A Unique Case of ′in Situ’ Bifluoride Triggered Formation of Supramolecular Organogels Using Isophthalamide Hydrogen Bond Donating Receptors
- Authors: Picci, G.; D'Anna, F.; Marullo, S.; Montis, R.; Lippolis, V.; Orton, J.; Coles, S.; Frontera, A.; Gomila, R.M.; Caltagirone, C.
- Publication year: 2025
- Type: Articolo in rivista
- OA Link: http://hdl.handle.net/10447/672047
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.