One- and two-electron reductions of a bulky BODIPY compound

The redox reaction between a bulky BODIPY and a magnesium(i) reducing agent leads to the formal one-electron reduction of the BODIPY, initially generating a dipyrromethene-centred radical compound that dimerises via C-C bond formation. In contrast, reduction with magnesium anthracene leads to the formal two-electron reduction of the BODIPY, resulting in the formation of the corresponding anion.