Synthesis and Evaluation of Supramolecular Assemblies Possessing Light Energy Conversion Properties

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A series of benzo[ghi]perylene and coronene derivatives substituted by electron-withdrawing imide and ester groups were systematically synthesized considering number of imide and ester groups, five- and six-membered imide groups, and the peripheral positions. The steady-state absorption and fluorescence spectra also become red-shifted and broadened as compared to those of reference unsubstituted benzo[ghi]perylene and coronene. Regarding the electrochemistry, with an increase in the number of imide groups, the reduction potentials are significantly shifted to the positive direction, which indicates the large enhancement of electron-accepting properties.Then, systematic comparison of quantum yields and rate constants of the excited-state dynamics also reveals that the intersystem crossing pathway was accelerated in both benzo[ghi]peryleneimide and coroneneimide derivatives, whereas the fluorescence property was dependent on the number of substituents and structural symmetry.