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

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 cycl...

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Bibliographic Details
Published in:RSC advances 2022-10, Vol.12 (45), p.29187-29196
Main Authors: Bandera, Yuriy, Jones, Haley W., Grant, Benjamin, Mell, Sarah, Foulger, Stephen H.
Format: Article
Language:English
Subjects:
Azides (organic)
Chemical synthesis
Chemistry
Cycloaddition
Monomers
Organic compounds
Polymer films
Polymerization
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Summary: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.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra03265a