SYNTHESIS AND HYDROPHOBIC BINDING-STUDIES ON A WATER-SOLUBLE TRITRIPTYCENE

The water soluble tritriptycene 1 was synthesized starting with triptycene trisquinone and anthracene. The hydrophobic binding of substrates to the benzene-walled cavities in 1 was studied by noting the up-field shift of substrate protons in the NMR of the substrate in the presence of aqueous 1. Small substrates, negatively charged substrates or substrates larger than the cavities do not bind as strongly as substrates about the same size as the cavities OT those bearing a positive charge. Based on differences in DELTAHz's, the bound substrates position themselves in the cavities so that polar groups are at the water interface.