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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (12): 2121-2125. 上一篇    下一篇

研究论文

含蒽醌基硫桥杯芳烃的点击合成及其对铝离子的荧光传感

赵邦屯*,1，曹世娜2，郭海明2，渠桂荣2   

  1. (1洛阳师范学院化学系 洛阳 471022)
    (2河南师范大学化学与环境科学学院 新乡 453007)
  • 收稿日期:2011-07-04 修回日期:2011-09-16 发布日期:2011-09-23
  • 通讯作者: 曹世娜 E-mail:csn407452454@yahoo.com.cn

Synthesis of Anthraquinone-Based Thiacalixarene via Click Chemis-try and Its Fluorescence Sensing Towards Al3＋

Zhao Bangtun*,1 Cao Shina2 Guo Haim-ing2 Qu Guirong2   

  1. (1 Department of Chemistry, Luoyang Normal University, Luoyang 471022)
    (2 College of Chemistry and Environmental Science, Henan Normal Univer-sity, Xinxiang 453007)
  • Received:2011-07-04 Revised:2011-09-16 Published:2011-09-23

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在二甲基甲酰胺(DMF)溶剂中, 下缘含端基溴的四取代硫桥[4]芳烃1和NaN3反应得到含叠氮端基硫桥[4]芳烃衍生物2, 利用点击反应, 以CuSO4/VcNa为催化剂, 叠氮基硫桥[4]芳烃衍生物2和端基炔蒽醌衍生物3反应合成了以三唑基为连接的蒽醌基硫桥杯芳烃衍生物4, 其通过了1H NMR, FT-IR, MS (MALDI-TOF)和元素分析等表征. 荧光光谱实验研究了化合物4对金属离子的荧光传感行为, 结果表明化合物4对Al3＋表现出了很好的荧光响应和良好的选择性. Job实验表明4对Al3＋的配比为1∶2|荧光滴定实验表明: 在室温条件下, 在CHCl3-CH3CN (V∶V＝3∶1)溶剂中, 4对Al3＋作用的键合常数Ks为2670 dm3•mol－1. 因此, 化合物4有望作为Al3＋的新型荧光传感器.

关键词: 硫桥杯[4]芳烃, 蒽醌, Al3＋离子, 荧光传感器

Tetrabromobutoxy thiacalix[4]arene (1) was reacted with sodium azide (NaN3) in dimentylformamide (DMF) to obtain tetraazidobutoxy thiacalix[4]arene (2). The sequent reaction of 2 with 1,8-bis(prop-2- ynyloxy)anthraquinone (3) catalyzed by CuSO4/VcNa to gave a novel anthraquinone-based thiacalixarene compound 4, which was characterized by 1H NMR, FT-IR, MS (MALDI-TOF) and elemental analysis. The fluorescence experiments have shown that compound 4 has a good selectivity with Al3＋ and the complexation of 4 with Al3＋ in a 1∶2 complex mode gives an enhanced fluorescence change at 559 nm. In CHCl3-CH3CN (V∶V＝3∶1) solvent, the binding constant for the complex 4 and Al3＋ is 2670 dm3•mol－1 at room temperature. Hence, compound 4 can be used as a new fluorescent sensor for the Al3＋ ion.

Key words: thiacalix[4]arene, anthraquinone, Al3＋ ion, fluorescent sensor