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Development of a Universal Alkoxyamine for “Living” Free Radical Polymerizations
Abstract
Examination of novel alkoxyamines has demonstrated the pivotal role that the nitroxide plays in mediating the “living” or controlled polymerization of a wide range of vinyl monomers. Surveying a variety of different alkoxyamine structures led to α-hydrido derivatives based on a 2,2,5-trimethyl-4-phenyl-3-azahexane-3-oxy, 1, skeleton which were able to control the polymerization of styrene, acrylate, acrylamide, and acrylonitrile based monomers. For each monomer set, the molecular weight could be controlled from 1000 to 200 000 amu with polydispersities typically 1.05−1.15. Block and random copolymers based on combinations of the above monomers could also be prepared with similar control. In comparison with 2,2,6,6-tetramethylpiperidinoxy (TEMPO), these new systems represent a dramatic increase in the range of monomers that can be polymerized under controlled conditions and overcome many of the limitations associated with nitroxide-mediated “living” free radical procedures. Monomer selection and functional group compatibility now approach those of ATRP-based systems.
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Citations
Cited by
Controlled/living radical polymerization: Features, developments, and perspectives
Braunecker, W. A., & Matyjaszewski, K. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.11.002 · Cited by 3,202
Barbey, R., Lavanant, L., Paripovic, D., Schüwer, N., Sugnaux, C., Tugulu, S., & Klok, H.-A. (2009) · Chemical Reviews · doi:10.1021/cr900045a · Cited by 1,753
Polymer brushes: surface-immobilized macromolecules
Zhao, B., & Brittain, W. J. (2000) · Progress in Polymer Science · doi:10.1016/s0079-6700(00)00012-5 · Cited by 1,628
Nitroxide-mediated polymerization
Nicolas, J., Guillaneuf, Y., Lefay, C., Bertin, D., Gigmes, D., & Charleux, B. (2013) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2012.06.002 · Cited by 1,380
Controlled/living radical polymerization in aqueous media: homogeneous and heterogeneous systems
Qiu, J., Charleux, B., & Matyjaszewski, K. (2001) · Progress in Polymer Science · doi:10.1016/s0079-6700(01)00033-8 · Cited by 595
Metadata
- Authors
- Benoit, D., Chaplinski, V., Braslau, R., & Hawker, C. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-04-01
- Volume
- 121
- Issue
- 16
- Pages
- 3904-3920
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1968922359
- Cited by
- 1,058
- References
- 0
- FWCI
- 42.07
- Type
- journal article
- Language
- en
- Open access
- closed
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- Benoit, D., Chaplinski, V., Braslau, R., & Hawker, C. J. (1999). Development of a Universal Alkoxyamine for “Living” Free Radical Polymerizations. Journal of the American Chemical Society. https://doi.org/10.1021/ja984013c
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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