Construction of perylene supramolecular assemblies with enhanced singlet oxygen generation for heteroatom photooxidation†

Abstract

In the dynamic field of photocatalysis, type II photosensitizers are crucial for efficiently generating reactive oxygen species (ROS), enabling a range of applications in organic synthesis, environmental remediation, and energy conversion. However, they are constrained by factors such as low catalytic activity, poor substrate selectivity, and limited generation efficiency of singlet oxygen (¹O₂). This study focuses on applying supramolecular strategies to develop type II photosensitizers based on perylene derivatives (PPDI). Through elaborate molecular design and utilization of host–guest interactions between PPDI and cucurbit[7]uril (CB[7]), a high-performance type II photosensitizer with excellent singlet oxygen (¹O₂) generation ability was successfully prepared. The performance of this photosensitizer in the organic photocatalytic oxidation reactions of sulfides, silanes, and arylphosphines was thoroughly investigated. The aim of this study is to overcome the drawbacks of traditional photosensitizers and provide efficient and green methods for organic synthesis. It not only shows great potential in solving the key problems of current photocatalytic oxidation reactions but also lays the foundation for the further development and application of supramolecular photocatalytic materials.