A unique case of ′in situ’ Bifluoride triggered formation of supramolecular organogels using isophthalamide hydrogen bond donating receptors
A unique case of ′in situ’ Bifluoride triggered formation of supramolecular organogels using isophthalamide hydrogen bond donating receptors
A novel isopthalamide based receptor H2L2 featuring two p-benzoic acid units has been synthesised and its anion binding properties analysed by 1H-NMR spectroscopy in DMSO-d6/0.5 % H2O. As expected, in the presence of tetrabutylammonium (TBA) fluoride the deprotonation of the carboxylic acid moieties was observed. However, the deprotonated receptor L22− was able to bind the in situ formed HF2− via the formation of H-bonds with the amide NHs. When H2L2 was dissolved in THF and 4 equivalents of TBAF were added in CH3CN a unique sol-gel transition occurred giving rise to a stable thixotropic supramolecular gel. Theoretical calculations elucidated the gelation mechanism and strongly support the findings observed experimentally.
Anion recognition, Non-covalent interactions, Self-assembly, Supramolecular chemistry, Supramolecular gels
Picci, Giacomo
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D'Anna, Francesca
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Marullo, Salvatore
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Montis, Riccardo
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Lippolis, Vito
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Orton, James
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Coles, Simon
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Frontera, Antonio
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Gomila, Rosa M.
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Caltagirone, Claudia
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3 March 2025
Picci, Giacomo
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D'Anna, Francesca
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Marullo, Salvatore
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Montis, Riccardo
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Lippolis, Vito
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Orton, James
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Coles, Simon
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Frontera, Antonio
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Gomila, Rosa M.
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Caltagirone, Claudia
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Picci, Giacomo, D'Anna, Francesca, Marullo, Salvatore, Montis, Riccardo, Lippolis, Vito, Orton, James, Coles, Simon, Frontera, Antonio, Gomila, Rosa M. and Caltagirone, Claudia
(2025)
A unique case of ′in situ’ Bifluoride triggered formation of supramolecular organogels using isophthalamide hydrogen bond donating receptors.
Chemistry - A European Journal, [e202404651].
(doi:10.1002/chem.202404651).
Abstract
A novel isopthalamide based receptor H2L2 featuring two p-benzoic acid units has been synthesised and its anion binding properties analysed by 1H-NMR spectroscopy in DMSO-d6/0.5 % H2O. As expected, in the presence of tetrabutylammonium (TBA) fluoride the deprotonation of the carboxylic acid moieties was observed. However, the deprotonated receptor L22− was able to bind the in situ formed HF2− via the formation of H-bonds with the amide NHs. When H2L2 was dissolved in THF and 4 equivalents of TBAF were added in CH3CN a unique sol-gel transition occurred giving rise to a stable thixotropic supramolecular gel. Theoretical calculations elucidated the gelation mechanism and strongly support the findings observed experimentally.
Text
Chemistry A European J - 2025 - Picci - A Unique Case of in Situ Bifluoride Triggered Formation of Supramolecular
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e-pub ahead of print date: 23 January 2025
Published date: 3 March 2025
Keywords:
Anion recognition, Non-covalent interactions, Self-assembly, Supramolecular chemistry, Supramolecular gels
Identifiers
Local EPrints ID: 498635
URI: http://eprints.soton.ac.uk/id/eprint/498635
ISSN: 0947-6539
PURE UUID: 9b28d1c0-e23e-46e8-994b-d3664ff7ebbc
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Date deposited: 24 Feb 2025 17:52
Last modified: 22 Aug 2025 01:44
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Contributors
Author:
Giacomo Picci
Author:
Francesca D'Anna
Author:
Salvatore Marullo
Author:
Riccardo Montis
Author:
Vito Lippolis
Author:
James Orton
Author:
Antonio Frontera
Author:
Rosa M. Gomila
Author:
Claudia Caltagirone
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