Fluorine substituted non-symmetric phenazines: A new synthetic protocol from polyfluorinated azobenzenes

A high ortho regioselectivity in nucleophilic aromatic substitution in low polar solvents is reported in the reaction of polyfluorinated azobenzenes with anilines. o-Anilino substituted derivatives could be easily transformed into non-symmetric phenazines by acid catalyzed electrocyclization. Phenazines are interesting compounds for their important properties as bioactive molecules. In addition, these fluorinated phenazines manifest interesting spectroscopic and electronic properties that make them candidates for n-type organic semiconductor. Furthermore, the prepared phenazines show reversible reduction with the LUMO and HOMO energy level controlled by the electronic nature of the substituent on the non-fluorinated ring of the system.