A new boron dipyrromethene–ferrocene (BODIPY–Fc) conjugate with pentafluorophenyl as the meso substituent and two Fc termini was synthesized and its spectroscopic and electrochemical features were analyzed. An intramolecular charge transfer from the donor Fc to the acceptor BODIPY has been predicted by theory and confirmed experimentally, leading to efficient fluorescence quenching when the dyad is
in the neutral state. Fluorescence can be triggered by oxidizing both ferrocenyl units either chemically
or electrochemically. Eventually, a fully reversible fluorescence switch is evidenced by coupling TIRF
microscopy with electrolysis in an electrochemical cell
