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A kind of aggregation-induced luminescent fluorescent material and its preparation method

A technology for aggregation-induced luminescence and fluorescent materials, which is used in the preparation of fluorescent materials, and the field of fluorescent materials with aggregation-induced luminescence properties, which can solve the problems of fluorescence quenching and low solid quantum yield, and achieve the effect of good solubility.

Active Publication Date: 2022-05-17
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are many literature reports on mitochondrial biological imaging, and the research on biological imaging has also attracted the interest of scientific researchers. However, traditional fluorescent materials are prone to fluorescence quenching at high concentrations and have low solid quantum yields.

Method used

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  • A kind of aggregation-induced luminescent fluorescent material and its preparation method
  • A kind of aggregation-induced luminescent fluorescent material and its preparation method
  • A kind of aggregation-induced luminescent fluorescent material and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Under nitrogen protection, add 668 μL N,N-dimethylformamide dropwise to 690 μL (8.5 mmol) POCl 3 , stirred at room temperature for 30 min to obtain a red solution, and then added the obtained red solution to 3 mL of N,N-dimethylformamide solution containing 341 mg (1 mmol) N,N-diphenylcoumarin (compound I-1) , stirred the reaction at 60°C for 24h, then added ice water to quench the reaction, adjusted the pH to 5.2 with NaOH, concentrated under reduced pressure, and column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate at a volume ratio of 40:1) liquid), the fluorescent material shown in formula II-1 was obtained, and the yield was 52%.

[0019]

[0020] The structural characterization data of the obtained fluorescent material is: 1 H NMR (300MHz, CDCl 3 )δ10.16(s,1H),8.28(s,1H),7.39(dd,J=12.6,4.9Hz,5H),7.29(s,1H),7.25-7.17(m,5H),6.84(dd ,J=8.8,2.2Hz,1H),6.73(d,J=2.1Hz,1H).

Embodiment 2

[0022] In this example, the N,N-diphenylcoumarin in Example 1 was replaced with an equimolar amount of N,N-xylylcoumarin (compound I-2), and the other steps were the same as in Example 1 , the fluorescent material represented by formula II-2 was obtained, and the yield was 47%.

[0023]

[0024] The structural characterization data of the obtained fluorescent material is: 1 H NMR (300MHz, CDCl 3 )δ10.14(s,1H),8.26(s,1H),7.34(d,J=8.8Hz,1H),7.15(dd,J=28.4,8.3Hz,8H),6.78(dd,J=8.8 ,2.1Hz,1H),6.67(d,J=2.1Hz,1H),2.37(s,6H).

[0025] The inventors tested the aggregation-induced luminescent properties of the fluorescent materials prepared in Examples 1-2 above. %, 99% acetonitrile aqueous solution, adding the fluorescent material into the resulting solution to obtain a concentration of 1×10 -5 mol / L fluorescent material solution, using Hitachi F-7000 fluorescence spectrophotometer to test the aggregation-induced luminescence properties of the fluorescent material, the results a...

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Abstract

The invention discloses a kind of aggregation-induced luminescent fluorescent material and a preparation method thereof. The general structural formula of the fluorescent material is as follows: R represents H, C 1 ~C 4 Alkyl, C 1 ~C 3 Any one of alkoxy and halogen, which is prepared by reacting N,N-diaryl coumarin with phosphorus oxychloride. Based on the simple skeleton of N,N-diaryl coumarin, the invention synthesizes a series of fluorescent materials with aggregation-induced luminescence by reacting with phosphorus oxychloride. The emission wavelength of this kind of fluorescent material can range from 550nm to 578nm. It has good solubility in organic solvents, but is almost insoluble in water. It can form aggregates in the aqueous phase and has significant aggregation-induced luminescence characteristics. , tissue and bacteria imaging, protein glycosylation analysis, and ion detection.

Description

technical field [0001] The invention belongs to the technical field of fluorescent materials for biomedicine, and in particular relates to a fluorescent material with aggregation-induced luminescence properties and a preparation method of the fluorescent material. Background technique [0002] Fluorescent materials have attracted great attention of scientists in recent years due to their great application value in optoelectronic devices, environmental sensors, biological sciences and other fields. Fluorescence detection not only has high sensitivity, but also overcomes a series of problems that require expensive and difficult-to-operate radioactive tracing reagents in biochemical experiments. Fluorescence imaging reveals the localization and measurement of molecules within cells, and sometimes enables detection at the single-molecule level. At present, there are many literature reports on mitochondrial bioimaging, and bioimaging research has also attracted the interest of s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06G01N21/6428G01N21/643C09K2211/1007C09K2211/1088
Inventor 李楠赵娜尹伟
Owner SHAANXI NORMAL UNIV
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