Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Photochemical E(trans)–Z(cis) Isomerization in 9-Anthraceneacrylic Esters
Majjigapu Janaki Ram ReddyUppalanchi SrinivasKolupula SrinivasVummadi Venkat ReddyVaidya Jayathirtha Rao
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2002 Volume 75 Issue 11 Pages 2487-2495

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Abstract

Several (16) 9-anthraceneacrylic esters were synthesized in order to study photochemical E(trans)–Z(cis) isomerization. All of the compounds 16 underwent selective E-to-Z isomerization upon direct excitation (> 400 nm) in organic solvents, leading to the formation of a thermodynamically less stable Z isomer over 96%. Triplet sensitized isomerization selectively produces the Z-to-E isomer in over 98%. The higher quantum yield of isomerization observed in the triplet-sensitized Z-to-E isomerization process informs us that a “quantum chain” process is in operation. Fluorescence data generated on all compounds indicate that the E-to-Z isomerization process involves a charge-transfer or polar singlet excited state.

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© 2002 The Chemical Society of Japan
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