Pd (0) fluorescence probe based on 7-nitro-1,2,3-benzoxadiazole and preparation method and application thereof

A technology of nitrofenfurazan and fluorescent probes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of low detection limit, simple synthesis process and high sensitivity

Inactive Publication Date: 2017-01-04
HENAN UNIV OF ANIMAL HUSBANDRY & ECONOMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are no literature and patent reports on the preparation method of Pd(0) fluorescent probes based on 7-nitrobenzofurazan derivatives at home and abroad.

Method used

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  • Pd (0) fluorescence probe based on 7-nitro-1,2,3-benzoxadiazole and preparation method and application thereof
  • Pd (0) fluorescence probe based on 7-nitro-1,2,3-benzoxadiazole and preparation method and application thereof
  • Pd (0) fluorescence probe based on 7-nitro-1,2,3-benzoxadiazole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Intermediate 4-amino-7-nitro-1,2,3-benzofurazan (NBD-NH 2 ) preparation

[0042] Wrap a 100 mL single-necked round-bottom flask with tin foil, add ammonia (1 mL, 20 mmol) solution dropwise to a methanol solution containing 1 mmol 4-chloro-7-nitrobenzofurazan (NBD-Cl), 4 The concentration of the methanol solution of -chloro-7-nitrobenzofurazan (NBD-Cl) is 40%. After stirring at room temperature for 20 hours, after fully reacting, the solid is obtained by distillation under reduced pressure. The solid is dissolved in 8 mL of ethyl acetate, and the Ethyl acetate and petroleum ether were used as eluents (volume ratio 1:1), and 108 mg of a tan solid was obtained by silica gel column chromatography, which was the intermediate NBD-NH 2 The product, yield 60%.

[0043] (2) Preparation of Pd(0) fluorescent probe

[0044] Under dark conditions, the intermediate NBD-NH 2 (180 mg, 1 mmol) and triethylamine (270 μL, 2 mmol) were mixed in 10 mL of dichloromethane solution, a...

Embodiment 2

[0047] The preparation method of Pd (0) fluorescent probe, the steps are as follows:

[0048] (1) Intermediate 4-amino-7-nitro-1,2,3-benzofurazan (NBD-NH 2 ) preparation

[0049] Wrap a 100 mL single-necked round-bottom flask with tinfoil, add 15 mmol ammonia solution dropwise to a methanol solution containing 1 mmol 4-chloro-7-nitrobenzofurazan (NBD-Cl), NBD-Cl in methanol The concentration of the solution is 60%. After stirring at room temperature for 25 hours, after sufficient reaction, the solvent is removed under reduced pressure, and the solid is dissolved in 6 mL of ethyl acetate, and ethyl acetate and petroleum ether are used as eluents (volume ratio: 1:5) , separated by silica gel column chromatography to obtain 100 mg of tan solid, which is the intermediate NBD-NH 2 The product, yield 50%.

[0050]

[0051] (2) Preparation of Pd(0) fluorescent probe

[0052] Under dark conditions, 1 mmol intermediate NBD-NH 2 Mix with 1.5mmol triethylamine in 10 mL dichlorome...

Embodiment 3

[0056] The preparation method of Pd (0) fluorescent probe, the steps are as follows:

[0057] (1) Intermediate 4-amino-7-nitro-1,2,3-benzofurazan (NBD-NH 2 ) preparation

[0058] Wrap a 100 mL single-necked round-bottom flask with tinfoil, add 30 mmol ammonia solution dropwise to a methanol solution containing 1 mmol 4-chloro-7-nitrobenzofurazan (NBD-Cl), 4-chloro-7 -The concentration of the methanol solution of nitrobenzenefurazan (NBD-Cl) is 70%. After stirring at room temperature for 30 hours, after sufficient reaction, the solvent is removed under reduced pressure, and the solid is dissolved in 10 mL of ethyl acetate. Ether was used as the eluent (volume ratio 1:10), and 120 mg of a tan solid was obtained by silica gel column chromatography, which was the intermediate NBD-NH 2 The product, yield 80%.

[0059] (2) Preparation of probes

[0060] Under dark conditions, 1 mmol intermediate NBD-NH 2 Mix with 5 mmol triethylamine in 10 mL dichloromethane solution, dropwise ...

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Abstract

The invention provides a Pd (0) fluorescence probe based on 7-nitro-1,2,3-benzoxadiazole and a preparation method and application thereof. The Pd (0) fluorescence probe has high-efficiency and specific selectivity on Pd (0), is capable of overcoming interference of common metal positive ions and negative ions in a system, is wide in pH application range (4-8) and is a high-efficiency Pd (0) fluorescence probe; (2) the Pd (0) fluorescence probe has the lowest detection limit of 15nM aiming at Pd (0); (3) the Pd (0) fluorescence probe disclosed by the invention has the advantages of simple synthetic process, low cost, simple and convenient operation, high selectivity, high sensitivity, low detection limit, wide application prospects and the like.

Description

technical field [0001] The invention relates to a palladium ion (Pd(0)) detection agent, in particular to a 7-nitrobenzofurazan-based Pd(0) fluorescent probe and its preparation method and application. Background technique [0002] The transition metal palladium is a good catalyst in the field of pharmaceuticals and organic synthesis, it can catalyze Buchwald-Hartwig coupling reaction, Heck reaction, Sonogashira reaction, Suzuki-Miyaura reaction and Tsuji-Trost reaction, in the process of manufacturing and synthesizing complex molecules , play an extremely important role. At the same time, palladium is also widely used in social life. For example, the use of palladium in automobile exhaust catalytic conversion devices can effectively improve the problem of exhaust pollution. However, while palladium is widely used, the potential harm of palladium to the environment and organisms cannot be ignored. Excessive palladium will cause great harm to the environment and organisms,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/12C09K11/06G01N21/64
CPCC07D271/12C09K11/06C09K2211/1048G01N21/6428
Inventor 马志伟刘志景刘俊桃吕全建童岩
Owner HENAN UNIV OF ANIMAL HUSBANDRY & ECONOMY
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