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Fluorescent molecular probe for detecting fluoride ions in aqueous solutions as well as synthesis method and application thereof

A technology of fluorescent molecular probes and fluorine ions, which is applied in the field of chemical analysis and detection, can solve the problem of short emission wavelength of the test system, and achieve the effects of wide detection range, high sensitivity and good selectivity

Active Publication Date: 2015-03-18
SUZHOU ROWLAND BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the large hydration energy of fluoride ions, there are few reports on fluorescent probes for detecting fluoride ions in aqueous solution, and the emission wavelength of the test system is relatively short, which is easily interfered by endogenous fluorescent substances in tissue cells. Therefore, it is of great practical significance to develop rapid and sensitive probes for the recognition of fluoride ions

Method used

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  • Fluorescent molecular probe for detecting fluoride ions in aqueous solutions as well as synthesis method and application thereof
  • Fluorescent molecular probe for detecting fluoride ions in aqueous solutions as well as synthesis method and application thereof
  • Fluorescent molecular probe for detecting fluoride ions in aqueous solutions as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of compound 2

[0030]In a 50 mL single-neck round bottom flask, add 1,4-diethyl-1,2,3,4-tetrahydro-7-hydroxyquinoxalin-6-al (23.4 mg, 0.1 mmol), 4-di Dissolve methylaminopyridine (16 mg, 0.13 mmol) and a drop of triethylamine in 10 mL of dichloromethane and stir at room temperature for 5 minutes. Tert-butyldimethylsilyl chloride (20 mg, 0.13 mmol) was added to the above reaction system, followed by stirring at room temperature for 1 hour. The reaction solution was poured into 30 mL of water to quench the reaction. Extracted with 30mL of dichloromethane, separated the organic phase and dried it with anhydrous sodium sulfate, distilled off the solvent, and purified by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain 30 mg of the product as a yellow liquid (yield: 86%).

[0031] 1 H NMR (400 MHz, CDCl 3 ) δ 10.14 (d, J = 7.2 Hz, 1H), 6.99 (d, J = 27.2 Hz, 1H), 5.91 (d, J = 15.7 Hz, 1H), 3.35 (t, J = 65.5 H...

Embodiment 2

[0032] Embodiment 2: Preparation of molecular fluorescent probe

[0033] In a 50 mL single-necked flask, compound 2 (34.8 mg, 0.1 mmol) and malononitrile (6.6 mg, 0.1 mmol) were dissolved in 5 mL of ethanol, 1 drop of piperidine was added, and reacted at room temperature for 30 minutes. The reaction solution was poured into water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by column chromatography (petroleum ether / dichloromethane=1:1) to obtain 21 mg of the product (yield: 53%) which was the probe compound.

[0034] 1 H NMR (400 MHz, CDCl 3 ) δ 7.84 (s, 1H), 7.43 (s, 1H), 5.92 (s, 1H), 3.59 – 3.52 (m, 2H), 3.35 (dq, J = 25.8, 7.1 Hz, 4H), 3.23 – 3.17 (m, 2H), 1.35 – 1.13 (m, 6H), 1.01 (s, 9H), 0.24 (s, 6H).

Embodiment 3

[0035] Example 3: Application of fluorescent molecular probes for detection of fluoride ions

[0036] Dissolve the probe in 30% acetonitrile:water solution at a concentration of 10 μM, add 1 mM sodium fluoride solution, and test the ultraviolet absorption spectrum; dissolve the probe in 30% acetonitrile:water solution at a concentration of 10 μM, first , adding different concentrations of sodium fluoride solution, additionally, adding different test substances (1 mM chloride ion, bromide ion, iodide ion, tetrabutylammonium cyanide, nitrate, hydrogen sulfate , perchlorate, acetate, thiocyanate, azide, cysteine, bovine serum albumin, carbonate, sulfate, reduced glutathione), and finally, in 1 mM coexisting substances (chloride ion , bromide ion, iodide ion, tetrabutylammonium cyanide, nitrate, hydrogen sulfate, perchlorate, acetate, thiocyanate, azide, cysteine, bovine serum albumin, carbonate, sulfuric acid root, reduced glutathione), 1 mM sodium fluoride solution was added...

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Abstract

The invention relates to a preparation method of a fluorescent molecular probe for detecting fluoride ions in aqueous solutions through fluorescence enhancement and an application of the fluorescent molecular probe to detecting fluoride ions. The fluorescent molecular probe is prepared by protecting 1,4-diethyl-1,2,3,4-tetrahydro-7-hydroxyquinoxaline-6-aldehyde taken as a raw material with silane and then condensing the raw material and malononitrile. The fluorescent molecular probe is simple and convenient to synthesize, and reaction conditions are mild. The fluorescent molecular probe has the specific characteristics that the probe molecule has stable optical properties and higher synthetic yield; the probe molecule has high sensitivity of detection of fluoride ions in the aqueous solutions and low lower limit of detection, and the limit of detection is 5.4mu M; the response range is 0-1mM and the detection range is wide; the probe molecule has good selectivity and has no responses to anions, such as chloride ions, bromide ions, iodide ions, tetrabutylammonium cyanide, nitrates radicals, hydrosulfate radicals, perchlorate radicals, acetate radicals, thiocyanate radicals, azide radicals, cysteine, bovine serum albumin, carbonate radicals, sulfate radicals and reduced glutathione; the fluorescent molecular probe has practical application values in the fields of biochemistry, environmental sciences and the like.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a fluorescent molecular probe for fluorescence enhancement detection of fluoride ions in an aqueous solution and an application of the fluorescent molecular probe in detecting fluorine ions. [0002] Background technique [0003] Molecular recognition plays an important role in life processes. As the smallest anion, fluoride ion has unique chemical properties. In the process of life, fluoride ion plays an important role as an essential element in the human body. Medical research has confirmed that fluoride ions can effectively prevent dental caries and treat osteoporosis. Fluoride ions widely exist in natural water bodies. When the content in surface water is too high, the water at this time is not suitable for drinking. Moreover, when the fluorine content in the human body exceeds the range required by oneself, it will cause fluo...

Claims

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Application Information

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IPC IPC(8): C07F7/18C09K11/06G01N21/64
Inventor 宋相志陈颂
Owner SUZHOU ROWLAND BIOTECH
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