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High-selectivity fluorescence probe for detecting cyanide ions in ratio mode and synthesis method and application thereof

A technology of cyanide ions and fluorescent molecular probes, which is applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, and luminescent materials, can solve the problems of influence and poor selectivity, and achieve stable optical properties, high sensitivity, and synthetic products. high rate effect

Active Publication Date: 2017-03-22
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the response principle of the currently developed probe molecules for the detection of cyanide ions is mostly single-wavelength fluorescence intensity-dependent, and the selectivity is not good enough. The test results of such probes are easily affected by the sample matrix and probe concentration.
However, ratiometric fluorescent probes (quantified by the ratio of the fluorescence emission intensities at two wavelengths) can overcome the above problems, and there are no related reports at present.

Method used

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  • High-selectivity fluorescence probe for detecting cyanide ions in ratio mode and synthesis method and application thereof
  • High-selectivity fluorescence probe for detecting cyanide ions in ratio mode and synthesis method and application thereof
  • High-selectivity fluorescence probe for detecting cyanide ions in ratio mode and synthesis method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0046] Example 1: Synthesis of Fluorescent Molecular Probes

[0047] Dissolve N-butyl-4-methylamino-1,8-naphthalimide (0.28g, 1.0mmol) and trifluoroacetic anhydride (0.28mL, 2.0mmol) in dichloromethane (10mL), add triethyl The amine (1 mL) was reacted at room temperature for 1 h. After the reaction was over, the solvent was distilled off under reduced pressure and separated by column chromatography (dichloromethane as the eluent) to obtain the product 0.32 as a white solid (yield: 85%). The product structural formula is as follows:

[0048]

[0049] 1 H NMR (400Hz, CDCl 3 ): δ8.70(dt, J=5.7, 2.8Hz, 1H), 8.66(t, J=5.7Hz, 1H), 8.14(dd, J=8.4, 0.8Hz, 1H), 7.91(dd, J= 8.4,7.3Hz,1H),7.70(d,J=7.7Hz,1H),4.20(dd,J=16.7,9.0Hz,2H),3.52(s,3H),1.79–1.66(m,2H), 1.54–1.41(m,2H),1.00(t,J=7.4Hz,3H).HRMS[ESI]:m / z,calcd for[M-H] - 363.0957; found 363.0973.

Embodiment 2

[0050] Embodiment 2: Fluorescent detection of probes to cyanide ions

[0051] The molecular probe prepared above was dissolved in a mixed solution of water and dimethyl sulfoxide (H 2 O / DMSO=9 / 1), prepared to 5μmol L -1 probe solution. Add 2 mL of prepared 5 μmol L to a 3 mL cuvette -1 Probe solution, and then add different concentrations of cyanide ions, mix and incubate for 10min, test its fluorescence spectrum, the results are as follows image 3 shown. The ratio of the fluorescence emission intensity of the solution at 535nm and 425nm is plotted against the concentration of cyanide ions, and the concentration of cyanide ions is 1.0–80 μmol L -1 In the range, there is a good linear relationship between the two ( Figure 4 ), according to the standard diagram, the quantitative detection of cyanide ion in the sample to be tested within this concentration range is realized, and the solution changes from colorless to yellow, which is also suitable for naked eye detection. ...

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Abstract

The invention discloses a high-selectivity fluorescence probe for detecting cyanide ions in a ratio mode and a synthesis method and application thereof, and belongs to the technical field of chemical analysis and detection. A 4-amino-1,8-naphthalimide skeleton and haloacetic acid or a derivative thereof are subjected to condensation reaction to obtain the probe, and the probe has the following structure (the structure is defined in the description). The fluorophore of the probe is of a naphthalimide skeleton structure, and the response group for the cyanide ions is a haloacetic acid unit. The probe molecule has high selectivity and sensitivity to the cyanide ions, the detection range is 1.0-80.0 micromol / L, and the detection limit is 0.23 micromol / L. The probe can be used for qualitatively and quantitatively detecting the cyanide ions in the water body and a practical sample.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a molecular probe for detecting cyanide ions by a ratio fluorescence method, a preparation method thereof and an application in detecting cyanide ions. Background technique [0002] Cyanide ion (CN - ) is a well-known toxic substance. Cyanide can be ingested by the human body through diet, inhalation or skin contact. The absorbed cyanide can have a strong binding effect with the heme in cytochrome c, thereby inhibiting extracellular respiration, resulting in a series of diseases and even death. The World Health Organization stipulates that the safe limit of cyanide ion in drinking water is 1.9 μmol L -1 . But on the other hand, cyanide is a very useful reagent, and has a wide range of industrial applications in the fields of printing and dyeing and metallurgy. This also leads to the inevitable discharge of cyanide ions into the environment...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64G01N21/78
CPCC07D221/14C09K11/06C09K2211/1029G01N21/643G01N21/6486G01N21/78
Inventor 郝远强常竹张银堂朱旭刘保霞崔亚丽瞿鹏徐茂田
Owner SHANGQIU NORMAL UNIVERSITY
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