Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry
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 modifi...
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| Format: | Article |
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American Chemical Society
2015
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| Online Access: | https://eprints.nottingham.ac.uk/39106/ |
| _version_ | 1848795764779646976 |
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| author | Francini, Nora Purdie, Laura Alexander, Cameron Mantovani, Giuseppe Spain, Sebastian G. |
| author_facet | Francini, Nora Purdie, Laura Alexander, Cameron Mantovani, Giuseppe Spain, Sebastian G. |
| author_sort | Francini, Nora |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:37:17Z |
| format | Article |
| id | nottingham-39106 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:37:17Z |
| publishDate | 2015 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-391062020-05-04T17:06:31Z https://eprints.nottingham.ac.uk/39106/ 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. 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. American Chemical Society 2015-04-17 Article PeerReviewed Francini, Nora, Purdie, Laura, Alexander, Cameron, Mantovani, Giuseppe and Spain, Sebastian G. (2015) Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry. Macromolecules, 48 (9). pp. 2857-2863. ISSN 1520-5835 http://dx.doi.org/10.1021/acs.macromol.5b00447 doi:10.1021/acs.macromol.5b00447 doi:10.1021/acs.macromol.5b00447 |
| spellingShingle | Francini, Nora Purdie, Laura Alexander, Cameron Mantovani, Giuseppe Spain, Sebastian G. Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry |
| title | Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry |
| title_full | Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry |
| title_fullStr | Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry |
| title_full_unstemmed | Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry |
| title_short | Multifunctional poly[N-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry |
| title_sort | multifunctional poly[n-(2-hydroxypropyl)methacrylamide] copolymers via postpolymerization modification and sequential thiol–ene chemistry |
| url | https://eprints.nottingham.ac.uk/39106/ https://eprints.nottingham.ac.uk/39106/ https://eprints.nottingham.ac.uk/39106/ |