基于查尔酮衍生物的铜离子探针的设计合成

doi:10.11944/j.issn.1000-0518.2020.11.200120

摘要/Abstract

摘要： 以N-丁基-吲哚-3-甲醛和2-乙酰吡啶作为原料,通过羟醛缩合反应设计合成一种查尔酮衍生物(E)-3-(1-丁基-1氢-吲哚基)-1-(2-吡啶基)丙烯基酮(L)。通过核磁共振波谱仪、质谱和傅里叶变换红外光谱技术手段表征了目标分子的结构。结果表明,探针L对Cu²⁺表现出专一的选择性和高的灵敏度,溶液颜色由淡黄色变为红色,能够直接通过肉眼识别,检测限低至27.8 nmol/L,探针L与Cu²⁺的配位比为1∶1,结合核磁滴定和理论计算研究了探针L对Cu²⁺的识别机制。

关键词: 铜离子探针, 查尔酮衍生物, 理论计算

Abstract: A novel chalcone derivative (E)-3-(1-butyl-1H-indol-3-yl)-1-(pyridin-2-yl)prop-2-en -1-one (L) was designed and synthesized from 1-butyl-1H-indole-3-carbaldehyde and 1-(pyridin-2-yl)ethan-1-one by condensation reaction. Compound L was characterized by nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS) and Fourier transform infrared (FT-IR) spectrometry. It is found that probe L exhibits a specific selectivity and high sensitivity to Cu²⁺ with a limit of detection (LOD) at 27.8 nmol/L, giving a noticeable color change from light yellow to red, which demonstrates that probe L can be used to recognize Cu²⁺ by “naked-eye”. Probe L binds to Cu²⁺by a 1∶1 stoichiometry. The mechanism for sensing Cu²⁺ was investigated using ¹H NMR titration and theoretical calculations.

Key words: Cu²⁺ probe, chalcone derivatives, theoretical calculations

中图分类号:

O625.6

李迪, 孙建强, 许丙嵩, 陈浩, 周乐, 胡磊, 王慧. 基于查尔酮衍生物的铜离子探针的设计合成[J]. 应用化学, 2020, 37(11): 1268-1275.

LI Di, SUN Jianqiang, XU Bingsong, CHEN Hao, ZHOU Le, HU Lei, WANG Hui. Design and Synthesis of Chalcone-Based Derivative for Sensing Cu(Ⅱ) Ion[J]. Chinese Journal of Applied Chemistry, 2020, 37(11): 1268-1275.

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