Poly(DCAQI): Synthesis and characterization of a new redox-active polymer

Redox-active anthraquinone based polymers are synthesized by the introduction of a polymerizable vinyl and ethynyl group, respectively, resulting in redox-active monomers, which electrochemical behaviors are tailored by the modification of the keto groups to N-cyanoimine moieties. These monomers can be polymerized by free radical polymerization and Rh-catalyzed polymerization methods, respectively. The resulting polymers are obtained in molar masses (Mn) of 4,400 to 16,800 g mol−1 as well as high yields of up to 97%. The monomers and polymers are furthermore electrochemically characterized by cyclic voltammetry. The monomers exhibit two one-electron redox reactions at about −0.6 and −1.0 V versus Fc+/Fc. The N-cyanoimine units are, however, partially hydrolyzed during the polymerization step or during the electrochemical measurements and degenerate to carbonyl groups, resulting in a new reduction signal at −1.26 V versus Fc+/Fc. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 1998–2003