Fibrous Networks with Incorporated Macrocycles: A Chiral Stimuli-Responsive Supramolecular Supergelator and Its Application to Biocatalysis in Organic Media

Authors

  • Zhenhui Qi,

    1. Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin (Germany), Fax: (+49) 30-838-55817
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  • Dr. Changzhu Wu,

    1. Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin (Germany), Fax: (+49) 30-838-55817
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  • Dr. Paula Malo de Molina,

    1. Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 124, 10624 Berlin (Germany)
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  • Han Sun,

    1. Max-Planck-Institut für Biophysikalische Chemie, Am Fassberg 11, 37073 Göttingen (Germany)
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  • Andrea Schulz,

    1. Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin (Germany), Fax: (+49) 30-838-55817
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  • Prof. Christian Griesinger,

    1. Max-Planck-Institut für Biophysikalische Chemie, Am Fassberg 11, 37073 Göttingen (Germany)
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  • Prof. Michael Gradzielski,

    1. Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 124, 10624 Berlin (Germany)
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  • Prof. Rainer Haag,

    1. Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin (Germany), Fax: (+49) 30-838-55817
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  • Prof. Marion B. Ansorge-Schumacher,

    1. Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 124, 10624 Berlin (Germany)
    2. Current address: Institut für Mikrobiologie, Technische Universität Dresden, 01062 Dresden (Germany)
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  • Prof. Christoph A. Schalley

    Corresponding author
    1. Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin (Germany), Fax: (+49) 30-838-55817
    • Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin (Germany), Fax: (+49) 30-838-55817

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Abstract

A new and versatile, crown ether appended, chiral supergelator has been designed and synthesized based on the bis-urea motif. The introduction of a stereogenic center improved its gelation ability significantly relative to its achiral analogue. This low-molecular-weight gelator forms supramolecular gels in a variety of organic solvents. It is sensitive to multiple chemical stimuli and the sol–gel phase transitions can be reversibly triggered by host–guest interactions. The gel can be used to trap enzymes and release them on demand by chemical stimuli. It stabilizes the microparticles in Pickering emulsions so that enzyme-catalyzed organic reactions can take place in the polar phase inside the microparticles, the organic reactants diffusing through the biphasic interface from the surrounding organic phase. Because of the higher interface area between the organic and polar phases, enzyme activity is enhanced in comparison with simple biphasic systems.

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