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Organic fluorescent small molecular material and preparation method and application thereof in fluorescence detection

A fluorescence detection and small molecule technology, applied in the field of fluorescence sensing, can solve the problems of long detection time, large-scale instruments, and complicated operations.

Active Publication Date: 2020-04-14
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Similarly, these techniques generally have disadvantages such as cumbersome preparation, complicated operation, long detection time, and large-scale instruments.

Method used

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  • Organic fluorescent small molecular material and preparation method and application thereof in fluorescence detection
  • Organic fluorescent small molecular material and preparation method and application thereof in fluorescence detection
  • Organic fluorescent small molecular material and preparation method and application thereof in fluorescence detection

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preparation example Construction

[0048] The present invention also provides a method for preparing the organic fluorescent small molecule material described in the above technical solution, comprising the following steps:

[0049] performing a Buchwald-Hartwig reaction on the compound having the structure shown in formula II and the first organic substance to obtain the organic fluorescent small molecule material shown;

[0050] The first organic compound is carbazole, phenothiazine, phenoxazine, diphenylamine, triphenylamine, benzene, biphenyl, fluorene or a derivative of fluorene;

[0051]

[0052]

[0053] Where: X is H, Cl or Br.

[0054] Unless otherwise specified, the raw materials used in the present invention are all commercially available products well known in the art or prepared by preparation methods well known to those skilled in the art.

[0055] In the present invention, the Buchwald-Hartwig reaction is preferably carried out in the presence of a catalyst, a solvent, an alkaline reagent an...

Embodiment 1

[0078] The synthesis of compound TTPA-TAZ, the reaction principle is shown in the following formula:

[0079]

[0080] Under the protection of argon, add palladium acetate Pd(OAc) into the 100mL two-necked bottle 2 (38mg, 0.1728mmol), tri-tert-butylphosphine t-Bu 3 P (104mg, 0.5184mmol) and 30mL of toluene, stirred in the room for 15min, palladium acetate and tri-tert-butylphosphine to form a new phosphine plus palladium complex, add 50mL of toluene, and then add the above monomer A1 (3.1g, 5.76mmol) in sequence , Sodium tert-butoxide NaOBu-t (1.99g, 17.28mmol), diphenylamine B1 (3.50g, 20.68mmol), heated to 110°C with stirring, stopped after 36h, and cooled to room temperature. Extract with dichloromethane and water, wash with water, collect the organic layer, wash with anhydrous MgSO 4 Dry, then place in a vacuum oven to dry. The crude product was purified by column chromatography and further recrystallized from dichloromethane and ethanol to give C1 as a white solid. ...

Embodiment 2

[0082] The synthesis of compound 3CZ-TAZ, the reaction principle is shown in the following formula:

[0083]

[0084] Under the protection of argon, add palladium acetate Pd(OAc) into the 100mL two-necked bottle 2 (38mg, 0.1728mmol), tri-tert-butylphosphine t-Bu 3 P (104mg, 0.5184mmol) and 30mL toluene, stirred at room temperature for 15min, palladium acetate and tri-tert-butylphosphine complex, add 50mL toluene, then add the above monomer A1 (3.1g, 5.76mmol), sodium tert-butoxide in sequence NaOBu-t (1.99g, 17.28mmol), carbazole B2 (3.47g, 20.68mmol), heated to 110°C with stirring, stopped after 36h, and cooled to room temperature. Extract with dichloromethane and water, wash with water, collect the organic layer, wash with anhydrous MgSO 4 Dry, then place in a vacuum oven to dry. The crude product was purified by column chromatography and further recrystallized from dichloromethane and ethanol to afford white solid C2. 1 H NMR (500MHz, CD 2 Cl 2 )8.24(d, J=7.64Hz, 2...

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Abstract

The invention provides an organic fluorescent small molecular material and a preparation method and application thereof in fluorescence detection, and belongs to the field of fluorescence sensing. According to the organic fluorescent small molecular material provided by the invention, the whole molecular skeleton is composed of 4H-1, 2, 4-triazole, a unit A, a unit B and a unit C, so that the organic fluorescent small molecular material has good electron transmission capability and high fluorescence efficiency; the 4H-1, 2, 4-triazole unit and the A / B unit not only serve as light-emitting construction units of the molecules, but also can be subjected to electron transfer or molecular recognition with different types of to-be-detected objects, so that the purpose of integrated detection ofvarious dangerous goods is achieved; compared with the prior art, the rigidity is high, a certain torsion angle is formed between every two adjacent structure units, intramolecular and intermolecularcavities can be formed, permeation and diffusion of molecules of a to-be-detected object are facilitated, sufficient contact and reaction between a film and molecules of the detected object can be improved, and explosion prevention and chemical prevention can be achieved at the same time.

Description

technical field [0001] The invention relates to the technical field of fluorescence sensing, in particular to an organic fluorescent small molecule material, a preparation method thereof and an application in fluorescence detection. Background technique [0002] Since the advent of explosives, they have been widely used in wars and various terrorist attacks because of their extreme destructiveness. Among them, nitro explosives, especially 2,4,6-trinitrotoluene (TNT) and 2,4-dinitrotoluene (DNT) have the characteristics of huge destructive power, strong power and safe storage. Nowadays, liquid explosives, especially peroxide explosives, are attracting more and more attention because of their extremely sensitive, explosive and powerful characteristics. In addition, explosives are not only extremely destructive, but the residues after the explosion will also cause serious pollution to the environment (such as water pollution and land pollution, etc.), which will further enter ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D403/14C07D403/10C09K11/06G01N21/64
CPCC07D249/08C07D403/10C07D403/14C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1059G01N21/643G01N2021/6432
Inventor 李峰张明郑平
Owner JILIN UNIV
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