Photoisomerization of cis-1-(3-methyl-2-naphthyl)-2-phenylethene in glassy methylcyclohexane at 77 K

The Journal of Physical Chemistry. a
Jack SaltielOlga Dmitrenko

Abstract

The cis-trans photoisomerizations of cis-1-(3-methyl-2-naphthyl)-2-phenylethene (c-3-MPE) was studied in methylcyclohexane (MCH) glass at 77 K. The fluorescence spectra of c- and t-3-MPE are excitation wavelength (λ(exc)) independent because the steric requirement of the methyl group restricts the conformational space of each isomer to a single conformer. Photocyclization, the dominant reaction pathway of c-3-MPE in solution, is entirely suppressed in MCH glass at 77 K. The only reaction on 313 nm irradiation of c-3-MPE in MCH glass is cis-trans isomerization. As the reaction progresses, the structureless fluorescence of c-3-MPE is replaced by the vibronically resolved fluorescence of the stable conformer of the trans isomer. The results are consistent with photoisomerization by the conventional one bond twist (OBT) pathway. Previously reported results on the photoisomerization of cis-1-(2-naphthyl)-2-(o-tolyl)ethene (c-NTE) are reinterpreted. Calculated geometries and energy differences for c- and t-3-MPE and c- and t-NTE [DFT using B3LYP/6-311+G(d,p)] are consistent with the interpretation of the experimental results.

References

Jan 1, 1985·Proceedings of the National Academy of Sciences of the United States of America·R S Liu, A E Asato
Jul 1, 1995·Journal of Photochemistry and Photobiology. B, Biology·J E Roberts
Sep 15, 1988·Physical Review A: General Physics·A D Becke
Oct 4, 2000·Proceedings of the National Academy of Sciences of the United States of America·R S Liu, G S Hammond
Dec 24, 2003·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Jack SaltielDonald F Sears
May 12, 2005·Journal of the American Chemical Society·Jack SaltielAndrzej M Turek
May 18, 2005·Accounts of Chemical Research·Robert S H Liu, George S Hammond
Apr 1, 2006·Chemical Communications : Chem Comm·Jack SaltielRonald J Clark
Oct 5, 2006·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Lan-Ying YangRobert S H Liu
Nov 22, 2007·Photochemistry and Photobiology·Lan-Ying Yang, Robert S H Liu
Apr 7, 2009·Chemistry, an Asian Journal·Yao-Peng ZhaoRobert S H Liu
Mar 2, 1998·Angewandte Chemie·Astrid M MüllerWerner Fuß

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Citations

Oct 21, 2014·Photochemistry and Photobiology·Christopher RedwoodJack Saltiel
Feb 25, 2017·The Journal of Physical Chemistry. a·Malgorzata BaydaJack Saltiel
Oct 11, 2012·The Journal of Physical Chemistry. a·Jack Saltiel, V K Ratheesh Kumar
Dec 25, 2012·The Journal of Physical Chemistry. a·Yoriko SonodaMasatoshi Kanesato

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