Preparation method of boron-nitrogen-containing small molecules and conjugated macromolecules and application in fluorine ion sensing

A technology of conjugated polymers and small molecules, applied in chemical instruments and methods, compounds containing elements of group 3/13 of the periodic table, analytical materials, etc., to achieve good selectivity, sensitive detection, and high sensitivity

Active Publication Date: 2018-08-17
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although boron-nitrogen (BN)-containing conjugated systems have excellent properties and great development prospects, there are still many difficulties in achieving efficient and simple design and synthesis of boron-nitrogen (BN) compounds

Method used

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  • Preparation method of boron-nitrogen-containing small molecules and conjugated macromolecules and application in fluorine ion sensing
  • Preparation method of boron-nitrogen-containing small molecules and conjugated macromolecules and application in fluorine ion sensing
  • Preparation method of boron-nitrogen-containing small molecules and conjugated macromolecules and application in fluorine ion sensing

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preparation example Construction

[0063] 1. Preparation of boron nitrogen (BN) compound

[0064] (1) Preparation of Compound A

[0065] Under the protection of argon, dissolve 4,4-dibromobiphenyl in absolute anhydrous ether and place it in a Shrek reaction bottle, slowly add n-butyllithium dropwise at -78°C, after the dropwise addition, slowly raise the temperature Keep it at room temperature for 3 hours, then place it at -78°C, dissolve dimethyl tin dichloride in absolute anhydrous ether and slowly add it dropwise to the above solution, slowly warm up to room temperature, continue stirring for 12 hours, and the reaction is complete. Remove the solvent under reduced pressure, add n-hexane and heat to dissolve at 40°C, let it stand for 30 minutes, filter with celite, and remove the solvent under reduced pressure to obtain the target product.

[0066] Its reaction equation is as follows:

[0067]

[0068] (2) Preparation of compound B

[0069] Under the protection of argon, dissolve the tin-containing comp...

Embodiment 1

[0088] (1) Synthesis of compound 1

[0089] Under the protection of argon, dissolve 2,2'-dibromobiphenyl (1g, 3.2mmol) in 30mL of absolute anhydrous ether, place it in a Shrek reaction bottle at -78°C, and slowly add n-butyl Lithium 2.56mL (2.5M, 6.4mmoL), after the dropwise addition is completed, slowly warm up to room temperature and keep for three hours, then place it at -78°C, dissolve dimethyl tin dichloride (0.71g, 3.2mmol) in Slowly add dropwise absolute anhydrous ether to the above solution, slowly raise the temperature to room temperature, and continue to stir for 12 hours. After the reaction is completed, remove the solvent under reduced pressure, add n-hexane to dissolve by heating at 40°C, let it stand for 30 minutes, and filter with diatomaceous earth. The solvent was removed under reduced pressure to obtain the target product.

[0090] (2) Synthesis of compound 2

[0091] Under the protection of argon, dissolve 2,2'-diiodo4,4'-dibromobiphenyl (1.685g, 3.0mmol) ...

Embodiment 2

[0111] According to the method for the synthesis of compound 2 in Example 1, the 2,2'-diiodo4,4'-dibromodiphenyl side chain substituent dibromine is replaced by Cl, and other steps in this step are the same as those in the corresponding Example 1 ( The methods of 2)(4)(6)(7) are the same.

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Abstract

The invention discloses a preparation method of boron-nitrogen-containing small molecules and conjugated macromolecules and application in fluorine ion sensing, and belongs to the technical field of preparation of fluorescent compounds and preparation of fluorescent probes. A boron ring compound is synthesized via BTE (boron-tin-exchange) reaction; the boron ring compound is subjected to ring-expanding reaction via azide molecules by utilizing Lewis acidity of high boron, and a series of boron-nitrogen-containing (BN-containing) small-molecular monomers are prepared; boron-nitrogen-containingconjugated macromolecules are successful prepared via Stille coupling. Both boron-nitrogen-containing small molecules and macromolecules are suitable for colorimetric selective recognition for fluorine ions. The preparation method of the boron-nitrogen-containing fluorescent compound is simple, and has mild reaction conditions; a prepared fluorescent probe has good opto-chemical stability, high sensitivity and good selectivity.

Description

technical field [0001] The invention belongs to the technical field of preparation of fluorescent compounds and fluorescent probes thereof, and specifically relates to a preparation method of a class of boron-nitrogen-containing small molecules and conjugated macromolecules and their application to fluoride ion sensing. Background technique [0002] As an emerging research field, organic optoelectronics is a new interdisciplinary subject that spans chemistry, materials, physics, and information. It has received extensive attention from academia and industry in recent years. At present, the rapid development of organic optoelectronic devices such as organic electroluminescent diodes, organic field effect transistors, organic photovoltaic cells, organic sensors, and organic information storage has demonstrated the incomparable advantages of inorganic semiconductor devices. [0003] In recent years, the impact of fluoride ions on humans has been increasing, because contact with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/22C08G61/12C09K11/06G01N21/64
CPCC07F5/02C08G61/122C08G61/126C08G2261/124C08G2261/18C08G2261/3223C08G2261/3244C08G2261/414C09K11/06C09K2211/1096C09K2211/1458C09K2211/1491G01N21/6428
Inventor 何刚张维东
Owner XI AN JIAOTONG UNIV
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