Regioselective E(trans)-Z(cis) photoisomerization in naphthyldiene derivatives |
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| Authors: | Maruthi Janaki Ram Reddy V Venkat Reddy U Srinivas M Janaki Ram Reddy and V Jayathirtha Rao |
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| Institution: | (1) Organic Chemistry Division II, Indian Institute of Chemical Technology, 500 007 Hyderabad, India |
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| Abstract: | Naphthyldiene derivatives,1-4, carrying electron-donating groups at one end and electron-withdrawing groups at the other, were synthesized to study the
photoisomerization process. All the compounds showed efficient photoisomerization upon direct excitation leading to the formation
of 4-Z isomer with high selectivity. Triplet sensitization studies indicated inefficientE-Z isomerization process. Room temperature fluorescence of1 and2 displayed fine structure in hexane solvent and the same was replaced by broad or structureless fluorescence in acetonitrile
and methanol solvents. A mechanism involving a polarized or charge transfer singlet excited state is proposed for the observed
photoisomerization in these naphthyldiene derivatives. |
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| Keywords: | Naphthyldiene derivatives regioselective photoisomerization direct excitation triplet sensitization fluorescence singlet excited state |
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