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Pyrene large conjugated system disciform liquid crystal compound and preparation method thereof

A technology of conjugated system and discotic liquid crystal, which is applied in the field of discotic liquid crystal compound and its preparation, can solve rare problems and achieve the effect of wide application prospect and good carrier transport efficiency

Inactive Publication Date: 2014-05-07
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This structure is an ideal structure required in organic solar cells and organic field effect transistors. However, there are few reports on columnar tetragonal discotic liquid crystal compounds with extremely regular arrangements.

Method used

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  • Pyrene large conjugated system disciform liquid crystal compound and preparation method thereof
  • Pyrene large conjugated system disciform liquid crystal compound and preparation method thereof
  • Pyrene large conjugated system disciform liquid crystal compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Take the R structure as: -C 5 h 11 The synthetic method of this compound is introduced as an example

[0020] 1: Friedel-Crafts acylation reaction of pyrene: Dissolve 10mmol pyrene (2g) in 30mL carbon disulfide, and place it in a 50mL single-necked bottle, add 1.5mmol acid chloride (3.26g), cool to 0 degrees in an ice bath, 0.02mol Aluminum trioxide (2.64g), heated to reflux for 16 hours, cooled the product and poured it into 100mL of ice water and stirred for 2 hours, extracted with dichloromethane, dried and filtered the organic phase through anhydrous magnesium sulfate, and recrystallized to obtain the product (a) 2.76g, yellow needle-like crystals, yield 72%.

[0021] 2: intermediate product bromination reaction: 5mmol product (a) (1.92g) gained in step 1 is dissolved in 50mL nitrobenzene, is placed in the 100mL single-necked bottle, and 20mmol liquid bromine (1.2mL) is gradually added dropwise at room temperature, After the dropwise addition, the reaction was st...

Embodiment 2

[0024] Take the R structure as: The synthetic method of this compound is introduced as an example

[0025] 1: Friedel-Crafts acylation reaction of pyrene: Dissolve 10mmol pyrene (2g) in 30mL carbon disulfide, and put it in a 50mL single-necked bottle, add 1.5mmol acid chloride (3.26g), cool to 0 degrees in an ice bath, add 0.02 mol of aluminum trioxide (2.64g), heated and refluxed for 12 hours, cooled the product and poured it into 100mL of ice water and stirred for 2 hours, separated the liquids with dichloromethane, dried and filtered the organic phase through anhydrous magnesium sulfate, and then recrystallized to obtain the intermediate product (a) 2.76g, yellow needle-like crystals, yield 72%.

[0026] 2: Intermediate product bromination reaction: 5 mmol product (a) (1.92 g) obtained in step 1 was dissolved in 50 mL nitrobenzene, placed in a 100 mL single-necked bottle, and 20 mmol liquid bromine (12 mL) was gradually added dropwise at room temperature. After the addit...

Embodiment 3

[0028] Example 3: The synthetic method of this compound is introduced as an example

[0029] 1: Friedel-Crafts acylation reaction of pyrene: Dissolve 10mmol pyrene (2g) in 30mL carbon disulfide and put it in a 50mL single-necked bottle, add 1.5mmol acid chloride (3.26g), cool to 0 degrees in an ice bath, add 0.02 mol of aluminum trioxide (2.64g); heated to reflux for 12 hours; the product was cooled and poured into 100mL of ice water and stirred for 2 hours, extracted with dichloromethane, and the organic phase was recrystallized after drying and filtering over anhydrous magnesium sulfate to obtain the product (a ) 2.76g, yellow needle-like crystals, yield 72%.

[0030] 2: intermediate product bromination reaction: 5mmol product (a) (1.92g) gained in step 1 is dissolved in 50mL nitrobenzene, is placed in the 100mL single-necked bottle, and 20mmol liquid bromine (1.2mL) is gradually added dropwise at room temperature, After the dropwise addition, the temperature was raised t...

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Abstract

The invention relates to a pyrene large conjugated system disciform liquid crystal compound and a preparation method thereof, belonging to the technical field of organic synthesis. The structure of the compound is disclosed in the specification, wherein n is a whole number ranging from 4 to 20. The preparation method of the compound comprises the following steps: Friedel-Crafts acylation reaction, intermediate product bromization reaction and Sonogashira coupling reaction. The pyrene large conjugated system disciform liquid crystal compound provided by the invention can easily form extremely regular cylindrical tetragonal-phase disciform liquid crystals. The extremely regular cylindrical tetragonal-phase disciform liquid crystals have the advantage of excellent current carrier transmission efficiency. The extremely regular cylindrical tetragonal-phase disciform liquid crystals are very rare, and such structure is an ideal structure required in the organic solar cell and organic field-effect transistor; and therefore, the compound has wide application prospects.

Description

technical field [0001] The invention relates to a discotic liquid crystal compound and a preparation method thereof, in particular to a discotic liquid crystal compound of a large conjugated pyrene system and a preparation method thereof. Background technique [0002] Liquid crystal is an intermediate phase between crystal and liquid. Liquid crystal has both liquid fluidity and crystal anisotropy. It partially or completely loses the order of its position and still retains the order of molecular orientation. Liquid crystal is a low-dimensional ordered fluid, and its molecular arrangement structure is not as three-dimensional as the crystal structure, and it is easy to deform. The application of liquid crystal materials, especially in the field of flat panel display, has developed by leaps and bounds in the past half century. At present, liquid crystal devices are continuously providing new application values ​​for human beings in various fields with their excellent quality....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/796C07C45/68C09K19/32
Inventor 杨槐李阳王磊王冬崔青李正强
Owner UNIV OF SCI & TECH BEIJING
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