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Issue 2, 2018

Photoacidity as a tool to rationalize excited state intramolecular proton transfer reactivity in flavonols

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Abstract

This work presents the determination of acidic strengths at the electronic ground and excited states (pKa and Image ID:c7pp00334j-t2.gif) of three flavonol derivatives using electronic absorption and fluorescence emission spectroscopy. The differences of the pKa and Image ID:c7pp00334j-t3.gif values were successfully correlated with the molecular structures according to the substitution pattern at the flavonol structure (hydrogen, diethylamino or fluoro moieties). In order to obtain more information about the observed photoacidity of these superacids, geometry optimizations and excitation energy calculations were performed at the CAM-B3LYP/6-311++G(d,p) level for their neutral, protonated and deprotonated species.

Graphical abstract: Photoacidity as a tool to rationalize excited state intramolecular proton transfer reactivity in flavonols

Supplementary files

Article information


Submitted
05 Sep 2017
Accepted
15 Dec 2017
First published
18 Dec 2017

Photochem. Photobiol. Sci., 2018,17, 231-238
Article type
Paper

Photoacidity as a tool to rationalize excited state intramolecular proton transfer reactivity in flavonols

L. G. T. A. Duarte, J. C. Germino, C. D. Á. Braga, C. A. Barboza, T. D. Z. Atvars, F. D. S. Santos and F. S. Rodembusch, Photochem. Photobiol. Sci., 2018, 17, 231 DOI: 10.1039/C7PP00334J

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