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

Greg J. McEntee, Peter J Skabara, Filipe Vilela, Steven Tierney, Ifor D. W. Samuel, Salvatore Gambino, Simon J. Coles, Michael B. Hursthouse, Ross W. Harrington, William Clegg

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)3000-3008
Number of pages9
JournalChemistry of Materials
Volume22
Issue number9
DOIs
Publication statusPublished - 11 May 2010

Keywords

  • FIELD-EFFECT TRANSISTORS
  • THIN-FILM TRANSISTORS
  • PI-CONJUGATED SYSTEMS
  • ORGANIC SOLAR-CELLS
  • HIGH-PERFORMANCE
  • POLYTHIOPHENE CHAINS
  • CARRIER MOBILITY
  • SMALL MOLECULES
  • SEMICONDUCTORS
  • POLYMERS

Cite this

McEntee, G. J., Skabara, P. J., Vilela, F., Tierney, S., Samuel, I. D. W., Gambino, S., Coles, S. J., Hursthouse, M. B., Harrington, R. W., & Clegg, W. (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), 3000-3008. https://doi.org/10.1021/cm100514r