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    Resolving Self-Assembly of Bile Acids at the Molecular Length Scale
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    Food and Soft Materials Science, Institute of Food, Nutrition and Health, ETH Zurich, Schmelzbergstrasse 9, LFO E23, CH-8092 Zürich, Switzerland
    *E-mail: [email protected]
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    Langmuir

    Cite this: Langmuir 2012, 28, 14, 5999–6005
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    https://doi.org/10.1021/la300384u
    Published March 13, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    The self-assembly behavior of the naturally occurring steroidal bile compounds cholic, deoxycholic, ursodeoxycholic, and lithocholic acid was studied by combining atomic force microscopy (AFM), polarized optical microscopy (POM), Fourier-transform infrared spectroscopy (FTIR), absorption spectroscopy (UV–vis), circular dichroism (CD), and wide-angle X-ray scattering (WAXS). Molecular solutions of these mono-, di-, and trihydroxyl substituted bile acids spontaneously evolved into supramolecular aggregates upon the incremental addition of H2O as a poor solvent. Highly crystalline nanostructured multilayered assemblies were formed, which revealed a very rich polymorphism of micro- and macro-structures depending on the chemical structure of the bile acid and the properties of the cosolvent (EtOH or DMSO) used. In particular, AFM allowed resolving the crystalline structure to an unprecedented level. It was thus possible to establish that bile acids associate into H-bonded chiral dimer building blocks, which organize in 2D layers of nanostructured lamellar surface topologies with unique facial amphiphilicity. The detailed understanding of the hierarchical organization in bile acid assemblies may contribute to develop strategies to design bioinspired materials with tailor-made nanostructured surface topologies.

    Copyright © 2012 American Chemical Society

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    Supporting Information

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    UV–vis absorption and CD spectra (Figure SI-1), FTIR spectra (Figure SI-2), WAXS spectra (Figure SI-3), 3D chemical structures of bile acids (Figure SI-4), AFM images (Figures SI-5 to SI-11), and tables of scattering vector q values from WAXS patterns with the corresponding AFM and FFT results (Table SI-1 and Table SI-2). This material is available free of charge via the Internet at http://pubs.acs.org.

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    Langmuir

    Cite this: Langmuir 2012, 28, 14, 5999–6005
    Click to copy citationCitation copied!
    https://doi.org/10.1021/la300384u
    Published March 13, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

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