Hybrid Corannulene-Perylene Dyes: Facile Synthesis and Optoelectronic Properties

Considering the peculiar topology of corannulene and extraordinary optoelectronic properties of perylene dyes, a series of hybrid corannulene-perylene dyes, namely corannulene-fused perylene-3,4-dicarboxylic acid monoimide (PMI) and corannulene-fused perylene-3,4,9,10-tetracarboxylic acid diimides (PDIs), were efficiently synthesized by a Suzuki coupling (carbon-carbon bond formation) and subsequent oxidative cyclization and photocyclization, respectively. Single crystal packing demonstrates that the solid state of the corannulene-fused PMI is arranged in back to back antiparallel dimers due to the strong dipole-dipole interactions. Integration of the corannulene unit to the perylene dyes along peri-positions makes the absorption bathochromically-shifted together with a much higher molar extinction coefficient, whereas integration of the corannulene unit to the perylene dyes along bay-positions has a much broader absorption. Strong and broad absorption properties, strong electron-accepting ability, and suitable LUMO levels close to that of [6,6]-phenyl-C-61-butyric acid methyl ester (PCBM) make hybrid corannulene-perylene dyes promising electron-acceptor materials for organic optoelectronic devices.