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A bifunctional probe for recognizing iron ions and fluorine ions and its preparation and application

A dual-function, iron ion technology, applied in the field of dual-function probes to identify iron ions and fluorine ions, to achieve the effect of simple synthesis steps, stable optical properties, and high synthesis yield

Active Publication Date: 2021-07-06
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In addition, using the same fluorescent probe to detect iron ions and fluoride ions respectively is rarely reported. Patent CN104788344A discloses a dual-functional probe with anthracene as the parent, which can detect iron ions and fluoride ions
However, no probes based on Schiff base compounds with this function have been reported.

Method used

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  • A bifunctional probe for recognizing iron ions and fluorine ions and its preparation and application
  • A bifunctional probe for recognizing iron ions and fluorine ions and its preparation and application
  • A bifunctional probe for recognizing iron ions and fluorine ions and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1: Preparation of bifunctional probes

[0053] 0.204g 3-acetyl-4-hydroxycoumarin and 0.144g 8-aminoquinoline were dissolved in 60mL methanol solution, stirred and heated to reflux for 8h; after the reaction mixture was concentrated by rotary evaporation, it was separated by column chromatography (petroleum ether / acetic acid Ethyl ester=7:3, v / v), rotary evaporation, and vacuum drying to obtain pure product 4-hydroxyl-3-[1-(quinoline-8-imino)-methyl]-chromen-2-one , yield 84.9%. NMR characterization is as follows: 1 H NMR (400MHz, CDCl 3 )δ, 9.10(d, J=4.2Hz, 1H), 8.37(d, J=8.2Hz, 1H), 8.19(d, J=8.2Hz, 1H), 7.93-7.98(m, 1H), 7.71( d,J=4.2Hz,2H),7.58-7.65(m,2H),7.27-7.32(m,2H),2.77(s,3H). 13 C NMR (400MHz, CDCl 3 )δ, 150.92, 134.07, 129.11, 128.20, 126.46, 123.64, 122.39, 116.64, 77.22, 21.67.

Embodiment 2

[0054] Example 2: Investigation of the ability of the bifunctional probe of the present invention to recognize iron ions

[0055] The probe molecule (prepared in Example 1) was formulated into 2×10 -5 M in DMF solution, and then add 10equiv of various metal ions Fe 3+ ,Hg 2+ ,Al 3+ ,Mn 2+ ,Mg 2+ ,Zn 2+ , measure the UV-Vis absorption spectrum of the blank solution and the mixed solution, the results are as follows figure 1 shown. It was found experimentally that only by adding Fe 3+ , the original probe molecule's maximum absorption peak at 324nm had a significant blue shift to 296nm (Δλ=28nm), and the maximum absorption intensity also increased from 0.26 to 0.76 (2.9 times). However, other metal ions do not change significantly, indicating that the bifunctional probe molecule of the present invention can selectively recognize iron ions.

Embodiment 3

[0056] Example 3: Investigation of the ability of the bifunctional probe of the present invention to recognize fluoride ions

[0057] The probe molecules and iron ions (Fe 3+ ) at a molar ratio of 1:1 to form a probe-iron ion complex, and the probe-iron ion complex was prepared as 2×10 -5 DMF solution of M, add various anions F - , Cl - , Br - , HSO 4 - , measure the UV-Vis absorption spectrum of the solution, the results are as follows figure 2 As shown, it was found that when 10 equiv of fluoride ions were added, the absorption intensity decreased significantly, which was at the same level as the recognition intensity of the probe molecule, which indicated that the probe-iron ion complex could further selectively recognize fluoride ions.

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Abstract

The invention discloses a bifunctional probe for recognizing iron ions and fluorine ions and its preparation and application. The rate is high; it can realize the detection of iron ion and fluorine ion, and the recognition of fluorine ion is also reversible.

Description

technical field [0001] The invention relates to the technical field of ion detection, in particular to a bifunctional probe for identifying iron ions and fluorine ions and its preparation and application. Background technique [0002] Iron ions are indispensable substances in many physiological processes of human beings. It is the core part of hemoglobin, participates in the synthesis of hemoglobin, myoglobin, cytochrome, cytochrome oxidase, peroxidase and catalase in the process of oxygen transfer, and plays an important role in metabolic activities; however, After water or food is contaminated by iron ions, if the content is too high after drinking or eating and entering the human body, it will cause great damage to the heart, liver, and pancreas, and even cause life-threatening in severe cases. Therefore, whether it is the lack of iron or excessive intake will cause the disorder of the life system, the detection of iron ions is widely concerned by the medical and biochem...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64G01N21/33G01N21/78
Inventor 刘志莲张书香牟佳伟杨震冯子琦王兆萱于诗雨
Owner UNIV OF JINAN
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