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Transition-Metal-Free Homopolymerization of Pyrrolo[2,3-d:5,4-d′]bisthiazoles via Nucleophilic Aromatic Substitution

Dey, S; Attar, S; Manley, EF; Moncho, S; Brothers, EN; Bazzi, HS; Bronstein, H; ... Al-Hashimi, M; + view all (2021) Transition-Metal-Free Homopolymerization of Pyrrolo[2,3-d:5,4-d′]bisthiazoles via Nucleophilic Aromatic Substitution. ACS Applied Materials & Interfaces , 13 (34) pp. 41094-41101. 10.1021/acsami.1c10858. Green open access

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Abstract

Novel methods to synthesize electron-deficient π-conjugated polymers utilizing transition-metal-free coupling reactions for the use of nonfunctionalized monomers are attractive due to their improved atom economy and environmental prospective. Herein we describe the use of iPrMgCl·LiCl complex to afford thiazole-based conjugated polymers in the absence of any transition metal catalyst, that enables access to well-defined polymers with good molecular weights. The mechanistically distinct polymerizations proceeded via nucleophilic aromatic substitution (SNAr) reaction supported by density functional theory (DFT) calculations. This work demonstrates the first example of fully conjugated thiazole-based aromatic homopolymers without the need of any transition metal catalyst.

Type: Article
Title: Transition-Metal-Free Homopolymerization of Pyrrolo[2,3-d:5,4-d′]bisthiazoles via Nucleophilic Aromatic Substitution
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acsami.1c10858
Publisher version: https://doi.org/10.1021/acsami.1c10858
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: thiazole, conjugated polymer, organic semiconductor, nucleophilic aromatic substitution, transition-metal-free
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10133938
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