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N-substituted carbazole-amide room temperature phosphorescent molecules and preparation method and application thereof

A room temperature phosphorescence and carbazole technology, which is applied in the directions of organic chemistry methods, chemical instruments and methods, luminescent materials, etc., can solve the problems of short lifespan of room temperature phosphorescence, and achieve the effects of long phosphorescence lifespan, simple post-processing, and simple synthesis steps.

Active Publication Date: 2017-03-29
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the room temperature phosphorescence lifetime of benzophenone and carbazole is very short. According to the solid matrix room temperature phosphorescence study on the crystals of the two, the room temperature phosphorescence lifetime of benzophenone is only 313 microseconds, and the room temperature phosphorescence lifetime of carbazole is only 313 microseconds. Only 470 milliseconds, therefore, it is necessary to develop an organic room temperature phosphorescent molecule with long room temperature phosphorescence lifetime

Method used

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  • N-substituted carbazole-amide room temperature phosphorescent molecules and preparation method and application thereof
  • N-substituted carbazole-amide room temperature phosphorescent molecules and preparation method and application thereof
  • N-substituted carbazole-amide room temperature phosphorescent molecules and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: the preparation of compound CPM

[0032]

[0033] Aluminum trichloride (1.33 g, 10 mmol) and carbon disulfide (10 mL) were added to the flask, and benzoyl chloride (1.2 mL, 10 mmol) was added dropwise with stirring. After stirring for 20 minutes, a solution of carbazole (0.836 g, 5 mmol) in carbon disulfide (40 mL) was added dropwise through a constant pressure dropping funnel, and the reactor was connected to an exhaust gas absorption device. After reacting at 40°C for three hours, dilute hydrochloric acid was slowly added dropwise to the flask to terminate the reaction, the reaction solution was extracted with dichloromethane (3×40mL), the organic phase was collected, and washed with anhydrous Na 2 SO 4 Dry and remove the solvent to give the crude product. A mixed solvent of petroleum ether and dichloromethane (v / v, 1 / 1) was used as an eluent, separated and purified by silica gel chromatography, and dried in vacuo to obtain a white solid (yield 30%)...

Embodiment 2

[0035] Embodiment 2: the preparation of compound CPM

[0036] Sodium hydride (0.34g, dispersed in mineral oil, content 70%, 9.9mmol) was added to the flask, then a solution of carbazole (0.835g, 5mmol) in DMF (20mL) was added, the reaction was stirred for half an hour, and benzyl was added dropwise Acid chloride (0.9 mL, 7.5 mmol) in DMF (10 mL) and the reaction was stirred overnight. Slowly add water to the reaction solution to terminate the reaction, the reaction solution was extracted with dichloromethane (3 × 40mL), washed with water several times to remove DMF, the organic phase was collected, and washed with anhydrous Na 2 SO 4 Dry and remove the solvent to give the crude product. Using a mixed solvent of petroleum ether and dichloromethane (v / v, 1 / 1) as an eluent, separate and purify using a silica gel column, and dry in vacuo to obtain CPM as a white solid.

Embodiment 3

[0037] Embodiment 3: the preparation of compound CMPM

[0038]

[0039] Sodium hydride (0.34g, dispersed in mineral oil, content 70%, 9.9mmol) was added to the flask, then a solution of carbazole (0.835g, 5mmol) in DMF (20mL) was added, and after stirring for half an hour, 4- Toluyl chloride (1 mL, 7.5 mmol) was dissolved in DMF (10 mL) and the reaction was stirred overnight. Slowly add water to the reaction solution to terminate the reaction, the reaction solution was extracted with dichloromethane (3 × 40mL), washed with water several times to remove DMF, the organic phase was collected, and washed with anhydrous Na 2 SO 4 Dry and remove the solvent to give the crude product. A mixed solvent of ethyl acetate and petroleum ether (v / v, 1 / 20) was used as an eluent, separated and purified by silica gel chromatography, and dried in vacuo to obtain a white solid (yield 49%). 1 H NMR, 13 C NMR, MS and EA characterize the structure, confirm that this white solid is compound C...

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Abstract

The invention discloses a room temperature phosphorescent compound and a preparation method, a single crystal culture method and application thereof in the field of anti-counterfeit. According to the invention, through acylation reaction with the participation of aluminum trichloride or sodium hydride, benzoyl chloride and derivatives thereof react with carbazole, benzoyl or derivatives thereof are connected with carbazole through N atoms, and by changing R groups connected with the benzoyl, three room temperature phosphorescent compounds CPM (R=H), CMPM (R=CH3) and CMOPM (R=OCH3) are obtained, and then the three compounds are cultured into single crystals through a solvent volatilization method by using two solvents with different solubility, boiling point and volatility. The obtained single crystals can be used in the field of anti-counterfeit, and can be matched with a material with better fluorescence-emission ability in use to complete two modes: color reliquid and time reliquid. Especially, the phosphorescence life of the obtained compound CPM at room temperature reaches 748ms, so that the compound CPM can be practically used in the field of anti-counterfeit.

Description

technical field [0001] The invention relates to the preparation of (carbazole) amide compounds by using carbazole, benzoyl chloride and derivatives thereof, crystal cultivation and application in the field of anti-counterfeiting. Background technique [0002] Materials with dual emission functions of fluorescence and phosphorescence simultaneously at room temperature have practical application value in the fields of organic light-emitting diodes, sensing, imaging, and data storage. Organic molecules with conjugation effects can generally emit fluorescence at room temperature. However, molecules capable of emitting phosphorescence at room temperature have been limited to inorganic molecules containing transition metals, because the heavy metal atoms contained in such materials have a strong spin-orbit coupling effect, which is conducive to enhancing the triplet excitons. Intersystem crossing effect, resulting in phosphorescence. But for organic molecules, the transition of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06
CPCC07B2200/13C07D209/86C09K11/06C09K2211/1029
Inventor 李振谢育俊
Owner WUHAN UNIV
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