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Unsymmetrical difunctionalization of cyclooctadiene under continuous flow conditions: expanding the scope of ring opening metathesis polymerization

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Abstract

Functionalized cyclooctenes (FCOEs) are important monomers in ring-opening metathesis polymerization (ROMP). Herein, a new library of disubstituted FCOEs bearing adjacent heteroatoms were synthesized and applied in ROMP. To address the issues associated with the handling of the reactive thienyl chloride intermediate, a two-step continuous flow method has been developed to prepare 5-thio-6-chlorocyclooctene compounds from abundant cyclooctadiene starting materials. These newly synthesized FCOE monomers were subsequently polymerized through ROMP, giving rise to a range of functionalized polymers with high molecular weights. Furthermore, we demonstrated that the thermal properties of these polymers could be fine-tuned by changing the functional groups in the FCOE monomers. We expect that this functionalization-polymerization strategy will enable the preparation of a range of polymeric materials with complex structures.

Graphical abstract: Unsymmetrical difunctionalization of cyclooctadiene under continuous flow conditions: expanding the scope of ring opening metathesis polymerization

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Publication details

The article was received on 23 Oct 2017, accepted on 05 Jan 2018 and first published on 08 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04580H
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Unsymmetrical difunctionalization of cyclooctadiene under continuous flow conditions: expanding the scope of ring opening metathesis polymerization

    X. Shen, H. Gong, Y. Zhou, Y. Zhao, J. Lin and M. Chen, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04580H

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