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Revisiting monomer synthesis and radical ring opening polymerization of dimethylated MDO towards biodegradable nanoparticles for enzymes

Gaitzsch, J; Welsch, PC; Folini, J; Schoenenberger, C-A; Anderson, JC; Meier, WP; (2018) Revisiting monomer synthesis and radical ring opening polymerization of dimethylated MDO towards biodegradable nanoparticles for enzymes. European Polymer Journal , 101 pp. 113-119. 10.1016/j.eurpolymj.2018.02.015. Green open access

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Abstract

Radical ring opening polymerization is a powerful tool to achieve a polyester via radical polymerization. We used it to obtain a dimethylated version of poly(caprolactone) (PdmCL) from dimethylated MDO (DMMDO). First, we revisited monomer synthesis and achieved a milder synthetic protocol by introducing a cobalt-based catalyst. We also developed a new route towards DMMDO via a cyclic carbonate using the Petasis chemistry. Amphiphilic block-copolymers were then generated by free radical polymerization of DMMDO with a PEG-based macroinitiator. The resulting polyesters self-assembled into nanoparticles that were biodegradable as well as biocompatible. The nanoparticles proved to be an effective protective shell for an entrapped enzyme that was released upon degradation of the polyester by esterase. We are confident that our results will spur further research into block-copolymers resulting from RROP.

Type: Article
Title: Revisiting monomer synthesis and radical ring opening polymerization of dimethylated MDO towards biodegradable nanoparticles for enzymes
Open access status: An open access version is available from UCL Discovery
DOI: 10.1016/j.eurpolymj.2018.02.015
Publisher version: http://dx.doi.org/10.1016/j.eurpolymj.2018.02.015
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: Science & Technology, Physical Sciences, Polymer Science, Radical ring opening polymerization, Cyclic ketene acetal, Self-assembly, Biodegradable, Amplex Red, CYCLIC KETENE ACETALS, XANTHATE-MEDIATED POLYMERIZATION, FUNCTIONAL DEGRADABLE POLYMERS, CONVENTIONAL VINYL MONOMERS, COPOLYMERIZATION, 4,7-DIMETHYL-2-METHYLENE-1,3-DIOXEPANE, 5,6-BENZO-2-METHYLENE-1,3-DIOXEPANE, NANOCONTAINERS, METHYLENATIONS, NANOREACTORS
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10049030
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