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Ethylene glycol-based ionic liquids via azide/alkyne click chemistry

Authors

  • Parvin Zare,

    1. Institute of Chemistry, Chair of Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin-Luther University Halle-Wittenberg, von Danckelmann-Platz 4, Halle 06120, Germany
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  • Maria Mahrova,

    1. Institute of Chemistry, Chair of Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin-Luther University Halle-Wittenberg, von Danckelmann-Platz 4, Halle 06120, Germany
    2. Department of Organic Chemistry, University of Vigo, 36310 Vigo, Spain
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  • Emilia Tojo,

    1. Department of Organic Chemistry, University of Vigo, 36310 Vigo, Spain
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  • Anja Stojanovic,

    Corresponding author
    1. Institute of Chemistry, Chair of Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin-Luther University Halle-Wittenberg, von Danckelmann-Platz 4, Halle 06120, Germany
    • Institute of Chemistry, Chair of Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin-Luther University Halle-Wittenberg, von Danckelmann-Platz 4, Halle 06120, Germany
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  • Wolfgang H. Binder

    Corresponding author
    1. Institute of Chemistry, Chair of Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin-Luther University Halle-Wittenberg, von Danckelmann-Platz 4, Halle 06120, Germany
    • Institute of Chemistry, Chair of Macromolecular Chemistry, Faculty of Natural Sciences II (Chemistry, Physics and Mathematics), Martin-Luther University Halle-Wittenberg, von Danckelmann-Platz 4, Halle 06120, Germany
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Abstract

A facile synthetic route for the preparation of dicationic ethylene glycol based-ionic liquids (ILs) via the azide/alkyne “click” reaction is presented. The copper(I) catalyzed, microwave-assisted azide/alkyne “click” reaction between diazido-ethylene glycols and the corresponding alkyne containing IL-head group enables a simple preparation of different sets of poly(ethylene glycol)-based ILs. Beside tetra- and hexa(ethylene glycol)-based ILs, also oligomeric (Mn = 400 g/mol) and polymeric ILs (Mn up to 1550 g/mol) could be prepared in good yield and with full conversion of the ionic head group. The prepared ILs were extensively characterized via NMR spectroscopy and ESI-time-of-flight (TOF) mass spectroscopy, revealing the formation of multiply charged ions in the negative mode. Thermal stability proved to be exceptionally high (up to 300 °C) together with low glass-transition temperatures. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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