Chiral and water-soluble poly(2-oxazoline)s

Authors

  • Robert Luxenhofer,

    1. Professur für Makromolekulare Chemie, Technische Universität Dresden, 01062 Dresden, Germany
    Current affiliation:
    1. Professur für Polymere Funktionswerkstoffe, Lehrstuhl für Chemische Technologie der Materialsynthese, Universität Würzburg, Röntgenring 11, 97070 Würzburg, Germany
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  • Stephan Huber,

    1. Wacker-Lehrstuhl für Makromolekulare Chemie, Technische Universität München, 85747 Garching, Germany
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  • Julia Hytry,

    1. Professur für Makromolekulare Chemie, Technische Universität Dresden, 01062 Dresden, Germany
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  • Jing Tong,

    1. Center for Drug Delivery and Nanomedicine, 985830 Nebraska Medical Center, Omaha, Nebraska 68198-5830
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  • Alexander V. Kabanov,

    1. UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599
    2. Laboratory of Chemical Design of Bionanomaterials, Faculty of Chemistry, M.V. Lomonosov Moscow State University, Moscow 119992, Russia
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  • Rainer Jordan

    Corresponding author
    1. Professur für Makromolekulare Chemie, Technische Universität Dresden, 01062 Dresden, Germany
    2. Wacker-Lehrstuhl für Makromolekulare Chemie, Technische Universität München, 85747 Garching, Germany
    • Professur für Makromolekulare Chemie, Technische Universität Dresden, Dresden 01069, Germany
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Abstract

We describe the synthesis and characterization of the first water-soluble and chiral poly(2,4-disubstituted-2-oxazoline)s. While poly(2,4-dimethyl-2-oxazoline)s are water soluble up to 100 °C, aqueous solutions of poly(2-ethyl-4-methly-2-oxazoline) exhibit a lower critical solution temperature. This is discussed in context with its constitutional isomers poly(2-oxazoline)s and poly(2-oxazine)s. Circular dichroism spectroscopy revealed strong Cotton effects, which are also responsive to temperature in aqueous solution. It is therefore hypothesized that structures, comparable to polyproline helices, are formed in aqueous solution. In contrast to polyproline, poly(2,4-disubstituted-2-oxazoline)s are highly water soluble and therefore represent very interesting pseudo-polypeptides that may be useful to develop responsive biomimetic biomaterials. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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