Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Letter
Facile Preparation of Poly(3-substituted thiophene) Block Copolymers by Nickel-catalyzed Deprotonative Polycondensation without External Generation of Thiophene Organometallic Species
Karin NakamuraShunsuke TambaAtsushi SugieAtsunori Mori
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2013 Volume 42 Issue 10 Pages 1200-1202

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Abstract

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.

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© 2013 The Chemical Society of Japan
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