Synthesis and properties of new tetrazines substituted by heteroatoms: towards the world's smallest organic fluorophores.
New tetrazines substituted by heteroatoms have been synthesized and their electrochemical and photochemical properties investigated. All compounds are reversibly electroactive with standard potentials shifting cathodically according to the donor character of the substituent. The tetrazine derivatives are also fluorescent with maximum emission wavelengths in the range 550-575 nm. Some of them show very long fluorescence lifetimes (several tens of ns) and remain fluorescent in the solid state without major changes in the spectral features. The fluorescence of one of the derivatives can be efficiently quenched by the presence of electron-rich compounds such as triphenylamines, phenol or anisole, which make them very promising compounds for sensor applications.
Audebert
Pierre
P
Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires, UMR 8531, Ecole Normale Supérieure de Cachan, 61 Av. du Pt Wilson, 94235 Cachan, France. audebert@ppsm.ens-cachan.fr
Miomandre
Fabien
F
Clavier
Gilles
G
Vernières
Marie-Claude
MC
Badré
Sophie
S
Méallet-Renault
Rachel
R