Pendent polymers of 1-methyl-2-oxo-4,5-dicyanoimidazole and their electrochemical properties

Abstract

The electron accepting 1-methyl-4,5-dicyanoimidazole group was attached to vinyl polymers, via an alkoxy link, by nucleophilic aromatic substitution (NAS) of 1-methyl-2-fluoro-4,5-dicyanoimidazole ( 1 ) with poly(vinyl alcohol), or conventional polymerizations of vinyl monomers containing 1-methyl-2-oxo-4,5-dicyanoimidazole. The cyclic voltammetry (CV) studies show that monomeric and oligomeric model compounds are electrochemically quasi-reversible and the degree of reversibility decreases as dicyanoimidazoles become more proximate within a molecule. On the other hand, the polymers show much less reversible reduction waves at −2.6∼−2.7 V vs Ag/Ag + , suggesting that there are chemical reactions among the pendent groups reduced at relatively high potential. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 3828–3838, 2000