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Preparation method of 2,3,6,7,10,11-substituted benzophenanthrene

A technology of triphenylene and o-dialkoxybenzene, which is applied in the field of liquid crystal materials and organic photoelectric functional materials, can solve the problems of high price and unsuitability for mass production, and achieve easy mass production, shortened reaction time, and good location regularity effect

Inactive Publication Date: 2013-04-17
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The researchers found that MoCl 5 , VOCl 3 etc. can effectively improve the yield of triphenylene, but it is expensive and not suitable for mass production

Method used

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  • Preparation method of 2,3,6,7,10,11-substituted benzophenanthrene
  • Preparation method of 2,3,6,7,10,11-substituted benzophenanthrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Put 2mmol 0.44g of o-dibutoxybenzene and 8mmol 1.30g powder anhydrous ferric chloride into a glass mortar, and grind it with a mortar for about 0.5 hours at room temperature. There is no obvious irritating gas in the mortar. The mixture was poured into ethanol containing 5% hydrochloric acid, stirred for 5 minutes, and the filtered precipitate was left to dry to obtain the primary product of 2,3,6,7,10,11-hexa-substituted triphenylene.

[0031] First add 2 mL of dichloromethane to the crude product to dissolve it, then add 10 mL of ethanol for precipitation, collect the precipitate and recrystallize with ethanol to finally obtain 0.41 g of a purple flaky solid with a yield of 93%.

[0032] Such as figure 1 , the chemical structure of the product was confirmed by H NMR and C NMR spectra.

Embodiment 2

[0034] Put 2mmol 0.44g of o-dibutoxybenzene and 4mmol 0.65g of powdered anhydrous ferric chloride into a glass mortar, grind with a mortar for 0.5 hours at room temperature, no obvious irritating gas is released in the mortar, The mixture was poured into ethanol containing 2% hydrochloric acid, stirred for 5 minutes, and the filtered precipitate was left to dry to obtain the primary product of 2,3,6,7,10,11-hexa-substituted triphenylene.

[0035] First add 2 mL of chloroform to the crude product to dissolve it, then add 10 mL of ethanol for precipitation, collect the precipitate and recrystallize with ethanol to finally obtain 0.25 g of a purple flaky solid with a yield of 56%.

[0036] The chemical structure of the product was confirmed by NMR spectrum and Fourier transform infrared spectrum.

Embodiment 3

[0038] Put 2mmol 0.44g of o-dibutoxybenzene and 6mmol 0.98g of powdered anhydrous ferric chloride into a glass mortar, grind with a mortar for 40min at room temperature, no obvious irritating gas is released in the mortar, and put The mixture was poured into ethanol containing 3% hydrochloric acid, stirred for 5 minutes, and the filtered precipitate was left to dry to obtain the primary product of 2,3,6,7,10,11-hexa-substituted triphenylene.

[0039] Add 2 mL of chloroform to the crude product to dissolve it, and then add 10 mL of ethanol for precipitation. After the precipitate was collected, it was recrystallized with ethanol to finally obtain 0.36 g of a purple flaky solid with a yield of 82%.

[0040] The chemical structure of the product was confirmed by NMR spectrum and Fourier transform infrared spectrum.

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Abstract

The invention relates to a preparation method of benzophenanthrene with substituent groups as alkoxy, belonging to the field of organic optoelectronics functional materials. The preparation method comprises the steps of: grinding monomer 5,6-alkoxyl benzene and anhydrous FeCl3 into mixed powder at room temperature to obtain a primary product; and 2, dissolving by using an organic solvent, adding an alcohols solvent with 4-5 times of weight by volume the organic solvent, stirring uniformly, standing and depositing, recrystallizing, and carrying out secondary drying to obtain a final product. Compared with the traditional solution oxidization coupling reaction, the invention reduces the environment pollution, lowers the production cost, has short reaction time for only 20-40min so that the production efficiency is improved, and improves the yield of reaching up to more than 90 percent. The obtained alkoxyl benzophenanthrene has a coil liquid crystal structure which has the characteristics of one-dimensional electron migration and energy transmission, electroluminescence effect, ferroelectric properties, surface self-assembly and the like. The benzophenanthrene can be used for light storage, solar cells, liquid crystal display materials, electronic transmission, LB membranes and the like.

Description

technical field [0001] The invention relates to a method for preparing a triphenylene whose substituent is an alkoxy group, and belongs to the field of organic photoelectric functional materials, in particular to the field of liquid crystal materials. Background technique [0002] Since Mannich synthesized triphenylene for the first time in 1907, the synthesis of various triphenylene and similar fused ring derivatives has aroused extensive interest of researchers. Dimensional electron migration and energy transport, electroluminescent effect, ferroelectric properties and surface self-assembly properties. These properties make discotic liquid crystals have potential applications in optical storage, organic semiconductors, materials for liquid crystal displays, electron transport, and LB films. The symmetrical 2,3,6,7,10,11-hexasubstituted triphenylene is the most common compound in the liquid crystal neighborhood, and the substituents are hexaalkoxy, thioether, selenoether, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/20C07C41/30
Inventor 白卫斌林金火
Owner FUJIAN NORMAL UNIV
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