Construction of perylene diimide supramolecular polymers: Study of photocatalytic reduction conversion from sulfoxide to thioether

Abstract

Exploring the redox window of current photoredox catalysis is a continuous task due to the intrinsic constraints of the technology. In this study, we present a novel supramolecular polymer PDI-CB[8] composed of perylene diimide derivative (PDI) and cucurbit[8]uril (CB[8]) through host-guest interactions, which can stabilize the excited states of PDI* and PDI radical anions (PDI^•−), resulting in a highly reducing photocatalytic unit PDI-CB[8]^•−* that can efficiently reduce inert sulfoxide to thioether by direct reduction. The supramolecular polymer approach successfully addresses the conventional energy limitations in photoredox catalysis. By exploiting higher-energy excitated illumination of PDI-CB[8], the efficient reduction of unactivated SO double bonds on various substrates was achieved, demonstrating the adaptable usefulness of this method in synthetic chemistry applications.