Synthesis of push–pull triarylamine dyes containing 5,6-difluoro-2,1,3-benzothiadiazole units by direct arylation and their evaluation as active material for organic photovoltaics

Tatiana Ghanem; Tony Vincendeau; Pablo Simón Marqués; Amir Hossein Habibi; Sana Abidi; Ali Yassin; Sylvie Dabos-Seignon; Jean Roncali; Philippe Blanchard; Clément Cabanetos

doi:10.1039/D1MA00798J

Synthesis of push–pull triarylamine dyes containing 5,6-difluoro-2,1,3-benzothiadiazole units by direct arylation and their evaluation as active material for organic photovoltaics†

Tatiana Ghanem,^a Tony Vincendeau,^a Pablo Simón Marqués,^a Amir Hossein Habibi,^a Sana Abidi,^ab Ali Yassin,^a Sylvie Dabos-Seignon,^a Jean Roncali,^c Philippe Blanchard

^a and Clément Cabanetos

*^ad

Author affiliations

* Corresponding authors

^a Univ Angers, CNRS, MOLTECH-ANJOU, SFR MATRIX, F-49000 Angers, France
E-mail: clement.cabanetos@cnrs.fr

^b École Nationale Supérieure d’Ingénieurs de Tunis (ENSIT), 13 Ave Taha Hussein, Tunis 1008, Tunisia

^c Babes-Bolyai University, Faculty of Chemistry and Chemical Engineering, Department of Chemistry and SOOMCC, Cluj-Napoca, 11 Arany Janos Str., Cluj-Napoca, Romania

^d Building Blocks for FUture Electronics Laboratory (2BFUEL), IRL2002, CNRS-Yonsei University, Seoul, South Korea

Abstract

Two push–pull molecules involving a triarylamine donor unit connected to a dicyanovinyl acceptor moiety by a difluorobenzothiadiazole-thienyl block have been synthesized. In order to simplify the synthesis, avoid intermediate halogenation reactions and the formation of toxic organometallic by-products, building blocks were connected by direct (hetero)-arylation. The optimization of the experimental conditions of the coupling reactions is thus reported herein as well as the preliminary evaluation of the potential of the target compounds as active material in simple air-processed organic solar cells.

This article is part of the themed collection: Organic Electronics – Ecofriendly and/or sustainable materials, processes, devices, and applications

Materials Advances

Synthesis of push–pull triarylamine dyes containing 5,6-difluoro-2,1,3-benzothiadiazole units by direct arylation and their evaluation as active material for organic photovoltaics†

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Synthesis of push–pull triarylamine dyes containing 5,6-difluoro-2,1,3-benzothiadiazole units by direct arylation and their evaluation as active material for organic photovoltaics

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