A Novel Electroneutral Anion Host Based on Organoboron Betaines

Host-guest binding of anions in organic solvents may find attractive applications in ion sensing and transport, if the host can extract the negatively charged guest species from its solvation sphere. The most powerful means to dismantle the anionic guest from solvent molecules that is required for selective binding is to provide positive charges in the host compound. They have to be counterbalanced by negatively charged subsites in order to conserve electroneutrality, but must avoid collapse into ion pairing with the cationic sites. According to this concept the cage compound 3 was constructed by attachment of anionic tetraphenylborate moieties to the parent macrotricyclic amine 1. The betainic product 3 was shown to be soluble in water-immiscible dipolar organic solvents like propylene carbonate and formed inclusion complexes with chloride and bromide in the gas phase as well as in solution.