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Bis-hydroquinone substituted 4,4´-bipyridinium is the formal dimer of an alkaloid isolated from Punica granatum and can exist as dication, cross-conjugated as well as pseudo-cross-conjugated mesomeric betaine, and dianion. It can moreover form persistent radicals in the solid state as well as in solution due to redox reactions of the reducing and oxidizing partial structures. A reversible coupled photocatalytic process with proflavine as the sensitizer and EDTA as the sacrificial donor is presented. We performed ESR and ENDOR spectroscopy as well as DFT calculations to gain additional knowledge about the radical species.

Coupled photocatalytic electron-transfers with 4,4´-bipyridinium derivatives of a betaine alkaloid from Punica granatum