DESIGN, SYNTHESIS, AND PROPERTIES OF CYCLOPHANES AS HOSTS HAVING ABILITY OF FORMING INCLUSION COMPLEXES

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Our earlier studies on cyclophanes such as QCP44 have suggested that they form inclusion complexes with anionic and neutral hydrophobic guests in aqueous solution. We intended to introduce the cyclophanes to stationary phase of column chromatography, and to design novel macrocyclic compounds as hosts for cationic guests.The skeleton of QCP44 was introduced to agarose gel with amide bond, and some structural isomers, such as 1- or 2-naphthalane sulfonic acids, could be effectively separated by the column containing this gel.Novel cyclophanes having carboxylates, ACP44 and ACP66, were synthesized, and were found to form stable 1:1 complexes with cationic guests. Stability constants (Ks) of their complexes were obtained using ^1H-NMR technique (Table 1). ACP44 exhibited the greatest value of K s for the complex with 1,4-bis(trimethylammoniummethyl)benzene. In contrast, ACP66 formed the most stable complex with 1,3-bis(trimethylammonium)propane.Investigation on novel macrocycles for selective and efficient artificial catalysts as an enzyme model is now in progress.