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Thiophene and selenophene copolymers incorporating fluorinated phenylene units in the main chain: Synthesis, characterization, and application in organic field-effect transistors

Thiophene and selenophene copolymers incorporating fluorinated phenylene units in the main chain: Synthesis, characterization, and application in organic field-effect transistors
Thiophene and selenophene copolymers incorporating fluorinated phenylene units in the main chain: Synthesis, characterization, and application in organic field-effect transistors
A series of thiophene oligomers bearing core phenylene and fluorinated phenylene units has been synthesized as potential semiconductor materials for organic field-effect transistors (OFETs). Polymerization of these compounds has been achieved using Stille and oxidative Coupling methods. Functionalization of the phenylene unit with fluorine atoms has a marked effect on the self-assembly and electronic properties of the parent materials: the optical band gaps and highest occupied molecular orbital levels are affected with the introduction Of fluorine atoms as a result of a combination of inductive effects and rigidification of the main chain. The design of these materials has focused on the self-assembly and solution processability of the materials. All the polymers are readily Soluble in common organic solvents. Self-assembly and planarization of the fluorinated materials in the solid state are identified by a combination of X-ray diffraction studies, absorption spectroscopy, and cyclic voltammetry. The organizational behavior of the films is in contrast to the conformational freedom observed in solution (absorption spectroscopy) and in the gas phase (computational Studies). Thin-film OFETs have been fabricated for the entire polymer series. Hole mobilities have been measured Lip to 10(-3) cm(2)/(V(.)s), with high current modulation (on/off ratios up to 10(5)) and low turn-on voltages (down to 2 V). For the Stille Coupled polymers, replacement of the bridging thiophene unit with selenophene generally increases the hole mobility of the polymers.
thin-film transistors, conjugated polymers, phase-behavior, solar-cells, semiconductors, derivatives, stacking, devices, sensors, oligothiophene
0897-4756
6567-6578
Crouch, David J.
b026fc2c-b90b-4c63-958e-ed3dd0a6437a
Skabara, Peter J.
7138e414-7d50-41c7-933e-0bccad2fa4cd
Lohr, Jan E.
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McDouall, Joseph J.W.
4ca54dfa-6b19-41d4-b531-a5cf701fdd68
Heeney, Martin
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McCulloch, Ian
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Sparrowe, David
bf6033db-64df-489d-9738-9ab4c931a86b
Shkunov, Maxim
2fff59a4-358b-4c89-a501-76ec445457d7
Coles, Simon J.
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Horton, Peter N.
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Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Crouch, David J.
b026fc2c-b90b-4c63-958e-ed3dd0a6437a
Skabara, Peter J.
7138e414-7d50-41c7-933e-0bccad2fa4cd
Lohr, Jan E.
8a0a591b-9815-4fc2-9ab7-973db79d5ad0
McDouall, Joseph J.W.
4ca54dfa-6b19-41d4-b531-a5cf701fdd68
Heeney, Martin
29360690-672c-4186-add3-f463f990e616
McCulloch, Ian
9a1a2fe0-0811-4305-8953-796102393f2b
Sparrowe, David
bf6033db-64df-489d-9738-9ab4c931a86b
Shkunov, Maxim
2fff59a4-358b-4c89-a501-76ec445457d7
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Horton, Peter N.
48f162d1-d6ce-43c1-aeef-d58b3ec702b8
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28

Crouch, David J., Skabara, Peter J., Lohr, Jan E., McDouall, Joseph J.W., Heeney, Martin, McCulloch, Ian, Sparrowe, David, Shkunov, Maxim, Coles, Simon J., Horton, Peter N. and Hursthouse, Michael B. (2005) Thiophene and selenophene copolymers incorporating fluorinated phenylene units in the main chain: Synthesis, characterization, and application in organic field-effect transistors. Chemistry of Materials, 17 (26), 6567-6578. (doi:10.1021/cm051563i).

Record type: Article

Abstract

A series of thiophene oligomers bearing core phenylene and fluorinated phenylene units has been synthesized as potential semiconductor materials for organic field-effect transistors (OFETs). Polymerization of these compounds has been achieved using Stille and oxidative Coupling methods. Functionalization of the phenylene unit with fluorine atoms has a marked effect on the self-assembly and electronic properties of the parent materials: the optical band gaps and highest occupied molecular orbital levels are affected with the introduction Of fluorine atoms as a result of a combination of inductive effects and rigidification of the main chain. The design of these materials has focused on the self-assembly and solution processability of the materials. All the polymers are readily Soluble in common organic solvents. Self-assembly and planarization of the fluorinated materials in the solid state are identified by a combination of X-ray diffraction studies, absorption spectroscopy, and cyclic voltammetry. The organizational behavior of the films is in contrast to the conformational freedom observed in solution (absorption spectroscopy) and in the gas phase (computational Studies). Thin-film OFETs have been fabricated for the entire polymer series. Hole mobilities have been measured Lip to 10(-3) cm(2)/(V(.)s), with high current modulation (on/off ratios up to 10(5)) and low turn-on voltages (down to 2 V). For the Stille Coupled polymers, replacement of the bridging thiophene unit with selenophene generally increases the hole mobility of the polymers.

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Published date: 2005
Keywords: thin-film transistors, conjugated polymers, phase-behavior, solar-cells, semiconductors, derivatives, stacking, devices, sensors, oligothiophene

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Local EPrints ID: 44413
URI: https://eprints.soton.ac.uk/id/eprint/44413
ISSN: 0897-4756
PURE UUID: 6526b073-9767-4475-bab3-2cc592164f5b

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Date deposited: 06 Mar 2007
Last modified: 13 Mar 2019 21:07

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Contributors

Author: David J. Crouch
Author: Peter J. Skabara
Author: Jan E. Lohr
Author: Joseph J.W. McDouall
Author: Martin Heeney
Author: Ian McCulloch
Author: David Sparrowe
Author: Maxim Shkunov
Author: Simon J. Coles
Author: Peter N. Horton
Author: Michael B. Hursthouse

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