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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
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 http://dx.doi.org/10.1071/CH12182
Submitted: 5 April 2012 Accepted: 1 May 2012 Published:
16
July
2012
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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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