Ketone functionalized nitroxides: Synthesis, evaluation of N-alkoxyamine initiators, and derivatization of polymer termini

Greg O'Bryan, Aaron Nilsen, Rebecca Braslau

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

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-(l-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.

Original languageEnglish (US)
Pages (from-to)7848-7854
Number of pages7
JournalMacromolecules
Volume40
Issue number22
DOIs
StatePublished - Oct 30 2007

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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