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Fluorescent probe for detecting cyanide ion and synthesis and application method thereof

A fluorescent probe, cyanide ion technology, applied in the field of chemical analysis and detection, can solve the problems of insufficient sensitivity, high cost, insufficient probe selectivity, etc., and achieves a simple synthesis method, fast response speed, and good application prospects. Effect

Active Publication Date: 2017-08-22
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most probe synthesis methods are complex, costly, and take a long time to detect in real time. Some detection systems are organic solvents, which make it difficult to detect cyanide ions in actual water samples. The sensitivity is not high enough, and it is rarely achieved. In addition, the selectivity of some reported probes is not good enough, and acetate and fluoride ions are likely to cause interference. Therefore, it is of great significance to develop fluorescent probes with high sensitivity and good selectivity that can detect cyanide ions in aqueous phase

Method used

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  • Fluorescent probe for detecting cyanide ion and synthesis and application method thereof
  • Fluorescent probe for detecting cyanide ion and synthesis and application method thereof
  • Fluorescent probe for detecting cyanide ion and synthesis and application method thereof

Examples

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Effect test

Embodiment 1

[0038] [Example 1] Synthesis of fluorescent probe HB molecules that detect cyanide ions

[0039] The present invention detects the synthesis of the fluorescent probe molecule of cyanide ion, is to take 2,4-dimethylpyrrole and 4-hydroxymethyl benzaldehyde as raw material, through condensation, oxidation, then with 1,2,3,3- Tetramethyl-3H-indole iodide salt is obtained by Ke Naowen Geier condensation reaction.

[0040] (1) Synthesis of 1,3,5,6-tetramethyl 8-(4(hydroxymethylphenyl)) boron fluoride dipyrrole (2):

[0041] Take a dry 500ml two-necked bottle, replace the bottle with nitrogen, add 2,4-dimethylpyrrole (2.2mL, 20.0mmol), benzaldehyde (1.4g, 10.0mmol), trifluoroacetic acid (0.11mL, 1mmol) and CH 2 Cl 2 (150mL), stirred at room temperature for 12h, then added 2,3-dichloro-5,6-dicyano-p-benzoquinone (2.3g, 10.0mmol), stirred at room temperature for 1h, added Et 3 N (30mL), cooled to 0°C in an ice bath, added BF 3 .Et 2 O (30mL), stirred at room temperature for 3h, a...

Embodiment 2

[0046] [Example 2] The recognition performance of the fluorescent probe HB for detecting cyanide ions to anions

[0047] 1. Study on the selectivity of fluorescent probes for cyanide ions

[0048] Dissolve HB in absolute ethanol to prepare 10 -3 mol L －1 stock solution; prepare F separately ─ , Cl ─ 、Br ─ , I ─ , NO 3 ─ , ClO 4 ─ 、HSO 4 ─ 、H 2 PO 4 ─ 、AcO ─ 、CN ─ Aqueous solution of 10 -2 mol L －1 . Add 25 μL of HB stock solution and 2475 μL of water and ethanol (V / V=1:1) mixed solution to the cuvette, detect the ultraviolet absorption spectrum and fluorescence emission spectrum, add 20 μL of ion stock solution respectively, the concentration of HB at this time 10×10 -6 mol L －1 , the concentration of the anion is 8 times that of the acceptor, and the detection ultraviolet absorption spectrum and fluorescence emission spectrum (λ ex =383nm), observe the response of fluorescent probe HB to various anions.

[0049] The results show that HB has absorption p...

Embodiment 3

[0064] [Example 3] HB is used for the detection of actual water samples

[0065] Take 50mL of tap water, lake water and mineral water respectively in beakers, put them into sample tubes and centrifuge them with a centrifuge, and collect the supernatant after centrifugation. Add 25 μL of HB stock solution and 2475 μL (tap water / ethanol=1 / 1) mixed solution into the cuvette. Shake and check the fluorescence emission spectrum. Add 5 μmol·L to the cuvette －1 CN － , shake, detect the fluorescence emission spectrum, repeat this operation three times. Repeat the above operation for each water sample.

[0066] The results showed that the concentrations of cyanide ions in all three water samples were lower than 1.9 μmol L －1 , add 5 μmol·L －1 CN － After that, CN was measured in tap water, lake water and mineral water － The concentration is 5.27±0.19μmol L －1 , 5.23±0.11 μmol L －1 , 5.13±0.18 μmol L －1 . The recoveries of standard addition were 105.46±3.67%, 104.05±2.03%, 102...

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Abstract

The invention discloses a fluorescent probe for detecting a cyanide ion and a synthesis and application method thereof. A cyanide ion fluorescent probe takes boron fluoride dipyrrole (BODIPY) as a fluorescent signal group and hemicyanine as a recognition site, and the probe is obtained by carrying out Knoevenagel condensation reaction on 1,3,5,6-tetramethyl 8-(4(formylphenyl)) boron fluoride dipyrrole and 1,2,3,3-tetramethyl-3H-indolium iodide. Ultraviolet absorption and fluorescence emission spectroscopy research finds that the probe can solely identify the cyanide ion, the lowest detection limit can reach 59 nM, the identification process is not interfered by other negative ions, and response speed is high. The fluorescent probe disclosed by the invention can be used for detection of the actual water sample, and relative standard deviation is less than 5%. Besides, the fluorescent probe is simple in synthesis method and relatively low in cost and has a good application prospect in cyanide ion detection.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a fluorescent probe for detecting cyanide ions, its preparation and application in detecting cyanide ions. Background technique [0002] As we all know, cyanide is extremely toxic and can be absorbed into the human body through the respiratory tract or skin, and a very small amount can cause death. The World Health Organization stipulates that CN in drinking water － The maximum content of 1.9μmol L －1 . The poisoning mechanism is that after the cyanide ion is absorbed into the blood circulation by the human body, it complexes with the ferric ion of cytochrome oxidase, causing the ferric ion to lose the ability to transfer electrons, interrupt the respiratory chain, and finally lead to the body's hypoxia and death. die. The fields of application of cyanide are very wide, for example, the metallurgical industry, gold mining and electroplating ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1055G01N21/643
Inventor 喻艳华舒婷婷喻冰洁董长治付成邓云
Owner JIANGHAN UNIVERSITY
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