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; Evan W. Culver; Furqan Almyahi; Paul C. Dastoor; Seth C. Rasmussen

doi:10.1055/s-0037-1610299

Synlett, Table of Contents

Synlett 2018; 29(19): 2542-2546
DOI: 10.1055/s-0037-1610299

cluster

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

^aDepartment 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

^aDepartment 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

^bCentre for Organic Electronics, University of Newcastle, Callaghan, NSW 2308, Australia

,

Paul C. Dastoor

^bCentre for Organic Electronics, University of Newcastle, Callaghan, NSW 2308, Australia

,

Seth C. Rasmussen*

^aDepartment of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108, USA Email: seth.rasmussen@ndsu.edu

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Abstract

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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

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References

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