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Dynamics of excited-state intramolecular proton-transfer in 2-amino-3-(2′-benzazolyl)quinoline cations

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Abstract

It was found that cations formed by the protonation of 2-amino-3-(2′-benzoxazolyl)-quinoline (ABO) and 2-amino-3-(2′-benzothiazolyl)-quinoline (ABT) at the nitrogen atom of the quinoline ring exhibit excited-state intramolecular proton transfer (ESIPT). The two-band fluorescence of these cations is due to the emission from two species: the initial tautomer (short-wavelength band) and the ESIPT product (long-wavelength band). The relative intensity of the long-wavelength band depends on the basicity of the proton-accepting moiety and temperature. Quantum-chemical calculations demonstrated that ESIPT in cations involves overcoming a significant potential barrier, which increases with the decreasing basicity of the proton-accepting benzazole moiety. Using femtosecond absorption spectroscopy and nanosecond fluorescence spectroscopy, the effective ESIPT time in the studied cations was determined, which increased with decreasing temperature.

Graphical abstract: Dynamics of excited-state intramolecular proton-transfer in 2-amino-3-(2′-benzazolyl)quinoline cations

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Publication details

The article was received on 21 Mar 2017, accepted on 16 May 2017 and first published on 17 May 2017


Article type: Paper
DOI: 10.1039/C7PP00104E
Citation: Photochem. Photobiol. Sci., 2017, Advance Article
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    Dynamics of excited-state intramolecular proton-transfer in 2-amino-3-(2′-benzazolyl)quinoline cations

    M. N. Khimich, V. L. Ivanov, M. Ya. Melnikov, I. V. Shelaev, F. E. Gostev, V. A. Nadtochenko and B. M. Uzhinov, Photochem. Photobiol. Sci., 2017, Advance Article , DOI: 10.1039/C7PP00104E

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