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Article

Synthesis and evaluation of an ester-functional alkoxyamine for nitroxide-mediated polymerization

  1. Anna C. Greene1,
  2. Robert B. Grubbs1,2,*

Article first published online: 22 OCT 2009

DOI: 10.1002/pola.23675

Issue

Journal of Polymer Science Part A: Polymer Chemistry

Journal of Polymer Science Part A: Polymer Chemistry

Volume 47, Issue 23, pages 6342–6352, 1 December 2009

Additional Information

How to Cite

Greene, A. C. and Grubbs, R. B. (2009), Synthesis and evaluation of an ester-functional alkoxyamine for nitroxide-mediated polymerization. J. Polym. Sci. A Polym. Chem., 47: 6342–6352. doi: 10.1002/pola.23675

Author Information

  1. 1

    Department of Chemistry, Dartmouth College, 6128 Burke Laboratory, Hanover, New Hampshire 03755

  2. 2

    Department of Chemistry, State University of New York, Stony Brook, New York 11794

*Department of Chemistry, Dartmouth College, 6128 Burke Laboratory, Hanover, New Hampshire 03755

Publication History

  1. Issue published online: 22 OCT 2009
  2. Article first published online: 22 OCT 2009
  3. Manuscript Accepted: 3 AUG 2009
  4. Manuscript Received: 19 JUN 2009

Funded by

  • NSF. Grant Numbers: DMR-0239697, DMR-0804792

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Keywords:

  • chain-end functionality;
  • controlled radical polymerization;
  • functional alkoxyamines;
  • functionalization of polymers;
  • nitroxide-mediated polymerization;
  • radical polymerization;
  • UV-vis spectroscopy

Abstract

The ester-functional alkoxyamine 2,2-dimethyl-3-(1-(4-(methoxycarbonyl)phenyl)ethoxy)-4-(4-(methoxycarbonyl)phenyl)-3-azapentane (2) was efficiently synthesized for use as a functional initiator in nitroxide-mediated polymerization. Two equivalents of 1-(4-(methoxycarbonyl)phenyl)ethyl radical were added across the double bond of 2-methyl-2-nitrosopropane to form alkoxyamine 2, which was found to control the polymerization of styrene, isoprene, and n-butyl acrylate. The ester moieties were hydrolyzed for subsequent esterification with 1-pyrenebutanol to form a dipyrene-labeled initiator that was used to probe nitroxide end-group fidelity after styrene polymerization. High retention of nitroxide was confirmed by UV-vis studies over a range of monomer conversions. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 6342–6352, 2009

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