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A kind of coumarin-pyridine compound, preparation method and application thereof

A technology of coumarin and compounds, which is applied in the field of organic small molecule fluorescent probes, can solve the problems of high cost and complex synthesis methods, and achieve the effects of fast response speed, high product yield and rapid response

Active Publication Date: 2021-03-23
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, through literature analysis, we found that there are few reports of this type of compound, and the synthesis method is more complicated and the cost is higher

Method used

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  • A kind of coumarin-pyridine compound, preparation method and application thereof
  • A kind of coumarin-pyridine compound, preparation method and application thereof
  • A kind of coumarin-pyridine compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Synthesis of coumarin-pyridine compound L 6-(7-N,N-diethylaminocoumarin-3-yl)-2-methylpyridine-3-carboxylic acid ethyl ester

[0034] Add 0.5g (1.93mmol) 3-acetyl-7-diethylaminocoumarin, 1.15g (9.65mmol) DMFDMA to a 50mL two-necked bottle, then add 15mL anhydrous isopropanol, 0.06g acetic acid, heat and stir Dissolve the solid. Reflux for 8 hours, TLC traced the complete reaction of 3-acetyl-7-diethylaminocoumarin, and cooled to room temperature to obtain enaminone intermediate 1 liquid. In the above-mentioned reaction flask, add 0.26g (1.91mmol) ethyl acetoacetate, 0.85g (11.13mmol) ammonium acetate, stir to dissolve, then add 0.08g piperidine, stir and reflux, after 5 hours, TLC traces the middle Body 1 was completely reacted, cooled to room temperature, suction filtered, washed with 25°C ethanol (mass fraction 95%), recrystallized from a mixed solvent of ethanol and water, dried and weighed to obtain yellow needle-shaped crystals, yield 77.82%, m.p.: 136 ...

Embodiment 2

[0036] Embodiment 2 Solvent influences on the spectrum of coumarin-pyridine compound L

[0037] Prepare 1mM pH fluorescent probe stock solution in DMF, add 20μL 1mM pH fluorescent probe stock solution, after shaking evenly, test its fluorescence spectrum. The test conditions are: excitation wavelength 365nm, slit width 5nm / 5nm, voltage 500V.

[0038] Such as figure 1 As shown, the peak position of the UV absorption peak of probe L did not move significantly with the change of solvent polarity, and the profile of the UV peak did not change, indicating that the polarity of the solvent did not have much influence on the UV absorption of probe L. However, with the increase of solvent polarity, the maximum emission wavelength of probe L shifted 27nm from toluene to acetonitrile, and the maximum emission wavelength red-shifted obviously, indicating that there may be intramolecular charge transfer.

Embodiment 3

[0039] Embodiment 3 coumarin-pyridine compound L is the same as metal ion and H + UV-Vis Absorption and Fluorescence Emission Spectra

[0040] Prepare 14 groups of buffer solutions with a pH value of 7.53 of V (methanol): V (PBS buffer solution) = 9:1, use HCl and NaOH to adjust and configure 1 group of solutions with a pH value of 1.97, and use the above solution with a pH value of 7.48 Concentration of 1mM Al was prepared respectively 3+ , Ca 2+ , Cr 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Ag + , Cd 2+ , Ba 2+ , Hg 2+ For the ionic solution, take 2 mL of each of the above 15 groups of solutions and add 20 μL of the fluorescent probe stock solution with a concentration of 1 mM to dissolve 20 μL. After shaking evenly, test its ultraviolet absorption spectrum and fluorescence emission spectrum (test conditions: excitation wavelength 365 nm, slit width 5 nm / 5nm, voltage 500V).

[0041] Such as figure 2 As shown, when the pH value of the solution is 7...

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Abstract

The invention discloses a coumarin-pyridine compound and a preparation method and application in H+ detection thereof. The structural formula of a compound L is 6-(7-diethylamino)coumarin-3-base)-2-dimethylpyridine-3-carboxylic acid ethyl ester. Coumarin ethyl ketone is taken as a raw material, condensation is conducted between the coumarin ethyl ketone and DMFDMA to obtain an enaminone intermediate product, the intermediate product is not separated and purified, and one-pot tandem synthesis is conducted on the intermediate product and acetacetic ester to obtain the compound. The compound L has a lower pKa value and the significant advantages of being sensitive in response to H+, rapid, reversal, good in selectivity, high in interference performance, suitable for pH detection in strong acidic environments and the like, and the compound L has extensive application prospect in environmental monitoring, ecological protection, disease diagnosis, industrial production and sewage discharginginspection.

Description

technical field [0001] The present invention relates to the field of organic small molecule fluorescent probes, in particular to a compound L 6-(7-N,N-diethylaminocoumarin-3-yl)-2-methylpyridine-3-carboxylic acid ethyl Esters, methods of preparation and applications thereof. Background technique [0002] pH is a key parameter in a wide range of fields, and has applications in human health, bioengineering, environmental protection, sewage detection, ecological protection, and chemical production. Especially in industrial production, a large amount of strongly acidic industrial wastewater is often produced, which has caused great pressure on the environment and ecological protection. Therefore, it is of great significance to accurately measure the pH value, especially the pH in a strongly acidic system. Compared with other methods for detecting pH such as glass electrode method, nuclear magnetic resonance method and indicator method, among the spectroscopic methods, absorptio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C09K11/06G01N21/31G01N21/64
CPCC07D405/04C09K11/06C09K2211/1029C09K2211/1088G01N21/31G01N21/643
Inventor 但飞君曾晓燕唐倩潘常乐
Owner CHINA THREE GORGES UNIV