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Symmetry Breaking in the Self-Assembly of Partially Fluorinated Benzene-1,3,5-tricarboxamides

Authors

  • Patrick J. M. Stals,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Peter A. Korevaar,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Martijn A. J. Gillissen,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Dr. Tom F. A. de Greef,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Dr. Carel F. C. Fitié,

    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Prof. Dr. Rint P. Sijbesma,

    Corresponding author
    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
    • Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Dr. Anja R. A. Palmans,

    Corresponding author
    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
    • Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • Prof. Dr. E. W. Meijer

    Corresponding author
    1. Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
    • Institute for Complex Molecular Systems and Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven (The Netherlands)
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  • This work was supported by the European Research Council (ERC advanced grant number 246829). Charley Schaeffer is acknowledged for assisting with measurements, the ICMS animation studio (TU/e) is acknowledged for providing the artwork. Prof. Dr. Willi Bannwarth (Freiburg University), Dr. Ilja Voets (Eindhoven University of Technology), and Prof. Dr. Jim Feast (Durham University) are acknowledged for stimulating discussions.

Abstract

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The interplay of two subsequent aggregation processes results in a symmetry-breaking phenomenon in an achiral self-assembling system. Partially fluorinated benzene-1,3,5-tricarboxamide molecules self-assemble into a racemic mixture of one-dimensional P- and M-helical aggregates, followed by bundling into optically active higher-order aggregates or fibers (see picture).

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