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).
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