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Malononitrile phorone fluorine-ion fluorescence probe and preparation method and application thereof

A technology of malononitrile phorone and fluorescent probe, which is applied in the field of analysis and detection, can solve the problems of large error, short fluorescence emission wavelength of fluorescent probe, low sensitivity, etc., achieve small error, avoid fluorescence self-quenching and fluorescence Effect of detection error and low detection limit

Inactive Publication Date: 2019-09-24
YANGTZE NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For the above-mentioned deficiencies existing in the prior art, the object of the present invention is to provide a kind of malononitrile phorone fluoride ion fluorescent probe, solve the problem that the fluorescent emission wavelength of the existing fluorescent probe is short, resulting in low sensitivity and large error, etc. question

Method used

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  • Malononitrile phorone fluorine-ion fluorescence probe and preparation method and application thereof
  • Malononitrile phorone fluorine-ion fluorescence probe and preparation method and application thereof
  • Malononitrile phorone fluorine-ion fluorescence probe and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0033] A synthetic process route of malononitrile phorone class fluoride ion fluorescent probe is as follows:

[0034]

[0035] Specifically include the following steps:

[0036] Preparation of malononitrile phorone-based fluoride ion fluorescent probe:

[0037] 3-(4-Hydroxystyryl)-5,5-dimethyl-cyclohex-2-en-1-ylidene]propanedicyano (290mg, 1mmol), triisopropylchlorosilane (384mg , 2mmol) and imidazole (272mg 4mmol) were added to 10mL of tetrahydrofuran solution, stirred at room temperature (25~35°C) for 3h, then 10mL of water was added to the reacted mixed solution to quench the reaction and the organic layer was extracted, and anhydrous sodium sulfate After drying, the solvent was removed by rotary evaporation under reduced pressure, and then the crude product was purified by column chromatography with petroleum ether / dichloromethane (v / v)=2:1 eluent to obtain 400 mg of the target product I, namely malononitrile fo A ketone-based fluoride ion fluorescent probe compound....

Embodiment 2

[0042] A synthetic process route of malononitrile phorone class fluoride ion fluorescent probe is as follows:

[0043]

[0044] Specifically include the following steps:

[0045] Preparation of malononitrile phorone-based fluoride ion fluorescent probe:

[0046] 3-(4-Hydroxystyryl)-5,5-dimethyl-cyclohex-2-en-1-ylidene]propanedicyano (290mg, 1mmol), triisopropylchlorosilane (768mg , 4mmol) and imidazole (544mg, 8mmol) were added in 10mL of acetonitrile solution, stirred at room temperature for 5h, then 10mL of water was added to the reacted mixed solution to quench the reaction and the organic layer was extracted, dried with anhydrous sodium sulfate, and spun under reduced pressure After evaporating the solvent, the crude product was purified by column chromatography with petroleum ether / dichloromethane (v / v)=2:1 eluent to obtain 400 mg of the target product I, namely malononitrile phorone fluoride ion Fluorescent Probe Probe Compounds.

Embodiment 3

[0048] A synthetic process route of malononitrile phorone class fluoride ion fluorescent probe is as follows:

[0049]

[0050] Specifically include the following steps:

[0051] Preparation of malononitrile phorone-based fluoride ion fluorescent probe:

[0052] 3-(4-Hydroxystyryl)-5,5-dimethyl-cyclohex-2-en-1-ylidene]propanedicyano (290mg, 1mmol), triisopropylchlorosilane (384mg , 2mmol) and imidazole (272mg 4mmol) were added to 10mL of tetrahydrofuran solution, stirred at room temperature for 3h, then 10mL of water was added to the reacted mixed solution to quench the reaction and the organic layer was extracted, dried with anhydrous sodium sulfate, and rotary evaporated under reduced pressure After the solvent was removed, the crude product was purified by column chromatography with petroleum ether / dichloromethane (v / v)=2:1 eluent to obtain 400 mg of the target product I, namely malononitrile phorone fluoride ion fluorescence Probe Probe Compound.

[0053] 2. The appl...

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Abstract

The invention discloses a malononitrile phorone fluorine-ion fluorescence probe and a preparation method and application thereof, and belongs to the technical field of analysis and detection. The chemical structural formula of the probe is shown in the description. The malononitrile phorone fluorine-ion fluorescence probe has the advantages of having a good optical property, being capable of highly selectively identifying fluorine ions, having large Stokes displacement and the long fluorescence emission wave length, being high in sensitivity and good in selectivity and the like; the probe is simple in synthesis route, high in yield, easy to separate, high in purity and capable of being used for identifying and detecting the content of fluorine ions in water environment, under the effect between fluorine and the probe, a macroscopic color change is generated, and whether or not the fluorine ions exist in the water environment is conveniently identified by naked eyes; the monitoring speed is relatively high, and interference of other ion elements in the water cannot cause influence. The raw materials are simple and easy to obtain, and the malononitrile phorone fluorine-ion fluorescence probe is low in cost and capable of easily achieving industrialized production, and has good application prospects in environment monitoring and a living body system.

Description

technical field [0001] The invention belongs to the field of analysis and detection, and in particular relates to a malononitrile phorone-based fluoride ion fluorescent probe and a preparation method and application thereof. Background technique [0002] Fluoride ion is an essential trace element for human beings. It is closely related to some life activities of the human body, such as the metabolism of teeth and bone tissue. Multiple organ lesion values. It should be noted that with the wide application of fluoride ions in industry, wastewater discharged from industries such as fluorine-containing ore mining, coke, glass, aluminum processing, electroplating, electronics, and chemical fertilizers often contains high concentrations of fluoride, causing environmental damage Irreversible pollution and damage are also increasingly evident. Therefore, it is becoming more and more important to realize accurate and rapid detection of fluoride ions in the environment and in vivo. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C09K11/06G01N21/64
CPCC07F7/1804C07F7/188C09K11/06C09K2211/1007C07C2601/16G01N21/6428G01N21/643G01N2021/6432
Inventor 张义斌
Owner YANGTZE NORMAL UNIVERSITY
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