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Issue 10, 2003
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Preparation and spectroelectrochemical behaviour of a new alternate copolymer of 3,3′-di-n-octyl-2,2′-bithiophene and fluoren-9-one

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Abstract

The synthesis and spectroelectrochemical behaviour of a new solution processible conjugated polymer, namely poly[{5,5′-(3,3′-di-n-octyl-2,2′-bithiophene)}-alt-(2,7-fluoren-9-one)] (abbreviated as PDOBTF), are described. PDOBTF can be considered as the first member of a new family of conjugated copolymers—poly(oligothiophene-alt-fluoren-9-one)s—whose properties can be tuned by changing the length of the oligothiophene segments and their regiochemistry. PDOBTF can be obtained by oxidative polymerisation of 2,7-bis(4-octylthien-2-yl)-fluoren-9-one or by condensation polymerisation of 2,7-bis(5-bromo-4-octylthien-2-yl)-fluoren-9-one using a modification of Yamamoto coupling. Both preparation methods lead to a mixture of polymeric and oligomeric species and require post-polymerisation fractionating if high molecular fractions are to be obtained. Oxidative polymerisation gives product of a higher molecular weight (Mn = 41.0 kDa, Mw/Mn = 1.81 for the highest molecular weight fraction) as compared to the one prepared by Yamamoto condensation polymerisation (Mn = 13.3 kDa, Mw/Mn = 1.45 for the highest molecular weight fraction).

Electrochemical oxidation of PDOBTF in an nonaqueous electrolyte (0.1 M Bu4NBF4/acetonitrile) gives rise to an anodic peak at E = 835 mV, which can be ascribed to the p-type doping of the copolymer. The extension of the potential to E = 1500 mV results in the oxidative degradation of the copolymer and induces total loss of its electroactivity. UV-Vis-NIR and Raman spectroelectrochemical data are consistent with the oxidative doping. The latter technique enables the monitoring of the doping-induced changes in both structural sub-units of the copolymer: the bithiophene sub-unit and the fluoren-9-one one.

Graphical abstract: Preparation and spectroelectrochemical behaviour of a new alternate copolymer of 3,3′-di-n-octyl-2,2′-bithiophene and fluoren-9-one

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Publication details

The article was received on 24 Apr 2003, accepted on 08 Jul 2003 and first published on 28 Aug 2003


Article type: Paper
DOI: 10.1039/B304551J
New J. Chem., 2003,27, 1479-1484

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    Preparation and spectroelectrochemical behaviour of a new alternate copolymer of 3,3′-di-n-octyl-2,2′-bithiophene and fluoren-9-one

    R. Demadrille, B. Divisia-Blohorn, M. Zagorska, S. Quillard, P. Rannou, J. Pierre Travers and A. Pron, New J. Chem., 2003, 27, 1479
    DOI: 10.1039/B304551J

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