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

P.J. Skabara, G.J. McEntee, F. Vilela, S. Tierney

Research output: Contribution to journalArticle

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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. Non-covalent 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.
Original languageEnglish
Pages (from-to)3000-3008
Number of pages8
JournalJournal of Materials Chemistry
Volume22
Issue number9
DOIs
Publication statusPublished - 2010

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Thiophenes
Electropolymerization
Thiophene
Molecules
Hole mobility
Conformations
Polymers
Single crystals
X ray diffraction

Keywords

  • synthesis
  • electropolymerization
  • hexadecyl functionalized bithiophene
  • materials chemistry

Cite this

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title = "Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units",
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. Non-covalent 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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Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units. / Skabara, P.J.; McEntee, G.J.; Vilela, F.; Tierney, S.

In: Journal of Materials Chemistry, Vol. 22, No. 9, 2010, p. 3000-3008.

Research output: Contribution to journalArticle

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AU - Skabara, P.J.

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AU - Vilela, F.

AU - Tierney, S.

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N2 - 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. Non-covalent 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.

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. Non-covalent 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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