1) 固有掌性芳杯螢光感測器之合成與光學純化及其掌性分子辨識 (2) 下緣鄰位蒽三唑及酯基取代芳杯螢光感測器之合成及其金屬離子辨識

Abstract

In this thesis, my research is focused on two topics. the first part is the synthesis and optical recognition of fluorescent inherently chiral calix[4]arenes and their chiral recognition. The second part is the synthesis of cailx[4]arenes with lower-rim triazole and ester groups as cationic binding site and anthracene as the fluorophores. In part one, we synthesized novel calix[4]arene of AABH-type with inherent chirality through the reaction of racemic calix[4]arene derivatives 40a and 40b with 1-phenylethylamine (both R-form and S-form), follow by the separation of the diastereomers by column chromatography. Compounds 41-44 are optically pure inherently chiral calix[4]arenes. Based on the X-ray structure of 41, we could determine the absolute configurations of all three chiral cailx[4]arenes. We farther modified the lower-rim propargyl groups by Click Chemistry to add an anthracene groups as the fluorophores. The optically pure inherently chiral calyx[4]arenes were used for chiral recognition studies. In second part, we synthesized a series of calix[4]arenes with lower-rim triazole and ester groups as the cationic binding sites, and anthracene as the fluorophores. When a cosolvent of methanol and chloroform (v/v = 99:1), both compound 49 and 51 have good selectivity toward Ag+ and Hg2+. Compared with 57, we confirmed that when thenumber of triazole and ester groups increased, their binding ability toward metal ions increased. The binding construct about 103~1010 (M-1).