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Functional degradable polymers by radical ring-opening copolymerization of MDO and vinyl bromobutanoate : synthesis, degradability and post-polymerization modification
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Hedir, Guillaume, Bell, Craig A., O’Reilly, Rachel K. and Dove, Andrew P. (2015) Functional degradable polymers by radical ring-opening copolymerization of MDO and vinyl bromobutanoate : synthesis, degradability and post-polymerization modification. Biomacromolecules, 16 (7). pp. 2049-2058. doi:10.1021/acs.biomac.5b00476 ISSN 1525-7797.
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Official URL: http://dx.doi.org/10.1021/acs.biomac.5b00476
Abstract
The synthesis of vinyl bromobutanoate (VBr), a new vinyl acetate monomer derivative obtained by the palladium-catalyzed vinyl exchange reaction between vinyl acetate (VAc) and 4-bromobutyric acid is reported. The homopolymerization of this new monomer using the RAFT/MADIX polymerization technique leads to the formation of novel well-defined and controlled polymers containing pendent bromine functional groups able to be modified via postpolymerization modification. Furthermore, the copolymerization of vinyl bromobutanoate with 2-methylene-1,3-dioxepane (MDO) was also performed to deliver a range of novel functional degradable copolymers, poly(MDO-co-VBr). The copolymer composition was shown to be able to be tuned to vary the amount of ester repeat units in the polymer backbone, and hence determine the degradability, while maintaining a control of the final copolymers’ molar masses. The addition of functionalities via simple postpolymerization modifications such as azidation and the 1,3-dipolar cycloaddition of a PEG alkyne to an azide is also reported and proven by 1H NMR spectroscopy, FTIR spectroscopy, and SEC analyses. These studies enable the formation of a novel class of hydrophilic functional degradable copolymers using versatile radical polymerization methods.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
Library of Congress Subject Headings (LCSH): | Polymers, Biopolymers, Biodegradable plastics | ||||||||
Journal or Publication Title: | Biomacromolecules | ||||||||
Publisher: | American Chemical Society | ||||||||
ISSN: | 1525-7797 | ||||||||
Official Date: | 13 July 2015 | ||||||||
Dates: |
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Volume: | 16 | ||||||||
Number: | 7 | ||||||||
Page Range: | pp. 2049-2058 | ||||||||
DOI: | 10.1021/acs.biomac.5b00476 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 29 December 2015 | ||||||||
Date of first compliant Open Access: | 29 December 2015 | ||||||||
Funder: | University of Warwick, British Petroleum Company (BP), Engineering and Physical Sciences Research Council (EPSRC), European Research Council (ERC) | ||||||||
Grant number: | 615142 |
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