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

Ravell Bengiat, Maayan Gil, Asne Klein, Orit Cohen, Benny Bogoslavsky, Shmuel Cohen, Faina Dubnikova, Joseph Almog*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

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.

Original languageEnglish
Pages (from-to)2429-2439
Number of pages11
JournalTetrahedron
Volume72
Issue number19
DOIs
StatePublished - 12 May 2016

Bibliographical note

Publisher Copyright:
© 2016 Elsevier Ltd.

Keywords

  • Alkali metal fluorides
  • Ion-pair recognition
  • Ninhydrin
  • Self-assembled
  • Supramolecular chemistry
  • Vasarene

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