標題: | Synthesis of upper-rim allyl- and p-methoxyphenylazocalix[4]arenes and their efficiencies in chromogenic sensing of Hg2+ ion |
作者: | Ho, I-Ting Lee, Gene-Hsiang Chung, Wen-Sheng 應用化學系 Department of Applied Chemistry |
公開日期: | 30-三月-2007 |
摘要: | A series of upper-rim p-allyl and p-methoxyphenylazocalix[4]arenes (6, 8, 9a, b, and 10a,b) were synthesized and shown to exhibit substantial color changes upon complexation with Hg2+ ion. Both the upper-rim p-allyl- and p-methoxyphenylazo groups on calix[4]arenes are proven to be key components in the recognition of Hg2+ ion. Job's plots revealed 1:1 binding stoichiometry for all these p-allyl- and p-arylazo-coupled calix[4]arenes with Hg2+ ions and Benesi-Hilderbrand plots were used for determination of their association constants. Our results also demonstrated that two p-methoxyphenylazo groups prefer to bind Hg2+ in a distal orientation rather than a proximal one, and if there are three p-methoxyphenylazo groups, the third flanking p-methoxyphenylazo group plays a role in disturbing the binding of the two distal diazo groups. Furthermore, it should be noted that triazocalix[4]arenes (6, 9a, and 9a) responded to all 14 metal ions without showing much preference among the eight transition-metal ions screened in this work (Cr3+, Ni2+, Cu2+, Ag+, Cd2+, Hg+, Hg2+, and Pb2+). |
URI: | http://dx.doi.org/10.1021/jo062280s http://hdl.handle.net/11536/11000 |
ISSN: | 0022-3263 |
DOI: | 10.1021/jo062280s |
期刊: | JOURNAL OF ORGANIC CHEMISTRY |
Volume: | 72 |
Issue: | 7 |
起始頁: | 2434 |
結束頁: | 2442 |
顯示於類別: | 期刊論文 |