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Dehalogenative or Deprotonative? The Preparation Pathway to the Organometallic Monomer for Transition‐Metal‐Catalyzed Catalyst‐Transfer‐Type Polymerization of Thiophene Derivatives
Author(s) -
Shibuya Yushin,
Mori Atsunori
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905653
Subject(s) - thiophene , polythiophene , polymerization , monomer , polymer chemistry , catalysis , polymer , materials science , transition metal , chemistry , combinatorial chemistry , organic chemistry , conductive polymer
Due to a wide range of applications in electronic materials, polythiophenes attract considerable attention in organic and polymer syntheses as well as in materials science. For the purpose of developing the practical synthetic protocol, this review focuses on the deprotonative pathway in the preparation of thiophene organometallic monomer, which was shown to be effective employing 2‐halo‐3‐substituted thiophene as a monomer precursor. The thus metallated thiophene monomer was shown to undergo polymerization by nickel(II) complex catalysis, with which highly regioregular head‐to‐tail (HT)‐type polythiophenes were obtained with controlled molecular weight and molecular weight distribution. Several polythiophene derivatives with modified thiophene‐ring and side‐chain structures were shown to be designed in order to achieve the designed functionality as materials.