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Copper ion detection probe based on o-alkynyl benzoxazole as well as preparation method and application thereof

A copper ion detection and benzoxazole technology, applied in the field of chemical analysis and detection, can solve problems such as difficult application, and achieve the effects of low detection limit, sensitive identification and strong specificity

Active Publication Date: 2020-01-21
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The copper ion probes reported above are basically fluorescent quenching, and most of them are realized in pure organic solvents, so it is not easy to be widely used in natural environments and water-phase environmental systems such as living organisms.

Method used

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  • Copper ion detection probe based on o-alkynyl benzoxazole as well as preparation method and application thereof
  • Copper ion detection probe based on o-alkynyl benzoxazole as well as preparation method and application thereof
  • Copper ion detection probe based on o-alkynyl benzoxazole as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of fluorescent probes of the present invention

[0040] The preparation route of fluorescent probe of the present invention is as follows:

[0041]

[0042] Dissolve compound 1 and o-aminothiophenol in a solvent, the ratio of the amount of compound 1 to o-aminothiophenol is 1:1, heat and stir at 60 degrees for 10 hours, after the reaction of the raw materials is completed, rotary evaporation under reduced pressure The solvent was removed, and the crude product was purified by column chromatography to obtain compound I as a pale yellow solid; that is, the copper ion detection probe represented by formula (I).

[0043] Yellow solid, yield 85%, 1 H NMR (500 MHz, CDCl 3 ) δ 8.53-8.51 (m, 1H), 8.21 (d, J = 10.0 Hz, 1H), 8.01 (d, J = 10.0 Hz, 1H), 7.75 – 7.72 (m, 1H), 7.56 – 7.54(m, 3H), 7.48 – 7.42 (m, 3H), 6.71 (d, J = 11.0 Hz, 1H), 3.44 (q, J = 9.0 Hz,4H), 1.22 (t, J = 9.0 Hz, 6H). 13 C NMR (125 MHz, CDCl 3 ) δ166.3, 152.6, 148.0, 136.2, 134....

Embodiment 2

[0045] Ratiometric Fluorescent Probe Molecular Working Curve

[0046] Take 2 mL of the prepared aqueous dispersion solution of ratiometric fluorescent probe molecules, add 20 μL of sulfuric acid with different concentrations (0, 0.4, 0.6, 0.8, 1.0, 2.0, 4.0, 6.0, 8.0, 10.0, 20.0, 50.0 μmol / L) After the copper aqueous solution was left for 60 minutes, the fluorescence spectrometer recorded the changes of the fluorescence intensity at 455nm and 566nm respectively. Taking the fluorescence intensity as the ordinate and the copper ion concentration as the abscissa, the working curve of the ratio fluorescent probe molecule is obtained by fitting. In the present embodiment, the ratiometric fluorescent probe is used for the measurement of the concentration of copper ions. Under the excitation of 375nm excitation light, the relationship diagram of the fluorescence intensity changing with the concentration of copper ions is as follows figure 1 shown.

Embodiment 3

[0048] Fluorescent Probe Molecular Cation Selectivity Determination

[0049] Take 2mL of the water-dispersed solution of the ratio fluorescent probe molecule prepared in Example 2, add 20 μL of Li with a concentration of 0.01M + 、K + 、Na + 、Sr 2+ 、Ba 2+ , Mg 2+ , Ca 2+ , Zn 2+ 、Ni 2+ 、Co 2+ , Hg 2+ , Pb 2+ , Pd 2+ , Fe 2+ , Mn 2+ 、Al 3+ 、Cr 3+ 、Cd 2+ , Fe 3+ After the aqueous solution was left for 60 minutes, the fluorescence spectrometer recorded the changes of the fluorescence intensity at 455nm and 566nm respectively. Experimental results show that, except copper ions, other ions do not cause significant changes in the fluorescence at 455nm, and have no effect on the fluorescence at 566nm. Mercury ions directly quench the fluorescence at 566nm, indicating that the probe molecules of the present invention have a large good selectivity. In this embodiment, the molecular selectivity of the fluorescent probe is measured, and the relationship diagram of the fl...

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Abstract

The invention discloses a copper ion detection probe based on o-alkynyl benzoxazole as well as a preparation method and application thereof. The structure of the fluorescent probe is shown as a formula I, and the fluorescent probe is prepared with 2-(4-ethylenediamine phenylethynyl) benzaldehyde as a raw material by forming a benzothiazole derivative with o-aminothiophenol. The fluorescent probe is stable in optical performance, high in copper ion detection sensitivity and low in detection lower limit, the detection limit is 3.08 nM, and the response range is 0.4-4.0 [mu]M. The selectivity isgood, and no response is made to silver ions, barium ions, calcium ions, lithium ions, sodium ions, potassium ions, magnesium ions, aluminum ions, nickel ions, zinc ions, mercury ions, cobalt ions, lead ions, palladium ions and strontium ions. The synthesis is simple, the conditions are mild, and the yield is high. The fluorescent molecular probe provided by the invention has practical applicationvalue in the fields of copper ion detection in biochemistry and environmental chemistry and the like.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a copper ion detection probe based on o-alkynyl benzoxazole and its preparation method and application. Background technique [0002] Copper ions are essential elements in the human body, and are also one of the chief culprits of environmental pollution. It plays an integral role in the fields of biology, chemistry and environmental science. The normal content of copper in the human body is 0.0001%, second only to iron and zinc. It usually exists in the body in the form of copper protein or copper enzyme. When the copper content is too low, it will lead to metabolic disorders in the human body and affect normal growth. Copper can also form copper-zinc superoxide dismutase with zinc, which is an important antioxidant enzyme that can remove oxygen free radicals in the human body, inhibit cardiovascular and cerebrovascular diseases, autoimmune diseases, emph...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D277/66G01N21/64
CPCC09K11/06C07D277/66G01N21/643G01N2021/6432C09K2211/1037
Inventor 赵云辉罗月阳刘立华周智华
Owner HUNAN UNIV OF SCI & TECH
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