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 pK_a units, to promote the conversion of protons and electrons into H-atoms for transfer to substrate molecules.

Keywords: BODIPY; H-atom transfer; fluorescent dyes; proton-coupled electron transfer; redox chemistry.