A kind of coumarin nickel ion fluorescent probe and its preparation method, crystal preparation method and application

A fluorescent probe, coumarin-based technology, applied in fluorescence/phosphorescence, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of poor anti-interference ability, low sensitivity, long response time, etc.

Inactive Publication Date: 2020-07-07
ZHEJIANG INT STUDIES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on nickel ion fluorescent probes based on coumarin derivatives, and they generally have disadvantages such as low sensitivity, poor anti-interference ability, and long response time.

Method used

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  • A kind of coumarin nickel ion fluorescent probe and its preparation method, crystal preparation method and application
  • A kind of coumarin nickel ion fluorescent probe and its preparation method, crystal preparation method and application
  • A kind of coumarin nickel ion fluorescent probe and its preparation method, crystal preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: This embodiment provides the preparation method of preparing required hydrazide intermediate, and its reaction equation is as follows:

[0032]

[0033] Specific steps are as follows:

[0034] Add methyl phenylpyrazolylcarboxylate (2.02g, 0.01mol), 20mL methanol, and 5mL 80% hydrazine hydrate into a 50mL round-bottomed flask, reflux the mixed solution in an oil bath at 80-90°C for 2h, and cool to room temperature , the solvent was removed from the resulting mixture under reduced pressure, and the filter residue was washed with water to obtain a white solid, which was the hydrazide intermediate, with a yield of 93%.

Embodiment 2

[0035] Embodiment 2: This embodiment provides the synthesis method of phenylpyrazole acylhydrazone diethylaminocoumarin fluorescent probe, and its reaction equation is as follows:

[0036]

[0037] In a 50mL round-bottomed flask, add the hydrazide intermediate (1.01g, 0.005mol) prepared in Example 1, 3-acetyl-7-(diethylamino)coumarin (1.30g, 0.005mol), 2 Drop formic acid, then add 10 mL of absolute ethanol, reflux the mixed solution in an oil bath at 80-90°C for 3 hours, cool to room temperature, filter the filter residue under reduced pressure, and wash the obtained solid with absolute ethanol and ether in sequence to obtain a yellow powder. Phenylpyrazolehydrazone-based diethylaminocoumarin fluorescent probe with a yield of 86%.

[0038] M.p.190-192℃; IR (KBr, pellet, cm-1): ν3419(br), 1710(s), 1665(s), 1622(s); 1H NMR(500MHz, CDCl3, ppm): 8.10(s , 1H, Aryl-H), 7.88-7.81 (m, 4H, Aryl-H), 7.55-7.39 (m, 3H, Aryl-H), 6.97 (d, J=7.4Hz, 1H, Aryl-H), 6.55 (s, 1H, CH-pyrazole)...

Embodiment 3

[0039] Embodiment 3: This embodiment provides the synthesis method of phenylpyrazole acylhydrazone diethylaminocoumarin fluorescent probe:

[0040] In a 50mL round-bottomed flask, add the hydrazide intermediate (1.01g, 0.005mol) prepared in Example 1, 3-acetyl-7-(diethylamino)coumarin (1.30g, 0.005mol), 2 Drop formic acid, then add 10 mL of absolute ethanol, reflux the mixed solution in an oil bath at 80-90°C for 5 hours, cool to room temperature, filter the filter residue under reduced pressure, and wash the obtained solid with absolute ethanol and ether in sequence to obtain a yellow powder. Phenylpyrazolehydrazone-based diethylaminocoumarin fluorescent probe with a yield of 86%.

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Abstract

The invention provides a coumarins nickel ion fluorescent probe and a preparation method thereof, a preparation method of a crystal and application. The structure of a coumarins compound is as follows: a formula is shown in the description. Compared with the prior art, the fluorescent probe prepared by the method has the advantages and active effects of simple synthesis steps, high yield and highly-specific selectivity on nickel ions; the fluorescent probe is not influenced by other metal ions and can be used for effectively identifying the nickel ions under a physiological environment with the pH (Potential of Hydrogen) of 7.4; the fluorescent probe has the characteristics of rapidness, convenience, good selectivity and the like and has a potential application prospect.

Description

technical field [0001] The invention relates to a coumarin-based nickel ion fluorescent probe, a preparation method thereof, a crystal preparation method and application, and belongs to the field of preparation methods and applications of fluorescent probes. Background technique [0002] Nickel is a transition metal that exists in nature and in organisms. It has a wide range of uses in chemical industry, environment, medicine and other fields. However, its pollution to the environment cannot be ignored, and it is also toxic to organisms. The human body contains too much Too much nickel ions often lead to organ failure and even carcinogenicity. Too little nickel ions in the human body will affect the normal operation of various enzymes in the body, resulting in a series of diseases. Therefore, it is extremely urgent to develop a detection technology with high selectivity and high sensitivity for nickel ions. [0003] Fluorescent probe technology has the characteristics of hi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/06G01N21/64
CPCC07B2200/13C07D405/12C09K11/06C09K2211/1007C09K2211/1044C09K2211/1088G01N21/643G01N2021/6432
Inventor 齐德强游金宗张一平冯启倪婉敏
Owner ZHEJIANG INT STUDIES UNIV
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