Facile Preparation of Poly(3-substituted thiophene) Block Copolymers by Nickel-catalyzed Deprotonative Polycondensation without External Generation of Thiophene Organometallic Species

Thiophene-based block copolymers are synthesized by addition of bromothiophene and the Knochel–Hauser base (TMPMgCl·LiCl). Nickel-catalyzed deprotonative C–H coupling polycondensation of 3-substituted-thiophenes proceeds to give head-to-tail-type poly(3-substituted thiophen-2,5-diyl) bearing nickel...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry letters 2013-10, Vol.42 (10), p.1200-1202
Main Authors: Nakamura, Karin, Tamba, Shunsuke, Sugie, Atsushi, Mori, Atsunori
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Thiophene-based block copolymers are synthesized by addition of bromothiophene and the Knochel–Hauser base (TMPMgCl·LiCl). Nickel-catalyzed deprotonative C–H coupling polycondensation of 3-substituted-thiophenes proceeds to give head-to-tail-type poly(3-substituted thiophen-2,5-diyl) bearing nickel at the polymer end. Block copolymers of thiophene derivatives are obtained by successive addition of 2-bromo-3-alkylthiophene and magnesium amide to a living polythiophene end. The use of nickel catalyst bearing an o-tolyl group gives the tolyl-group-terminated thiophene diblock copolymers in high efficiency. Triblock copolymer is also synthesized by the iterative addition of bromothiophene and TMPMgCl·LiCl.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.130523