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

doi:10.1021/cm100514r

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 journal › Article › peer-review

45 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 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 language	English
Pages (from-to)	3000-3008
Number of pages	9
Journal	Chemistry of Materials
Volume	22
Issue number	9
DOIs	https://doi.org/10.1021/cm100514r
Publication status	Published - 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

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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

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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.",

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

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

year = "2010",

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doi = "10.1021/cm100514r",

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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 J

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

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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. 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.

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 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.

KW - FIELD-EFFECT TRANSISTORS

KW - THIN-FILM TRANSISTORS

KW - PI-CONJUGATED SYSTEMS

KW - ORGANIC SOLAR-CELLS

KW - HIGH-PERFORMANCE

KW - POLYTHIOPHENE CHAINS

KW - CARRIER MOBILITY

KW - SMALL MOLECULES

KW - SEMICONDUCTORS

KW - POLYMERS

U2 - 10.1021/cm100514r

DO - 10.1021/cm100514r

M3 - Article

SN - 0897-4756

VL - 22

SP - 3000

EP - 3008

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 9

ER -

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

Abstract

Keywords

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