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Benzophenanthrene asymmetrical disk compound and preparation method thereof

A triphenylene and asymmetric technology, applied in the field of new triphenanthrene-like discotic compounds and their preparation, can solve the problems of few and few luminescent materials of derivatives of triphenanthrene, and achieve good organic electrophoresis The effect of luminescent effect

Inactive Publication Date: 2012-06-27
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are few studies on triphenanthrene derivatives used in luminescent materials, especially on asymmetric triphenylene derivatives.

Method used

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  • Benzophenanthrene asymmetrical disk compound and preparation method thereof
  • Benzophenanthrene asymmetrical disk compound and preparation method thereof
  • Benzophenanthrene asymmetrical disk compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment one : Synthesis and Characterization of Compound 1

[0032]

[0033] 1: Friedel-Crafts acylation reaction of triphenylene: Dissolve 21.90mmol triphenylene (5.00g) in 60mL dichloromethane and put it in a 250mL one-necked bottle, add 23.00mmol p-benzoyl chloride (3.23g) , cooled to 0 degrees Celsius in an ice bath, gradually added 31.30mmol of aluminum oxide (4.17g); heated to reflux for 10 hours; the product was cooled and poured into 500mL of ice water and stirred overnight, extracted with dichloromethane, and the organic phase was passed through After drying and filtering with magnesium sulfate in water, it was purified with a silica gel column (the developer was a 1:1 mixed solvent of petroleum ether and dichloromethane) to obtain 3.25 g of benzoyl chloride-substituted triphenylene as a pale yellow solid, with a yield of 45%.

[0034]2: bromination reaction: 3.00mmol benzoyl chloride-substituted triphenylene (1.00g) obtained in step 1 was dissolved in ...

Embodiment 2

[0039] Embodiment two : Synthesis and Characterization of Compound 2

[0040]

[0041] 1: Friedel-Crafts acylation reaction of triphenylene: Dissolve 21.90mmol triphenylene (5.00g) in 60mL dichloromethane and put it in a 250mL one-necked bottle, add 23.00mmol p-benzoyl chloride (3.23g) , cooled to 0 degrees Celsius in an ice bath, gradually added 31.30mmol of aluminum oxide (4.17g); heated to reflux for 10 hours; the product was cooled and poured into 500mL of ice water and stirred overnight, extracted with dichloromethane, and the organic phase was passed through After drying and filtering with magnesium sulfate in water, it was purified with a silica gel column (the developer was a 1:1 mixed solvent of petroleum ether and dichloromethane) to obtain 3.25 g of benzoyl chloride-substituted triphenylene as a pale yellow solid, with a yield of 45%.

[0042] 2: bromination reaction: 3.00mmol benzoyl chloride-substituted triphenylene (1.00g) obtained in step 1 was dissolved in...

Embodiment 3

[0046] Embodiment three : Synthesis and Characterization of Compound 3

[0047]

[0048] 1: Friedel-Crafts acylation reaction of triphenylene: Dissolve 21.90mmol triphenylene (5.00g) in 60mL dichloromethane and put it in a 250mL one-necked bottle, add 23.00mmol p-benzoyl chloride (3.23g) , cooled to 0 degrees Celsius in an ice bath, gradually added 31.30mmol of aluminum oxide (4.17g); heated to reflux for 10 hours; the product was cooled and poured into 500mL of ice water and stirred overnight, extracted with dichloromethane, and the organic phase was passed through After drying and filtering with magnesium sulfate in water, it was purified with a silica gel column (the developer was a 1:1 mixed solvent of petroleum ether and dichloromethane) to obtain 3.25 g of benzoyl chloride-substituted triphenylene as a pale yellow solid, with a yield of 45%.

[0049] 2: bromination reaction: 3.00mmol benzoyl chloride-substituted triphenylene (1.00g) obtained in step 1 was dissolved ...

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Abstract

The invention relates to a benzophenanthrene asymmetrical disk compound and a preparation method thereof, belonging to the technical field of organic synthesis. The structure of the compound is shown in a figure in the specifications, wherein n is an integer ranging from 1 to 20. The preparation method of the compound comprises a friedel-crafts acylation of benzophenanthrene, a bromination reaction, a Sonogashira coupling reaction, a trimethyl silicane removing reaction or a bromo-chain connecting reaction and a click chemical reaction. The benzophenanthrene asymmetrical disk compound prepared with the method has a special disk conjugated structure, so that the compound has a good photoluminescence effect. Moreover, the benzophenanthrene asymmetrical disk compound has high side chain modification property, so that the compound can be connected with different conjugate groups and chromophore, and great help is provided for the preparation of a novel efficient luminous material. The compound has wide use.

Description

technical field [0001] The present invention relates to a novel triphenylene-like discotic compound and its preparation method, in particular to an asymmetric triphenylene-like discotic organic compound with relatively large π-electron conjugated system and its preparation method. Background technique [0002] The triphenylene compound composed of three benzene rings was first isolated from the pyrolysis product of benzene, and was first called Triphenylene (triphenylene) by Schultz. Triphenylene has good optical and electrical properties due to its special structure. At present, with the breakthrough of organic and polymers in the field of optoelectronics, people pay more and more attention to triphenylene derivatives with special structures, and more and more studies are being made on the synthesis of triphenylene and its derivatives. [0003] In the field of luminescence, the research of organic materials has been paid more and more attention by people. Because there a...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07C255/42C07C253/30C09K11/06
Inventor 杨洲弥永胜王冬梁蓬霞金召奎杜政才
Owner UNIV OF SCI & TECH BEIJING
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