Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP
Ring-opening metathesis polymerization of norbornene-based (macro)monomers is a powerful approach for the synthesis of macromolecules with diverse compositions and complex architectures. Nevertheless, a fundamental limitation of polymers prepared by this strategy is their lack of facile degradabilit...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Springer Science and Business Media LLC
2020
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| Online Access: | https://hdl.handle.net/1721.1/127831 |
| _version_ | 1826199407186411520 |
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| author | Shieh, Peyton Nguyen, Hung V. -T. Johnson, Jeremiah A. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Shieh, Peyton Nguyen, Hung V. -T. Johnson, Jeremiah A. |
| author_sort | Shieh, Peyton |
| collection | MIT |
| description | Ring-opening metathesis polymerization of norbornene-based (macro)monomers is a powerful approach for the synthesis of macromolecules with diverse compositions and complex architectures. Nevertheless, a fundamental limitation of polymers prepared by this strategy is their lack of facile degradability, limiting their utility in a range of applications. Here we describe a class of readily available bifunctional silyl ether-based cyclic olefins that copolymerize efficiently with norbornene-based (macro)monomers to provide copolymers with backbone degradability under mildly acidic aqueous conditions and degradation rates that can be tuned over several orders of magnitude, depending on the silyl ether substituents. These monomers can be used to manipulate the in vivo biodistribution and clearance rate of polyethylene glycol-based bottlebrush polymers, as well as to synthesize linear, bottlebrush and brush-arm star copolymers with degradable segments. We expect that this work will enable preparation of degradable polymers by ROMP for biomedical applications, responsive self-assembly and improved sustainability. ©2019, The Author(s), under exclusive licence to Springer Nature Limited. |
| first_indexed | 2024-09-23T11:19:42Z |
| format | Article |
| id | mit-1721.1/127831 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T11:19:42Z |
| publishDate | 2020 |
| publisher | Springer Science and Business Media LLC |
| record_format | dspace |
| spelling | mit-1721.1/1278312022-10-01T02:52:07Z Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP Shieh, Peyton Nguyen, Hung V. -T. Johnson, Jeremiah A. Massachusetts Institute of Technology. Department of Chemistry Ring-opening metathesis polymerization of norbornene-based (macro)monomers is a powerful approach for the synthesis of macromolecules with diverse compositions and complex architectures. Nevertheless, a fundamental limitation of polymers prepared by this strategy is their lack of facile degradability, limiting their utility in a range of applications. Here we describe a class of readily available bifunctional silyl ether-based cyclic olefins that copolymerize efficiently with norbornene-based (macro)monomers to provide copolymers with backbone degradability under mildly acidic aqueous conditions and degradation rates that can be tuned over several orders of magnitude, depending on the silyl ether substituents. These monomers can be used to manipulate the in vivo biodistribution and clearance rate of polyethylene glycol-based bottlebrush polymers, as well as to synthesize linear, bottlebrush and brush-arm star copolymers with degradable segments. We expect that this work will enable preparation of degradable polymers by ROMP for biomedical applications, responsive self-assembly and improved sustainability. ©2019, The Author(s), under exclusive licence to Springer Nature Limited. National Institutes of Health (grant no. 1R01CA220468-01) 2020-10-07T16:58:58Z 2020-10-07T16:58:58Z 2019-10 2019-02 2020-09-15T17:30:47Z Article http://purl.org/eprint/type/JournalArticle 1755-4349 https://hdl.handle.net/1721.1/127831 Shieh, Peyton et al., "Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP." Nature Chemistry 11, 12 (December 2019): 1124–32 doi. 10.1038/s41557-019-0352-4 ©2019 Authors en https://dx.doi.org/10.1038/S41557-019-0352-4 Nature Chemistry Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf Springer Science and Business Media LLC PMC |
| spellingShingle | Shieh, Peyton Nguyen, Hung V. -T. Johnson, Jeremiah A. Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP |
| title | Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP |
| title_full | Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP |
| title_fullStr | Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP |
| title_full_unstemmed | Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP |
| title_short | Tailored silyl ether monomers enable backbone-degradable polynorbornene-based linear, bottlebrush and star copolymers through ROMP |
| title_sort | tailored silyl ether monomers enable backbone degradable polynorbornene based linear bottlebrush and star copolymers through romp |
| url | https://hdl.handle.net/1721.1/127831 |
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