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

The water soluble tritriptycene 1 was synthesized starting with tripty cene trisquinone and anthracene. The hydrophobic binding of substrates to the benzene-walled cavities in 1 was studied by noting the up-fiel d shift of substrate protons in the NMR of the substrate in the presen ce of aqueous 1. Small substrates, negatively charged substrates or su bstrates larger than the cavities do not bind as strongly as substrate s about the same size as the cavities OT those bearing a positive char ge. Based on differences in DELTAHz's, the bound substrates position t hemselves in the cavities so that polar groups are at the water interf ace.