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Colorimetric probe based on naphthalimides derivative and preparation method and application thereof

A technology of hydrazinonaphthalimide and naphthalimide, which is applied in the field of naphthalimide derivatives and its preparation, can solve problems such as decreased arterial elasticity, elevated cholesterol, and elevated blood pressure, achieving strong selectivity and sensitivity High and easy-to-obtain raw materials

Inactive Publication Date: 2017-03-08
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, if the metabolic balance of copper ions in the body is destroyed, it may cause metabolic disorders and many diseases, such as increased cholesterol, decreased arterial elasticity, and increased blood pressure.

Method used

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  • Colorimetric probe based on naphthalimides derivative and preparation method and application thereof
  • Colorimetric probe based on naphthalimides derivative and preparation method and application thereof
  • Colorimetric probe based on naphthalimides derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of Naphthalimide Derivatives

[0025]

[0026] Dissolve 0.195 g of ethyl 5-formyl-2,4-dimethylpyrrole-3-carboxylate in 10 mL of absolute ethanol, then add 0.271 g of N-hydroxyethyl-4-hydrazinonaphthalimide, usually Stir under pressure at 78°C for 3 h, cool to room temperature and precipitate a large amount of solid, filter under reduced pressure, recrystallize the filter residue with acetonitrile to obtain a red solid which is the target product, and the yield of the target product is 78.2%.

[0027] Naphthalimide derivative NMR analysis results are as follows:

[0028] 1 H NMR (400 MHz, DMSO- d 6 ), δ (ppm): 11.62 (s, 1H, OH), 11.25 (s, 1H, NH),8.73-8.75 (d, 1H, Aryl-H), 8.47-8.49 (d, 1H, Aryl-H) , 8.40 (s, 1H, CH=N),8.33-8.35 (d, 1H, Aryl-H), 7.76-7.84 (m, 2H, Aryl-H), 4.79-4.82 (t, 1H, OH),4.13 -4.20 (m, 4H, 2CH 2 ), 3.59-3.63 (q, 2H, CH 2 ), 2.33 (s, 3H, CH 3 ), 1.29-1.31(t, 3H, CH 3 ).

[0029] Single crystal structure: see the crystal struct...

Embodiment 2

[0032] The preparation method of the colorimetric probe based on naphthalimide derivatives: 0.001 mol of 5-formyl-2,4-dimethylpyrrole-3-carboxylic acid ethyl ester was dissolved in 50ml of absolute ethanol, Then add 0.01 mol of N-hydroxyethyl-4-hydrazinonaphthalimide, reflux and stir at 70°C under normal pressure for 1h, cool to room temperature and precipitate a solid, filter under reduced pressure, and recrystallize the filter residue with acetonitrile to obtain a naphthalene-based Colorimetric probes for imine derivatives.

Embodiment 3

[0034] The preparation method of the colorimetric probe based on naphthalimide derivatives: 0.01mol of 5-formyl-2,4-dimethylpyrrole-3-carboxylic acid ethyl ester is dissolved in 10 ml of absolute ethanol , then add 0.001 of N-hydroxyethyl-4-hydrazinonaphthalimide, stir at 90°C under normal pressure for 3h, cool to room temperature and precipitate a solid, filter under reduced pressure, and recrystallize the filter residue with acetonitrile to obtain Naphthaloyl-based Colorimetric probes for imine derivatives.

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Abstract

The invention provides a colorimetric probe based on naphthalimides derivative and a preparation method and an application thereof. A chemical structural formula of the naphthalimides derivative is shown as follows, the naphthalimides derivative is capable of selectively effecting with bivalent copper ion, red is turned to colourless, the naphthalimides derivative has colorimetric decrease effect, can realize naked-eye discrimination and detection, and can be taken as the colorimetric probe for conveniently detecting the copper ions in a water sample.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to naphthalimide derivatives and their preparation methods and applications. Background technique [0002] Copper is an important trace element in the human body. It plays a very important role in different physiological processes such as mitochondrial respiration, iron absorption, and enzyme redox. However, if the metabolic balance of copper ions in the body is destroyed, it may cause metabolic disorders and many diseases, such as elevated cholesterol, decreased arterial elasticity, and increased blood pressure. In addition, copper has also become an important metal pollutant due to the large amount of copper ions mined and widely used. In view of its importance to life and the environment, scientists have been working on the detection of copper ions in biological and environmental systems using selective colorimetric and fluorescent sensing probes. Contents of the in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12G01N21/33G01N21/78
CPCC07D401/12G01N21/33G01N21/78
Inventor 吴伟娜王元陈兴颖陈泽华李慧军徐周庆吴浩
Owner HENAN POLYTECHNIC UNIV
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