Organic molecule containing boron-nitrogen coordination bond and preparation method thereof

An organic molecule and coordination bond technology, applied in the field of organic molecules containing boron-nitrogen coordination bonds and their preparation, can solve the problems of low yield of key steps, long synthesis route, lack of structural diversity, etc., and achieve good application Effects of foreground, fewer synthesis steps, small Stokes shift

Pending Publication Date: 2022-03-01
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing boron-nitrogen compounds have the problem of long synthetic routes or low yields of key steps in the process of p

Method used

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  • Organic molecule containing boron-nitrogen coordination bond and preparation method thereof
  • Organic molecule containing boron-nitrogen coordination bond and preparation method thereof
  • Organic molecule containing boron-nitrogen coordination bond and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0069] Example 1:

[0070] Key precursor synthesis:

[0071]

[0072] The exact weighed monomer 1 (7.30 g, 14.25 mmol) was dissolved with thiazol butyl tin salt (16.00 g, 42.76 mmol), and a palladium catalyst was dissolved in 150 ml of toluene, and the argon was protected, 120 ° C was heated and refluxed. , The reaction is 20 h, the system is cooled to room temperature, and the reaction solvent is removed. Solvents, column chromatography collected from 6.89 g of product, yield 93%. [M + ] = 521.

Example Embodiment

[0073] Example 2-21

[0074] Example 2-21 The synthesis step similar to that of Example 1 is used to replace only the reaction to the corresponding reactants. The corresponding reactants and target products are now listed in the table in the table.

[0075]

[0076]

[0077]

[0078]

[0079]

Example Embodiment

[0080] Example 22: Accurate Weighing Raw Material 2a (2.08 g, 4.0 mmol) is dispersed in a 50 mln-dimethylformamide solvent, and trifluoroacetic acid (5 ml) is added, and NBS (1.50 g 8.42 mmol) is added 5 times. To the reaction system, at 25 ° C for 12 h, a saturated sodium hydrogencarbonate solution and trifluoroacetic acid, quenched reaction, and remove most of N'N-dimethylformamide and water, 100 mL of ethyl acetate extract system three times. Ethyl acetate was washed with EtOAc EtOAc EtOAc EtOAc. + ] = 677.

[0081]

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Abstract

The invention relates to an organic molecule containing a boron-nitrogen coordination bond and a preparation method of the organic molecule, and particularly belongs to the field of organic compound synthesis and organic dyes. The organic molecule containing the boron-nitrogen coordination bond is shown as a formula (I) and a formula (II) and is a novel boron-nitrogen coordination bond basic building unit derivatization organic molecule, the preparation process is simple and easy to implement, rich structure expansion can be achieved by selecting and coupling different substituent groups containing coordination nitrogen atoms and central nuclei, and the organic molecule containing the boron-nitrogen coordination bond can be used for preparing the organic molecule containing the boron-nitrogen coordination bond. And abundant structural selectivity is provided for functional derivation of the compound. Meanwhile, based on the characteristics of narrow band gap, molecular skeleton planarity, narrow emission spectrum and the like of the boron-nitrogen coordination bond unit, the derivative of the boron-nitrogen coordination bond unit has good application potential in the fields of organic photoelectric devices, fluorescence labeling, biological imaging and the like.

Description

technical field [0001] The invention relates to the technical fields of organic compound synthesis and organic dyes, in particular to an organic molecule containing a boron-nitrogen coordination bond and a preparation method thereof. Background technique [0002] Organoboron compounds, especially organic molecules containing boron-nitrogen coordination bonds, have good planarity, delocalized π electrons on the conjugated skeleton, and Strong visible to near-infrared light absorption and fluorescent properties. It is widely used in optoelectronic devices such as organic light-emitting diodes, organic solar cells, organic field-effect transistors, photodetectors, and organic thermoelectrics. At the same time, it also has important applications in biological cell imaging, ion detection fluorescent probes, etc. [0003] However, the types of organoboron compounds containing boron-nitrogen coordination bonds are still limited to derivatives of several compounds. The existing b...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06
CPCC07F5/022C07F5/02C09K11/06C09K2211/1085
Inventor 刘俊邵兴鑫王利祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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