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

Magalie Delecluse (1) , Cédric Colomban (1) , Delphine Moraleda (1) , Innocenzo de Riggi (1) , Françoise Duprat , Sabine Michaud-Chevallier (1) , Jean-Pierre Dutasta (2) , Vincent Robert (3) , Bastien Chatelet (1) , Alexandre Martinez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 LC - Laboratoire de Chimie - UMR5182
3 LCQMM - Laboratoire de chimie quantique et de modélisation moléculaire

The synthesis of a hemicryptophane cage combining a CTV unit with a C 3 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 tetramethy-lammonium bromide (TMABr) salt, which was confirmed and rationalized by DFT calculations.

Domaines: Chimie

Magalie Delecluse, Cédric Colomban, Delphine Moraleda, Innocenzo de Riggi, Françoise Duprat, et al.. Positive Cooperative Effect in Ion‐Pair Recognition by a Tris‐urea Hemicryptophane Cage. Chemistry - A European Journal, 2019, 25 (13), pp.3337-3342. ⟨10.1002/chem.201805534⟩. ⟨hal-02098293⟩