Stable Near-Infrared Anionic Polymethine Dyes: Structure, Photophysical, and Redox Properties

Pierre-Antoine Bouit (1) , Emmanuel Di Piazza (2) , Stéphane Rigaut (2) , Boris Le Guennic (1) , Christophe Aronica (1) , Loic Toupet (3) , Chantal Andraud (1) , Olivier Maury (1)

1 LC - Laboratoire de Chimie - UMR5182
2 ISCR - Institut des Sciences Chimiques de Rennes
3 GMCM - Groupe matière condensée et matériaux

The concept of cyanine has been successfully extended to anionic heptamethine dye featuring tricyanofuran (TCF) moieties in terms of structure, reactivity and photophysical properties. Importantly, absorption and emission are red-shifted compared to its classical cationic analog without any cost in term of thermal stability. In addition to its "cyanine" behavior, this molecule exhibits further redox properties: oxidation and reduction led to the reversible formation of radical species whose absorption is in marked contrast with that of cyanines.

Domaines: Chimie de coordination

Pierre-Antoine Bouit, Emmanuel Di Piazza, Stéphane Rigaut, Boris Le Guennic, Christophe Aronica, et al.. Stable Near-Infrared Anionic Polymethine Dyes: Structure, Photophysical, and Redox Properties. Organic Letters, 2008, 10 (19), pp.4159-4162. ⟨10.1021/ol801416n⟩. ⟨hal-00369219⟩