Solution-processed perylenediimides (PDIs) with varying peri and bay substituents are characterized in order to better understand the relationships between molecular structure, solid state order, charge transport, and photovoltaic performance. It was found that bulky bay substituents interfere with molecular packing, leading to low charge transport and photovoltaic efficiencies compared to PDIs with fewer or less disruptive substituents. We assessed the potential of PDIs as acceptors for organic photovoltaics (OPVs) by utilizing a solution-processed bilayer OPV device architecture with the donor benzoporphyrin. At AM1.5G illumination, power conversion efficiencies (PCEs) up to 2.0% are obtained for solution-processed bilayer OPVs employing PDIs as acceptors. These results demonstrate the potential of PDIs as photovoltaic acceptor materials while elucidating the relationships between molecular structure and material properties.
A new donor–acceptor doubly bridged perylenediimide–fullerene dyad (PDI–C60, DB-3), where the perylenediimide (PDI) acts as a donor, has been synthesized and studied by time-resolved absorption spectroscopy. The DB-3 undergoes an electron transfer (ET) in both polar and non-polar media under photo-excitation. Structurally the DB-3 dyad resembles four other recently studied dyads (R. K. Dubey et al., Chem. Eur. J., 2013, 19, 6791–6806). Analysis of the ET reactions in this series of dyads was carried out in frame of both classic and semi-quantum ET theories. The result of the analysis for DB-3 suggests that the electronic coupling for the ET reaction is roughly 0.005 eV, internal reorganization energy is 0.16 eV, and outer sphere or solvent reorganization energy is 0.5 and 0.3 eV in benzonitrile and toluene, respectively.
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