N-allylpyrrole as a bifunctional precursor to electrically conducting and filmable organic polymers: synthesis and preliminary characterization

Abstract We have begun to evaluate the potentialities of N -allypyrrole as a precursor monomer to electrically conducting organic polymers. Ab initio calculations carried out on tetramers of the correlated poly( N -vinylpyrrole) are reported and evaluated. A chemical synthetic route using FeCl 3 as the oxidizing agent allowed us to obtain a dark product which is presumably the poly(2,5- N -allypyrrole). An electrochemical synthesis carried out at constant applied potential gave very good black films on a Pt electrode. The chemical and the electrochemical polymers have nearly the same conductivity which is of the order of 10 −4 S/cm. IR spectra demonstrate the survival of the allyl double bond in the conductive materials. Attempts to polymerize the N -allylpyrrole on the allyl double bond in order to obtain a polymeric insulating precursor to a ladder conducting polymer were largely unsuccessful.