. K. Gollnick, T. Franken, G. Schade, and G. Dorhofer. Ann. N.Y. Acad. Sci. 171, 89 (1970).
52. A. Streitwieser, Jr., R.H. Jagow, R.C. Fahey, and S. Suzuki. J. Am. Chem. Soc. 80, 2326 (1958).
53. For relevant early examples, see: M. Matsuoka and M. Szwarc. J. Am. Chem. Soc. 83, 1260 (1961).
54. (a) J. Gersdorf and J. Mattay. J. Photochem. 28, 405 (1985);
55. (b) M. Mac and J. Wirz. Chem. Phys. Lett. 211, 20 (1993);
56. (c) M. Mac, P. Kwiatkowski, and A.M. Turek. Chem. Phys. Lett. 250, 104 (1996);
57. (d) M. Mac and J. Wirz. Photochem. Photobiol. Sci. 1, 24 (2002).
58. For a typical example, see: J.L. Charlton, D.E. Townsend, B.D. Watson, P. Shannon, J. Kowalewska, and J. Saltiel. J. Am. Chem. Soc. 99, 5992 (1977).