A novel one-pot procedure for the fast and efficient conversion of RAFT polymers into hydroxy-functional polymers

Gruendling, T., Dietrich, M., & Barner-Kowollik, C. (2009) A novel one-pot procedure for the fast and efficient conversion of RAFT polymers into hydroxy-functional polymers. Australian Journal of Chemistry, 62(8).

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We report on the successful quantitative transformation of methacrylate and acrylate-type polymers prepared by reversible additionfragmentation chain transfer (RAFT) polymerization carrying a dithioester-end-group into hydroxy-functional polymers. The simple reaction procedure involves stirring a solution of the dithioester-capped polymer and an azo-initiator in tetrahydrofuran at elevated temperatures (T = 60°C) in the presence of air. This reaction quantitatively yields hydroperoxide functionalities that can be efficiently reduced to hydroxy groups in a one-pot procedure using triphenylphosphine. Size exclusion chromatography - electrospray mass spectrometry was employed to monitor the progress of the reaction. The new backbone-linked hydroxy group provides a versatile anchor for chemical end-group conversions and conjugation reactions with prepared RAFT polymers, which alleviates problems with the rather limited ability of the dithioester-end-group to undergo non-radical transformations. © 2009 CSIRO.

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ID Code: 99210
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :28
Export Date: 5 September 2016
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@polymer.uni-karlsruhe.de
Keywords: Azoinitiator, Dithioesters, Electrospray mass spectrometry, Elevated temperature, End groups, Hydroperoxides, Hydroxy groups, One-pot procedures, Quantitative transformation, Radical transformation, Reversible addition-fragmentation chain transfer polymerization, Simple reaction, Tetra-hydrofuran, Triphenyl phosphines, Chromatographic analysis, Free radical polymerization, Mass spectrometry, Organic polymers, Polymers, Size exclusion chromatography, Functional polymers
DOI: 10.1071/CH09080
ISSN: 00049425
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 25 Oct 2016 23:41

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