DEVELOPMENT OF NEW FUNCTIONALIZED HOST MOLECULES VIA HIGH PRESSURE REACTION

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High-pressure S_NAr reaction was first applied to the synthesis of a new family of macrocyclic host molecules, which incorporated various heteroaromatics as potential cation binding sites in a unique fashion. In CH_2Cl_2 liquid membrane transport experiments, several macrocycles having thiazole, oxazole, pyrazine and pyridazine rings exhibited a perfect Ag^+ ion selectivity. Cation extraction and ^<13>C NMR titration experiments revealed that attachment of unique heterocycle to the parent macro-ring, if in the proper position, significantly offered excellent Ag^+ ion specificity. Since binding and transport selectivities of these macrocycles were apparently higher than those with conventional crown ethers, the present study provided a useful method for synthesis of a new, specific host molecule.