Oxidation-State-Dependent Photochemistry of Sulfur-Bridged Aza-Anthracenes

J Org Chem. 2025 May 2;90(17):5788-5794. doi: 10.1021/acs.joc.4c02786. Epub 2025 Apr 16.

Abstract

Aromatic systems with bridged sulfur units in varying oxidation states have enabled photoresponsive materials for anticounterfeiting and supramolecular assembly. However, only a few sulfoxide-bridged chromophores exhibit photoinduced sulfur extrusion, leading to drastic photophysical changes that make them useful as stimuli-responsive materials. Here, we present nitrogen-substituted anthracene (aza-anthracene) with a sulfur bridge in different oxidation states. Overall, aza-anthracene produces red-shifted green-to-red chromophores with similar sulfoxide photoconversion behavior compared to the anthracene analog.