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

29 November 2023, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

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 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 meta-lated 3-hexylthiophene with 2-chloro-3-hexylthiophene employing Ni(cod)(dq) with IPr proceeded with a remarkably re-duced amount of homocoupling byproduct. Polymerization of 2-chloro-3-hexylthiophene with Ni(cod)(dq)/DPPP also re-sulted to reduce the regioregularity defect.

Keywords

Ni(cod)(dq)
oligothiophene
polythiophene
cross coupling reaction
N-heterocyclic carbene

Supplementary materials

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Description
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Supporting Information
Description
Experimental details and copies of 1H and 13C{1H }NMR spec-tra
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