Nanomaterials 2019, 9(2), 249; https://doi.org/10.3390/nano9020249
Straightforward Immobilization of Phosphonic Acids and Phosphoric Acid Esters on Mesoporous Silica and Their Application in an Asymmetric Aldol Reaction
Christian Weinberger
, Tatjana Heckel, Patrick Schnippering, Markus Schmitz, Anpeng Guo, Waldemar Keil, Heinrich C. Marsmann, Claudia Schmidt *, Michael Tiemann * and René Wilhelm *
, Tatjana Heckel, Patrick Schnippering, Markus Schmitz, Anpeng Guo, Waldemar Keil, Heinrich C. Marsmann, Claudia Schmidt *, Michael Tiemann * and René Wilhelm *
Department of Chemistry, Paderborn University, Warburger Str. 100, D-33098 Paderborn, Germany
*
Authors to whom correspondence should be addressed.
Received: 31 December 2018 / Revised: 27 January 2019 / Accepted: 4 February 2019 / Published: 12 February 2019
(This article belongs to the Special Issue Functional Nanoporous Materials)
Abstract
The combined benefits of moisture-stable phosphonic acids and mesoporous silica materials (SBA-15 and MCM-41) as large-surface-area solid supports offer new opportunities for several applications, such as catalysis or drug delivery. We present a comprehensive study of a straightforward synthesis method via direct immobilization of several phosphonic acids and phosphoric acid esters on various mesoporous silicas in a Dean–Stark apparatus with toluene as the solvent. Due to the utilization of azeotropic distillation, there was no need to dry phosphonic acids, phosphoric acid esters, solvents, or silicas prior to synthesis. In addition to modeling phosphonic acids, immobilization of the important biomolecule adenosine monophosphate (AMP) on the porous supports was also investigated. Due to the high surface area of the mesoporous silicas, a possible catalytic application based on immobilization of an organocatalyst for an asymmetric aldol reaction is discussed. View Full-TextKeywords:
mesoporous silica; organocatalysis; host–guest materials; magic-angle spinning NMR (MAS-NMR)
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Weinberger, C.; Heckel, T.; Schnippering, P.; Schmitz, M.; Guo, A.; Keil, W.; Marsmann, H.C.; Schmidt, C.; Tiemann, M.; Wilhelm, R. Straightforward Immobilization of Phosphonic Acids and Phosphoric Acid Esters on Mesoporous Silica and Their Application in an Asymmetric Aldol Reaction. Nanomaterials 2019, 9, 249.
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