Synthesis, electropolymerization and functionalization click chemistry of -alkynylated dithieno[3,2-:2',3'-]pyrrole.

A new N-alkynylated dithieno[3,2-:2',3'-]pyrrole (DTP) monomer was synthesized using a Buchwald-Hartwig amination of 3,3'-dibromo-2,2'-bithiophene with pent-4-yn-1-amine. The obtained monomer was investigated for the possibility of a pre-polymerization modification Huisgen 1,3-dipolar cycloaddition ("click") reaction with azide-containing organic compounds. The synthesized N-alkynylated DTP monomer is soluble in a number of organic solvents and reacts with organic azides "click" reactions in mild conditions, achieving high yields. The N-alkynylated DTP monomer and its "click"-modified derivative can be electropolymerized to form polymeric films. Herein, the synthesis and characterization of a "click" modified DTP monomer, its pre-modified derivative, and their corresponding polymers are described. The developed method is a facile route to synthesize a new generation of various N-functionalized DTP homopolymers.