Diphenylacetylene butene liquid crystal compound and synthesis method thereof

A technology of toluene butylene and liquid crystal compound, which is applied in the field of tolan butylene liquid crystal compound and its synthesis, can solve the problems of high melting point and high viscosity, and achieve low melting point, good low temperature performance, high product yield and The effect of high purity

Inactive Publication Date: 2018-06-15
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] In order to overcome the shortcomings of existing liquid crystal materials such as high viscosity and high melting point, the present invention proposes a toluene butylene-based liquid crystal compound with low melting point, low viscosity, wide liquid crystal phase range, and good low-temperature performance, and is a new product for this type of liquid crystal Compounds offer a simple, easy-to-operate preparation method

Method used

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  • Diphenylacetylene butene liquid crystal compound and synthesis method thereof
  • Diphenylacetylene butene liquid crystal compound and synthesis method thereof
  • Diphenylacetylene butene liquid crystal compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 1-{2-[4-(but-3-enyl)phenyl]ethynyl}-4-[2-(4-propylcyclohexyl)ethyl]benzene of the following synthetic structure

[0035]

[0036] 1. Under the protection of nitrogen, add 1.29g (3mmol) 2-{4-{2-{4-[2-(4-propyl Cyclohexyl)ethyl]phenyl}ethynyl}phenethyl}-1,3-dioxolane, 50mL tetrahydrofuran, 27.6g (0.6mol) formic acid, heated to 55°C, stirred at constant temperature for 5 hours, cooled to room temperature Dilute with water, extract with dichloromethane, wash the organic phase with water until neutral, dry with anhydrous magnesium sulfate, filter, evaporate the solvent, concentrate, recrystallize the solid with ethyl acetate, and dry to obtain 0.9g of yellow solid 3-{4 -{2-{4-[2-(4-Propylcyclohexyl)ethyl]phenyl}ethynyl}phenyl}propanal, gas chromatography purity 98%, yield 80.8%.

[0037] 2. Under the protection of nitrogen, add 0.82g (2.3mmol) methyl bromide triphenylphosphine salt and 50mL tetrahydrofuran successively to a 100mL three-neck flask equipped with a condense...

Embodiment 2

[0042] Synthesis of 1-{2-[4-(but-3-enyl)-2-fluorophenyl]ethynyl}-4-[2-(4-ethylcyclohexyl)ethyl]benzene with the following structural formula

[0043]

[0044]1. Under the protection of nitrogen, add 0.86g (2mmol) 2-(3-fluoro-4-(2-(4-(2-( 4-Ethylcyclohexyl)ethyl)phenyl)ethynyl)phenethyl)-1,3-dioxolane, 50mL tetrahydrofuran, 18.4g (0.4mol) formic acid, heated to 55°C, stirred at constant temperature for 5 hours , cooled to room temperature, diluted with water, extracted with dichloromethane, washed the organic phase with water until neutral, dried with anhydrous magnesium sulfate, filtered, evaporated to remove solvent, concentrated, solid recrystallized with ethyl acetate, dried to obtain 0.6g yellow solid 3-{4-{2-{4-[2-(4-Ethylcyclohexyl)ethyl]phenyl}ethynyl}-3-fluorophenyl}propanal, gas chromatography purity 98%, yield 80 %.

[0045] 2. Under the protection of nitrogen, add 0.5g (1.4mmol) methyl bromide triphenylphosphine salt and 50mL tetrahydrofuran successively into a...

Embodiment 3

[0050] Synthesis of 1-{2-[4-(but-3-enyl)-2-fluorophenyl]ethynyl}-4-[2-(4-propylcyclohexyl)ethyl]benzene with the following structural formula

[0051]

[0052] 1. Under the protection of nitrogen, add 0.67g (1.5mmol) 2-(3-fluoro-4-(2-(4-(2- (4-Propylcyclohexyl)ethyl)phenyl)ethynyl)phenethyl)-1,3-dioxolane, 50mL tetrahydrofuran, 13.9g (0.3mol) formic acid, heated to 55°C, stirred at constant temperature for 5 hours, cooled to room temperature, diluted with water, extracted with dichloromethane, washed the organic phase with water until neutral, dried with anhydrous magnesium sulfate, filtered, evaporated to remove solvent, concentrated, solid recrystallized with ethyl acetate, dried to obtain 0.5g yellow Solid 3-{4-{2-{4-[2-(4-propylcyclohexyl)ethyl]phenyl}ethynyl}-3-fluorophenyl}propanal, gas chromatography purity 98%, yield 83%.

[0053] 2. Under the protection of nitrogen, add 0.4g (1.1mmol) methyl bromide triphenylphosphine salt and 50mL tetrahydrofuran successively in...

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Abstract

The invention discloses a diphenylacetylene butene liquid crystal compound and a synthesis method thereof. The structural formula of the compound is shown as the specification, wherein (F)x and (F)y both represent fluorine atom substitution, x and y indicate the substitution number of fluorine atom, and can be 0 or 1, and R represents C1-C15 alkyl or C1-C15 alkoxy. The method provided by the invention employs acetal deprotection and Witting reaction to prepare the diphenylacetylene butene liquid crystal compound, the preparation method is simple in operation, the product yield and purity are high, and the obtained compound has the characteristics of low melting point, low viscosity, wide liquid crystal phase interval, good low temperature performance, direct preparation of liquid crystal mixture and the like, and is suitable for liquid crystal display, especially for TFT liquid crystal display technology.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, and in particular relates to a toluene butylene liquid crystal compound and a synthesis method thereof. Background technique [0002] With the accelerated development of liquid crystal display technology, higher requirements are put forward for liquid crystal materials. In order to improve the response speed of the liquid crystal panel, it is necessary to reduce the viscosity of the liquid crystal or reduce the thickness of the liquid crystal cell. The development of new low-viscosity liquid crystal materials is an effective shortcut, and this type of material also has a good application prospect. At present, the most widely used liquid crystal compounds of tolanyl acetylene are liquid crystal compounds with alkyl or fluorine as the terminal group. These compounds show the advantages of a wide liquid crystal phase range, but they have a high melting point, and there are smectic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/30
CPCC09K19/3059
Inventor 安忠维赵亮秦元元陈然陈新兵陈沛
Owner SHAANXI NORMAL UNIV
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