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Liquid crystal compound 4'-n-heptyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof

A technology of azobenzene carboxylic acid and liquid crystal compound, applied in the field of organic synthesis, can solve the problems of low viscosity and low working voltage, and achieve the effects of high clearing point, wide liquid crystal range and stable chemical properties

Inactive Publication Date: 2008-09-10
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there have been many reports on liquid crystal materials, not all of them are suitable for use in display devices, because liquid crystal materials for display must meet a wide operating temperature range, low operating voltage, low viscosity, fast response, high Stability and other requirements

Method used

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  • Liquid crystal compound 4'-n-heptyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof
  • Liquid crystal compound 4'-n-heptyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof
  • Liquid crystal compound 4'-n-heptyloxy-4-phenylazobenzoic acid-3-fluoro-4-cyanobenzene ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] 1) Dissolve 0.01mol p-hydroxyazobenzenecarboxylic acid and 0.02mol potassium hydroxide in 40ml 95% (volume fraction) ethanol, add 0.03mol bromo-n-heptane dropwise at a speed of about 1ml / min, and reflux reaction After 24 hours, 16 ml of 70% (volume fraction) ethanol solution of 0.02 mol potassium hydroxide was added, and the reflux was continued for 2 hours. Add 100ml of water, 20ml of concentrated hydrochloric acid, heat for 15min, cool and filter, wash with distilled water, dry, and then recrystallize with 95% (volume fraction) ethanol to obtain 4'-n-heptyloxy-4-azobenzenecarboxylic acid, It is orange-red flaky crystal, and the yield is 53%.

[0016] 2) Add 0.01mol of 4'-heptyloxy-4-azobenzenecarboxylic acid and 20ml of anhydrous tetrahydrofuran into a three-necked flask, stir to dissolve completely, then add 0.01mol of DCC (N,N-dicyclohexyl Carbodiimide), after turbidity appears, dissolve 0.01mol 2-fluoro-4-hydroxybenzonitrile and a small amount of DMAP[4-(N,N-dimet...

Embodiment 2

[0018] 1) Dissolve 0.02mol of p-hydroxyazobenzenecarboxylic acid and 0.05mol of potassium hydroxide in 120ml of 95% (volume fraction) ethanol, then add 0.06mol of n-heptane iodide, and react under reflux for 56h. Then add 40 ml of 0.03 mol potassium hydroxide in 70% (volume fraction) ethanol solution, and continue to reflux for 2 h. Add 100ml of water and 40ml of concentrated hydrochloric acid, mix well, heat for 20min, cool and filter, wash with distilled water, dry, and recrystallize with 95% (volume fraction) ethanol to obtain 4'-n-heptyloxy-4-azobenzene Carboxylic acid, orange-red flaky crystal, yield 50%.

[0019] 2) Add 0.015mol of 4'-heptyloxy-4-azobenzenecarboxylic acid and 50ml of anhydrous tetrahydrofuran into a three-necked flask, stir to dissolve completely, then add 0.01mol of DCC (N,N-dicyclohexyl Carbodiimide), after turbidity appeared, 0.015mol 2-fluoro-4-hydroxybenzonitrile and a small amount of DMAP[4-(N,N-dimethylamino)pyridine] were completely dissolved in...

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Abstract

The present invention relates to one kind of substituted azophenyl carboxylate containing fluorine atom and cyan group as liquid crystal compound and its preparation process. The compound has the chemical structure of 4'-heptyloxy-4- azophenyl carboxylic acid-3-fluoro-4-cyan phenyl ester. The preparation process includes the first Williamson etherification to introduce heptyloxy radical to the 4'-place of p-hydroxy azophenyl carboxylic acid so as to produce 4'-heptyloxy-4-azophenyl carboxylic acid; and the subsequent DCC dehydrating condensation of 4'-heptyloxy-4-azophenyl carboxylic acid and 2-fluoro-4-hydroxyl phenyl nitrile to obtain the required compound.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a substituted azobenzenecarboxylate liquid crystal compound containing a fluorine atom and a cyano group, a preparation method and an application thereof. Background technique [0002] In recent years, liquid crystal compounds and liquid crystal materials have become one of the hot spots in the research of applied chemistry and material chemistry, and have been widely used in electronics, optics, acoustics, bioengineering, chemical industry, etc., and the most extensive and important It is its application in electronic display. With the development of the information industry, the requirements for liquid crystal materials are constantly increasing. Although there have been many reports on liquid crystal materials, not all of them are suitable for use in display devices, because liquid crystal materials for display must meet a wide operating temperature range, low opera...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/24
Inventor 张书圣任锐颜连忠黄学青
Owner QINGDAO UNIV OF SCI & TECH