Synthesis of oligomeric p-phenyleneimine by self-condensation reaction of a novel monomer

A new approach for the synthesis of poly(phenylenimines) and related conjugated polymers is presented. A novel bifunctional monomer, N-Boc-indoaniline 4 is synthesized as shown in scheme I. Thermolysis of the latter, either as solid, thin film or in solution of high boiling solvents, leads to polycondensation of the bifunctional monomer and results in the formation of poly(phenyleneimine) or its reduced form. Scope and limitation of this approach in the synthesis of various poly(aryleneimines) is also described.