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Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry

Francini, Nora; Purdie, Laura; Alexander, Cameron; Mantovani, Giuseppe; Spain, Sebastian G.

Authors

Nora Francini

Laura Purdie

Sebastian G. Spain sebastian.spain@nottingham.ac.uk



Abstract

Poly[N-(2-hydroxypropyl)methacrylamide] is a promising candidate material for biomedical applications. However, synthesis of functional pHPMA via compolymerization results can lead to variations in monomer composition, molar mass, and dispersity making comparison difficult. Postpolymerization modification routes, most commonly aminolysis of poly[active ester methacrylates], have alleviated some of these problems, but ester hydrolysis can lead to other problems. Here we report the synthesis of multifunctional pHPMA via a simple two-step derivatization of pHPMA homopolymer using readily available standard reagents and atom-efficient procedures. First, treatment with allyl isocyanate yields the corresponding carbamate with predictable incorporation of side-chain functionality. Allyl-pHPMA can then be derivatized further via radical thiol–ene reactions to generate pHPMA with multiple diverse functionalities but without adverse effects on the molecular weight and dispersity of the polymer. The applicability of the method to production of biologically relevant materials is demonstrated by cytocompatibility and cell labeling experiments with easily prepared ligand-functionalized pHPMA in the HCT 116 model cell line.

Journal Article Type Article
Publication Date Apr 17, 2015
Journal Macromolecules
Print ISSN 0024-9297
Electronic ISSN 1520-5835
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
Volume 48
Issue 9
APA6 Citation Francini, N., Purdie, L., Alexander, C., Mantovani, G., & Spain, S. G. (2015). Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry. Macromolecules, 48(9), doi:10.1021/acs.macromol.5b00447
DOI https://doi.org/10.1021/acs.macromol.5b00447
Publisher URL http://dx.doi.org/10.1021/acs.macromol.5b00447
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
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