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Preparation of Bifunctional Mesoporous Silica Nanoparticles by Orthogonal Click Reactions and Their Application in Cooperative Catalysis

Authors

  • Arne T. Dickschat,

    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6523
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  • Frederik Behrends,

    1. Physikalisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 28/30, 48149 Münster (Germany)
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  • Martin Bühner,

    1. nanoAnalytics GmbH, Heisenbergstrasse 11, 48149 Münster (Germany)
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  • Dr. Jinjun Ren,

    1. Physikalisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 28/30, 48149 Münster (Germany)
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  • Mark Weiß,

    1. Physikalisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 28/30, 48149 Münster (Germany)
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  • Prof. Dr. Hellmut Eckert,

    Corresponding author
    1. Physikalisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 28/30, 48149 Münster (Germany)
    • Physikalisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 28/30, 48149 Münster (Germany)
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  • Prof. Dr. Armido Studer

    Corresponding author
    1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6523
    • Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149 Münster (Germany), Fax: (+49) 251-833-6523
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Abstract

The synthesis of bifunctional mesoporous silica nanoparticles is described. Two chemically orthogonal functionalities are incorporated into mesoporous silica by co-condensation of tetraethoxysilane with two orthogonally functionalized triethoxyalkylsilanes. Post-functionalization is achieved by orthogonal surface chemistry. A thiol–ene reaction, Cu-catalyzed 1,3-dipolar alkyne/azide cycloaddition, and a radical nitroxide exchange reaction are used as orthogonal processes to install two functionalities at the surface that differ in reactivity. Preparation of mesoporous silica nanoparticles bearing acidic and basic sites by this approach is discussed. Particles are analyzed by solid state NMR spectroscopy, elemental analysis, infrared-spectroscopy, and scanning electron microscopy. As a first application, these particles are successfully used as cooperative catalysts in the Henry reaction.

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