A relay-recognition fluorescent probe and its synthesis and application

A technology of fluorescent probes and probes, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, which can solve the problems of expensive instruments, cumbersome operations, etc., and achieve low detection limits, high sensitivity, and good results. Effect

Active Publication Date: 2020-06-09
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Mass spectrometry, electrochemical method, atomic absorption spectrometry, electron-coupled plasma atomic emission spectrometry, etc. have many disadvantages, such as expensive instruments, high cost, cumbersome operation, etc.

Method used

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  • A relay-recognition fluorescent probe and its synthesis and application
  • A relay-recognition fluorescent probe and its synthesis and application
  • A relay-recognition fluorescent probe and its synthesis and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the synthesis of intermediate compound 2

[0045]

[0046] (1) Synthesis of compound 3

[0047] A mixture of 8-hydroxy-2-methylquinoline (1.6 g, 10.05 mmol), ethyl bromoacetate (1.7 g, 10.18 mmol) and anhydrous potassium carbonate (5 g, 36.18 mmol) in acetone (20 mL) was heated Reflux for 24 hours. After cooling, the mixture was filtered and the resulting filtrate was evaporated to dryness to give a crude residue. The final product was purified by chromatography (eluent, dichloromethane / ethyl acetate=10:1) to obtain 1.98 g of light yellow oily product, namely compound 3.

[0048] (2) Synthesis of Compound 2

[0049] At 65 °C, 0.75 g of SeO2 was added to a solution of 3 (1.5 g, 6 mmol) in 1,4-dioxane (20 mL), and the temperature of the above mixture was raised to 80 °C. After reacting for 2 hours, it was cooled to room temperature. The precipitate was filtered off. The organic phase was concentrated in vacuo. The final product was obtained as a ye...

Embodiment 2

[0051] Embodiment 2: Synthesis of fluorescent probes based on quinoline structure

[0052]

[0053] Add 0.58g (4mmol) 5-chloro-2-hydroxyaniline and 1.04g compound 2 (4mmol) to a 100mL round-bottomed flask, then add 20mL ethanol solvent to dissolve, add 3 drops of acetic acid and 5 mg of ZnO as a catalyst, 50 ° C The reaction was stirred for 4 hours. The reaction process was monitored by TLC (developing solvent: petroleum ether / ethyl acetate=1:2), and the reaction of compound 2 was the end point. The crude product was recrystallized from ethanol and purified by column chromatography (eluent: petroleum ether / dichloromethane=0.5:1). Finally, 1.13 g of a light yellow solid, namely probe 1, was obtained with a yield of 73.8%.

Embodiment 3

[0054] Embodiment 3: Synthesis of fluorescent probes based on quinoline structure

[0055] Add 1.75g ​​(12mmol) of 5-chloro-2-hydroxyaniline and 3.12g of compound 2 (12mmol) into a 100mL round bottom flask, then add 40mL of ethanol solvent to dissolve, add 10 drops of acetic acid and 20 mg of ZnO as a catalyst, and then heat at 80°C The reaction was stirred for 8 hours. The reaction process was monitored by TLC (developing solvent: petroleum ether / ethyl acetate=1:2), and the reaction of compound 2 was the end point. The crude product was recrystallized from ethanol and purified by column chromatography (eluent: petroleum ether / dichloromethane=0.5:1). Finally, 3.25 g of a light yellow solid, namely probe 1, was obtained with a yield of 70.8%.

[0056] Its NMR image is figure 2 and 3 Shown: 1 H NMR (400MHz, DMSO-d6) δ8.6(dd,1H),8.45(dd,1H),8.05(dd,1H),8.0(dd,1H),7.82–7.56(m,3H),7.23( dd,1H),5.18(s,2H),4.22(q,2H),1.24(t,3H); 13 C NMR (101MHz, DMSO-d6) δ169.15, 163.40, 154...

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Abstract

The invention relates to the field of preparation of fluorescent compounds and application of metal ion detection, in particular to a relay identification type fluorescent probe and synthesis and application thereof. A certain amount of a compound C14H13O4N and 5-chloro-2-hydroxyaniline are dissolved in alcohol, stirring is conducted in an oil bath pot at a certain temperature and reflux reactionis conducted after a certain amount of acetic acid and ZnO are added; after the reaction is completed, the mixture is cooled to room temperature, settled impurities are filtered out, a coarse productis obtained after rotary evaporation is conducted on filter liquid, and a light yellow product, namely the novel quinoline fluorescent probe, is obtained through recrystallization. The obtained probehas high sensitivity on detection of Cu<2+> and Cd<2+> ions, a measured detection limit is low, and the effect is good. The preparation method is simpler in synthesis route compared with other complexsynthesis methods, a nano ZnO material is adopted as a catalyst, the productive rate is higher, and the cost is lower.

Description

technical field [0001] The invention relates to the field of preparation of a fluorescent compound and the application of metal ion detection, in particular to a relay recognition fluorescent probe and its synthesis and application. Background technique [0002] As we all know, with the continuous development of the industrialization process of human society, the problem of environmental pollution is becoming more and more serious, and the problem of metal ion pollution to the environment has always been concerned. Copper is the third most abundant transition metal element after iron and zinc in the human body, and copper ions play a vital role in physiological processes. However, the imbalance of copper ion concentration in organisms can also cause a series of diseases, such as Parkinson's syndrome, Menkes' syndrome, Alzheimer's disease, Wilson's disease, familial amyotrophic lateral sclerosis and so on. As a highly toxic heavy metal, cadmium can accumulate in the human bo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/04C09K11/06G01N21/64
CPCC07D413/04C09K11/06C09K2211/1029C09K2211/1033G01N21/643
Inventor 韩娟王赟王蕾唐旭倪良刘仁杰李红昀郑洲
Owner JIANGSU UNIV
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