Construction of a novel pyrene-based two-dimensional supramolecular organic framework and the selective regulation of reactive oxygen species for photocatalysis

Abstract

The regulation of type I and type II photosensitizers during the generation of reactive oxygen species (ROS) is a challenging issue in photooxidation reactions. In this study, a novel pyrene-based two-dimensional supramolecular organic framework (SOF) was constructed in water using the host–guest interactions between the methylated vinylpyridine arms of the pyrene derivative (Pmvp) and cucurbit[8]uril (CB[8]), in which the four methylated vinylpyridine arms can be encapsulated by the cavity of CB[8] to form a stable framework structure with periodic pore structure and homogeneous solubility. More importantly, the construction of the SOF can realize the regulation of singlet oxygen (¹O₂) and superoxide anion radical (O₂˙⁻) generation capacity in ROS production. Specifically, the ¹O₂ generation capacity decreases, while the O₂˙⁻ generation capacity increases, and the SOF exhibits high photocatalytic conversion efficiency in the photocatalysis of the aerobic oxidation of thioanisoles and the oxidative hydroxylation of arylboronic acids in water, with yields up to 87% and 99%, respectively. This study presents an approach based on the concept of SOFs for the effective management of ROS in photooxidation reactions.