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

Organophosphorus chemical warfare agent simulant DMMP promotes structural reinforcement of urea-based chiral supramolecular gels
Organophosphorus chemical warfare agent simulant DMMP promotes structural reinforcement of urea-based chiral supramolecular gels
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.
2046-2069
12287-12292
Piana, Francesca
26f205ad-2e31-498e-96e2-e42f48c1df80
Facciotti, Marco
4c7dc014-3d52-4fdb-98f2-867f81b3447b
Pileio, Giuseppe
13f78e66-0707-4438-b9c9-6dbd3eb7d4e8
Hiscock, Jennifer R.
99a8a34c-a869-48e2-b713-1e69e4741032
Van Rossom, Wim
4a3f4484-88e4-4bf8-aa7e-e36b646386b5
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Piana, Francesca
26f205ad-2e31-498e-96e2-e42f48c1df80
Facciotti, Marco
4c7dc014-3d52-4fdb-98f2-867f81b3447b
Pileio, Giuseppe
13f78e66-0707-4438-b9c9-6dbd3eb7d4e8
Hiscock, Jennifer R.
99a8a34c-a869-48e2-b713-1e69e4741032
Van Rossom, Wim
4a3f4484-88e4-4bf8-aa7e-e36b646386b5
Brown, Richard C. D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943

Piana, Francesca, Facciotti, Marco, Pileio, Giuseppe, Hiscock, Jennifer R., Van Rossom, Wim, Brown, Richard C. D. and Gale, Philip A. (2015) Organophosphorus chemical warfare agent simulant DMMP promotes structural reinforcement of urea-based chiral supramolecular gels. RSC Advances, 5 (16), 12287-12292. (doi:10.1039/C4RA15241G).

Record type: Article

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.

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Accepted/In Press date: 8 January 2015
e-pub ahead of print date: 2015
Published date: 23 January 2015
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 373800
URI: https://eprints.soton.ac.uk/id/eprint/373800
ISSN: 2046-2069
PURE UUID: ddefde98-3c13-4d98-9ea7-f7d40fcbe391
ORCID for Giuseppe Pileio: ORCID iD orcid.org/0000-0001-9223-3896
ORCID for Richard C. D. Brown: ORCID iD orcid.org/0000-0003-0156-7087
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

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Date deposited: 02 Feb 2015 11:35
Last modified: 20 Jul 2019 01:16

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