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Quinoline fluorescent compound, preparation method and application thereof

A fluorescent compound and compound technology, applied in the field of fluorescent dyes, can solve the problems of low excitation wavelength, short excitation and emission wavelength, and limit the application of quinoline, and achieve the effects of large displacement value, high quantum yield, and excellent fluorescence performance

Active Publication Date: 2019-08-06
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the benzopyridine ring of the basic core structure of quinoline has no fluorescence, and its fluorescence needs to be obtained by modifying benzopyridine. Therefore, the excitation and emission wavelengths of quinoline fluorescent dyes usually available on the market are relatively short, which limits the use of quinoline in laser light. , Electroluminescence, and developments in the fields of nonlinear optical materials
At the same time, quinoline, as a common metal ion chelate, has weak specific recognition effect on metal ions, low excitation wavelength, and the N atom on the quinoline ring is easy to form hydrogen bonds in polar solutions. These characteristics It also limits the application of quinoline in the fields of bioluminescence sensing and chemical sensing

Method used

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  • Quinoline fluorescent compound, preparation method and application thereof
  • Quinoline fluorescent compound, preparation method and application thereof
  • Quinoline fluorescent compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of 2-Chloro-7-diethylaminoquinoline-3-carbaldehyde (1)

[0050] Add 1.00g (4.8mmol) 2-diethylaminoacetanilide, 0.9g (4.7mmol) DMF to a 50ml two-necked bottle, add 2.5g (8.4mmol) solid phosgene to a 50mL one-necked bottle, add 5mL1, 2-dichloroethane to completely dissolve the solid phosgene, and add the solid phosgene dropwise in an ice-salt bath. The dropwise addition was completed in half an hour. Reaction at 60°C. TLC traced until the reaction was complete. The reaction solution was poured into 50 mL of water, hydrolyzed for 5 min, the organic solvent was spin-dried, filtered with suction, dried, recrystallized from toluene, and dried with suction to obtain 0.82 g of a tan solid. Yield 66%. 1 H NMR (400MHz, Chloroform-d) δ10.40(s,1H),8.48(s,1H),7.72(d,J=9.2Hz,1H),7.11(dd,J=9.2,2.6Hz,1H) , 7.01(d, J=2.5Hz, 1H), 3.53(q, J=7.1Hz, 4H), 1.28(t, J=7.1Hz, 6H).

Embodiment 2

[0052] Preparation of 2-chloro-7-diethylaminoquinoline-3-carbonitrile (2)

[0053] Add 0.30g (1.1mmol) of 3-chloro-7-diethylaminoquinoline-3-carbaldehyde into a one-necked bottle, add 3mL tetrahydrofuran to dissolve, add 0.5g (1.9mmol) of iodine, 7mL ammonia water, stir at room temperature for 3-5h, TLC tracking, until the reaction is completely completed, the reaction solution is poured into water, filtered with suction, and dried. Silica gel column chromatography, eluent: petroleum ether: ethyl acetate (100:0-10, v / v), gave 0.24 g of a yellow solid. Yield: 80%. IR(KBr)cm -1 : 2215(C≡N), 1620(C=N), 688(C-Cl).

Embodiment 3

[0055] Preparation of 2-chloro-7-diethylaminoquinoline-3-carboxylic acid (3)

[0056] Add 0.20g (0.8mmol) 3-chloro-7-ethylenediaminoquinoline-3-carbonitrile into a single-necked bottle, add 2mL of acetic acid, 5mL of 70% sulfuric acid, heat and reflux for 2-3h, TLC traces to the completion of the reaction, Pour the reaction solution into water, filter it with suction, dissolve the obtained solid in 1,2-dichloroethane, add 0.25g (0.84mmol) of solid phosgene, a drop of DMF, reflux for 3-5h, trace by TLC until the reaction is complete, and use a silica gel column Chromatography, eluent: petroleum ether: ethyl acetate, 100:0-50, v / v), eluted to give 0.18g of yellow-green solid, namely the product 2-chloro-7-diethylaminoquinoline-3- Formic acid (3). Yield: 81%.

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Abstract

The invention discloses a quinoline fluorescent compound and a preparation method thereof, wherein the structural formula of the compound is as shown in the specification, X is Cl or OH; and R is anyone of CHO, CH2OH, COOH, CN and CH = NOH. The compound is obtained by taking m-diethylaminoacetanilide as a raw material to carry out Vilsmeier-Hacck reaction to obtain 2-chloroquinoline-3-formaldehyde, and subsequently obtaining a series of quinoline derivatives. The reaction conditions are mild and the operation is simple. The series of organic materials are synthesized through mutual conversionamong groups, and the absorption spectrum and the emission spectrum of the compound can be adjusted. At the same time, the disclosed compounds all have large stroke' s shift value and fluorescence quantum yield, and most of the compounds can also emit light in solid state, and can be used to develop fluorescent probes, blue luminescent materials and fluorescent whitening agents.

Description

technical field [0001] The present invention relates to quinoline compounds, in particular to a fluorescent dye based on a D-π-A mechanism. Background technique [0002] Organic small molecule fluorescent compounds play a key role in the development and application of fluorescence technology. The development of dye-sensitized solar cells, organic light-emitting diodes, information storage, photodynamic anti-tumor drugs, bioluminescent imaging, and chemical sensing technologies all depend on the development of corresponding fluorescent compounds. At present, organic small molecule fluorescent compounds that have been widely used include fluorescein, rhodamine, coumarin, BODIPY, etc., which have excellent fluorescence quantum yield, spectral stability, and low cytotoxicity. However, their Stokes shift is not large enough, and they emit weak or no light in the aggregated state, which affects their wide application in the above fields. [0003] Quinoline is an organic heterocy...

Claims

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Application Information

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IPC IPC(8): C07D215/38C07D215/48C09K9/02C09K11/06G01N21/64
CPCC07D215/38C07D215/48C09K9/02C09K11/06G01N21/6428G01N21/643C09K2211/1029
Inventor 但飞君马尚虎潘彤唐倩潘常乐杨得瑾
Owner CHINA THREE GORGES UNIV
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