Synthesis and characterization of new redox-active polymers based on 10-(1,3-dithiol-2-ylidene)anthracen-9(10H)-one derivatives

Abstract

Redox-active materials based on a 10-(1,3-dithiol-2-ylidene)anthracen-9(10H)one core were synthesized by the introduction of a polymerizable vinyl group in 3-position, resulting in a redox-active monomer, which possess both electron donating and electron accepting properties. The electron accepting properties can be tailored by straightforward one-step modifications of the carbonyl functionality to N-cyanoimine, dicyanomethylene or thione moieties, respectively, leading to bipolar compounds. These monomers can be polymerized by free radical polymerization. The resulting polymers could be obtained with molar masses of 6,500 to 24,300 g/mol as well as yields of up to 92% and were examined with 1H NMR and SEC. Their electrochemical behavior reveals reversible reductions comparable with the redox properties of the corresponding monomers. After further optimization, these materials could become potentially interesting for applications in organic batteries.