A Ni0(cod)(dq) (COD: 1,5-cycloctadiene; DQ: duroquinone) complex as a catalyst precursor for oligothiophene and polythiophene synthesis

Naoki Noda; Seiha Yamaoka; Ukyo Ogi; Masaki Horie; Kentaro Okano; Atsunori Mori

doi:10.1039/D4OB00210E

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A Ni⁰(cod)(dq) (COD: 1,5-cycloctadiene; DQ: duroquinone) complex as a catalyst precursor for oligothiophene and polythiophene synthesis†

Naoki Noda,^a Seiha Yamaoka,^a Ukyo Ogi,^a Masaki Horie,

^b Kentaro Okano

^a and Atsunori Mori

*^ac

Author affiliations

* Corresponding authors

^a Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan
E-mail: amori@kobe-u.ac.jp

^b Department of Chemical Engineering, National Tsing Hua University, 101, Sec. 2, Kuang-Fu Road, Hsinchu 30013, Taiwan

^c Research Center for Membrane and Film Technology, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan

Abstract

Nickel-catalyzed syntheses of oligothiophene and polythiophene were carried out with Ni(cod)(dq) (COD: 1,5-cycloctadiene; DQ: duroquinone) as a catalyst precursor. Studies on the ligand exchange of Ni(cod)(dq) revealed that a high temperature was necessary to replace COD and DQ with PPh₃ and N-heterocyclic carbene IPr. A coupling reaction of a metalated 3-hexylthiophene with 2-chloro-3-hexylthiophene employing Ni(cod)(dq) with IPr proceeded with a remarkably reduced amount of homocoupling byproduct. Polymerization of 2-chloro-3-hexylthiophene with Ni(cod)(dq)/DPPP also resulted in the reduction of the regioregularity defect.

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Article information

DOI: https://doi.org/10.1039/D4OB00210E
Article type: Paper
Submitted: 09 Feb 2024
Accepted: 29 Feb 2024
First published: 05 Mar 2024

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Org. Biomol. Chem., 2024,22, 2574-2579

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A Ni⁰(cod)(dq) (COD: 1,5-cycloctadiene; DQ: duroquinone) complex as a catalyst precursor for oligothiophene and polythiophene synthesis

N. Noda, S. Yamaoka, U. Ogi, M. Horie, K. Okano and A. Mori, Org. Biomol. Chem., 2024, 22, 2574 DOI: 10.1039/D4OB00210E

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Organic & Biomolecular Chemistry