Utilization of a Fluorescent Dye Molecule as a Proton and Electron Reservoir

Abstract

Fluorescent dyes have been widely utilized as chemical sensors and in photodynamic therapy, but exploitation of their redox‐active nature in chemical reactions has remained mostly unexplored. This report describes the isolation of a 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY)‐based radical. The redox‐active nature of the BODIPY compound can be utilized in combination with a guanidine center, the basicity of which can be manipulated by greater than 14 pKa units, to promote the conversion of protons and electrons into H‐atoms for transfer to substrate molecules.