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Light initiated E–Z and Z–E isomerization of isatinphenylsemicarbazones: Tautomeric equilibrium effect

Paper ID Volume ID Publish Year Pages File Format Full-Text
26544 43961 2014 10 PDF Available
Title
Light initiated E–Z and Z–E isomerization of isatinphenylsemicarbazones: Tautomeric equilibrium effect
Abstract

•Efficient isatinphenylsemicarbazone colorimetric sensors for anions were investigated.•The light and thermally initiated mutual E- and Z-isomer transformations were studied.•The reaction mechanism of E–Z isomerization was suggested.•The absence of back Z–E isomerization is discussed in terms of activation energies.•Theoretical calculations confirm the obtained experimental results.

The light and thermally initiated mutual E- and Z-isomer transformations of two efficient isatin N-phenylsemicarbazone colorimetric sensors for strongly basic anions differing in sensitivity, selectivity and sensing mechanism were investigated in solvents of different polarity. The reaction mechanism of photochemically and thermally initiated E–Z isomerization and the absence of back Z–E isomerization is discussed in terms of self-aggregate formation, hydrazide-hydrazonol tautomeric equilibrium, the role of intra- and inter-molecular hydrogen bonds, excited-state proton transfer, solvent polarity and concentration effects. The effect of the activation energies related to conformational and geometric changes of the isomers and the possible analytical application were investigated. Theoretically calculated properties are in good agreement with obtained experimental results and support the proposed reaction mechanism.

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Keywords
Isatinphenylsemicarbazones; Light initiated E–Z and Z–E isomerization; Thermally initiated back reaction; Tautomeric equilibrium effect
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Light initiated E–Z and Z–E isomerization of isatinphenylsemicarbazones: Tautomeric equilibrium effect
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 288, 15 August 2014, Pages 60–69
Authors
, , , , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Price was $35.95
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Price after discount Only $4.95
100% Money Back Guarantee
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