Synthesis of Arylated Perylene Bisimides through C−H Bond Cleavage under Ruthenium Catalysis

Treatment of perylene bisimide (PBI) with various arylboronates in the presence of a ruthenium catalyst provides tetraarylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The electronic nature of the introduced aryl substituents has a significant impact on their optical and electronic properties. This protocol has been applied to the synthesis of a water-soluble emissive PBI derivative.