Reactive groups on polymer-coated electrodes, 9. New electroactive polythiophenes with epoxy and cyclic carbonate groups

Abstract

Two new functionalized thiophene derivatives bearing epoxy and carbonate groups were synthesized. The electrooxidative polymerization of both monomers led to stable electroactive polymers, while the functional groups remained unchanged during the polymerization process. Electrochemical and spectroscopic data of the resulting homopolymers reveal that these polymers possess an extended conjugated π-electron system comparable to unfunctionalized poly(3-alkylthiophene)s. Both monomers can also easily copolymerize with 3-methylthiophene to form the corresponding conducting copolymers. SEM photographs show that the obtained homopolymers and copolymers exhibit a very compact homogeneous morphology, indicating that the new thiophene monomers have good formability of polymer films. The measurement of electrical conductivity of these polymers by means of two-probe method gave values in the range of 10 2 to 10 -1 S . cm -1 . Using butylamine and 2-aminoanthraquinone as model compounds, it was demonstrated that amino compounds easily react with pendant epoxy and cyclic carbonate groups and are convalently attached to the new electroactive polymer surfaces. Thus, a new type of conducting polymers with pendant reactive groups was developed.