Aggregation-induced luminescent material containing quinoline and coumarin functional groups and preparation method thereof

A technology of aggregation-induced luminescence, coumarin, applied in luminescent materials, chemical instruments and methods, material analysis by optical means, etc. mild conditions

Active Publication Date: 2021-12-31
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention provides an aggregation-induced luminescence material containing quinoline and coumarin functional groups and Preparation

Method used

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  • Aggregation-induced luminescent material containing quinoline and coumarin functional groups and preparation method thereof
  • Aggregation-induced luminescent material containing quinoline and coumarin functional groups and preparation method thereof
  • Aggregation-induced luminescent material containing quinoline and coumarin functional groups and preparation method thereof

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preparation example Construction

[0037] The specific preparation method of 2-oxo-N'-(2-(quinolin-8-yloxy)acetyl)-2H-benzopyran-3-carboxhydrazide comprises the following steps:

[0038] 1), prepare 2-(quinolin-8-yloxy)ethyl acetate, refer to the literature (Both visual and ratiometricfluorescent sensor for Zn 2+ based on spirobenzopyran platform, Tetrahedron Letters 53 (2012) 2001-2004.) Preparation;

[0039] The reaction equation is:

[0040]

[0041] 2), preparation of 2-(quinolin-8-yloxy)acetylhydrazide, refer to the literature (Both visual and ratiometricfluorescent sensor for Zn 2+ based on spirobenzopyran platform, Tetrahedron Letters 53 (2012) 2001-2004.) Preparation;

[0042] The reaction equation is:

[0043]

[0044] 3), preparation of 2-oxo-N'-(2-(quinolin-8-yloxy)acetyl)-2H-benzopyran-3-carboxhydrazide,

[0045] Dissolve coumarin-3-carboxylic acid, N-hydroxysuccinimide and dicyclohexylcarbodiimide in DMF, react at room temperature for 8h-10h, filter the product with suction, collect the f...

Embodiment 1

[0048]1), add 0.51g 8-hydroxyquinoline (3.5mmol), 0.48g potassium carbonate (3.5mmol) and 10mL acetone in the 25mL there-necked flask that stirring magnet is housed, reflux and stir for 30 minutes; Then 0.83g bromoacetic acid Ethyl ester (5.0mmol) was added to the stirred solution at one time, and then the reaction mixture was refluxed and stirred for 6h; after the reaction was completed, the solvent was spin-off, extracted with ethyl acetate and saturated brine, the combined organic layers were washed with anhydrous magnesium sulfate After drying and evaporation under reduced pressure, the crude product was obtained. Subsequent separation by column chromatography, select ethyl acetate:petroleum ether (1:3) as eluent, obtain 0.65g yellow oily matter 2-(quinolin-8-yloxy)ethyl acetate (2.8mmol), produce Rate 80%.

[0049] 2), 0.23g of 2-(quinolin-8-yloxy)ethyl acetate (1.0mmol) was dissolved in 5mL of methanol, and 0.51g of hydrazine hydrate (10mmol) was added to react at room ...

Embodiment 2

[0052] 1), add 0.51g 8-hydroxyquinoline (3.5mmol), 0.48g potassium carbonate (3.5mmol), 0.83g ethyl bromoacetate (5.0mmol) and 10mL in a 25mL three-necked flask equipped with a stirring magnet. Acetone, and then the reaction mixture was refluxed and stirred for 6 h; after the reaction was completed, the solvent was removed, extracted with ethyl acetate and saturated brine, the organic layers were combined, dried with anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain a crude product, which was separated by column chromatography. Ethyl acetate:petroleum ether (1:3) was used as eluent to obtain 0.51 g of yellow oily ethyl 2-(quinolin-8-yloxy)acetate (2.2 mmol), with a yield of 62%.

[0053] 2), with embodiment 1.

[0054] 3), 0.19g coumarin-3-carboxylic acid (1.0mmol), 0.14g N-hydroxysuccinimide (1.2mmol) and 0.25g dicyclohexylcarbodiimide (1.2mmol) were dissolved in 5mL DMF , react at room temperature for 10 h, filter the product with suction, collect...

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Abstract

The invention belongs to the technical field of organic luminescent materials. In order to solve the technical problems of complex structures of aggregation-induced luminescent materials with specific functions and the high cost of raw materials used in the preparation of the aggregation-induced luminescent materials, it provides a functional compound containing quinoline and coumarin. Aggregation-induced luminescent material of groups, the preparation method of which is as follows: quinoline derivatives and coumarin derivatives are used as raw materials, quinoline derivatives are substituted with ethyl bromoacetate to obtain ethyl acetate containing quinoline functional groups, and quinoline functional group-containing Ethyl acetate is then reacted with hydrazine hydrate to obtain acetyl hydrazide containing quinoline functional groups, and finally the acetyl hydrazide containing quinoline functional groups is reacted with coumarin derivatives to obtain an aggregation-induced luminescent material containing quinoline and coumarin functional groups. The preparation method of the invention is simple to operate, and the reaction conditions are mild. The aggregation-induced luminescence material containing quinoline and coumarin functional groups of the invention has a simple structure, and the raw materials used for the preparation are cheap.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, in particular to an aggregation-induced luminescent material containing quinoline and coumarin functional groups and a preparation method. Background technique [0002] Traditional organic light-emitting materials have strong fluorescence in dilute solution, but in high concentration or solid state, due to the phenomenon of aggregation-quenched fluorescence (ACQ), the fluorescence of these molecules is weak or no light, which limits the application of these materials. application. Aggregation-induced emission (AIE) molecules are just the opposite. They have weak fluorescence or almost no light in good solvents, and the molecules aggregate in poor solvents, and the fluorescence is significantly enhanced. This property makes AIE molecules more versatile in the fields of electronics, optics, and biology. Among the reported AIE molecules, there are tetraphenylethylene derivati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/06G01N21/64
CPCC07D405/12C09K11/06G01N21/643C09K2211/1029C09K2211/1088G01N2021/6417
Inventor 王云侠牛伟平王皓萍冯丽恒
Owner SHANXI UNIV
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