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Polymerization of 1-chloro-2-benzaldehyde-acetylene using an NHC-Pd/AgOTf catalyst and post-polymerization modification

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Abstract

We report the synthesis of a poly(1-chloro-2-phenylacetylene) derivative with an electron-withdrawing substituent on the phenyl group. A combination of an N-heterocyclic carbene-based Pd catalyst (NHC-Pd) with silver trifluoromethyl sulfonate (AgOTf) formed an active catalytic system for the polymerization of 1-chloro-2-(para-substituted)-phenylacetylenes. Based on this active catalytic system, functional poly(di-substituted acetylene) (PDSA) bearing an aldehyde group (P3) was obtained in high yield. The exceptional P3 bearing a reactive aldehyde group on its side chain was used as a precursor to be subsequently modified with amines to generate a novel PDSA (P3-ppm) possessing Schiff-base functionalities in good yield.

Graphical abstract: Polymerization of 1-chloro-2-benzaldehyde-acetylene using an NHC-Pd/AgOTf catalyst and post-polymerization modification

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Publication details

The article was received on 04 Jul 2017, accepted on 03 Aug 2017 and first published on 04 Aug 2017


Article type: Paper
DOI: 10.1039/C7PY01110E
Citation: Polym. Chem., 2017, Advance Article
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    Polymerization of 1-chloro-2-benzaldehyde-acetylene using an NHC-Pd/AgOTf catalyst and post-polymerization modification

    Y. Wang, W. Wang, X. Wang, X. Cheng, A. Qin, J. Z. Sun and B. Z. Tang, Polym. Chem., 2017, Advance Article , DOI: 10.1039/C7PY01110E

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