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J Org Chem. 2008 Sep 19;73(18):7067-71. doi: 10.1021/jo800712q. Epub 2008 Aug 20.

Calix[6]tris(thio)ureas: heteroditopic receptors for the cooperative binding of organic ion pairs.

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  • 1URCOM, Université du Havre, FST, 25 rue Philippe Lebon, BP 540, 76058 Le Havre cedex, France.


The straightforward syntheses of C3v symmetrical calix[6]trisureas and -thiourea have been achieved. NMR studies have shown that these flexible compounds possess a major cone conformation. While these neutral hosts can strongly bind anions such as AcO(-) or HSO4(-) through induced fit processes, they can also behave as unique heteroditopic receptors for organic ion pairs with a remarkable positive cooperativity in the complexation process, the anion acting as an allosteric effector.

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