Thiophene fluorination to enhance photovoltaic performance in low band gap donor–acceptor polymers

Zhuping Fei; Munazza Shahid; Nir Yaacobi-Gross; Stephan Rossbauer; Hongliang Zhong; Scott E. Watkins; Thomas D. Anthopoulos; Martin Heeney

doi:10.1039/c2cc35079c

Thiophene fluorination to enhance photovoltaic performance in low band gap donor–acceptor polymers

Zhuping Fei, Munazza Shahid, Nir Yaacobi-Gross, Stephan Rossbauer, Hongliang Zhong, Scott E. Watkins, Thomas D. Anthopoulos, Martin Heeney

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66 Scopus citations

Abstract

We report the first synthesis of a tetrafluorinated 4,7-bis(3,4-difluorothiophen-2-yl)-2,1,3-benzothiadiazole monomer and its polymerisation with dithieno[3,2-b:2′,3′-d]germole by Stille coupling to afford a low band gap polymer with a high ionisation potential. Direct comparison to the non-fluorinated analogue demonstrates that fluorination results in an increase in ionisation potential with no change in optical band gap, and enhanced aggregation over the non-fluorinated polymer. These desirable properties result in a significant enhancement in OPV device performance in blends with PC71BM. © 2012 The Royal Society of Chemistry.

Original language	English (US)
Pages (from-to)	11130-11132
Number of pages	3
Journal	Chemical Communications
Volume	48
Issue number	90
DOIs	https://doi.org/10.1039/c2cc35079c
State	Published - Oct 17 2012
Externally published	Yes

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title = "Thiophene fluorination to enhance photovoltaic performance in low band gap donor–acceptor polymers",

abstract = "We report the first synthesis of a tetrafluorinated 4,7-bis(3,4-difluorothiophen-2-yl)-2,1,3-benzothiadiazole monomer and its polymerisation with dithieno[3,2-b:2′,3′-d]germole by Stille coupling to afford a low band gap polymer with a high ionisation potential. Direct comparison to the non-fluorinated analogue demonstrates that fluorination results in an increase in ionisation potential with no change in optical band gap, and enhanced aggregation over the non-fluorinated polymer. These desirable properties result in a significant enhancement in OPV device performance in blends with PC71BM. {\textcopyright} 2012 The Royal Society of Chemistry.",

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T1 - Thiophene fluorination to enhance photovoltaic performance in low band gap donor–acceptor polymers

AU - Fei, Zhuping

AU - Shahid, Munazza

AU - Yaacobi-Gross, Nir

AU - Rossbauer, Stephan

AU - Zhong, Hongliang

AU - Watkins, Scott E.

AU - Anthopoulos, Thomas D.

AU - Heeney, Martin

N1 - Generated from Scopus record by KAUST IRTS on 2023-02-14

PY - 2012/10/17

Y1 - 2012/10/17

N2 - We report the first synthesis of a tetrafluorinated 4,7-bis(3,4-difluorothiophen-2-yl)-2,1,3-benzothiadiazole monomer and its polymerisation with dithieno[3,2-b:2′,3′-d]germole by Stille coupling to afford a low band gap polymer with a high ionisation potential. Direct comparison to the non-fluorinated analogue demonstrates that fluorination results in an increase in ionisation potential with no change in optical band gap, and enhanced aggregation over the non-fluorinated polymer. These desirable properties result in a significant enhancement in OPV device performance in blends with PC71BM. © 2012 The Royal Society of Chemistry.

AB - We report the first synthesis of a tetrafluorinated 4,7-bis(3,4-difluorothiophen-2-yl)-2,1,3-benzothiadiazole monomer and its polymerisation with dithieno[3,2-b:2′,3′-d]germole by Stille coupling to afford a low band gap polymer with a high ionisation potential. Direct comparison to the non-fluorinated analogue demonstrates that fluorination results in an increase in ionisation potential with no change in optical band gap, and enhanced aggregation over the non-fluorinated polymer. These desirable properties result in a significant enhancement in OPV device performance in blends with PC71BM. © 2012 The Royal Society of Chemistry.

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DO - 10.1039/c2cc35079c

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SP - 11130

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JO - Chemical Communications

JF - Chemical Communications

IS - 90

ER -

Thiophene fluorination to enhance photovoltaic performance in low band gap donor–acceptor polymers

Abstract

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