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Issue 28, 2015
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Supramolecular polymers for organocatalysis in water

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Abstract

A water-soluble benzene-1,3,5-tricarboxamide (BTA) derivative that self-assembles into one-dimensional, helical, supramolecular polymers is functionalised at the periphery with one L-proline moiety. In water, the BTA-derivative forms micrometre long supramolecular polymers, which are stabilised by hydrophobic interactions and directional hydrogen bonds. Furthermore, we co-assemble a catalytically inactive, but structurally similar, BTA with the L-proline functionalised BTA to create co-polymers. This allows us to assess how the density of the L-proline units along the supramolecular polymer affects its activity and selectivity. Both the supramolecular polymers and co-polymers show high activity and selectivity as catalysts for the aldol reaction in water when using p-nitrobenzaldehyde and cyclohexanone as the substrates for the aldol reaction. After optimisation of the reaction conditions, a consistent conversion of 92 ± 7%, deanti of 92 ± 3%, and eeanti of 97 ± 1% are obtained with a concentration of L-proline as low as 1 mol%.

Graphical abstract: Supramolecular polymers for organocatalysis in water

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Publication details

The article was received on 08 May 2015, accepted on 09 Jun 2015 and first published on 09 Jun 2015


Article type: Paper
DOI: 10.1039/C5OB00937E
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Citation: Org. Biomol. Chem., 2015,13, 7711-7719
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    Supramolecular polymers for organocatalysis in water

    L. N. Neumann, M. B. Baker, C. M. A. Leenders, I. K. Voets, R. P. M. Lafleur, A. R. A. Palmans and E. W. Meijer, Org. Biomol. Chem., 2015, 13, 7711
    DOI: 10.1039/C5OB00937E

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