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Synthesis and Electropolymerization of Hexadecyl Functionalized Bithiophene and Thieno[3,2-b]thiophene End-Capped with EDOT and EDTT Units

Lookup NU author(s): Dr Ross Harrington, Emeritus Professor Bill Clegg

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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 center dot center dot center dot 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 x 10(-5) cm(2) V-1 s(-1) for compound 1 and 1.5 x 10(-5) cm(2) V-1 s(-1) for 2.


Publication metadata

Author(s): McEntee GJ, Skabara PJ, Vilela F, Tierney S, Samuel IDW, Gambino S, Coles SJ, Hursthouse MB, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: Chemistry of Materials

Year: 2010

Volume: 22

Issue: 9

Pages: 3000-3008

Print publication date: 02/04/2010

ISSN (print): 0897-4756

ISSN (electronic): 1520-5002

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/cm100514r

DOI: 10.1021/cm100514r


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