Radical Approach to Thioester-Containing Polymers
Abstract
A new approach to radical ring-opening polymerization is presented that employs a new thionolactone monomer to generate polymers with thioester-containing backbones. The use of a thiocarbonyl acceptor overcomes longstanding reactivity problems in the field to give complete ring-opening and quantitative incorporation into a variety of acrylate polymers. The resulting copolymers readily degrade under hydrolytic conditions, in addition to cysteine-mediated degradation through transthioesterification. The strategy is compatible with reversible addition-fragmentation chain transfer (RAFT) polymerization and permits the synthesis of block polymers for the preparation of well-defined macromolecular structures.
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The rROP approach requires delicate design of the cyclic monomer to achieve high reactivity and to control the ratio of ring-opened and cyclic structures.
“However, the rROP approach requires delicate design of the cyclic monomer to achieve high reactivity and to control the ratio of ring-opened and cyclic structures.”
From Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones (2023) · cites this paper as [24]
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- Authors
- Smith, R. A., Fu, G., McAteer, O., Xu, M., & Gutekunst, W. R.
- Affiliations
- Georgia Institute of Technology (US)
- Corresponding author
- Gutekunst, Will R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-01-12
- Volume
- 141
- Issue
- 4
- Pages
- 1446-1451
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2910869068
- Cited by
- 248
- References
- 61
- Citations by year
- 2026: 41 · 2025: 39 · 2024: 50 · 2023: 49 · 2022: 38 · 2021: 16 · 2020: 12 · 2019: 3
- FWCI
- 6.77
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Georgia Institute of Technology
- American Chemical Society Petroleum Research Fund (59312-DNI7)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Photopolymerization techniques and applications
- Keywords
- radical ring-opening polymerization, acrylate copolymers, hydrolytic degradation, RAFT polymerization, block copolymers
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