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Organocatalytic tunable amino acid polymers prepared by controlled radical polymerization
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Evans, Amanda C., Lu, Annhelen, Ondeck, Courtney, Longbottom, Deborah A. and O'Reilly, Rachel K.. (2010) Organocatalytic tunable amino acid polymers prepared by controlled radical polymerization. Macromolecules, Vol.43 (No.15). pp. 6374-6380. ISSN 0024-9297
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Official URL: http://dx.doi.org/10.1021/ma1008447
Abstract
Two families of organocatalytically active polystyrene-based copolymers with tunable incorporations of 4-hydroxyproline have been synthesized using two different controlled radical polymerization technologies: nitroxide-mediated polymerization (NMP) and reversible addition-fragmentation chain transfer (RAFT) polymerization. Both of these methodologies allow ready access to a number of polymeric species with controllable molecular weights, narrow molecular weight distributions (ca. 1.2), and reliable functionality incorporations (between 3 and 26%). The organocatalytic activity and selectivity of the NMP-derived family of copolymers with variable incorporations of L-proline have been investigated using the aldol reaction, which provided high conversion to products ( > 95%) with very good diastereo- and enantioselectivities. We propose that these materials have potential as highly efficient recoverable organocatalyst supports whose solubility and loading can be readily tailored to the desired application.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Chemistry |
| Library of Congress Subject Headings (LCSH): | Polymers, Amino acids, Polymerization, Polystyrene, Catalysis |
| Journal or Publication Title: | Macromolecules |
| Publisher: | American Chemical Society |
| ISSN: | 0024-9297 |
| Date: | 10 August 2010 |
| Volume: | Vol.43 |
| Number: | No.15 |
| Number of Pages: | 7 |
| Page Range: | pp. 6374-6380 |
| Identification Number: | 10.1021/ma1008447 |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Funder: | Royal Society (Great Britain), Leverhulme Trust (LT), Engineering and Physical Sciences Research Council (EPSRC) |
| URI: | http://wrap.warwick.ac.uk/id/eprint/5365 |
Data sourced from Thomson Reuters' Web of Knowledge
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