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Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units

Skabara, P.J. and McEntee, G.J. and Vilela, F. and Tierney, S. (2010) Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units. Journal of Materials Chemistry, 22 (9). pp. 3000-3008. ISSN 0959-9428

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Abstract

The synthesis of three novel thiophene-based conjugated molecules (1-3) is presented. We report the electronic and redox properties of these compounds along with the corresponding electrochemically prepared polymers. The structures of compounds 1 and 2 have been confirmed by single-crystal X-ray diffraction studies. Non-covalent S…O interactions in 1 act to hold the molecule in a planar conformation and this is in stark contrast to the twisted nature of the 3,4-ethylenedithiothiophene (EDTT) analogue. The degree of planarity within the molecules dictates the effective conjugation length within the materials and also the packing of the molecules in the solid state. CGL-TOF studies give hole mobilities up to 4 × 10-5 cm2 V-1 s-1 for compound 1 and 1.5 × 10-5 cm2 V-1 s-1 for 2.