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Issue 35, 2016
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A new class of N–H excited-state intramolecular proton transfer (ESIPT) molecules bearing localized zwitterionic tautomers

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Abstract

A series of new amino (NH)-type intramolecular hydrogen-bonding (H-bonding) compounds have been strategically designed and synthesized. These molecules comprise a 2-(imidazo[1,2-a]pyridin-2-yl)aniline moiety, in which one of the amino hydrogens was replaced with substituents of different electronic properties. This, together with the versatile capability for modifying the parent moiety, makes feasible comprehensive spectroscopy and dynamics studies of excited-state intramolecular proton transfer (ESIPT) as a function of N–H acidity. Different from other (NH)-type ESIPT systems where the ESIPT rate and exergonicity increase with an increase in the N–H acidity and hence the H-bonding strength, the results reveal an irregular relationship among ESIPT dynamics, thermodynamics and H-bond strength. This discrepancy may be rationalized by the localized zwitterionic nature of 2-(imidazo[1,2-a]pyridin-2-yl)aniline in the proton-transfer tautomer form, which is different from the π-delocalized tautomer form in other (NH)-type ESIPT systems.

Graphical abstract: A new class of N–H excited-state intramolecular proton transfer (ESIPT) molecules bearing localized zwitterionic tautomers

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Publication details

The article was received on 28 Jul 2016, accepted on 11 Aug 2016 and first published on 11 Aug 2016


Article type: Paper
DOI: 10.1039/C6CP05236C
Citation: Phys. Chem. Chem. Phys., 2016,18, 24428-24436

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    A new class of N–H excited-state intramolecular proton transfer (ESIPT) molecules bearing localized zwitterionic tautomers

    A. J. Stasyuk, Y. Chen, C. Chen, P. Wu and P. Chou, Phys. Chem. Chem. Phys., 2016, 18, 24428
    DOI: 10.1039/C6CP05236C

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