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Aggregation-induced emission type fluorescent materials, preparation method and application

A technology of aggregation-induced luminescence and fluorescent materials, applied in the application field of labeling lipid droplets, can solve the problems of fluorescence quenching and low solid quantum yield, and achieve good biocompatibility

Inactive Publication Date: 2019-06-21
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are many literature reports on lipid droplet bioimaging, and the study of bioimaging has also attracted the interest of scientific researchers, but traditional fluorescent materials are prone to fluorescence quenching at high concentrations and have low solid quantum yields.

Method used

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  • Aggregation-induced emission type fluorescent materials, preparation method and application
  • Aggregation-induced emission type fluorescent materials, preparation method and application
  • Aggregation-induced emission type fluorescent materials, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1. In a nitrogen atmosphere, add 2mL (17.86mmol) m-aminoanisole, 10mL (89.3mmol) iodobenzene, 10g (89.1mmol) potassium tert-butoxide into 30mL toluene, then add 644mg (3.572mmol) 1, 10-phenanthroline and 680 mg (3.572 mmol) of cuprous iodide were reacted under reflux at 125° C. for 24 hours, and purified by column chromatography (pure petroleum ether as the eluent) to obtain compound I with a yield of 75%.

[0040]

[0041] 2. Dissolve 2g (7.27mmol) of compound I in 10mL of dry dichloromethane, then add 5mL of dichloromethane solution containing 1.03mL (10.9mmol) boron tribromide under an ice bath, then connect a condenser tube to condense Connect the drying tube on the tube, stir the reaction for 24 hours after naturally warming up to normal temperature, add water to quench after the reaction is completed, spin off the dichloromethane, extract with ethyl acetate and water, then column chromatography (eluent is petroleum ether and acetic acid Ethyl ester volume ratio...

Embodiment 2

[0049]In step 4 of this embodiment, the p-fluoroaniline in embodiment 1 is replaced with equimolar p-methoxyaniline (formula IV-2), and the other steps are the same as in embodiment 1 to obtain the fluorescent material shown in VI-2, Its yield is 35%.

[0050]

[0051] The structural characterization data of the obtained fluorescent material is: 1 H NMR (300MHz, DMSO) δ8.78(s, 1H), 7.67-7.17(m, 13H), 7.05(d, J=8.7Hz, 2H), 6.41(d, J=7.4Hz, 1H), 6.05 (s,1H),3.80(s,3H).

Embodiment 3

[0053] In step 4 of this embodiment, the p-fluoroaniline in embodiment 1 is replaced with equimolar p-cyanoaniline (formula IV-2), and the other steps are the same as in embodiment 1 to obtain the fluorescent material shown in VI-3, which The yield was 32%.

[0054]

[0055] The structural characterization data of the obtained fluorescent material is: 1 H NMR (300MHz, CDCl 3 )δ8.13(s,1H),7.75(d,J=8.7Hz,2H),7.64(d,J=8.5Hz,2H),7.41(t,J=7.6Hz,4H),7.29(d, J=7.4Hz, 2H), 7.23(dd, J=11.0, 3.7Hz, 5H), 6.51(dd, J=8.9, 2.2Hz, 1H), 6.42(d, J=1.9Hz, 1H).

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Abstract

The invention discloses aggregation-induced emission type fluorescent materials, a preparation method and an application. The general structural formula of the fluorescent materials is shown in the description, wherein R represents a hydrogen atom, cyano group, halogen, C1-C4 alkyl, C1-C3 alkoxy, hydroxyl or N,N-dimethyl. The fluorescent materials are formed as follows: a salicylaldehyde derivative and para-substituted aniline are used as raw materials, and intermediate imine is obtained through a simple dehydration condensation reaction and then subjected to a reaction with boron trifluoridediethyl etherate. The fluorescent materials have the aggregation-induced emission characteristic, can specifically mark lipid droplets in living cells and are excellent lipid droplet imaging dyes.

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, a preparation method of the fluorescent material and an application in marking lipid droplets. 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 reports on biological imaging of lipid droplets, and the research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
Inventor 赵娜李楠马诚成
Owner SHAANXI NORMAL UNIV
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