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Polymerization of 1-chloro-2-phenylacetylene derivatives by using a Brookhart-type catalyst

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Abstract

We report the polymerization of a series of disubstituted acetylenes including nonpolar and highly polar groups by a Brookhart-type α-diimine methyl palladium catalyst [(α-diimine)PdMeCl] with high molecular weight for the first time. 1-Chloro-2-(para-substituted)-phenylacetylenes with a highly polar carboxy group were polymerized in the polar solvent tetrahydrofuran by the combination of (α-diimine)PdMeCl and silver trifluoromethyl sulfonate (AgOTf), affording a molecular weight of 27 400 and a narrow polydispersity index of 1.12. Both the AgOTf and sodium tetrakis[3,5-bis-(trifluoro-methyl)phenyl]borate (NaBAF) are workable cocatalysts for the polymerization of 1-chloro-2-(para-substituted)-phenylacetylenes; the activity of the (α-diimine)PdMeCl/AgOTf catalyst system is higher than that of (α-diimine)PdMeCl/NaBAF under the same reaction conditions. The present work has enlarged the application range of the Brookhart-type catalyst and the types of polymerizable disubstituted acetylenes.

Graphical abstract: Polymerization of 1-chloro-2-phenylacetylene derivatives by using a Brookhart-type catalyst

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Publication details

The article was received on 02 Jul 2019, accepted on 04 Aug 2019 and first published on 05 Aug 2019


Article type: Paper
DOI: 10.1039/C9PY00974D
Polym. Chem., 2019, Advance Article

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    Polymerization of 1-chloro-2-phenylacetylene derivatives by using a Brookhart-type catalyst

    F. Yang, S. Zhang, T. Shen, J. Ni, J. Zhang, X. Cheng, J. Z. Sun, Z. Fu and B. Z. Tang, Polym. Chem., 2019, Advance Article , DOI: 10.1039/C9PY00974D

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