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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.617-624
Published online, 3rd April, 2014
DOI: 10.3987/COM-14-S(K)11
Studies on the Effect of N-Heterocyclic Carbene as a Ligand for Nickel(II)-Catalyzed Polymerization of Thiophenes

Atsunori Mori,* Makoto Fujio, and Shunsuke Tamba

*Chemical Science & Technology, Graduate School of Engineering, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan

Abstract

Effect of N-heterocyclic carbene (NHC) ligand in the nickel-catalyzed polythiophene synthesis is studied. One-pot protocol to form nickel-NHC ligand with the corresponding HCl salt of NHC and Ni(acac)2 in the presence of a base and following deprotonation and polymerization smoothly affords poly(3-hexylthiophen-2,5-diyl) (2a). Among NHC ligands examined, imidazolidine derived NHC bearing 2,6-diisopropylphenyl group as an N-substituent is found to be the optimum ligand.