Synthesis and characterization of polyisocyanides derived from alanine and glycine dipeptides

Authors

  • Jeroen J. L. M. Cornelissen,

    1. Department of Organic Chemistry, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
    Current affiliation:
    1. IBM Almaden Research Center, 650 Harry Road, San Jose, CA, 95120
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  • W. Sander Graswinckel,

    1. Department of Organic Chemistry, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • P. J. H. M. Adams,

    1. Department of Organic Chemistry, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
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  • Gerda H. Nachtegaal,

    1. Department of Physical Chemistry, University of Nijmegen, Nijmegen, The Netherlands
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  • Arno P. M. Kentgens,

    1. Department of Physical Chemistry, University of Nijmegen, Nijmegen, The Netherlands
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  • Nico A. J. M. Sommerdijk,

    Corresponding author
    1. Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    • Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
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  • Roeland J. M. Nolte

    1. Department of Organic Chemistry, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands
    2. Laboratory for Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
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Abstract

The synthesis and characterization of polymers derived from isocyanopeptides are described. Optically pure dipeptides based on alanine and glycine were equipped with an isocyano function and subsequently polymerized with a Ni(II) catalyst. Infrared and NMR spectroscopy indicated that the side chains of the polymers were connected by well-defined arrays of intramolecular hydrogen bonds. The weight-average molecular weights of the polymers were determined by atomic force microscopy to be 200–400 kg/mol (polydispersity index = 1.4–1.7). © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 4255–4264, 2001

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