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

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 <i>ortho</i> 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.