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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 preparation, and lack of structural diversity due to the limitation of synthetic methods in the process of structure expansion.

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

Embodiment 1

[0070] Synthesis of key precursors:

[0071]

[0072] Accurately weigh brominated monomer 1 (7.30g, 14.25mmol), thiazobutyltin salt (16.00g, 42.76mmol), palladium catalyst 0.50g (0.43mmol) and dissolve in 150mL of toluene, under the protection of argon, heat to reflux at 120°C , react for 20h, cool the system to room temperature, remove the reaction solvent by distillation under reduced pressure, extract the system three times with 100mL dichloromethane and water, collect the dichloromethane and wash the organic phase with 200mL saturated brine, dry the organic phase with anhydrous sodium sulfate, concentrate the organic phase to remove Solvent, collected by column chromatography to obtain 6.89g product, yield 93%. [M + ]=521.

Embodiment 2-21

[0074] Examples 2-21 adopt the similar synthesis steps as Example 1, only the reactants are replaced with corresponding reactants. The corresponding reactants and target products and corresponding mass spectrometry detection values ​​and yields are listed in the table now.

[0075]

[0076]

[0077]

[0078]

[0079]

Embodiment 22

[0080] Example 22: Accurately weigh raw material 2a (2.08g, 4.0mmol) and disperse it in 50mL N'N-dimethylformamide solvent, add trifluoroacetic acid (5mL), and add NBS (1.50g 8.42mmol) in 5 times To the reaction system, react at 25°C for 12h, add saturated sodium bicarbonate solution to neutralize trifluoroacetic acid, quench the reaction, distill off most of N'N-dimethylformamide and water under reduced pressure, and extract the system three times with 100mL ethyl acetate , collected ethyl acetate and washed the organic phase with saturated brine, dried the organic phase over anhydrous sodium sulfate, concentrated the organic phase to remove the solvent, collected by column chromatography to obtain 2.24g product, yield 83%, [M + ] = 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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