Functional degradable polymers by radical ring-opening copolymerization of MDO and vinyl bromobutanoate: synthesis, degradability and post-polymerization modification

Hedir, Guillaume G., 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: 2049-2058. doi:10.1021/acs.biomac.5b00476


Author Hedir, Guillaume G.
Bell, Craig A.
O'Reilly, Rachel K.
Dove, Andrew P.
Title Functional degradable polymers by radical ring-opening copolymerization of MDO and vinyl bromobutanoate: synthesis, degradability and post-polymerization modification
Journal name Biomacromolecules   Check publisher's open access policy
ISSN 1526-4602
1525-7797
Publication date 2015-07-13
Sub-type Article (original research)
DOI 10.1021/acs.biomac.5b00476
Volume 16
Issue 7
Start page 2049
End page 2058
Total pages 10
Place of publication Washington, DC, United States
Publisher American Chemical Society
Collection year 2016
Language eng
Formatted 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.
Keyword Vinyl bromobutanoate
Vinyl acetate monomer derivative
Vinyl acetate (VAc)
4-bromobutyric acid
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

 
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