Substituent effect on the cis-trans photoisomerization of trans,trans,trans-1,6-diphenyl-1,3,5-hexatrienes

Chemistry Letters

Volumn , Issue 4, 1998, Pages 349-350

  Sonoda, Yoriko ^a   Morii, Hisayuki ^b   Sakuragi, Masako ^a   Suzuki, Yasuzo ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

^b NATL INST BIOSCI HUM TECHNOL   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032371290     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.349     Document Type: Article

References (17)

1. Y. Sonoda and Y. Suzuki, J. Chem. Soc., Perkin Trans. 2, 1996, 401.
2. Y. Sonoda and Y. Suzuki, Chem. Lett., 1996, 659.
3. K. Lunde and L. Zechmeister, J. Am. Chem. Soc., 76, 2308 (1954).
4. J. Saltiel, D. -H. Ko, and S. A. Fleming, J. Am. Chem. Soc., 116, 4099 (1994).
5. All photolyses were carried out using a spectroirradiator (2kW Xe lamp) and quartz cells. Irradiation light wavelength was set around the absorption maximum of each ttt isomer (Table 1).
6. 7
7. C. W. Spangler, R. K. McCoy, A A. Dembek, L. S. Sapochak, and B. D. Gates, J. Chem. Soc., Perkin Trans. 1, 1989, 151; C. C. Leznoff and R. J. Hayward, Can. J. Chem., 50, 528 (1972), T. Mitsudo, W. Fischetti, and R. F. Heck, J. Org. Chem., 49, 1640 (1984).
8. C. W. Spangler, R. K. McCoy, A A. Dembek, L. S. Sapochak, and B. D. Gates, J. Chem. Soc., Perkin Trans. 1, 1989, 151; C. C. Leznoff and R. J. Hayward, Can. J. Chem., 50, 528 (1972), T. Mitsudo, W. Fischetti, and R. F. Heck, J. Org. Chem., 49, 1640 (1984).
9. C. W. Spangler, R. K. McCoy, A A. Dembek, L. S. Sapochak, and B. D. Gates, J. Chem. Soc., Perkin Trans. 1, 1989, 151; C. C. Leznoff and R. J. Hayward, Can. J. Chem., 50, 528 (1972), T. Mitsudo, W. Fischetti, and R. F. Heck, J. Org. Chem., 49, 1640 (1984).
10. S. L. Murov, I. Carmichael, and G. L. Hug, "Handbook of Photochemistry", 2nd ed, revised and expanded, Marcel Dekker, Inc., New York (1993), pp 345-348.
11. P. C. Alford and T. F. Palmer. Chem. Phys. Lett., 86, 248 (1982).
12. 3
13. S. Misumi and M. Nakagawa, Bull. Chem. Soc. Jpn., 36, 399 (1963).
14. 2 Singlet lifetime was evaluated from fluorescence lifetime, which was measured by the single photon counting method A gated pico-second nitrogen laser provided excitation with half-band width of 1.0125 ns. Sample solution in acetonitrile was degassed with argon Concentrations were 0.03-0.04 OD at the excitation wavelength.
15. W. A. Yee, S. J. Hug, and D. S. Kliger, J. Am. Chem. Soc., 110, 2164 (1988).
16. The presence of a ground-state s-cis conformer, which is ignored in the present study, may be important in quantum yield measurement of cis-trans isomerization of polyenes, because the double bond isomerization of s-cis conformer is considered to be sterically hindered The fluorescence spectrum of s-cis conformer(s) of ttt-DPH is red-shifted compared to that of all-s-trans conformer. Therefore, to understand the role of s-cis conformer(s) in the isomerization of the diphenylhexatrienes, it is necessary to investigate the product distribution after extreme red edge excitation of theabsorption spectrum of the ttt isomer.
17. J. Saltiel, D. F. Sears, Jr., Y. -P. Sun, and J.-O. Choi, J. Am. Chem. Soc., 114, 3607 (1992).