Polymerization of acetylenes bearing proxyl radical and their redox property

A nitroxide radical is stable at ambient conditions and has two redox couples; nitroxide radical is oxidized to oxoammonium cation (p-type doping) and reduced to aminoxyl anion (n-type doping). Based on these electrochemical properties, the nitroxide radical is expected as an electrode active material of secondary battery. In this report, we synthesized new polyacetylene derivatives bearing 2,2,5,5-tetramethylpyrrolidine-N-oxyl(proxyl radical) and studied their electrochemical properties. Two monomers were synthesized by Grignard reaction (from nitrone). The obtained acetylene monomer was polymerized by coordination polymerization and oxidized to its radical derivative. Poly(proxyl radical)s were identified by IR, ESR, SQUID measurement, and elemental analysis. Redox property of these poly(proxyl radical)s was examined by cyclic voltammetry.