Axially Aligned Confinement of 1,4-Bis(triethylammoniomethyl)benzene by Two p-Sulfonatocalix[4]arenes

A multiple component bi-layer complex containing 1,4- bis(triethylammoniomethyl)benzene and mono-phosphonium cations, and p-sulfonatocalix[4]arene involves preferential binding of the ammonium cation in the cavities of two geometrically opposed calixarenes with the mono-phosphonium cation embedded within a bilayer of calixarenes. The complex has channels between bilayers ∼14 Å in diameter which are lined with both polar sulfonate groups and the hydrophobic surface of the central part of the ammonium cation. ¹H NMR and 1D-ROESY experiments establish the formation of supermolecules of the bis-triethylammonium cation and two calixarenes in solution.