Redox Chemistry of BODIPY Dyes

Abstract

The implementation of BODIPY dyes in electron transfer reactions is an exciting new frontier that expands the toolbox of the dye molecule that has primarily been implemented in biological and chemical sensing applications. BODIPY dyes are capable of reversible reductions at the average reduction potential of −1.53 V vs. ferrocene/ferrocenium, varying about 700 mV from this average value depending on the substitution of the BODIPY core. BODIPY dyes are also capable of reversible oxidations, exhibiting an average oxidation potential of 610 mV with the ability to manipulate the oxidation potential up to 600 mV from the average potential. The respective azaBODIPY dyes are on average about 600 mV easier to reduce (more positive potentials) and are oxidized at almost identical oxidation potentials to the respective BODIPY dyes. The oxidation and reduction potentials of BODIPY dyes are heavily dependent on substitution of the BODIPY core, which allows for a high degree of tunability in the redox potentials. This characteristic makes BODIPY dye molecules good candidates for use as photoredox catalysts, redox flow batteries, redox-active ligands, light harvesting antenna, and many other applications in materials science, biology, and chemical synthesis.