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Electrochemical and spectral properties of meta-linked 1,3,5-tris(aryl)benzenes and 2,4,6-tris(aryl)-1-phenoles, and their polymers |
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| Authors: | Krzysztof R Idzik Przemyslaw Ledwon Sylwia Golba Mieczyslaw Lapkowski |
| Affiliation: | a Institute of Organic and Macromolecular Chemistry, Friedrich Schiller Universität Jena, Humboldstraße 10, D-07743 Jena, Germany b Department of Chemistry, Faculty of Medicinal Chemistry and Microbiology, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland c Silesian University of Technology, Faculty of Chemistry, Strzody 9, 44-100 Gliwice, Poland d Centre of Polymer and Carbon Materials, Polish Academy of Sciences, ul. Sowinskiego 5, 44-121 Gliwice, Poland e Technische Universität Darmstadt, Eduard-Zintl-Institut für Anorganische und Physikalische Chemie, Petersenstr. 20, 64287 Darmstadt, Germany |
| Abstract: | We present electrochemical and spectral properties of symmetric monomers 1,3,5-tris(aryl)benzenes and 2,4,6-tris(aryl)-1-phenols and their polymers. These compounds contain thienyl, furyl or EDOT moieties attached to central benzene or phenol ring at the meta-position, synthesized by a Stille cross-coupling procedure. All monomers are electroactive and undergo electropolymerization creating thin films on an electrode surface. Polymers with meta-linkages were obtained by electrochemical oxidation. Detailed cyclic voltammetry and in situ UV-vis spectroelectrochemistry show that polymers with hydroxy groups exhibit higher conductivity and better stability than with benzene core. Interesting and different behavior occurs for 2,4,6-tris(2-thienyl)-1-phenol, for which the characteristic, sharp, redox peak is observed. |
| Keywords: | Stille coupling procedure Meta-linkage Branched polymers Electrochemical polymerization Hydroxyl substituent |
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