Bromination of the benzothioxanthene Bloc: Toward new π-conjugated systems for organic electronic applications

Pierre Josse; Shi Li; Sergey Dayneko; Damien Joly; Antoine Labrunie; Sylvie Dabos-Seignon; Magali Allain; Benjamin Siegler; Renaud Demadrille; Gregory C. Welch; Chad Risko; Philippe Blanchard; Clément Cabanetos

doi:10.1039/c7tc05245f

Bromination of the benzothioxanthene Bloc: Toward new π-conjugated systems for organic electronic applications

Pierre Josse, Shi Li, Sergey Dayneko, Damien Joly, Antoine Labrunie, Sylvie Dabos-Seignon, Magali Allain, Benjamin Siegler, Renaud Demadrille, Gregory C. Welch, Chad Risko, Philippe Blanchard, Clément Cabanetos

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

A selective and efficient method to afford a monobrominated benzothioxanthene (Br-BTXI) derivative is reported. Br-BTXI was extensively employed in common palladium catalyzed coupling reactions. Finally, as a proof of concept, a BTXI based molecular donor was synthesized and evaluated in bulk heterojunction solar cells.

Original language	English
Pages (from-to)	761-766
Number of pages	6
Journal	Journal of Materials Chemistry C
Volume	6
Issue number	4
DOIs	https://doi.org/10.1039/c7tc05245f
State	Published - 2018

Bibliographical note

Funding Information:
The Ministère de la Recherche and the RFI LUMOMAT from the Région Pays de la Loire are acknowledged for the PhD grants of P. Josse and A. Labrunie respectively. Authors thank the PIAM (Plateforme d’Ingénierie et Analyses Moléculaires) of the University of Angers for the characterization of organic compounds. GCW acknowledges NSERC DG (435715-2013), CFI JELF (34102) and the Canadian Research Chairs Program. CR acknowledges the Department of the Navy, ONR (award no. N00014-16-1-2985) and the UK Vice President for start-up research funds. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the UK Information Technology Department and Center for Computational Sciences (CCS).

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

ASJC Scopus subject areas

Chemistry (all)
Materials Chemistry

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10.1039/c7tc05245f

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Josse, P., Li, S., Dayneko, S., Joly, D., Labrunie, A., Dabos-Seignon, S., Allain, M., Siegler, B., Demadrille, R., Welch, G. C., Risko, C., Blanchard, P., & Cabanetos, C. (2018). Bromination of the benzothioxanthene Bloc: Toward new π-conjugated systems for organic electronic applications. Journal of Materials Chemistry C, 6(4), 761-766. https://doi.org/10.1039/c7tc05245f

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title = "Bromination of the benzothioxanthene Bloc: Toward new π-conjugated systems for organic electronic applications",

abstract = "A selective and efficient method to afford a monobrominated benzothioxanthene (Br-BTXI) derivative is reported. Br-BTXI was extensively employed in common palladium catalyzed coupling reactions. Finally, as a proof of concept, a BTXI based molecular donor was synthesized and evaluated in bulk heterojunction solar cells.",

author = "Pierre Josse and Shi Li and Sergey Dayneko and Damien Joly and Antoine Labrunie and Sylvie Dabos-Seignon and Magali Allain and Benjamin Siegler and Renaud Demadrille and Welch, {Gregory C.} and Chad Risko and Philippe Blanchard and Cl{\'e}ment Cabanetos",

note = "Funding Information: The Minist{\`e}re de la Recherche and the RFI LUMOMAT from the R{\'e}gion Pays de la Loire are acknowledged for the PhD grants of P. Josse and A. Labrunie respectively. Authors thank the PIAM (Plateforme d{\textquoteright}Ing{\'e}nierie et Analyses Mol{\'e}culaires) of the University of Angers for the characterization of organic compounds. GCW acknowledges NSERC DG (435715-2013), CFI JELF (34102) and the Canadian Research Chairs Program. CR acknowledges the Department of the Navy, ONR (award no. N00014-16-1-2985) and the UK Vice President for start-up research funds. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the UK Information Technology Department and Center for Computational Sciences (CCS). Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

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doi = "10.1039/c7tc05245f",

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Josse, P, Li, S, Dayneko, S, Joly, D, Labrunie, A, Dabos-Seignon, S, Allain, M, Siegler, B, Demadrille, R, Welch, GC, Risko, C, Blanchard, P & Cabanetos, C 2018, 'Bromination of the benzothioxanthene Bloc: Toward new π-conjugated systems for organic electronic applications', Journal of Materials Chemistry C, vol. 6, no. 4, pp. 761-766. https://doi.org/10.1039/c7tc05245f

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T1 - Bromination of the benzothioxanthene Bloc

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AU - Josse, Pierre

AU - Li, Shi

AU - Dayneko, Sergey

AU - Joly, Damien

AU - Labrunie, Antoine

AU - Dabos-Seignon, Sylvie

AU - Allain, Magali

AU - Siegler, Benjamin

AU - Demadrille, Renaud

AU - Welch, Gregory C.

AU - Risko, Chad

AU - Blanchard, Philippe

AU - Cabanetos, Clément

N1 - Funding Information: The Ministère de la Recherche and the RFI LUMOMAT from the Région Pays de la Loire are acknowledged for the PhD grants of P. Josse and A. Labrunie respectively. Authors thank the PIAM (Plateforme d’Ingénierie et Analyses Moléculaires) of the University of Angers for the characterization of organic compounds. GCW acknowledges NSERC DG (435715-2013), CFI JELF (34102) and the Canadian Research Chairs Program. CR acknowledges the Department of the Navy, ONR (award no. N00014-16-1-2985) and the UK Vice President for start-up research funds. Supercomputing resources on the Lipscomb High Performance Computing Cluster were provided by the UK Information Technology Department and Center for Computational Sciences (CCS). Publisher Copyright: © 2018 The Royal Society of Chemistry.

PY - 2018

Y1 - 2018

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AB - A selective and efficient method to afford a monobrominated benzothioxanthene (Br-BTXI) derivative is reported. Br-BTXI was extensively employed in common palladium catalyzed coupling reactions. Finally, as a proof of concept, a BTXI based molecular donor was synthesized and evaluated in bulk heterojunction solar cells.

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Bromination of the benzothioxanthene Bloc: Toward new π-conjugated systems for organic electronic applications

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