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Issue 19, 2021
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Oxanorbornenes: promising new single addition monomers for the metathesis polymerization

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Abstract

Higher ring-opening metathesis propagation rates of exo-norbornene derivatives over endo derivatives are well established in the literature. Here, we report for the first time that endo-isomers of oxanorbornene derivatives show higher reactivity towards ring-opening metathesis with Grubbs' 3rd generation catalyst (G3) than the corresponding exo-isomers. A very high selectivity for the reaction of G3 with endo over the exo-isomers could be shown. Furthermore, single molecular addition of the endo-isomers with G3 was observed. On the other hand, pure exo-monomers could successfully be homopolymerized. Mixtures of exo- and endo- monomers, however, prevented the homopolymerization of the exo-monomer. Such mixtures could successfully be copolymerized with cycloalkenes, resulting in alternating copolymers. An oxanorbornadiene derivative could be shown to undergo single addition reactions, exploited in the preparation of mono-end functional ROMP polymers. These could be selectively derivatized via endgroup selective thiol-ene click reactions. A thiol and alcohol end functional ROMP polymer was synthesized, and the efficient end functionalization was confirmed by 1H NMR spectroscopy and MALDI-ToF spectrometry.

Graphical abstract: Oxanorbornenes: promising new single addition monomers for the metathesis polymerization

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Supplementary files

Article information


Submitted
04 Jan 2021
Accepted
31 Mar 2021
First published
07 Apr 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 6705-6711
Article type
Edge Article

Oxanorbornenes: promising new single addition monomers for the metathesis polymerization

S. Pal, M. Alizadeh, P. Kong and A. F. M. Kilbinger, Chem. Sci., 2021, 12, 6705
DOI: 10.1039/D1SC00036E

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