Preparation method and application of a near-infrared fluorescent probe for detecting selenite

A fluorescent probe and near-infrared technology, which is applied in the field of preparation of near-infrared fluorescent probes, can solve the problems of failing to meet the requirements for detecting selenite, low detection limit, and inability to use anionic selenite for detection.

Active Publication Date: 2022-04-05
河南省农业科学院农业质量标准与检测技术研究所 +1
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Problems solved by technology

In the past few decades, the research on fluorescent probes has made great progress; patent 201510178114.X discloses a kind of malononitrile isophorone copper ion fluorescent probe and its preparation method, which can be used in Selective recognition of copper ions in buffer solution, characterized by low detection limit (only 0.2µM), large Stokes shift, fluorescence enhancement, long-wavelength emission and discoloration under visible light, copper ions can be detected by using its fluorescence enhancement and visible light discoloration Naked eye detection; using its fluorescence enhancement response to copper ions can be used for qualitative or quantitative analysis of copper ions; but it is mainly used to study the quantitative and qualitative analysis of cation-copper ions, and the minimum detection limit of the probe is high, its chemical The recognition group in the structure cannot be used for anion detection, so it cannot be applied to the detection of anion selenite; patent 201310125465.5 discloses the method of detecting the content of selenate ion and reducing it to selenite ion on-line, which is used to convert the hexavalent The selenate ion is reduced to tetravalent selenite ion online, so as to realize the speciation analysis method of selenate ion high-sensitivity vapor generation-atomic fluorescence detection combined liquid chromatography / ion chromatography and atomic fluorescence. This patent is through chromatography method and atomic fluorescence combined analysis and detection of selenite ion, the detection limit of the method is far below the requirements of detecting selenite in the environment, and the detection method is complicated, which is not conducive to real-time rapid detection. The fluorescent detector adopted in the present invention Acupuncture analysis, which directly detects tetravalent selenite ions, is fundamentally different from the above-mentioned patented method; therefore, the development of fluorescent probes for highly sensitive and selective recognition of inorganic selenium is still huge. challenges that also bring great rewards

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  • Preparation method and application of a near-infrared fluorescent probe for detecting selenite
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  • Preparation method and application of a near-infrared fluorescent probe for detecting selenite

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preparation example Construction

[0036] The preparation method of intermediate 1 is:

[0037] .

[0038] Commercial raw materials (3,5,5-trimethylcyclohex-2-enylidene) malononitrile (compound A, 186 mg, 1 mmol) and p-hydroxybenzaldehyde (244 mg, 2 mmol) were dissolved in 6 One to two drops of piperidine and acetic acid were added dropwise to the above system in mL of ethanol solution, heated to reflux for 4 hours, and cooled to room temperature after the reaction was complete as monitored by TLC. The above reaction solution was poured into 15 ml of ice-water mixture, and a precipitate was formed. The precipitate was filtered out and redissolved in dichloromethane, and the product was separated by column chromatography to obtain a yellow solid product which was intermediate 1 (203 mg), and the yield was 70%.

Embodiment 1

[0040] The preparation method of the near-infrared fluorescent probe of the detection selenite of the present embodiment, the steps are:

[0041] Levulinic acid (116.0 mg, 1.0 mmol) was dissolved in 10 mL of anhydrous dichloromethane, EDC (96 mg, 0.5 mmol) and DMAP (12.2 mg, 0.1 mmol) were added and stirred at room temperature for 10 minutes. Dissolve Intermediate 1 (145 mg, 0.5 mmol) in 10 mL of anhydrous dichloromethane solution, add it dropwise to the above mixed solution at room temperature, react for 8 hours after the dropwise addition, and wash the reaction solution with 10 mL of saturated chlorine The sodium chloride solution was washed 3 times, the organic phase was dried with anhydrous sodium sulfate, filtered, the solvent was removed under reduced pressure, ethyl acetate and petroleum ether were used as detergents (volume ratio 1:3), and 77.6 mg product SeP1, 40% yield.

[0042] NMR determination: 1 H NMR (CDCl 3 , 400 MHz) δ 1.10 (s, 6 H), 2.25 (s, 3 H),2.48 (s, ...

Embodiment 2

[0045] The preparation method of the near-infrared fluorescent probe of the detection selenite of the present embodiment, the steps are:

[0046] Levulinic acid (116.0 mg, 1.0 mmol) was dissolved in 10 mL of anhydrous dichloromethane, EDC (192 mg, 1 mmol) and DMAP (61 mg, 0.5 mmol) were added and stirred at room temperature for 20 minutes. Dissolve intermediate 1 (290 mg, 1 mmol) in 15 mL of anhydrous dichloromethane solution, add it dropwise to the above mixed solution at room temperature, react for 10 hours after the dropwise addition, and use 10 mL of saturated chlorinated The sodium solution was washed 3 times, the organic phase was dried with anhydrous sodium sulfate, filtered, the solvent was removed under reduced pressure, ethyl acetate and petroleum ether were used as detergents (volume ratio 1:6), and 213.4 mg was obtained by silica gel column chromatography The product SeP1, namely the fluorescent probe, has a yield of 55%.

[0047] NMR determination of fluorescent ...

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Abstract

The invention belongs to selenite (SeO 3 2‑ ) detection field, and relates to a preparation method and application of a near-infrared fluorescent probe for detecting selenite. Activation of levulinic acid by catalyst EDC and DMAP, the activation product and malononitrile isophorone intermediate 1 (2-[3-(4-hydroxystyryl)-5,5-dimethyl ‑cyclohex‑2‑ene‑1‑ylidene] malononitrile) to carry out condensation acylation reaction to obtain a compound based on malononitrile isophorones, which can be used as selenous It is a highly selective fluorescent probe for acid radicals, and its fluorescence emission wavelength is above 650 nm, which realizes near-infrared fluorescence spectrum identification. The results show that the probe SeP1 has high efficiency and specific selectivity to selenite, and has strong anti-interference ability. The minimum detection limit of the probe for selenite is 0.068 μM, and has practical value in the detection of selenite in the environment.

Description

technical field [0001] The invention belongs to selenite (SeO 3 2- ) detection field, and relates to a preparation method and application of a near-infrared fluorescent probe for detecting selenite. Background technique [0002] Selenium is one of the essential trace elements in the human body. It participates in the synthesis of various selenium-containing enzymes and selenoproteins in the human body, and has various physiological functions such as anti-oxidation and anti-tumor. Due to the important role of selenium, adequate supplementation of selenium in the human body can prevent organ aging and disease, delay aging, enhance immunity, and resist harmful heavy metals. [0003] Selenium exists in nature in two forms: organic selenium and inorganic selenium. Organic selenium is formed by the combination of selenium and amino acids through biotransformation. It mainly exists in the form of selenomethionine, participates in the synthesis of proteins in organisms, and plays...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/38C07C253/30C07C253/34C09K11/06G01N21/64
CPCC07C255/38C07C253/30C07C253/34C09K11/06G01N21/643C07C2601/16C09K2211/1007
Inventor 马志伟张迪刘继红李漫王铁良王红旗徐孟生王允曹成王俊艳郑嘉
Owner 河南省农业科学院农业质量标准与检测技术研究所
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