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Issue 2, 2018
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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

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Publication details

The article was received on 05 Sep 2017, accepted on 15 Dec 2017 and first published on 18 Dec 2017


Article type: Paper
DOI: 10.1039/C7PP00334J
Citation: Photochem. Photobiol. Sci., 2018,17, 231-238
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    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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