Controlled Supramolecular Oligomerization of C3-Symmetrical Molecules in Water: The Impact of Hydrophobic Shielding

Authors

  • Dr. Pol Besenius,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Dr. Kelly P. van den Hout,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Harald M. H. G. Albers,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Dr. Tom F. A. de Greef,

    1. Department of Biomedical Engineering, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Luuk L. C. Olijve,

    1. Department of Biomedical Engineering, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Dr. Thomas M. Hermans,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Bas F. M. de Waal,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Paul H. H. Bomans,

    1. Laboratory of Materials and Interface Chemistry and Soft Matter CryoTEM Research Unit, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Dr. Nico A. J. M. Sommerdijk,

    1. Laboratory of Materials and Interface Chemistry and Soft Matter CryoTEM Research Unit, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Dr. Giuseppe Portale,

    1. BM26 - DUBBLE, European Synchrotron Radiation Facility (ESRF), 6 rue Jules Horowitz, BP220, 38043 Grenoble (France)
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  • Dr. Anja R. A. Palmans,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Dr. Marcel H. P. van Genderen,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Dr. Jef A. J. M. Vekemans,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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  • Prof. Dr. E. W. Meijer

    Corresponding author
    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
    • Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands), Fax: (+31) 40-2474706
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Abstract

The supramolecular oligomerization of three water-soluble C3-symmetrical discotic molecules is reported. The compounds all possess benzene-1,3,5-tricarboxamide cores and peripheral GdIII–DTPA (diethylene triamine pentaacetic acid) moieties, but differ in their linker units and thus in their propensity to undergo secondary interactions in H2O. The self-assembly behavior of these molecules was studied in solution using circular dichroism, UV/Vis spectroscopy, nuclear magnetic resonance, and cryogenic transmission electron microscopy. The aggregation concentration of these molecules depends on the number of secondary interactions and on the solvophobic character of the polymerizing moieties. Hydrophobic shielding of the hydrogen-bonding motif in the core of the discotic is of paramount importance for yielding stable, helical aggregates that are designed to be restricted in size through anti-cooperative, electrostatic, repulsive interactions.

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