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Issue 9, 2005
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Cyclohexane bis-urea compounds for the gelation of water and aqueous solutions

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Abstract

A new class of efficient hydrogelators has been developed by a simple modification of the peripheral substituents of cyclohexane bis-urea organogelators with hydrophilic hydroxy or amino functionalities. These bis-urea hydrogelators were synthesised in two or three steps using an alternative procedure to the common isocyanate method. Gelation was obtained with organic solvents, water and strongly basic aqueous solutions like 25% ammonia. Hydrogelation was found to depend on a delicate balance between the hydrophobicity of the alkyl chains, hydrophilicity of the terminal substituents and the enantiomeric purity of the compound. The hydrogels consisted of a network of fibers, in which all urea groups are involved in intermolecular hydrogen bonding. Most likely, gelation is driven by hydrophobic interactions of the methylene units, whereas hydrogen bond formation between the urea groups provides the necessary anisotropy of the aggregation and the high thermal stability of the gels.

Graphical abstract: Cyclohexane bis-urea compounds for the gelation of water and aqueous solutions

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Supplementary files

Article information


Submitted
19 Jan 2005
Accepted
03 Mar 2005
First published
21 Mar 2005

Org. Biomol. Chem., 2005,3, 1631-1639
Article type
Paper

Cyclohexane bis-urea compounds for the gelation of water and aqueous solutions

M. de Loos, A. Friggeri, J. van Esch, R. M. Kellogg and B. L. Feringa, Org. Biomol. Chem., 2005, 3, 1631
DOI: 10.1039/B500837A

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