Two- and Three-Phase Self-assembly of Molecular Capsules

Two- and three-phase molecular encapsulations of Me4N+ or C7H7+ in the hydrogen-bonded dimers of resorcin[4]arene tetraphosphates enable ion pair separations, dissolution of solid capsule components, and stabilization of capsule-separated ion pairs in solution. Self-assembly of the capsular ion pairs, the exchange of the encapsulated cations and external anions as well as the formation of heterodimeric capsular complexes are slow on hours time scale in heterogeneous systems and instantaneous in solutions. Spectroscopic studies and molecular modeling related the properties of the capsule-separated ion pairs to the energies of induced conformational changes, hydrogen bonding, host-guest interactions, ion pair separation, and the relative polarity of the solvent.