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Torsion-induced fluorescence quenching in excited-state intramolecular proton transfer (ESIPT) dyes

Paper ID Volume ID Publish Year Pages File Format Full-Text
28866 44099 2007 6 PDF Available
Title
Torsion-induced fluorescence quenching in excited-state intramolecular proton transfer (ESIPT) dyes
Abstract

Fluorescence quenching behaviors of four known excited-state intramolecular proton transfer (ESIPT) molecules have been studied by semiempirical and ab initio calculations. The ESIPT compounds studied in this work are assorted into two sets depending on the N-containing ring structure (5- and 6-membered rings). It has been found that twisted intramolecular charge transfer (TICT) process in the excited keto state (K*) after ESIPT, one of the possible quenching pathways of ESIPT fluorescence, is significantly influenced by the geometrical properties of intramolecular hydrogen (H) bond associated with the N-containing ring structure. The compounds with 5-membered ring have efficient ESIPT emission with large barrier to fluorescence-quenching TICT state, due to appropriate stabilization of planar K* through intramolecular H bond. For the compounds with 6-membered ring, however, ESIPT emission is completely quenched due to significantly lowered barrier resulting from too short H-bond length. The effect of intramolecular H bond on the TICT reaction potential has been discussed in detail from the viewpoints of molecular structure and torsional motion, with the help of elaborate model compound studies.

Keywords
Twisted intramolecular charge transfer (TICT); Intramolecular hydrogen bond; Excited-state intramolecular proton transfer (ESIPT); Fluorescence quenching; Semiempirical and ab initio calculations
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Torsion-induced fluorescence quenching in excited-state intramolecular proton transfer (ESIPT) dyes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 191, Issue 1, 7 September 2007, Pages 19–24
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