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

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

Org Biomol Chem. 2024 Mar 27;22(13):2574-2579. doi: 10.1039/d4ob00210e.

Authors

Naoki Noda¹, Seiha Yamaoka¹, Ukyo Ogi¹, Masaki Horie², Kentaro Okano¹, Atsunori Mori^{1

3}

Affiliations

¹ Department of Chemical Science and Engineering, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan. amori@kobe-u.ac.jp.
² Department of Chemical Engineering, National Tsing Hua University, 101, Sec. 2, Kuang-Fu Road, Hsinchu 30013, Taiwan.
³ Research Center for Membrane and Film Technology, Kobe University, 1-1 Rokkodai, Nada, Kobe 657-8501, Japan.

PMID: 38482726
DOI: 10.1039/d4ob00210e

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.