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Issue 18, 2018
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Efficient polymerization and post-modification of N-substituted eight-membered cyclic carbonates containing allyl groups

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Abstract

Aliphatic polycarbonates are promising materials in the biomedical field due to their low toxicity, biocompatibility, and biodegradability. A popular approach in obtaining these materials is through the organocatalyzed ring-opening polymerization (ROP) of cyclic carbonates. Functional polycarbonates can be obtained by (co)polymerizing allyl-functional cyclic monomers, which can be chemically modified via radical thiol–ene click reactions after the ROP process. To date, allyl-bearing 6-membered cyclic carbonates have been reported, however their polymerization kinetics are slow. In previous works, larger cyclic carbonates (e.g. N-substituted eight membered cyclic carbonates) have demonstrated superior reactivities over their smaller counterparts and hence, in this work, we investigated the preparation and ROP of two allyl bearing N-substituted eight membered cyclic carbonates. One of these monomers, with a pendent carbamate group, displayed substantially enhanced polymerization kinetics that allowed for efficient homopolymerizations and co-polymerizations with commercially available monomers (e.g. trimethylene carbonate, or TMC). Lastly, the polymers underwent almost quantitative post-polymerization modification via thiol–ene chemistry to yield different functionalized polycarbonates. We also demonstrated that the post-polymerization reaction could be used to form polycarbonate-based gels with multifunctional thiols.

Graphical abstract: Efficient polymerization and post-modification of N-substituted eight-membered cyclic carbonates containing allyl groups

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Publication details

The article was received on 09 Feb 2018, accepted on 26 Mar 2018 and first published on 27 Mar 2018


Article type: Paper
DOI: 10.1039/C8PY00231B
Citation: Polym. Chem., 2018,9, 2458-2467
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    Efficient polymerization and post-modification of N-substituted eight-membered cyclic carbonates containing allyl groups

    A. Y. Yuen, A. Bossion, A. Veloso, D. Mecerreyes, J. L. Hedrick, A. P. Dove and H. Sardon, Polym. Chem., 2018, 9, 2458
    DOI: 10.1039/C8PY00231B

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