Wavily Curved Perylene Diimides: Synthesis, Characterization, and Photovoltaic Properties

Solubility enhancement is a key issue for developing the perylene diimide-based functional materials. Introduction of curved structure proved an effective solubilizing method without employing steric repulsion. In this work, wavily curved perylene diimides were developed as a new family of highly soluble curved perylene diimides. Moreover, their conformational dynamics, aggregating properties, electronic properties, and photovoltaic performances were thoroughly examined in comparison to the previously reported isomer exhibiting an arched curvature. The waved isomer demonstrated heightened rigidity and a greater propensity for aggregation compared to the arched isomer, likely attributed to its more planar structure. Each benzoxepin unit played a role in cancelling out the curvature on the opposite side. While the difference in the molecular curvature did not cause significant alterations in the photophysical and electron-accepting properties, we identified that the modulation of the curved structure is effective in controlling the morphology of the photoelectric conversion layer. Wavily curved perylene diimides have been developed and their structure-property relationship has been investigated with comparing to the arched isomer. While no significant alterations were conformed in their photophysical and electron-accepting properties, the waved isomer showed higher rigidity and aggregation tendency probably due to the overall more planar structure. image