Vasarene and vasarene-analogues: synthesis and characterization of self-assembled, voluminous ligands with specific affinity to M+F− ion-pairs

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 encapsulati...

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Bibliographic Details
Published in:Tetrahedron 2016-05, Vol.72 (19), p.2429-2439
Main Authors: Bengiat, Ravell, Gil, Maayan, Klein, Asne, Cohen, Orit, Bogoslavsky, Benny, Cohen, Shmuel, Dubnikova, Faina, Almog, Joseph
Format: Article
Language:English
Subjects:
Alkali metal fluorides
Ion-pair recognition
Ninhydrin
Self-assembled
Supramolecular chemistry
Vasarene
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.03.065