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New acetophenone-functionalized thiophene monomer for conducting films on electrodes in chemical ion-sensorics: The synthesis and spectroelectrochemical study

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Abstract

A new acetophenone-functionalized thiophene monomer, 2-hydroxy-6-[2-(thiophene-3-yl)ethoxy]acetophenone, is synthesized by the reaction of 2.6-dihydroxyacetophenone with 2-(thiophene-3-yl)ethane-1-ol under mild conditions. The synthesis is performed in order to study its electrochemical oxidation and prepare a functionalized conducting material for ion sensors with a receptor group for divalent heavy-metal cations. The redox behavior of the functionalized thiophene is studied by simultaneous in situ ESR and Vis-NIR spectroscopy. The formation of soluble thiophene oligomeric structures during the electrochemical oxidation of the monomer is found. Direct evidence for the formation of oligomers is given by ex situ MALDI-TOF and LDI-TOF mass spectrometry. The acetophenone-functionalized monomer and 3-methylthiophene are electrochemically copolymerized and the copolymeric nature of the product is proved by MALDI-TOF mass spectrometry as well. The copolymer film at the electrode surface is characterized in its redox behavior.

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Authors and Affiliations

  1. Heyrovský Institute of Physical Chemistry, Dolejškova 3, CZ-182 23, Prague 8, Czech Republic

    J. Tarábek

  2. Institute for Macromolecular and Textile Chemistry, Dresden University of Technology, Mommsenstrasse 4, D-010 69, Dresden, Germany

    E. Jähne, D. Ferse & H. -J. Adler

  3. Slovak University of Technology, Radlinského 9, SK-812 37, Bratislava, Slovak Republic

    P. Rapta

  4. Leibniz Institute for Solid State and Materials Research, Helmholtzstrasse 20, D-010 69, Dresden, Germany

    J. Tarábek, P. Rapta & L. Dunsch

Authors
  1. J. Tarábek
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  2. E. Jähne
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  3. P. Rapta
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  4. D. Ferse
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  5. H. -J. Adler
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  6. L. Dunsch
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Corresponding author

Correspondence to L. Dunsch.

Additional information

Published in Russian in Elektrokhimiya, 2006, Vol. 42, No. 11, pp. 1302–1311.

Based on the report delivered at the 8th International Frumkin Symposium “Kinetics of the Electrode Processes,” October 18–22, 2005, Moscow.

The text was submitted by the authors in English.

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Tarábek, J., Jähne, E., Rapta, P. et al. New acetophenone-functionalized thiophene monomer for conducting films on electrodes in chemical ion-sensorics: The synthesis and spectroelectrochemical study. Russ J Electrochem 42, 1169–1176 (2006). https://doi.org/10.1134/S1023193506110036

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  • DOI: https://doi.org/10.1134/S1023193506110036

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