Herein we report on the first successful coupling of the dithienophosphole (S2PO) functional building block with three types of heteroaryl end caps using direct (hetero)arylation C–H bond functionalization methods.
We report six tetrameric compounds synthesized via direct (hetero)arylation methods based on phthalimide, naphthalimide, and perylene diimide end groups with fused thiophene cores.
Herein we study the effects of borane incorporation in a perylene diimide (PDI)-based non-fullerene acceptor (NFA). We have previously demonstrated that a PDI-bithiophene-PDI ((PDI) 2 Th 2 ) compound can be synthesized via direct (hetero)arylation techniques and is easily modified to incorporate a phosphole in the bithiophene core ((PDI) 2 Th 2 PO) to tune the electronic and geometric properties. In this work, we have synthesized the borane analogue ((PDI) 2 Th 2 B) and demonstrated that the organoboron moiety heavily influences the optical, electronic, and geometric properties. To determine the effects of borane functionalization on device performance, green solvent solution-processed bulk-heterojunction solar cells were fabricated using a medium-gap donor polymer TTFQx-T1 and each PDI compound as the NFA, respectively. Devices with the new borane-containing compound provided the highest efficiency, more than twice that for the other compounds, which was attributed to a highly twisted structure allowing for a more favorable active-layer morphology to be formed.
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%.
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