Construction of supramolecular dimer photosensitizers based on triphenylamine derivatives and cucurbit[8]uril for photocatalysis

Abstract

Enhancing the capability for generating reactive oxygen species (ROS) and improving the photocatalytic efficiency of organic photocatalysts have been longstanding significant challenges. In the present study, we designed and synthesized two triphenylamine derivatives (MATM and MeOTPPy) with aggregation-induced emission (AIE) properties, which can interact with CB[8] through host–guest interactions in aqueous solution to construct supramolecular dimers (2MeOTPPy-CB[8] and 2MATM-CB[8]). In contrast to the D–A configuration observed in 2MATM-CB[8], the D–π–A configuration of 2MeOTPPy-CB[8] exhibits remarkable intersystem crossing (ISC) performance through the introduction of the thiophene group, which can significantly improve the ROS generation capacity, especially singlet oxygen (¹O₂), resulting in exceptional catalytic efficiency during the photocatalytic oxidation of thioanisole with a high yield of 94%. This work provides an efficient supramolecular dimer strategy for the preparation of novel photosensitizers.