Synthesis and preliminary characterization of two copper(I) chromophore–acceptor dyads as potential photoredox catalysts

Abstract

The development of sustainable alternatives to fossil fuel-derived chemical feedstocks is imperative as we move towards decarbonization. Here, we report two Cu(I) chromophore–acceptor dyads bearing a 1,8-naphthalene monoimide electron-accepting moiety with a pendant Lewis basic pyridine for halogen bonding in the hopes of driving C–Br cleavage reactions using visible light. The photophysical and electrochemical properties are documented and both complexes were found to have favourable driving force for intramolecular charge shift in the excited state. However, neither complex was capable of C–Br cleavage and C–C bond formation in our hands. This study highlights that there are many structural and electronic factors that must be considered to successfully drive photoredox transformations, and the reported photosensitizers have potential uses in other applications owing to the synthetically versatile pyridine on the accepting ligand.