Ketone Functionalized Nitroxides:  Synthesis, Evaluation of N-Alkoxyamine Initiators, and Derivatization of Polymer Termini

Two ketone-bearing N-alkoxyamines have been prepared and evaluated as initiators in nitroxide-mediated polymerization. N-(1-Phenethyloxy)-5,5,8-trimethyl-7-phenyl-azanonan-2-one (1) forms polymers with excellent control of molecular weight and low polydispersities, whereas N-(1-phenethyloxy)-5,8-dim...

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Bibliographic Details
Published in:Macromolecules 2007-10, Vol.40 (22), p.7848-7854
Main Authors: O'Bryan, Greg, Nilsen, Aaron, Braslau, Rebecca
Format: Article
Language:English
Subjects:
Applied sciences
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Polymerization
Preparation, kinetics, thermodynamics, mechanism and catalysts
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Summary:Two ketone-bearing N-alkoxyamines have been prepared and evaluated as initiators in nitroxide-mediated polymerization. N-(1-Phenethyloxy)-5,5,8-trimethyl-7-phenyl-azanonan-2-one (1) forms polymers with excellent control of molecular weight and low polydispersities, whereas N-(1-phenethyloxy)-5,8-dimethyl-5,7-phenyl-azanonan-2-one (2) does not effect controlled polymerization at 125 °C. Polymers prepared from initiator 1 retain the ketone functionality on the nitroxide terminus. Near-quantitative functionalization is demonstrated via hydrazone formation.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma071039s