Fluoride binding by an anionic receptor: tuning the acidity of amide NH groups for basic anion hydrogen bonding and recognitionElectronic supplementary information (ESI) available: General methods, synthetic details for the synthesis of H2L1 and H2L2, stack plots for the 1H-NMR titrations of H2L1 with OH−, AcO−, BzO−, HPpi3−, Cl−, stack plots of the 19F-NMR titrations of H2L2 with TBAF, crystallization conditions, details of the crystal data, structure refinement and crystal packing description

• Main Authors: Montis, Riccardo, Bencini, Andrea, Coles, Simon J, Conti, Luca, Fusaro, Luca, Gale, Philip A, Giorgi, Claudia, Horton, Peter N, Lippolis, Vito, Mapp, Lucy K, Caltagirone, Claudia
• Format: Article
• Language: English
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c8cc09962f

Here we report a family of bis-amide receptors for anion binding that contain carboxylic acid groups vicinal to the amide function. Deprotonation of the carboxylic acids decreases the acidity of amide NHs, switching on the anion binding ability of the deprotonated receptors with selectivity for fluoride complexation. The proposed systems represent a unique example of anionic receptors able to bind anions via H-bonding. Here we report the first family of bis-amide receptors able to bind fluoride in their anionic form.