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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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Supplementary files

Article information


Submitted
08 May 2015
Accepted
09 Jun 2015
First published
09 Jun 2015

This article is Open Access

Org. Biomol. Chem., 2015,13, 7711-7719
Article type
Paper
Author version available

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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