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Preparation method and application of dicarbazole and derivative thereof

A technology for biscarbazole and derivatives is applied in the field of preparation of biscarbazole and its derivatives, which can solve the problems of high cost, complicated post-processing and purification, low yield and the like, and achieves low cost, simple post-processing process and high yield. high rate effect

Inactive Publication Date: 2021-11-02
陕西维世诺新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Based on the current problems of complex purification, low yield and high cost in the preparation and post-processing of biscarbazole and its derivatives, the application provides a preparation method of biscarbazole and its derivatives

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  • Preparation method and application of dicarbazole and derivative thereof

Examples

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Embodiment 1

[0038] This embodiment provides a method for preparing a biscarbazole luminescent material, specifically, the method includes the following steps:

[0039] (1) Under the protection of nitrogen, 560g of phenylhydrazine hydrochloride (molecular weight 144.60, 3.87mol), 200g of 1,3-cyclohexanedione (molecular weight 112.13, 1.78mol), and 3000mL of ethanol were added to the , in the reaction bottle of the reflux condenser (mainly for reflux condensation), thermometer (mainly for temperature monitoring) and oil bath heating device (mainly for heating the reaction). Slowly add 20 g of concentrated sulfuric acid (molecular weight 98, 0.20 mol) dropwise, heat up to 80°C, react for 4 hours and end the reaction, cool to room temperature, then filter, wash with ethanol (to remove impurities adsorbed on the solid material) to obtain a brown solid W1 ((1E,3E)-1,3-bis(2-phenylhydrazino)cyclohexane) 521.5g (molecular weight 292.39, 1.78mol); yield was 100%, MS(FAB): m / z 292( M+);

[0040] ...

Embodiment 2

[0044] This example provides a preparation method of biscarbazole luminescent material (5-phenyl-12-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)-5,12-diindole And [3,2-a] carbazole), specifically, the method comprises the steps:

[0045] (1) Under the protection of argon, mix 194g of phenylhydrazine hydrochloride (molecular weight 144.60, 1.34mol), 100g of 1,3-cyclohexanedione (molecular weight 112.13, 0.89mol), the ratio of which is not within the above range, and ethanol 1000m L , into the reaction flask with mechanical stirring, reflux condenser, thermometer and oil bath heating device. Slowly add 10 g of concentrated sulfuric acid (molecular weight 98.08, 0.10 mol) dropwise, heat up to 80°C, react for 4 hours and end the reaction, cool to room temperature, then filter, wash with ethanol, and purify with column chromatography to obtain 117.10 g of brown solid W1 ( Molecular weight 292.39, 0.40mol); The yield is 45%, MS (FAB): m / z 292 (M+);

[0046] (2) Under the protection of arg...

Embodiment 3

[0050] This embodiment provides a method for preparing a biscarbazole luminescent material, specifically, the method includes the following steps:

[0051] (1) Under the protection of nitrogen, mix 386.08g of phenylhydrazine hydrochloride (molecular weight 144.60, 2.67mol), 100g of 1,3-cyclohexanedione (molecular weight 112.13, 0.89mol), the proportion is not within the above range, ethanol 1000m L , into the reaction flask with mechanical stirring, reflux condenser, thermometer and oil bath heating device. 10 g of concentrated sulfuric acid was slowly added dropwise, the temperature was raised to 80 ° C, the reaction was completed after 4 hours of reaction, cooled to room temperature, then filtered and washed with ethanol to obtain 234.20 g of brown solid W1 (molecular weight 292.39, 0.80 mol); the yield was 90%, MS (FAB): m / z 292 (M+);

[0052] (2) Under the protection of nitrogen, W1, 100g (molecular weight 292.39, 0.34mol), trifluoroacetic acid 116.30g (molecular weight 1...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method and application of dicarbazole and derivatives thereof. At present, the preparation of dicarbazole and derivatives thereof is complicated in post-treatment purification, low in yield and high in cost. The invention provides a preparation method of dicarbazole and derivatives thereof. The preparation method comprises the following steps: carrying out condensation reaction on 1, 3-cyclohexanedione and phenylhydrazine hydrochloride to prepare W1; carrying out cyclization reaction on the W1 to obtain W2; carrying out the coupling of the W2 with iodobenzene to prepare W3; and carrying out the coupling of the W3 with 9-(4-bromophenyl)-9-phenyl fluorene to prepare the dicarbazole or the dicarbazole derivative. The method has the advantages of mild reaction conditions, simple post-treatment purification, high yield and low cost.

Description

technical field [0001] The application belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method and application of biscarbazole and its derivatives. Background technique [0002] Halides at different substituent positions on carbazole were prepared by different methods. At present, 3-bromocarbazole, 2-bromocarbazole, 1-bromocarbazole, 4-bromocarbazole and other carbazole derivatives have been widely reported. Most of its synthetic methods are obtained by direct bromination, cardogen ring closure or Fischer indole synthesis. [0003] At present, the preparation, post-treatment and purification of biscarbazole and its derivatives are complex, low yield and high cost. Contents of the invention [0004] 1. Technical problems to be solved [0005] Based on the current problems of complex purification, low yield, and high cost in the post-preparation and post-treatment purification of biscarbazole and its derivatives, the...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 吕钟闫喜亮
Owner 陕西维世诺新材料有限公司
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