含螢光Isoxazoline與Isoxazole取代的芳杯之合成研究

Abstract

芳杯因具有特殊的立體結構，若作以適當的官能基修飾，可促使芳杯對於客體分子具有高度的選擇性或產生特殊的物理性質。 利用下緣單及雙取代丙烯基的芳杯作為起始物和具有不同螢光基團取代的hydroximoyl chloride衍生物進行1,3偶極環化加成反應，將可以得到於下緣具有不對稱中心及螢光基團的isoxazoline芳杯化合物。此類化合物不僅可以作為是一般金屬螢光感測器，同時也預期能夠針對掌性化合物分子具有選擇性。此外，若將其五員雜環藉由不同方式進行開環產生不同的多官能基，亦有輔助芳杯對於客體分子選擇性的效果。 本論文中我們亦利用下緣單及雙取代丙炔基取代的芳杯作為起始物和具有不同螢光基團取代的hydroximoyl chloride衍生物進行1,3偶極環化加成反應，可以得到在下緣具有螢光基團的isoxazole官能基的芳杯化合物，期望未來對於客體分子有更好的辨識系統。

Flexibility endows the calixarenes with a dimension that at times can be frustrating but that also makes possible the fashioning of cavities of highly varied shapes and contours, and forming complexes with specific guests. Modifying the mono- and di-substituted allyl groups on the lower rim of calix[4]arenes by 1,3-dipolar cycloaddition reaction may lead to chiral and fluorescent isoxazoline calix[4]arenes, which are not only useful for sensor of metal ion but also good for chiral recognition. Besides, ring-opening reactions of the isoxazoline calix[4]arenes can produce several multi-functional compounds which are also useful in molecular recognition studies. When the lower rim of calix[4]arenes are modified with mono- and di-substituted propagyl groups, they can undergo 1,3-dipolar cycloaddition reaction and give fluorescent isoxazole substituted calix[4]arenes, which may be also useful for metal ion sensing.