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

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-pi-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. We have designed and constructed supramolecular dimers between triphenylamine derivatives with AIE properties and CB[8] through host-guest interactions, which can be used as photosensitizers for photooxidation reactions of thioanisole.

Automated summary

In this study, we designed and synthesized two triphenylamine derivatives with aggregation-induced emission (AIE) properties and constructed supramolecular dimers with CB[8] through host-guest interactions. The D-pi-A configuration of 2MeOTPPy-CB[8] exhibited remarkable intersystem crossing (ISC) performance, enhancing the generation of reactive oxygen species (ROS), especially singlet oxygen (1O2), and resulting in exceptional catalytic efficiency in the photocatalytic oxidation reaction.