Electrochromic and electrofluorochromic properties of a new boron dipyrromethene-ferrocene conjugate

Olivier Galangau (1) , Isabelle Fabre-Francke (2) , Sorin Munteanu (1) , Cécile Dumas-Verdes (1) , Gilles Clavier (1) , Rachel Méallet-Renault (1) , Robert Bernard Pansu (1, 3) , Frantisek Hartl (4) , Fabien Miomandre (1)

1 PPSM - Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires
2 LPPI - Laboratoire de Physico-chimie des Polymères et des Interfaces
3 IDA - Institut d'Alembert
4 Department of Chemistry [Reading]

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 analysed. 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.

Mots clés: Boron dipyrromethene Ferrocene Electrochromic Fluorescence Redox switch

Domaines: Chimie théorique et/ou physique

Olivier Galangau, Isabelle Fabre-Francke, Sorin Munteanu, Cécile Dumas-Verdes, Gilles Clavier, et al.. Electrochromic and electrofluorochromic properties of a new boron dipyrromethene-ferrocene conjugate. Electrochimica Acta, 2012, 87, pp.809-815. ⟨10.1016/j.electacta.2012.09.048⟩. ⟨hal-00906515⟩