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Pyrene asymmetrical double-shaft discotic liquid crystal compound and preparation method thereof

A liquid crystal compound, asymmetric technology, applied in the field of discotic liquid crystal compound and its preparation, can solve the problem of few reports, etc., and achieve the effect of wide application prospect

Inactive Publication Date: 2011-05-18
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on asymmetric pyrene-like discotic liquid crystal compounds.

Method used

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  • Pyrene asymmetrical double-shaft discotic liquid crystal compound and preparation method thereof
  • Pyrene asymmetrical double-shaft discotic liquid crystal compound and preparation method thereof
  • Pyrene asymmetrical double-shaft discotic liquid crystal compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] with R 1 The structure is: R 2 The structure is:

[0021] The synthetic method of this compound is introduced as an example

[0022] Step 1: Friedel-Crafts acylation reaction of pyrene: dissolve 10mmol pyrene (2g) in 30mL carbon disulfide, and place in a 50mL single-necked bottle, add 1.5mmol p-bromobenzoyl chloride (3.26g), and cool in an ice bath to 0 degrees, gradually add 0.02mol aluminum oxide (2.64g); heat and reflux for 12 hours; pour the product into 100mL ice water and stir for 2 hours after cooling, separate the liquid with dichloromethane, and dry and filter the organic phase through anhydrous magnesium sulfate After recrystallization, 2.76 g of p-bromobenzoyl chloride-substituted pyrene was obtained as yellow needle-like crystals, with a yield of 72%.

[0023] Step 2: Bromination reaction of intermediate product: Dissolve 5mmol of p-bromobenzoyl chloride monosubstituted pyrene (1.92g) obtained in step 1 in 50mL of nitrobenzene, place it in a 100mL sin...

Embodiment 2

[0029] with R 1 structured as R 2 The structure is - C 5 h 11

[0030] The synthetic method of this compound is introduced as an example:

[0031] 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 p-bromobenzoyl chloride (3.26g), and cool to 2.5mL in an ice bath degree, gradually add 0.02mol aluminum oxide (2.64g); heat and reflux for 14 hours; pour the product into 100mL ice water and stir for 3 hours after cooling, separate the liquid with dichloromethane, dry and filter the organic phase through anhydrous magnesium sulfate, and reconstitute Crystallization to obtain 2.76 g of p-bromobenzoyl chloride-substituted pyrene, yellow needle-like crystals, yield 72%;

[0032] 2: Intermediate product bromination reaction: 5mmol p-bromobenzoyl chloride monosubstituted pyrene (1.92g) obtained in step 1 was dissolved in 50mL nitrobenzene, placed in a 100mL single-necked bottl...

Embodiment 3

[0037] with R 1 The structure is:

[0038] R 2 The structure is:

[0039] The synthetic method of this compound is introduced as an example

[0040] 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 p-bromobenzoyl chloride (3.26g), and cool to 5mL in an ice bath degree, gradually added 0.02mol aluminum oxide (2.64g); heated and refluxed for 16 hours; cooled the product and poured it into 100mL ice water and stirred for 4 hours, separated with dichloromethane, and the organic phase was dried and filtered through anhydrous magnesium sulfate and reconstituted. Crystallization gave 2.76 g of p-bromobenzoyl chloride monosubstituted pyrene, yellow needle-like crystals, and the yield was 72%.

[0041] 2: Intermediate product bromination reaction: 5mmol p-bromobenzoyl chloride monosubstituted pyrene (1.92g) obtained in step 1 was dissolved in 50mL nitrobenzene, placed in...

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Abstract

The invention belongs to the technical field of organic synthesis and relates to a pyrene asymmetrical double-shaft discotic liquid crystal compound and a preparation method thereof. The compound has a typical columnar hexagonal-phase discotic liquid crystal structure. The preparation method of the compound comprises the following steps of: carrying out a friedel-crafts acylation reaction on pyrene; carrying out a bromination reaction on an intermediate product; carrying out a Sonogashira coupling reaction; carrying out reaction for removing trimethyl silicon; and carrying out reaction for connecting bromination chains. The pyrene asymmetrical double-shaft discotic liquid crystal compound has biaxial orientation, i.e. a disk is used as a shaft, and an asymmetrical rod molecular chain is used as a shaft. Compared with the prior art, the invention has the advantages that the discotic liquid crystal compound with an asymmetrical structure is easier to form biaxial nematic discotic liquid crystal which has quicker refresh rate and low energy consumption, and has strong fluorescence and wide application prospect.

Description

technical field [0001] The invention relates to a discotic liquid crystal compound and a preparation method thereof, in particular to a pyrene asymmetric discotic liquid crystal compound and a preparation method thereof. Background technique [0002] Liquid crystal is an intermediate phase between crystal and liquid. In a certain temperature range or in a suitable solvent, it has the fluidity of liquid from the outside, and has the optical birefringence of crystal at the same time. It has been more than a hundred years since the discovery of liquid crystal materials. Although our research on liquid crystal theory is not very deep, the application of liquid crystal materials, especially in the field of flat panel display, has developed by leaps and bounds in the past half a century. . At present, liquid crystal devices are continuously providing new application values ​​for human beings in various fields with their excellent quality. [0003] When the discotic liquid crysta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/32C07C49/796C07C45/68
Inventor 杨槐王冬李阳崔晓鹏李正强王磊
Owner UNIV OF SCI & TECH BEIJING
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