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%.
Highlights
Direct heteroarylation (DHA) is an efficient carbon-carbon (C–C) cross-coupling technique that has significant advantages over traditional methods [1,2,3,4]
We have optimized several DHA reactions with perylene diimide (PDI)-Br [16,38,39,40]; in this study, we extend this reactivity to the coupling of TPD and PDI–Br together
We have reported on the syntheses of two electron deficient molecules comprised of a TPD core with PDI terminal units using direct heteroarylation methods
Summary
Direct heteroarylation (DHA) is an efficient carbon-carbon (C–C) cross-coupling technique that has significant advantages over traditional methods [1,2,3,4]. While traditional methods require transmetallation reagents to drive aromatic C–C bond formation, DHA can activate C–H and C–Br bonds via a concerted metallation-deprotonation (CMD) mechanism [5,6]. Transmetallation reagents for Suzuki [7], Negishi [8], and Stille [9]. DHA can be performed under milder conditions with fewer reagents and in fewer steps [10,11]. The substrate scope for DHA is more limited . The aromatic C–H bonds of a given substrate must be sufficiently active for coupling to occur. DHA reactions are often much more sensitive to issues of selectivity and reactivity
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