Synthesis of perylene dyes with multiple triphenylamine substituents

Perylene monoimide (PMI) was brominated to give tetra- and tribrominated molecules, which underwent a Suzuki coupling reaction with 4-(diphenylamino) phenylboronic acid to give PMI derivatives. The photophysical and electrochemical properties of the synthesized compounds were investigated, and theoretical calculations were performed. Single crystals of tetrasubstituted PMI were grown and studied in detail. The structure-property relationships were examined to reveal the effect of the position and number of substituents on the perylene core unit. All molecules showed a broad absorption up to 750 nm. Corresponding anhydrides of PMIs were used for fabrication of dye-sensitized solar cells. The molecule with four triphenylamine units on perylene monoanhydride showed the highest power conversion efficiency.