Synthesis, complete characterization, and enantioselective electrokinetic separation of functionalized ruthenium complex enantiomers

Authors

  • Elisabeth Holder,

    1. Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology and Dutch Polymer Institute, Eindhoven, The Netherlands
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  • Oliver Trapp,

    1. Department of Chemistry, Stanford University, Stanford, California
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  • Gabriele Trapp,

    1. Department of Chemistry, Stanford University, Stanford, California
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  • Veronica Marin,

    1. Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology and Dutch Polymer Institute, Eindhoven, The Netherlands
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  • Richard Hoogenboom,

    1. Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology and Dutch Polymer Institute, Eindhoven, The Netherlands
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  • Ulrich S. Schubert

    Corresponding author
    1. Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology and Dutch Polymer Institute, Eindhoven, The Netherlands
    • Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology and Dutch Polymer Institute, P.O. Box 513, 5600 MB Eindhoven, The Netherlands

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Abstract

Electrokinetic chromatography was employed to separate the enantiomers of two novel functionalized ruthenium(II) complexes with different polypyridyl coordination spheres. The use of anionic carboxymethyl-β-cyclodextrin as chiral mobile phase additive resulted in maximum efficiency and resolution for the enantiomer separation of both transition metal complexes. The syntheses of the [4-(3-hydroxypropyl)-4′-methyl-2,2′-bipyridine]-bis(2,2′-bipyridine)rethenium(II)-bis(tetrafluoroborate) and [4-(3-hydroxypropyl)-4′-methyl-2,2′-bipyridine]-bis(4,4′-dimethyl-2,2′-bypyridine)ruthenium(II)-bis(tetrafluoroborate) complexes and their complete characterization by means of two-dimensional 1H and 13C{1H} NMR techniques (1H–1H COSY and 1H–13C HMQC) as well as elemental analyses and MALDI-TOFMS are described in detail. The functionalized complexes can be used as building blocks for further reactions with polymers, biopolymers, surfaces and nanoparticles. Chirality 16:363–368, 2004. © Wiley-Liss, Inc.

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