Development of Calixarene Derivatives Having Molecular Recognition Ability and Catalytic Ability

点击翻译按钮获取中文摘要

The synthesis and properties of calixarene derivatives have been studied with the intention of developing materials having a high molecular recognition ability and a high catalytic ability. The results obtained are summarized below.1. Calix[4]quinone and calix[4]hydroquinone were synthesized starting with p-H-calix[4]arene, and their conformational properties were elucidated.2. p-Phenylazocalix[4]and[6]arenes exhibited the high ability of capturing heavy metal ions such as Ag^+, Hg^+, and Hg^<2+>. They also exhibited a chromotropic property.3. The p-t-butylcalix[6]arene derivative bearing 3,6,9-trioxadecyl group at six phenolic oxygens showed the high ability of capturing K^+ion. By utilizing this ability, new esterification reaction and dichlorocarbene generation reaction were developed.4. The above calixarene derivative served as catalysts for the KMnO_4oxidation of alkenes, alkynes, and primary alcohols to yield carboxylic acids and also for the oxidation of secondary alcohols to ketones.5. The above calixarene derivatives also exhibited the ability of including diene-iodine complexes.Moreover, the calixarene derivative enhanced the reactivity and selectivity in the Ti-complex catalyzed hydroboration of isolated dienes with NaBH_4.6. The method for technical production of p-t-butylcalix[6]arene was established.