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Issue 16, 2015
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Organophosphorus chemical warfare agent simulant DMMP promotes structural reinforcement of urea-based chiral supramolecular gels

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Abstract

Six urea-based supramolecular gels have been obtained in situ by mixing either (R)-(−)-1-(1-naphthyl)ethyl isocyanate or (±)-1-(1-naphthyl)ethyl isocyanate with various amines. This allowed a comparative study on the effects of chirality on the response of the molecular gels to the presence of the neutral organophosphate guest dimethyl methylphosphonate (DMMP). The inversion test results show that the absence of enantiomeric purity causes marked instability of the gel network in the presence of the guest. DSC and rheology measurements reveal the promotion of a structural reinforcement of the gels when 0.01 mL of DMMP interacts with the enantiomerically pure systems. This effect was investigated by means of electrostatic potential surface calculations and 31P–{1H} NMR spectroscopy.

Graphical abstract: Organophosphorus chemical warfare agent simulant DMMP promotes structural reinforcement of urea-based chiral supramolecular gels

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Supplementary files

Article information


Submitted
25 Nov 2014
Accepted
08 Jan 2015
First published
23 Jan 2015

RSC Adv., 2015,5, 12287-12292
Article type
Paper
Author version available

Organophosphorus chemical warfare agent simulant DMMP promotes structural reinforcement of urea-based chiral supramolecular gels

F. Piana, M. Facciotti, G. Pileio, J. R. Hiscock, W. Van Rossom, R. C. D. Brown and P. A. Gale, RSC Adv., 2015, 5, 12287
DOI: 10.1039/C4RA15241G

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