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Proton-driven “one-way” photoisomerization due to energy transfer switching in styrylquinoline–merocyanine dyad

Paper ID Volume ID Publish Year Pages File Format Full-Text
27143 44004 2014 6 PDF Available
Title
Proton-driven “one-way” photoisomerization due to energy transfer switching in styrylquinoline–merocyanine dyad
Abstract

•Forster resonance energy transfer (FRET) occurs in bichromophoric dyad.•FRET quenches trans → cis photoisomerization of styrylquinoline (SQ) moiety.•SQ trans → cis photoisomerization is switched on in protonated dyad.•Effect of “one-way” photoisomerization in the dyad is kinetic in nature.

Photophysical and photochemical properties of the novel bichromophoric covalently linked dyad SQ3MC, where 2-styrylquinoline (SQ) and merocyanine (MC) chromophoric groups are connected by dioxytrimethylene bridge O-(CH2)3O, in comparison with model compounds 2-(4-methoxystyryl)quinoline MeSQ and 1-ethyl-2-(4-methoxystyryl)quinolinium perchlorate, which is O-methylated merocyanine MeMC, are investigated. In dyad SQ3MC, trans → cis photoisomerization of SQ moiety is quenched because of competing Forster resonance energy transfer (FRET) to MC fragment. However, reaction is switched on in protonated quasisymmetric dyad where positively charged SQ fragment obtains the same chromophoric π-system as in MC chromophore. After deprotonation, photoisomerization of SQ fragment in trans → cis direction is again switched off but goes in cis → trans direction. Effect of “one-way” photoisomerization in the dyad SQ3MC is kinetic in nature and based on the difference in rates of competing processes in the excited state, in contrast to well-known one-way reactivity of diarylethylenes with large aryl substituents, where effect is thermodynamic in nature and based on the difference in energies of the excited-state isomers and conformers.

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Keywords
Bichromophoric dyad; Styrylquinoline; Merocyanine; Electronic energy transfer; Photoisomerization
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Proton-driven “one-way” photoisomerization due to energy transfer switching in styrylquinoline–merocyanine dyad
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 279, 1 April 2014, Pages 59–64
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us