Positive Cooperative Effect in Ion-Pair Recognition by a Tris-urea Hemicryptophane Cage.

The synthesis of a hemicryptophane cage combining a CTV unit with a C symmetrical moiety bearing three urea functions is reported. This host was found to bind anions with higher binding constants than other previously reported hemicryptophanes. Due to its heteroditopic character this cage proved to be an efficient ion-pair receptor. The best cooperativity effect was observed for the tetramethylammonium bromide (TMABr) salt, which was confirmed and rationalized by DFT calculations.