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Aminolysis of Polymers with Thiocarbonylthio Termini Prepared by RAFT Polymerization: The Difference between Polystyrene and Polymethacrylates
Abstract
Aminolysis of polystyrene and poly(methyl methacrylate) (PMMA) prepared by reversible addition−fragmentation chain transfer (RAFT) polymerization was investigated. The product of the former contains predominantly double molecular weight species by the formation of disulfide bond, whereas the latter formed coupled species which consequently cleaved to unimolecular weight species. MALDI−TOF MS (matrix-assisted laser desorption ionization time-of-flight mass spectrometry), elemental analysis and 1 H NMR indicated that thiolactone terminus was formed after aminolysis of PMMA. We propose that the thiol end groups generated during the aminolysis of PMMA tend to cyclize through “backbiting” to form thiolactone structure. A similar reaction was observed in the case of poly( N, N -dimethylaminoethyl methacrylate) and poly(laury methacrylate). Despite this, the preparation of thiol-end functionalized PMMA was achieved by introducing a short block of polystyrene after the RAFT polymerization of MMA.
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Citations
Cited by
Thiol-ene “click” reactions and recent applications in polymer and materials synthesis
Lowe, A. B. (2010) · Polym. Chem. · doi:10.1039/b9py00216b · Cited by 1,563
Radical addition–fragmentation chemistry in polymer synthesis
Moad, G., Rizzardo, E., & Thang, S. H. (2008) · Polymer · doi:10.1016/j.polymer.2007.11.020 · Cited by 1,397
Bioapplications of RAFT Polymerization
Boyer, C., Bulmus, V., Davis, T. P., Ladmiral, V., Liu, J., & Perrier, S. (2009) · Chemical Reviews · doi:10.1021/cr9001403 · Cited by 1,015
End group removal and modification of RAFT polymers
Willcock, H., & O'Reilly, R. K. (2010) · Polym. Chem. · doi:10.1039/b9py00340a · Cited by 607
Metadata
- Authors
- Xu, J., He, J., Fan, D., Wang, X., & Yang, Y.
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-11-10
- Volume
- 39
- Issue
- 25
- Pages
- 8616-8624
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W2092077565
- Cited by
- 181
- References
- 0
- FWCI
- 8.57
- Type
- journal article
- Language
- en
- Open access
- closed
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- Xu, J., He, J., Fan, D., Wang, X., & Yang, Y. (2006). Aminolysis of Polymers with Thiocarbonylthio Termini Prepared by RAFT Polymerization: The Difference between Polystyrene and Polymethacrylates. Macromolecules. https://doi.org/10.1021/ma061961m
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