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Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-

DOI: 10.1021/cm100514r DOI Help

Authors: Greg J. Mcentee (University of Strathclyde, U.K.) , Peter J. Skabara (University of Strathclyde, U.K.) , Filipe Vilela (University of Strathclyde, U.K.) , Steven Tierney (Merck Chemicals, U.K.) , Ifor D. W. Samuel (University of St. Andrews, U.K.) , Salvatore Gambino (University of St. Andrews, U.K.) , Simon Coles (University of Southampton) , Michael B. Hursthouse (University of Southampton, U.K.) , Ross Harrington (Newcastle University) , William Clegg (Newcastle University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry Of Materials , VOL 22 (9) , PAGES 3000 - 3008

State: Published (Approved)
Published: May 2010
Diamond Proposal Number(s): 987

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.

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 28/09/2012 11:02

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