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Molecules 2018, 23(4), 931; https://doi.org/10.3390/molecules23040931

Direct (Hetero)Arylation for the Synthesis of Molecular Materials: Coupling Thieno[3,4-c]pyrrole-4,6-dione with Perylene Diimide to Yield Novel Non-Fullerene Acceptors for Organic Solar Cells

Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, AB T2N 1N4, Canada
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Received: 1 April 2018 / Revised: 12 April 2018 / Accepted: 15 April 2018 / Published: 17 April 2018
(This article belongs to the Special Issue Direct (Hetero)Arylation: A New Tool for Organic Electronics)
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Abstract

Herein we report on the synthesis of an N-annulated perylene diimide (PDI) disubstituted thieno[3,4-c]pyrrole-4,6-dione (TPD) molecular acceptor (PDI–TPD–PDI) by direct heteroarylation (DHA) methods. Three sets of DHA conditions that explore the effects of solvent, temperature, and catalyst were employed to find the optimal conditions for the synthesis of two PDI–TPD–PDI derivatives. We then selected one PDI–TPD–PDI for use as a non-fullerene acceptor in organic solar cell devices with the donor polymer PBDB-T. Active layer bulk-heterojunction blends were modified using several post-deposition treatments, including thermal annealing, solvent vapour annealing, and high boiling solvent additives. It was found that active layers cast from o-dichlorobenzene with a 3% v/v diphenylether additive yielded films with adequate phase separation, and subsequently gave the best organic solar cell performance, with power conversion efficiencies greater than 3%. View Full-Text
Keywords: organic dyes; non-fullerene acceptors; direct heteroarylation; bulk heterojunction solar cells; perylene diimide; thieno[3,4-c]pyrrole-4,6-dione organic dyes; non-fullerene acceptors; direct heteroarylation; bulk heterojunction solar cells; perylene diimide; thieno[3,4-c]pyrrole-4,6-dione
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Welsh, T.A.; Laventure, A.; Welch, G.C. Direct (Hetero)Arylation for the Synthesis of Molecular Materials: Coupling Thieno[3,4-c]pyrrole-4,6-dione with Perylene Diimide to Yield Novel Non-Fullerene Acceptors for Organic Solar Cells. Molecules 2018, 23, 931.

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