Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
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Enhanced Spin-capturing Polymerization and Radical Coupling Mediated by Cyclic Nitrones

Kayte Ranieri A , Matthias Conradi A , Pierre-Yves Chavant B , Veronique Blandin B , Christopher Barner-Kowollik C D and Thomas Junkers A D
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- Author Affiliations

A Polymer Reaction Design Group, Institute for Materials Research, Universiteit Hasselt, Agoralaan, Gebouw D, BE-3590 Diepenbeek, Belgium.

B Département de Chimie Moléculaire, UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP-53, 38041 Grenoble Cedex 9, France.

C Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe, Germany.

D Corresponding authors. Email: christopher.barner-kowollik@kit.edu; thomas.junkers@uhasselt.be

Australian Journal of Chemistry 65(8) 1110-1116 https://doi.org/10.1071/CH12182
Submitted: 5 April 2012  Accepted: 1 May 2012   Published: 16 July 2012

Abstract

A series of cyclic nitrones have been tested for their spin-trapping activity in the enhanced spin-capturing polymerization of styrene and in nitrone-mediated radical coupling reactions. rac-2-Isopropyl-2,3-dimethyl-1-oxy-2,3-dihydro-imidazol-4-one was found to be the most efficient nitrone. The specific polystyrene macroradical addition rate to this nitrone was determined to be 8.0 × 103 L mol–1 s–1, which is by a factor of 10 higher than for previously studied compounds. Via enhanced spin-capturing polymerization, polymers in the range of oligomers to 30000 g mol–1 were obtained. A strong dependence of molecular weight on monomer conversion was observed, which can be explained by the high trapping rate. In nitrone-mediated radical coupling, almost ideal coupling of bromine-functional polymers was obtained and the successful introduction of the residual alkoxyamine functionality confirmed.


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