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Synthesis process for fluorine-containing diphenylacerylene liquid crystal of lactic acid chiral derivative

A technology of diphenylacetylene and synthesis process, which is applied in liquid crystal materials, preparation of organic compounds, preparation of carboxylic acid esters, etc., can solve the problems of narrow blue phase temperature range and limited application research, and achieve chemical stability, low viscosity, dual High refraction effect

Inactive Publication Date: 2016-06-01
陈玉梅
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the temperature range of the blue phase is very narrow, but about 1°C, it limits its application research

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Add 2.00g (7.56mmol) of perfluorophenyltrimethylsilylacetylene, 2.00g (14.4mmol) of potassium carbonate, 2.60g (28mmol) of n-pentanol and 60mL of DMF to 100mL of three ports in sequence In the flask, stir magnetically at room temperature, stop the reaction after 72h of reaction (TLC tracking); add 50mL of water, extract with methyl tert-butyl ether (50mL×3), obtain the organic phase, dry it with anhydrous sodium sulfate, and depressurize The solvent was evaporated, and petroleum ether was used to pass through the column to obtain 1.2 g of yellow liquid.

Embodiment 2

[0019] Example 2: Under nitrogen protection, 5 g of terephthaloyl chloride was added into a 100 mL three-neck flask with 40 mL of dioxane as a solvent, and magnetically stirred to dissolve the terephthaloyl chloride. Continue to add 3.6 g of p-iodophenol and 0.1 g of DMAP, and then drop a few drops of pyridine under reflux for reaction for 24 h. After cooling, 2.9 g of ethyl lactate was added under the protection of nitrogen, and then heated to reflux for 24 h to stop the reaction. Wash with 5% acetic acid three times successively, wash three times with saturated sodium chloride solution, extract three times with dichloromethane, then combine the organic phases, dry, concentrate and pass through the column (petroleum ether: ethyl acetate: dichloromethane=30: 1:0.5) to obtain 2.3 g of light yellow solid.

Embodiment 3

[0020] Embodiment 3: the compound of 560mg (1.2mmol), the Pd of 50mg (PPh 3 ) 2 Cl ２ , 60mg of CuI and 35mL of triethylamine were added to a 50mL three-necked flask under nitrogen protection, magnetically stirred, and reacted under reflux conditions. After 4.5h, the reaction was stopped, cooled, suction filtered, and the solid was washed with methyl tert-butyl ether , and then washed with water (50mL×3) to obtain a yellow organic phase, dried over anhydrous sodium sulfate, evaporated the solvent under reduced pressure, and used petroleum ether (bp60~90°C):ethyl acetate:dichloromethane=30:1:0.5 The eluent was passed through the column to obtain a white solid, which was recrystallized from methanol to obtain 0.51 g.

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PUM

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Abstract

The invention provides a synthesis process for a fluorine-containing diphenylacerylene liquid crystal of a lactic acid chiral derivative. The method is to synthesize a target compound 1-[(4-alkyloxy-2,3,5,6-tetrafluorophenyl)acetylenyl]phenyl,4-[(1-ethoxcarbonyl)ethyl]terephthalate and comprises the following concrete steps: successively adding 2.00 g (7.56 mmol) of perfluorophenyltrimethylsilylacetylene, 2.00 g (14.44 mmol) of potassium carbonate, 2.60 g (28 mmol) of n-amyl alcohol and 60 mL of DMF into a three-neck flask with a volume of 100 mL and carrying out stirring; (2) adding 5 g of paraphthaloyl chloride into a 40-mL three-neck flask with a solvent dioxane under the protection of nitrogen, carrying out magnetic stirring to dissolve paraphthaloyl chloride, continuing to add 3.6 g of p-iodophenol and 0.1 g of DMAP, then adding a few drops of pyridine drop by drop and carrying out a reflux reaction for 24 h; and (3) adding 560 mg (1.2 mmol) of a compound, 650 mg of Pd (PPh3)2Cl2, 60 mg of CuI and 35 mL of triethylamine into a three-neck flask with a volume of 50 mL under the protection of nitrogen and successively carrying out stirring, a reflux reaction, cooling and pumping filtration.

Description

technical field [0001] The invention specifically relates to a synthesis process of a fluorine-containing tolan liquid crystal of a lactic acid chiral derivative. Background technique [0002] The performance of liquid crystal displays depends on the birefringence and dielectric anisotropy of liquid crystal compounds. The well-known twisted nematic mode (TN), super twisted nematic mode (STN), and thin film transistor mode (TFT) all depend on the birefringence and dielectric anisotropy of liquid crystal materials. TFT-LCD has become the mainstream of today's flat panel display technology. [0003] In addition to the above-mentioned technologies, technologies related to cholesteric liquid crystal materials are also research hotspots. One of them is reflective display technology. The cholesteric liquid crystal material for display is prepared from a wide temperature nematic liquid crystal composition and a chiral composition. Compared with other liquid crystal materials, the...

Claims

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Application Information

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IPC IPC(8): C07C67/343C09K19/18C09K19/20
Inventor 陈玉梅
Owner 陈玉梅
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