Synthesis of End-Functionalized polyanilines

Eelkema R, Anderson HL

Insulated polyaniline (PANI) polyrotaxane molecular wires were synthesized to apply them as advanced materials in photovoltaic devices and light emitting diodes. Benzylamine-substituted polyaniline is constructed through the synthesis and deprotection of tert-butoxycarbonyl (Boc) protected PANI using Pd-catalyzed polymerization. The synthesis was conducted by a three-component step-growth polymerization, using diamine and dibromide monomers and a monobromide chain stopper with a protected benzylamine functionality. The results show exclusive degradation of monobromide due to the removal or migration of one of the Boc protecting groups. Covalent incorporation of conjugated polymers in organic, inorganic, and biological systems shows that it is possible to couple protected acetylene and allylphenol. Deprotection of Boc-protected PANI is generally achieved by thermal elimination of the Boc group at 150°C.