Controlling optoelectronic properties and aggregation of planar dipoles through symmetry-preserving modifications

Abstract

Planar and symmetric molecular architectures with defined donor–acceptor distributions offer exceptional versatility for optoelectronic applications. Perylene monoimides exemplify these features, and here we systematically explore strategies to tune their dipole-like distribution while preserving symmetry. Correlating optical properties in solution and solid states with electron-donating and/or -withdrawing groups at the ortho positions reveals how subtle modifications control the intermolecular interactions and therefore, aggregation and optoelectronics. Single-crystal X-ray diffraction further uncovers distinct stacking modes, highlighting the decisive role of molecular design in tailoring functionality for diverse applications.