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Solvent effect on the anodic oxidation of tannic acids: EPR/UV–Vis spectroelectrochemical and DFT theoretical study

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Abstract

Cyclic voltammetry of tannic acid mixture (TAM) in water, dimethylsulfoxide (DMSO), and acetonitrile (ACN) indicates the highest oxidation potential for TAM in ACN, followed by the slightly lowered potential in DMSO and a strongly shifted oxidation potential in water solutions, confirming its pH-dependent redox behavior. In situ EPR and UV–Vis spectroelectrochemical experiments were performed to follow the oxidation reactions of TAM in protic and aprotic media. The formation of an unstable semiquinone anion radical formed upon anodic oxidation of TAM was proved by in situ EPR spectroelectrochemistry both in DMSO and water solutions. The quantum chemical calculations of the model pyrogallol derivatives and tannic acid molecules with four and ten galloyl moieties estimated the role of the spatial hydrogen bonds on the proton affinities and suggested the possible interpretation of experimentally detected redox and spectroelectrochemical behaviors.

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Acknowledgments

This work was supported by the Scientific Grant Agency of the Slovak Republic (Projects 1/0735/13 and 1/0307/14). We are grateful to the HPC center at the Slovak University of Technology in Bratislava, which is a part of the Slovak Infrastructure of High Performance Computing (SIVVP project, ITMS code 26230120002, funded by the European Region Development Funds, ERDF) for the computational time and resources made available.

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Authors and Affiliations

  1. Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic

    Vladimír Lukeš, Denisa Darvasiová, Ivana Hubertová & Peter Rapta

  2. Institute of Biotechnology and Food Science, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37, Bratislava, Slovak Republic

    Katarína Furdíková

Authors
  1. Vladimír Lukeš
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  2. Denisa Darvasiová
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  3. Katarína Furdíková
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  4. Ivana Hubertová
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  5. Peter Rapta
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Correspondence to Vladimír Lukeš.

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Dedicated to Prof. Mikhail A. Vorotyntsev in the occasion of his 70th birthday

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Lukeš, V., Darvasiová, D., Furdíková, K. et al. Solvent effect on the anodic oxidation of tannic acids: EPR/UV–Vis spectroelectrochemical and DFT theoretical study. J Solid State Electrochem 19, 2533–2544 (2015). https://doi.org/10.1007/s10008-015-2921-9

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  • DOI: https://doi.org/10.1007/s10008-015-2921-9

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