TY - JOUR
T1 - Vasarene and vasarene-analogues
T2 - Synthesis and characterization of self-assembled, voluminous ligands with specific affinity to M+F- ion-pairs
AU - Bengiat, Ravell
AU - Gil, Maayan
AU - Klein, Asne
AU - Cohen, Orit
AU - Bogoslavsky, Benny
AU - Cohen, Shmuel
AU - Dubnikova, Faina
AU - Almog, Joseph
N1 - Publisher Copyright:
© 2016 Elsevier Ltd.
PY - 2016/5/12
Y1 - 2016/5/12
N2 - 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.
AB - 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.
KW - Alkali metal fluorides
KW - Ion-pair recognition
KW - Ninhydrin
KW - Self-assembled
KW - Supramolecular chemistry
KW - Vasarene
UR - http://www.scopus.com/inward/record.url?scp=84962178065&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2016.03.065
DO - 10.1016/j.tet.2016.03.065
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AN - SCOPUS:84962178065
SN - 0040-4020
VL - 72
SP - 2429
EP - 2439
JO - Tetrahedron
JF - Tetrahedron
IS - 19
ER -