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Aggregation-induced emission-based copper ion detection probe and preparation method and application thereof

A technology of aggregation-induced luminescence and copper ion detection, applied in the field of chemical analysis and detection, to achieve the effect of sensitive identification, strong specificity and low detection limit

Inactive Publication Date: 2017-07-18
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Divalent copper ions have extremely strong quenching properties on fluorescent molecules, so most of the reported copper ion fluorescent probes are fluorescence quenching fluorescent probes, and they are all realized in pure organic solvents. It is not easy to be widely used in the natural environment and water environment systems such as living organisms

Method used

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  • Aggregation-induced emission-based copper ion detection probe and preparation method and application thereof
  • Aggregation-induced emission-based copper ion detection probe and preparation method and application thereof
  • Aggregation-induced emission-based copper ion detection probe and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Synthesis of fluorescent probes of the present invention

[0046] The preparation route of fluorescent probe of the present invention is as follows:

[0047]

[0048] (1) Preparation of intermediate compound 2

[0049]

[0050] Dissolve compound 1 and hexamethylenetetramine (HMTA) in trifluoroacetic acid, the ratio of the amount of compound 1 to HMTA is 1:1, heat and stir for 5 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 2 as a yellow solid;

[0051] (2) Preparation of fluorescent probe I

[0052]

[0053] Get compound 2, the hydrazine hydrate that mass fraction is 80% is dissolved in dehydrated alcohol, and the ratio of the amount of described compound 2 and hydrazine hydrate substance is 2:1,60 o Stirred under the condition of C for 2 hours, the solid was completely precipitated, filtered, and th...

Embodiment 2

[0056] Ratiometric Fluorescent Probe Molecular Working Curve

[0057] Take 2 mL of the prepared water-dispersed solution of ratiometric fluorescent probe molecules, add 20 μL of copper sulfate aqueous solution with different concentrations (0, 0.5, 1, 2.5, 5, 10, 20, 50, 100 μmol / L), and let it stand for 60 minutes , Fluorescence spectrometer recorded the change of fluorescence intensity at 581nm 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 to measure the concentration of copper ions. Under the excitation of 380nm excitation light, the relationship between the fluorescence intensity and the concentration of copper ions is as follows: figure 1 shown.

Embodiment 3

[0059] Fluorescent Probe Molecular Cation Selectivity Determination

[0060] Take 2mL of the water-dispersed solution of the ratio fluorescent probe molecule prepared in Example 2, and add 20 μL of Ag with a concentration of 0.01M + , Ba 2+ , Ca 2+ , Li + , Mg 2+ , NH 4 + , Ni 2+ , Zn 2+ , Pb 2+ , Co 3+ , Hg 2+ After the aqueous solution was left for 60 minutes, the fluorescence spectrometer recorded the changes of the fluorescence intensity at 581nm respectively. Experimental results show that, except for copper ions, other particles do not cause obvious changes in fluorescence, indicating that the probe molecules of the present invention have good selectivity. In the present embodiment, the molecular selectivity of the fluorescent probe is measured, and the relationship diagram of the fluorescence intensity changing with the concentration of copper ions under the excitation of 380nm excitation light is as follows figure 2 shown.

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Abstract

The invention discloses an aggregation-induced emission-based copper ion detection probe and a preparation method and application thereof. The structure of the fluorescent probe is as shown in a formula I, and the fluorescent probe is prepared through formylating hydroxytetrstyrene as a raw material and forming triphenylethylene-based salicylaldehyde azine together with hydrazine hydrate. The probe is stable in optical property, high in copper ion detection sensitivity and low in lower detection limit, the detection limit is 30.9nM and the response range is 0.5-7.5muM; the probe is good in selectivity and free of response to cations such as a silver ion, a barium ion, a calcium ion, a lithium ion, a magnesium ion, an ammonium ion, a nickel ion, a zinc ion, a mercury ion, a cobalt ion and a lead ion; and the probe is simple in synthesis, mild in condition and high in yield. The fluorescent molecular probe has practical application value in the field of copper ion detection in biochemistry and environmental chemistry.

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 aggregation-induced luminescence and its preparation method and application. Background technique [0002] Copper is an important trace element and essential nutrient in living systems. The toxicity of copper is very small, and if the copper element is deficient in the human body, it will lead to growth and metabolic disorders. Copper is known to be an essential component of respiratory pigments and is detected in a growing number of proteins and enzymes. Changes in the concentration balance of copper in cells can lead to suppressive neurological diseases such as Menkes syndrome, familial lateral sclerosis, Alzheimer , s disease, Wilson disease and prion disease, etc., so the distribution of copper in the cell should be strictly controlled. The detection of copper ions is of great significance in chemistry, environm...

Claims

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Application Information

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IPC IPC(8): C07C251/88C07C249/16C09K11/06G01N21/64
CPCC07C251/88C07C249/16C09K11/06C09K2211/1003C09K2211/1014G01N21/6428
Inventor 赵云辉周智华龙云飞
Owner HUNAN UNIV OF SCI & TECH
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