REDOX-ACTIVE POLYMERS - SYNTHESIS AND EXCHANGE-REACTION OF AMINO-COMPOUNDS CONTAINING A CYCLIC DISULFIDE

Two monoamidated amino compounds, bearing the cyclic disulfide moiety of lipoic acid, were prepared by imidazole group transfer with aliphat ic diamines (1,3-diaminopropane and piperazine). The products, charact erized by spectroscopic methods (H-1 nuclear magnetic resonance and Fo urier-transform infra-red), were studied in solution. Basicity constan ts for the protonation of the basic nitrogens were evaluated in aqueou s media, and redox properties in dimethylsulfoxide, by cyclic voltamme try. Insoluble polymers were obtained by polymer-analogue exchange rea ction of the monoamidated compound with a benzotriazole residue presen t in preformed poly(N-acryloylbenzotriazole). A copolymer of the same monomer with N-vinylpyrrolidinone was soluble in solvents, giving a re sponse in cyclic voltammetry. Its positive anode peak was slightly hig her than that of the simple monoamidated compounds.