Design and Synthesis of Chalcone-Based Derivative for Sensing Cu(Ⅱ) Ion

doi:10.11944/j.issn.1000-0518.2020.11.200120

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (11): 1268-1275.DOI: 10.11944/j.issn.1000-0518.2020.11.200120

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Design and Synthesis of Chalcone-Based Derivative for Sensing Cu(Ⅱ) Ion

LI Di, SUN Jianqiang, XU Bingsong, CHEN Hao, ZHOU Le, HU Lei^*, WANG Hui^*

College of Pharmacy,Wannan Medical College,Wuhu,Anhui 241002,China

Received:2020-04-25 Revised:2020-06-16 Accepted:2020-07-06 Published:2020-11-01 Online:2020-11-04
Contact: WANG Hui, lecturer; Tel:0553-3932472; E-mail:wanghias@126.com; Research interests:fluorescent probe
Co-corresponding author:HU Lei, assistant experimenter; Tel:0553-3932472; E-mail:hulei@wnmc.edu.cn; Research interests:fluorescent probe
Supported by:
Supported by Anhui Provincial Natural Science Foundation(No.1908085QB50), and the Training Program of Innovation and Entrepreneurship Education for College Students in Anhui Province(No.S201910368079)

Abstract

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

CLC Number:

O625.6

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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Design and Synthesis of Chalcone-Based Derivative for Sensing Cu(Ⅱ) Ion

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