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Tetrazolium imine coumarin copper ion fluorescent probe and preparation method thereof

A technology of coumarins and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of endangering human health, drug damage, etc., achieve weakened fluorescence intensity, easy to obtain raw materials, and synthesize simple effect

Active Publication Date: 2016-01-20
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Copper ions are also often used in pesticides and fungicides to inhibit the growth of bacteria and fungi, but improper use can cause phytotoxicity, and even directly endanger human health through the prevention and control of bioaccumulation

Method used

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  • Tetrazolium imine coumarin copper ion fluorescent probe and preparation method thereof
  • Tetrazolium imine coumarin copper ion fluorescent probe and preparation method thereof
  • Tetrazolium imine coumarin copper ion fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 : Synthesis of copper ion fluorescent probe 1-B, where R 1 is diethylamino, R 2 For hydrogen, n=2.

[0032]

[0033] 5-Phenyl-1-H-tetrazole: 515.6mg (5mmol) benzonitrile, 390mg (6mmol, 1.2eq) NaN 3 , 818mg (6mmol, 1.2eq) ZnCl 2 Dissolve in 10mL of water, stir at 100°C for reaction, follow the reaction by TLC, complete the reaction after 24 hours, cool, adjust the pH to 1 with 3M hydrochloric acid solution, filter, and dry in vacuo to obtain 0.6g of white solid with a yield of 82.1%.

[0034]2-acetonitrile-5-phenyltetrazole: 584.6mg (4mmol) 1-H-5-phenyltetrazole, 362.4mg (4.8mmol, 1.2eq) chloroacetonitrile, 331.7mg (2.4mmol, 0.6eq) K 2 CO 3 Dissolve in 8mL of DMF, stir at 60°C for reaction, follow the reaction by TLC, complete the reaction after 12h, cool to room temperature, dilute the reaction solution with 100mL of dichloromethane, wash with 60mL of water three times, dry the organic phase with anhydrous sodium sulfate, and let stand. Filtration, r...

Embodiment 2

[0037] Example 2: Synthesis of copper ion fluorescent probe 2-B, where R 1 is diethylamino, R 2 is hydrogen, n=1.

[0038]

[0039] 1-A Operation method see embodiment 1.

[0040] Fluorescent probe 2-B (shown in the above formula): the molar ratio of 1-A to 2-aminomethylpyridine is 1:5, and the reaction time is 30 h. See 1-B for postprocessing. Yield 70%. 1 HNMR (500MHz, CDCl 3 ): δ8.61-8.55(d,1H),8.34-8.26(m,2H),8.13-8.04(s,1H),7.73-7.65(m,1H),7.65-7.53(m,3H),7.39 -7.31(m,1H),7.28-7.15(dd,1H),7.16-7.05(d,1H),6.53-6.46(m,2H),5.66-5.58(s,2H),4.44-3.36(q, 4H),1.20-1.16(t,6H).

Embodiment 3

[0041] Example 3: Synthesis of Copper Ion Fluorescent Probe 3-B, where R 1 is hydroxyl, R 2 For hydrogen, n=2.

[0042]

[0043] Please refer to Example 1 for the synthesis operation method of 5-phenyl-1-H-tetrazole and 2-acetonitrile-5-phenyltetrazole.

[0044] Compound 3-A (shown in the above formula): the molar ratio of 2-acetonitrile-5-phenyltetrazole to 4-hydroxysalicylaldehyde is 1:1.2, piperidine is the base catalyst, the reaction temperature is 80°C, and the reaction time is 10h. Refer to 1-A for the post-processing method, and the yield was 86%. 1 HNMR(500MHz,DMSO): δ11.13(s,1H),8.77(s,1H),8.21-8.07(m,2H),7.76(d,J=8.6Hz,1H),7.61(dd,J= 4.9,2.5Hz,3H),6.94(dd,J=8.5,2.2Hz,1H),6.89(d,J=2.2Hz,1H).

[0045] Fluorescent probe 3-B (shown in the above formula): the molar ratio of 3-A to 2-aminoethylpyridine is 1:4, react at 80°C for 20 hours, refer to 1-B for the post-treatment method, and the yield is 60%. 1 HNMR(500MHz,DMSO)δ11.10(s,1H),8.73(s,1H),8.51-8.42(dd,2H),8...

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Abstract

The present invention relates to the preparation of a class of copper ion fluorescent probes based on tetrazolium imine coumarin structure. The general formula of this kind of fluorescent molecular probes is as follows: in the general formula, R1 is hydroxyl or diethylamino; R2 is hydrogen, 2 -chloro, 4-trifluoromethoxy or 4-methoxycarboxyl; n=1 or 2. This kind of fluorescent molecular probe with relatively simple structure and easy synthesis shows high selectivity and sensitivity to metal copper ions in ethanol / water solution, and the fluorescence quenching of copper ions can directly observe the color change of the solution with naked eyes. The lowest detectable copper ion concentration is 1×10-6mol / L.

Description

technical field [0001] The invention relates to the preparation of a class of copper ion fluorescent probes based on tetrazolium imine coumarin structure and the selective fluorescence detection of copper ions, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Copper is the third trace metal element in the body. The body has a very strict regulation mechanism for the content of copper ions in the cell. Excess or deficiency of copper will lead to neurological diseases, such as Wilson's disease and family hereditary lateral cord Sclerosis, Menkes syndrome, Alzheimers disease and Prion disease etc. Copper ions are also often used in pesticides and fungicides to inhibit the growth of bacteria and fungi, but improper use can cause phytotoxicity, and even directly endanger human health through the prevention and control of bioaccumulation. Copper is widely used in the production fields of electrical appliances, electronics, and mac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64G01N21/29
CPCC07D405/14C09K11/06C09K2211/1088G01N21/29G01N21/6428G01N2021/296G01N2021/6432
Inventor 董伟周湘湘刘洋洋谢阿明丰连东胡新宇
Owner NANJING UNIV OF SCI & TECH