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

23 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

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

Funding

The Minist\u00E8re de la Recherche and the RFI LUMOMAT from the R\u00E9gion Pays de la Loire are acknowledged for the PhD grants of P. Josse and A. Labrunie respectively. Authors thank the PIAM (Plateforme d\u2019Ing\u00E9nierie et Analyses Mol\u00E9culaires) 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).

Funders	Funder number
U.S. Navy Air Systems Command
Conseil Régional des Pays de la Loire
Ministère de l'Enseignement Supérieur et de la Recherche Scientifique
Natural Sciences and Engineering Research Council of Canada	435715-2013
Office of Naval Research Naval Academy	N00014-16-1-2985
Canada Foundation for Innovation	34102

ASJC Scopus subject areas

General Chemistry
Materials Chemistry

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10.1039/c7tc05245f

Cite this

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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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",

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doi = "10.1039/c7tc05245f",

language = "English",

volume = "6",

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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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AU - Dayneko, Sergey

AU - Joly, Damien

AU - Labrunie, Antoine

AU - Dabos-Seignon, Sylvie

AU - Allain, Magali

AU - Siegler, Benjamin

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AU - Welch, Gregory C.

AU - Risko, Chad

AU - Blanchard, Philippe

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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

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

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