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 aliphatic diamines (1,3-diaminopropane and piperazine). The products, characterized by spectroscopic methods (H-1 nuclear magnetic resonance and Fourier-transform infra-red), were studied in solution. Basicity constants for the protonation of the basic nitrogens were evaluated in aqueous media, and redox properties in dimethylsulfoxide, by cyclic voltammetry. Insoluble polymers were obtained by polymer-analogue exchange reaction of the monoamidated compound with a benzotriazole residue present in preformed poly(N-acryloylbenzotriazole). A copolymer of the same monomer with N-vinylpyrrolidinone was soluble in solvents, giving a response in cyclic voltammetry. Its positive anode peak was slightly higher than that of the simple monoamidated compounds.