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Method for synthesis of hexa-cata-hexabenzocoronene and derivatives thereof

A technology of benzophenone and its derivatives, which is applied in the field of synthesis of hexabenzophenone compounds and their derivatives, achieving the effects of mild reaction conditions and convenient operation

Inactive Publication Date: 2015-11-18
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the above-mentioned synthetic method of hexabenzophenone and its derivatives, and provide a kind of raw material that is cheap and easy to obtain, with simple and convenient synthesis steps, less environmental pollution, mild conditions, mass production and yield. Synthetic method of hexabenzophenone and its derivatives with high efficiency and no need for alkoxy group as directing group

Method used

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  • Method for synthesis of hexa-cata-hexabenzocoronene and derivatives thereof
  • Method for synthesis of hexa-cata-hexabenzocoronene and derivatives thereof
  • Method for synthesis of hexa-cata-hexabenzocoronene and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Taking the synthesis of hexabenzophenone with the following structural formula as an example, the specific synthesis method is as follows:

[0028]

[0029] 1. Friedel-Crafts acylation reaction

[0030] Add 2.19g (10mmol) of o-bromobenzoyl chloride and 50mL of dry dichloromethane to a 100mL three-necked flask, and add 1.33g (10mmol) of aluminum trichloride and 8.59g (11mmol) of benzene at 0°C under the protection of argon. , stirred at room temperature for 3 hours, quenched the reaction with saturated ammonium chloride, extracted three times with dichloromethane, combined the organic phases, dried with anhydrous sodium sulfate, and removed the solvent by rotary evaporation. The volume ratio of petroleum ether to ethyl acetate was The 10:1 mixed solution was used as a developing solvent to separate the product by column chromatography to obtain 2-bromobenzophenone with the following structural formula, and the yield was 98.2%.

[0031]

[0032] 2. Boronation react...

Embodiment 2

[0048] Taking the synthesis of 2,10,18-trimethylhexabenzophenone with the following structural formula as an example, the specific synthesis method is as follows:

[0049]

[0050] 1. Friedel-Crafts acylation reaction

[0051] Add 2.19g (10mmol) of o-bromobenzoyl chloride and 50mL of dry dichloromethane into a 100mL three-necked flask, add 1.33g (10mmol) of anhydrous aluminum trichloride at 0°C under the protection of argon, and stir the reaction until the trichloride Aluminum chloride was completely dissolved, then added 1.01g (11mmol) toluene to the mixed solution, stirred and reacted at 0°C for 3 hours, the solution turned from yellow to orange, TLC tracked and monitored no raw material point, quenched the reaction with saturated aqueous ammonium chloride solution to Neutral, extracted three times with dichloromethane, combined the organic phases, dried over anhydrous sodium sulfate, removed the solvent by rotary evaporation, and used the mixed solution of petroleum ethe...

Embodiment 3

[0069] Taking the synthesis of 2,10,18-trimethoxyhexabenzophenone with the following structural formula as an example, the specific synthesis method is as follows:

[0070]

[0071] 1. Friedel-Crafts acylation reaction

[0072] In step 1 of Example 2, the toluene used was replaced with equimolar anisole, and the reaction was stirred at 0°C for 2 hours. The other steps were the same as in Example 2 to obtain a white powder compound (2-bromophenyl ) (4-methoxyphenyl)methanone with a yield of 90.5%.

[0073]

[0074] 2. Boronation reaction

[0075] In step 2 of Example 1, the 2-bromobenzophenone used is replaced with equimolar (2-bromophenyl) (4-methoxyphenyl) ketone, and other steps are the same as in Example 1, A white powdery solid compound 2-(4-methoxy)benzoylphenylboronic acid pinacol ester with the following structural formula was obtained with a yield of 90.7%.

[0076]

[0077] 3. Coupling reaction

[0078] In step 3 of Example 1, the 2-benzoylphenylboronic a...

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Abstract

The invention discloses a method for synthesis of hexa-cata-hexabenzocoronene and derivatives thereof. The method comprises the steps: with 2-bromobenzoyl chloride as a raw material, carrying out a friedel-crafts acylation reaction and a boronation reaction with benzene or a substituent benzene to obtain 2-benzoyl benzeneboronic acid pinacol ester and derivatives thereof, further, carrying out a Suzuki coupling reaction with 1,3,5-tris(bromomethyl)benzene to construct a c-HBC skeleton-1,3,5-tris(((2-benzoyl)phenyl)methyl)benzene and derivatives thereof, and then successively carrying out a reduction reaction, a friedel-crafts reaction and a Scholl cyclization reaction to synthesize the hexa-cata-hexabenzocoronene and the derivatives thereof. The method is mild in reaction conditions and convenient to operate, enables the highest total yield of the products to reach more than or equal to 80%, and can be used for mass production; the synthesized hexa-cata-hexabenzocoronene and the derivatives thereof have no need of alkoxy as a guidance group and a positioning group; and the method is a simple and convenient method for synthesis of the hexa-cata-hexabenzocoronene and the derivatives thereof.

Description

technical field [0001] The invention belongs to the technical field of synthesis of polycyclic aromatic hydrocarbon compounds, and in particular relates to a synthesis method of a hexa-cata-hexabenzocorone (c-HBC) compound and derivatives thereof. Background technique [0002] The aromatic nuclei of c-HBC and its derivatives are distorted, and the distorted carbon atoms near the central carbon atom of the plane deviate from the plane by 20° due to space crowding. The structure is in a biconcave conformation, which can be combined with some special compounds, such as C 60 , forming geometrically complementary complexes. c-HBC also has structural units of linear acenes, which are well-known electronic materials. In addition, the discoid structure of c-HBC makes it a potential columnar liquid crystal core with good electron transport and good photoluminescence effect. Diodes have a wide range of potential applications. [0003] The Clar research group first reported the syn...

Claims

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Application Information

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IPC IPC(8): C07C15/20C07C1/20C07C43/20C07C41/18
Inventor 魏俊发卢琼琼李靖彭汗青杨奕辉施东辉程昆木
Owner SHAANXI NORMAL UNIV
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