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Synthesis and electropolymerisation of 3 ',4 '-bis(alkylsulfanyl)terthiophenes and the significance of the fused dithiin ring in 2,5-dithienyl-3,4-ethylenedithiothiophene (DT-EDTT)

Pozo-Gonzalo, Cristina and Khan, Tahir and McDouall, Joseph J.W. and Skabara, Peter J. and Roberts, Donna M. and Light, Mark E. and Coles, Simon J. and Hursthouse, Michael B. and Neugebauer, Helmut and Cravino, Antonio and Sariciftci, N. Serdar (2002) Synthesis and electropolymerisation of 3 ',4 '-bis(alkylsulfanyl)terthiophenes and the significance of the fused dithiin ring in 2,5-dithienyl-3,4-ethylenedithiothiophene (DT-EDTT). Journal of Materials Chemistry, 12 (3). pp. 500-510. ISSN 0959-9428

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Abstract

A new series of regioregular poly(terthiophenes), bearing bis( thioether) side groups, has been prepared by electrochemical oxidation. Cyclic voltammetry of the parent trimers reveals an increase in electron donating ability in cyclic thioether derivatives. For example, one compound containing a central ethylenedithiothiophene (EDTT) unit gives two irreversible oxidation peaks which are significantly lower than the corresponding values for the structurally analogous bis( methylthio) derivative (DeltaE(1ox) = 170 mV, DeltaE(2ox) = 30 mV). The difference in oxidation potentials of each terthiophene in acetonitrile solution can be explained by examining the highest occupied molecular orbital (HOMO) energies. The electrochemical behaviour of the polymers illustrates the increase in p-doping ability of the EDTT-containing polymer. The cyclic voltammograms and electronic absorption spectra of the polymers show that the polymers containing cyclic thioether units have the lowest bandgap in the series (ca. 1.4 V and 1.5 eV, respectively). Photoinduced IR spectroscopy of poly(dithienyl-3,4-ethylenedithiothiophene) provides evidence of a long-living photoexcited charged state in the polymer.

Item type: Article
ID code: 819
Keywords: x-ray structure, conducting polymers, conjugated polymers, crystal-strucutres, electrochemical synthesis, infrared activity, poly(3, 4-ethylenedioxythiophene), oligothiophenes, 3, 4-ethylenedioxythiophene, poly(thiophenes), Chemistry, Materials Chemistry, Chemistry(all)
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Related URLs:
Depositing user: Mr Derek Boyle
Date Deposited: 20 Apr 2006
Last modified: 04 Sep 2014 11:09
URI: http://strathprints.strath.ac.uk/id/eprint/819

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