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 Affiliations

Funding 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.
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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.

Supporting Information