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Metering type fluorinion fluorescence probe and preparation method

A fluorescent probe, fluoride ion technology, applied in biochemical equipment and methods, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problem of inability to complete fluoride ion detection, and achieve excellent selectivity, sensitivity, and yield. High and good water solubility

Inactive Publication Date: 2013-01-30
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this invention cannot complete the detection of fluoride ions in cells

Method used

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  • Metering type fluorinion fluorescence probe and preparation method
  • Metering type fluorinion fluorescence probe and preparation method
  • Metering type fluorinion fluorescence probe and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] In a (200 mL) round bottom flask, add pyrenemethanol (2 g, 8.6 mmol), under nitrogen protection, add 90 mL of tetrahydrofuran and triethylamine (2.64 mL, 18.9 mmol), and then add 1,1 , 2,2-Tetramethyldichlorodisilane (810 μL, 4.3 mmol), about 20 minutes, keep the reaction for 10 hours after the dropwise addition is completed. Then directly remove the precipitate by suction filtration, extract the filtrate three times with dichloromethane, wash three times with water, dry with anhydrous sodium sulfate, and separate with a chromatographic column (petroleum ether as eluent) to obtain the pure product 1 as a white solid, namely Quantitative fluoride ion fluorescent probe 1 (1.92 g) with the structural formula (A1), the yield was 77.3%.

[0031] 1 H NMR (400 MHz, CDCl 3 ) δ: 8.15-8.04(m, 10H), 8.01-7.93(m, 6H), 7.85(d, 2H), 5.42(s, 4H), 0.37 (s, 12H)

[0032] HR-MS: Calcd. for C 38 h 34 o 2 Si 2 [M + ] 578.8464. Found 578.8468.

[0033] The synthetic reaction equat...

Embodiment 2

[0037] In a (200 mL) round bottom flask, add pyrenemethanol (2 g, 8.6 mmol), under nitrogen protection, add 55 mL of tetrahydrofuran and triethylamine (2.64 mL, 18.9 mmol), and then add dimethyl Dichlorosilane (800 μL, 4.3 mmol), about 30 minutes, keep the reaction for 8 hours after the dropwise addition is completed. Then direct suction filtration to remove a large amount of precipitate, the filtrate was extracted three times with dichloromethane, washed three times with water, dried with anhydrous sodium sulfate, and separated by chromatography column (petroleum ether as eluent) to obtain the pure product of white solid 2 , that is, the quantitative fluoride ion fluorescent probe 2 (1.82g) with the structural formula (A2), and the yield was 81.2%.

[0038] 1 H NMR (400 MHz, CDCl 3 ) δ: 8.15-8.05(m, 10H), 8.05-7.98(m, 6H), 7.89(d, 2H), 5.40(s, 4H), 0.39 (s, 6H)

[0039] HR-MS: Calcd. for C 36 h 28 o 2 Si [M + ] 520.6918. Found 520.6919.

[0040] The structural formula...

Embodiment 3

[0044] In a (200 mL) round bottom flask, add 10 mmol of pyrenyl n-butyl alcohol, add 100 ml of diethyl ether and triethylamine (3.07 mL, 22.5 mmol) under the protection of argon, and then add dimethyl dimethicone dropwise Chlorosilane 5 mmol, about 25 minutes, keep the reaction for 10 hours after the dropwise addition is completed, use the method of Example 1 to carry out suction filtration and purification, and obtain the pure product 3 of white solid, that is, the metering type fluoride ion fluorescence with the structural formula (A3) Probe 3 (2.43 g), yield 80.3%.

[0045] 1 H NMR (400 MHz, CDCl 3 ) δ: 8.18-8.10(m, 10H), 8.08-7.90(m, 6H), 7.86(d, 2H), 5.42(s, 4H), 3.17 (t, 8H), 1.60-1.90 (m, 8H) 0.39 (s, 6H)

[0046] HR-MS: Calcd. for C 42 h 40 o 2 Si [M + ] 604.8513. Found 604.8517.

[0047] The structural formula is:

[0048]

[0049] (A3)

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Abstract

The invention relates to the organic chemistry field, which solves the requirement for a fluorescence probe used for determining the fluorinion with high selectivity and high sensitivity. The invention provides a metering type fluorinion fluorescence probe and a preparation method. The method comprises the following steps: in a container, adding alcohol with a luminescence group, then under the protection of inert gas, adding a solvent and triethylamine, adding a dichlorosilane compound, completing the droping in 15-30 minutes, reacting for 8-18 hours to obtain a metering type fluorinion fluorescence probe crude product, then performing pumping filtration on the obtained crude product according to a conventional method, and purifying to obtain a metering type fluorinion fluorescence probe pure product. The probe has good selectivity and sensitivity on the fluorinion, and can be used for detecting the fluorinion in a water phase system and cells; the preparation method of the probe is simple, and the equipment requirement is low, and the method of the invention is easy to be industrialized.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a proportional metering reaction type fluoride ion fluorescent probe. Background technique [0002] Fluoride ion is an important anion and one of the essential trace elements for human body. Fluorine is an indispensable element for bones and teeth. A small amount of fluorine can effectively prevent dental caries and osteoporosis. A large amount of fluorine exists in nature in the form of fluoride ions, and intake of a large amount of fluoride ions can easily cause fluorosis, which is a chronic systemic disease. For example: after excessive fluorine enters the human body, dental fluorosis will form, causing the teeth to be yellowish brown or dark brown, and gradually defect and fall off; symptoms such as joint stiffness, bending of lower limbs, bone deformation, and even paralysis; affect the normal development of children's intelligence and Therefore, the detection of fluoride ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F7/18G01N21/64C12Q1/02
Inventor 卢华盖立志李志芳来国桥蒋剑雄
Owner HANGZHOU NORMAL UNIVERSITY
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