A water-soluble type II photosensitizer for selective photooxidation reactions of hydroazaobenzenes, olefins, and hydrosilanes in water

Abstract

Despite the fact that water is a widely available, non-toxic, and safe solvent, its application in organic synthesis remains an ongoing challenge due to the insolubility of numerous catalysts, reactants and products in water. In this study, a triphenylamine modified cyanophenylenevinylene derivative (TPCI) is reported, which exhibits excellent water solubility and remarkable selectivity and efficiency for producing singlet oxygen (¹O₂) in water, rendering it perfectly suited for use as an efficient photosensitizer for photocatalytic reactions of hydroazaobenzenes, olefins, and hydrosilanes to obtain functional organic molecules of azoaromatics, carbonyls, and silanols with good functional-group tolerance as well as a broad substrate scope under blue light irradiation. The present study introduces a new type II photosensitizer that enables the synthesis of functional organic molecules through photocatalytic oxidation using visible light in water with high efficiency.