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

McEntee, Greg J. and Skabara, Peter and Vilela, Filipe and Tierney, Steven and Samuel, Ifor D. W. and Gambino, Salvatore and Coles, Simon J. and Hursthouse, Michael B. and Harrington, Ross W. and Clegg, William (2010) Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units. Chemistry of Materials, 22 (9). pp. 3000-3008. ISSN 0897-4756

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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. Noncovalent 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.