Synthesis, electropolymerization and functionalization via click chemistry of N-alkynylated dithieno[3,2- b:2',3'- d]pyrrole

Yuriy Bandera; Haley W Jones; Benjamin Grant; Sarah Mell; Stephen H Foulger

doi:10.1039/d2ra03265a

Synthesis, electropolymerization and functionalization via click chemistry of N-alkynylated dithieno[3,2- b:2',3'- d]pyrrole

RSC Adv. 2022 Oct 13;12(45):29187-29196. doi: 10.1039/d2ra03265a. eCollection 2022 Oct 11.

Authors

Yuriy Bandera^{1

2}, Haley W Jones^{1

2}, Benjamin Grant^{1

2}, Sarah Mell^{1

2}, Stephen H Foulger^{1

2

3}

Affiliations

¹ Center for Optical Materials Science and Engineering Technologies (COMSET), Clemson University Anderson SC 29625 USA.
² Department of Materials Science and Engineering, Clemson University Clemson SC 29634 USA.
³ Department of Bioengineering, Clemson University Clemson SC 29634 USA foulger@clemson.edu.

Abstract

A new N-alkynylated dithieno[3,2-b:2',3'-d]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 via 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 via "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.