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Issue 12, 2018
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Oxidation of pyrrole with p-benzoquinone to semiconducting products and their application in electrorheology

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Abstract

A low-molecular-weight organic semiconducting material was prepared by the redox interaction between pyrrole and p-benzoquinone. The reaction between pyrrole and p-benzoquinone in aqueous solutions of methanesulfonic acid proceeded smoothly at room temperature. The product with a globular morphology obtained in high yield in 0.1 M methanesulfonic acid had the highest conductivity, 4.6 × 10−6 S cm−1. On the other hand, the samples prepared in the absence of acid or at high acid concentration were non-conducting. EPR spectroscopy confirmed the presence of electronic species as charge carriers responsible for conductivity. The dominating component was proved to be a low-molecular-weight adduct composed of the quinhydrone complex and the pyrrole molecule. FTIR and Raman spectra were used to discuss the molecular structure in detail. A strong electrorheological effect with a very fast response time was demonstrated by the reproducible increase in the viscosity of suspensions in silicone oil after application of the electric field. The effect is discussed with the help of dielectric spectroscopy.

Graphical abstract: Oxidation of pyrrole with p-benzoquinone to semiconducting products and their application in electrorheology

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Publication details

The article was received on 15 Mar 2018, accepted on 30 Apr 2018 and first published on 02 May 2018


Article type: Paper
DOI: 10.1039/C8NJ01283K
Citation: New J. Chem., 2018,42, 10167-10176
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    Oxidation of pyrrole with p-benzoquinone to semiconducting products and their application in electrorheology

    J. Stejskal, P. Bober, M. Trchová, J. Horský, Z. Walterová, S. K. Filippov, T. Plachý and M. Mrlík, New J. Chem., 2018, 42, 10167
    DOI: 10.1039/C8NJ01283K

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