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Synlett 2018; 29(19): 2542-2546
DOI: 10.1055/s-0037-1610299
cluster
© Georg Thieme Verlag Stuttgart · New York

Poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline): Processible, Low-Bandgap, Ambipolar-Acceptor Frameworks via Direct Arylation Polymerization

Trent E. Anderson
a   Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108, USA   Email: seth.rasmussen@ndsu.edu
,
Evan W. Culver
a   Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108, USA   Email: seth.rasmussen@ndsu.edu
,
Furqan Almyahi
b   Centre for Organic Electronics, University of Newcastle, Callaghan, NSW 2308, Australia
,
Paul C. Dastoor
b   Centre for Organic Electronics, University of Newcastle, Callaghan, NSW 2308, Australia
,
Seth C. Rasmussen*
a   Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108, USA   Email: seth.rasmussen@ndsu.edu
› Author AffiliationsFunding provided by North Dakota State University and the American-Australian Fulbright Commission. The work was also performed in part at the Material’s Node of the Australian National Fabrication Facility, which is a company established under the National Collaborative Research Infrastructure Strategy to provide nano- and microfabrication facilities for Australia’s researchers. FA gratefully acknowledges the Office of the Prime Minister of Iraq through the Higher Committee for Education Development (HCED) for funding support.
Further Information

Publication History

Received: 14 July 2018

Accepted after revision: 11 September 2018

Publication Date:
11 October 2018 (online)

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Published as part of the Cluster Synthesis of Materials

Abstract

The synthesis of a new dialkyl-functionalized quinoxaline ­acceptor, 5,8-dibromo-2,3-dihexylquinoxaline, is reported, along with its cross-coupling with 2,3-dihexylthieno[3,4-b]pyrazine via direct arylation polymerization. The resulting ambipolar-acceptor polymer ­poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline) exhib­its a low bandgap of 1.07 eV and high solubility. The results of initial organic photovoltaic devices are also reported.

Key words

thieno[3,4-b]pyrazine - 2,3-dihexylquinoxaline - donor–­acceptor framework - low bandgap - direct arylation polymerization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610299.
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