The DOI matches its Crossref record.
Highly Efficient “Click” Functionalization of Poly(3-azidopropyl methacrylate) Prepared by ATRP
Abstract
To prepare polymers with pendant functionality capable of participating in highly efficient Cu I -catalyzed 1,3-dipolar cycloaddition of azide and alkynes, monomers with acetylene or azido groups were polymerized via controlled radical polymerization. Atom transfer radical polymerization (ATRP) of propargyl methacrylate (PgMA) resulted in high polydispersities ( M w / M n > 3), multimodal molecular weight distributions, and cross-linked networks at moderate to high conversion. The poor results obtained with this monomer were presumably due to addition of the propagating radicals to the acetylene group, transfer reactions, and/or interference with the catalyst. A novel monomer, 3-azidopropyl methacrylate (AzPMA), was polymerized via ATRP with good control of the polymer molecular weight distribution and retention of chain functionality. Poly(3-azidopropyl methacrylate) was coupled with propargyl alcohol, propargyl triphenylphosphonium bromide, propargyl 2-bromoisobutyrate, and 4-pentynoic acid via a highly efficient “click” reaction in the presence of a Cu I catalyst. The azido-functionalized polymer demonstrated enhanced reactivity as compared to small molecules with comparable structures. The ability of the coupling reactions to be conducted at room temperature without significant excess of reagents makes this an attractive alternative to preparing (co)polymers with high degrees of functionalization.
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Braunecker, W. A., & Matyjaszewski, K. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.11.002 · Cited by 3,202
Self-citationAtom Transfer Radical Polymerization (ATRP): Current Status and Future Perspectives
Matyjaszewski, K. (2012) · Macromolecules · doi:10.1021/ma3001719 · Cited by 2,606
Self-citationLutz, J. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200604050 · Cited by 1,516
Ouchi, M., Terashima, T., & Sawamoto, M. (2009) · Chemical Reviews · doi:10.1021/cr900234b · Cited by 1,257
Corrigan, N., Jung, K., Moad, G., Hawker, C. J., Matyjaszewski, K., & Boyer, C. (2020) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2020.101311 · Cited by 981
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Golas, P. L., & Matyjaszewski, K. (2010) · Chem. Soc. Rev. · doi:10.1039/b901978m · Cited by 863
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Xi, W., Scott, T. F., Kloxin, C. J., & Bowman, C. N. (2014) · Advanced Functional Materials · doi:10.1002/adfm.201302847 · Cited by 677
Ladmiral, V., Mantovani, G., Clarkson, G. J., Cauet, S., Irwin, J. L., & Haddleton, D. M. (2006) · Journal of the American Chemical Society · doi:10.1021/ja058364k · Cited by 586
Synthesis of Molecular Brushes by “Grafting onto” Method: Combination of ATRP and Click Reactions
Gao, H., & Matyjaszewski, K. (2007) · Journal of the American Chemical Society · doi:10.1021/ja0711617 · Cited by 584
Self-citation“Click”‐Chemistry in Polymer and Material Science: the Update
Binder, W. H. (2008) · Macromolecular Rapid Communications · doi:10.1002/marc.200800332 · Cited by 567
Lutz, J.-F., & Zarafshani, Z. (2008) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2008.02.004 · Cited by 549
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Fang, L., Olson, M. A., Benítez, D., Tkatchouk, E., Goddard III, W. A., & Stoddart, J. F. (2010) · Chem. Soc. Rev. · doi:10.1039/b917901a · Cited by 450
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Kennedy, D. C., McKay, C. S., Legault, M. C. B., Danielson, D. C., Blake, J. A., Pegoraro, A. F., Stolow, A., Mester, Z., & Pezacki, J. P. (2011) · Journal of the American Chemical Society · doi:10.1021/ja2083027 · Cited by 416
Telechelic polymers by living and controlled/living polymerization methods
Tasdelen, M. A., Kahveci, M. U., & Yagci, Y. (2011) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2010.10.002 · Cited by 393
Kempe, K., Krieg, A., Becer, C. R., & Schubert, U. S. (2012) · Chem. Soc. Rev. · doi:10.1039/c1cs15107j · Cited by 353
Combination of Living Radical Polymerization and Click Chemistry for Surface Modification
Ranjan, R., & Brittain, W. J. (2007) · Macromolecules · doi:10.1021/ma0705873 · Cited by 275
Li, X., Qian, Y., Liu, T., Hu, X., Zhang, G., You, Y., & Liu, S. (2011) · Biomaterials · doi:10.1016/j.biomaterials.2011.05.049 · Cited by 270
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Geng, Z., Shin, J. J., Xi, Y., & Hawker, C. J. (2021) · Journal of Polymer Science · doi:10.1002/pol.20210126 · Cited by 269
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Engler, A. C., Lee, H., & Hammond, P. T. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200904070 · Cited by 254
Hu, J., Qian, Y., Wang, X., Liu, T., & Liu, S. (2012) · Langmuir · doi:10.1021/la203992q · Cited by 124
Metadata
- Authors
- Sumerlin, B. S., Tsarevsky, N. V., Louche, G., Lee, R. Y., & Matyjaszewski, K.
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-08-04
- Volume
- 38
- Issue
- 18
- Pages
- 7540-7545
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W2018087879
- Cited by
- 452
- References
- 0
- FWCI
- 22.63
- Type
- journal article
- Language
- en
- Open access
- closed
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