Vasarene and vasarene-analogues: synthesis and characterization of self-assembled, voluminous ligands with specific affinity to M+F− ion-pairs. Issue 19 (12th May 2016)

• Record Type: Journal Article
• Authors: Bengiat, Ravell; Gil, Maayan; Klein, Asne; Cohen, Orit; Bogoslavsky, Benny; Cohen, Shmuel; Dubnikova, Faina; Almog, Joseph
• Is Part Of: Tetrahedron. Volume 72:Issue 19(2016)
• Page Start: 2429
• Page End: 2439
• Publication Date: 2016-05-12
• Subjects: Vasarene -- Alkali metal fluorides -- Self-assembled -- Ninhydrin -- Supramolecular chemistry -- Ion-pair recognition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.03.065
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Vasarene is a vase-shaped compound readily obtained by the reaction between ninhydrin and phloroglucinol (1, 3, 5-benzenetriol). Vasarene has shown a special affinity towards alkali fluoride ion-pairs, forming with them cage-like supramolecular structures composed of several vasarene units encapsulating the alkali fluoride salt. Here we report the preparation and characterization of a series of geometrically modified vasarenes containing only two 'side-walls' instead of three, and their derivatives. Synthesis under microwave conditions could be accomplished within minutes compared to hours for 'regular' solvent heating. Like vasarene, the new analogues have also demonstrated a selective affinity to alkali- and tetraalkyl ammonium-fluorides including inter alia their solubilization in organic solvents and precipitation from aqueous solutions. Graphical abstract: