A class of quinoline fluorescent compounds, preparation method and application thereof

A technology of fluorescent compounds and quinolines, which is applied in the field of fluorescent dyes, can solve problems such as low excitation wavelength, short excitation and emission wavelength, and limit the application of quinoline, and achieve large displacement values, high quantum yields, and excellent fluorescence properties. Effect

Active Publication Date: 2022-07-15
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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  • A class of quinoline fluorescent compounds, preparation method and application thereof
  • A class of quinoline fluorescent compounds, preparation method and application thereof
  • A class of quinoline fluorescent compounds, 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] In the double-necked flask of 50ml, add 1.00g (4.8mmol) 2-diethylaminoacetanilide, 0.9g (4.7mmol) DMF, add 2.5g (8.4mmol) solid phosgene in the single-necked flask of 50mL, add 5mL1, 2-dichloroethane, so that the solid phosgene is completely dissolved, and the solid phosgene is added dropwise under an ice-salt bath. Half an hour was added dropwise. 60°C reaction. Followed by TLC, the reaction was complete. The reaction solution was poured into 50 mL of water, hydrolyzed for 5 min, spin-dried the organic solvent, suction filtered, dried, recrystallized from toluene, suction filtered and dried to obtain 0.82 g of a yellow-brown solid. Yield 66%. 1 H NMR (400MHz, Chloroform-d) δ 10.40 (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 0.30 g (1.1 mmol) of 3-chloro-7-diethylaminoquinoline-3-carbaldehyde to the single-necked flask, add 3 mL of tetrahydrofuran to dissolve, add 0.5 g of iodine (1.9 mmol), 7 mL of ammonia water, stir at room temperature for 3-5 h, TLC tracking, when the reaction was completed, the reaction solution was poured into water, suction filtered, and dried. Silica gel column chromatography, eluent: petroleum ether: ethyl acetate (100:0-10, v / v), to obtain 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 0.20 g (0.8 mmol) of 3-chloro-7-ethylenediaminoquinoline-3-carbonitrile to a single-necked flask, add 2 mL of acetic acid, 5 mL of 70% sulfuric acid, heat under reflux for 2-3 h, TLC traces to after the reaction is complete, The reaction solution was poured into water, filtered with suction, the obtained solid was dissolved in 1,2-dichloroethane, 0.25 g (0.84 mmol) of solid phosgene was added, and a drop of DMF was refluxed for 3 to 5 h, followed by TLC until the reaction was completed, and a silica gel column Chromatography, eluent: petroleum ether: ethyl acetate, 100:0-50, v / v), eluted to obtain 0.18g of yellow-green solid, which is the product 2-chloro-7-diethylaminoquinoline-3- Formic acid (3). Yield: 81%.

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Abstract

The invention discloses a class of quinoline fluorescent compounds and a preparation method thereof. The structural formula of the compound is wherein X=Cl, OH; R=CHO, CH 2 Any of OH, COOH, CN, CH=NOH. The compound of the present invention uses m-diethylaminoacetanilide as a raw material to carry out Vilsmeier-Hacck reaction to obtain 2-chloroquinoline-3-formaldehyde, and subsequently obtain a series of quinoline derivatives. The reaction conditions are mild and the operation is simple. Through the mutual conversion between groups, the synthesized series of organic materials can adjust the absorption spectrum and emission spectrum of the compound. The compounds disclosed at the same time all have large stroke's shift values ​​and fluorescence quantum yields. Most of the compounds can also emit light in the solid state, and they can be used to develop fluorescent probes, blue light-emitting materials and fluorescent whitening agents.

Description

technical field [0001] The present invention relates to quinoline compounds, in particular to a fluorescent dye based on the 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 antitumor drugs, bioluminescence 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 the characteristics of excellent fluorescence quantum yield, spectral stability, and low cytotoxicity. However, their Stokes shifts are not large enough, and they emit weak or no light in the aggregated state, which affects their wide application in the above-mentioned fields. [0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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