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

Greg J. McEntee, Peter 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

33 Citations (Scopus)

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.
LanguageUndefined/Unknown
Pages3000-3008
Number of pages9
JournalChemistry of Materials
Volume22
Issue number9
DOIs
Publication statusPublished - 11 May 2010

Keywords

  • electropolymerization
  • hexadecyl functionalized bithiophene
  • EDTT units
  • planarity

Cite this

McEntee, G. J., Skabara, P., Vilela, F., Tierney, S., Samuel, I. D. W., Gambino, S., ... 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
McEntee, Greg J. ; Skabara, Peter ; Vilela, Filipe ; Tierney, Steven ; Samuel, Ifor D. W. ; Gambino, Salvatore ; Coles, Simon J. ; Hursthouse, Michael B. ; Harrington, Ross W. ; Clegg, William. / Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units. In: Chemistry of Materials. 2010 ; Vol. 22, No. 9. pp. 3000-3008.
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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.",
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McEntee, GJ, Skabara, P, Vilela, F, Tierney, S, Samuel, IDW, Gambino, S, Coles, SJ, Hursthouse, MB, Harrington, RW & 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, vol. 22, no. 9, pp. 3000-3008. https://doi.org/10.1021/cm100514r

Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units. / McEntee, Greg J.; Skabara, Peter; Vilela, Filipe; Tierney, Steven; Samuel, Ifor D. W.; Gambino, Salvatore; Coles, Simon J.; Hursthouse, Michael B.; Harrington, Ross W.; Clegg, William.

In: Chemistry of Materials, Vol. 22, No. 9, 11.05.2010, p. 3000-3008.

Research output: Contribution to journalArticle

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T1 - Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units

AU - McEntee, Greg J.

AU - Skabara, Peter

AU - Vilela, Filipe

AU - Tierney, Steven

AU - Samuel, Ifor D. W.

AU - Gambino, Salvatore

AU - Coles, Simon J.

AU - Hursthouse, Michael B.

AU - Harrington, Ross W.

AU - Clegg, William

PY - 2010/5/11

Y1 - 2010/5/11

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AB - 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.

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