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双杯[4]芳烃四三氮唑大环的合成、表征及 Cu(2+)引发的选择性荧光猝灭。

Synthesis, characterization and Cu(2+) triggered selective fluorescence quenching of Bis-calix[4]arene tetra-triazole macrocycle.

机构信息

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.

出版信息

J Hazard Mater. 2016 May 15;309:97-106. doi: 10.1016/j.jhazmat.2016.01.074. Epub 2016 Feb 4.

DOI:10.1016/j.jhazmat.2016.01.074
PMID:26878705
Abstract

A novel fluorescent bis-calix[4]arene macrocycle 9 incorporating metal-binding pockets was successfully prepared. The structure of macrocycle 9 and its precursors were characterized via EI-MS, MALDI-TOF-MS, ESI-MS, (1)H NMR, (13)CNMR, 2D NMR, and X-ray crystallography. The macrocycle 9 displayed selective fluorescence quenching after interacting with Cu(2+) in the presence competing metal cations including Mg(2+), Ca(2+), Ba(2+), Ag(+), Zn(2+), Ti(4+),Cd(2+), Hg(2+), Pb(2+), In(3+), La(3+), Cr(3+), Ni(2+), Sb(3+), V(5+), Fe(3+), Co(2+), Sn(2+), Sn(2+), and Tl(+). The Cu(2+) limit of detection was found to be 40 nM much lower than its threshold level (∼ 20 μM) in drinking water permitted by the U.S Environmental Protection Agency (EPA). Furthermore, drinking water samples from Karachi University (Pakistan) spiked with Cu(2+) were analysed with the sensing system and the results showed an excellent agreement with the fluorescence quenching phenomenon of macrocycle 9 examined in deionized water. Importantly, the chemosensor 9 could be used to detect Cu(2+) in living cells.

摘要

一种新型荧光双杯[4]芳烃大环 9 成功合成,其中包含金属结合口袋。大环 9 及其前体的结构通过 EI-MS、MALDI-TOF-MS、ESI-MS、(1)H NMR、(13)C NMR、2D NMR 和 X 射线晶体学进行了表征。大环 9 在存在竞争金属阳离子(包括 Mg(2+)、Ca(2+)、Ba(2+)、Ag(+)、Zn(2+)、Ti(4+)、Cd(2+)、Hg(2+)、Pb(2+)、In(3+)、La(3+)、Cr(3+)、Ni(2+)、Sb(3+)、V(5+)、Fe(3+)、Co(2+)、Sn(2+)和 Tl(+))时,与 Cu(2+) 相互作用后显示出选择性荧光猝灭。Cu(2+) 的检测限被发现为 40 nM,远低于美国环境保护署(EPA)允许的饮用水中允许的阈值水平(约 20 μM)。此外,用传感系统分析了来自巴基斯坦卡拉奇大学的含 Cu(2+) 的饮用水样品,结果与在去离子水中检查的大环 9 的荧光猝灭现象非常吻合。重要的是,该化学传感器 9 可用于检测活细胞中的 Cu(2+)。

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