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Difluoromethoxy liquid crystal compound containing benzoxazole heterocycle as well as synthesis method and application thereof

A technology of difluoromethoxyl and liquid crystal compounds, which is applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve problems such as the influence of the birefringence of liquid crystal molecules on the mesogenic phase type, and achieve a simple and easy synthesis method, Effect of High Refractive Index, Wide Mesophase Temperature Range

Inactive Publication Date: 2020-09-01
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, the introduction of highly polarizable heteroatoms will also affect the birefringence of liquid crystal molecules and the type of mesogenic phase.

Method used

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  • Difluoromethoxy liquid crystal compound containing benzoxazole heterocycle as well as synthesis method and application thereof
  • Difluoromethoxy liquid crystal compound containing benzoxazole heterocycle as well as synthesis method and application thereof
  • Difluoromethoxy liquid crystal compound containing benzoxazole heterocycle as well as synthesis method and application thereof

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preparation example Construction

[0079] Step S3 of the preparation method of the present invention has the advantage of simple reaction operation. Furthermore, the functionalization of transition metal-catalyzed carbon-hydrogen bonds conforms to the principles of green chemistry and atom economy. This method is used to construct CX(X=C, N, O, etc.) bonds have become a research hotspot in the field of organic chemistry. However, due to the unique physical properties of fluorine-containing groups, halogenated aromatic hydrocarbon substrates with difluoromethoxy groups as bridging bonds have not been reported, which makes their applications have certain limitations.

[0080] Therefore, the present invention uses Pd(AcO)2 as the catalyst, NiXantphos as the ligand, and NatOBu as the base to react in THF or DME at 65°C for 12h, which is the first realization of a halogen with difluoromethoxy as a bridge. Arylation reaction of substituted aromatic hydrocarbon substrates. The reaction operation is simple, and ordinary ...

Embodiment 1

[0086] The synthesis of 2-[4-(trans-4-(trans-4-n-propylcyclohexyl)cyclohexyldifluoromethoxy)phenyl]benzoxazole (5a) includes the following steps:

[0087] (1) Synthesis of 1-(4-(4-(trans-4-n-propylcyclohexyl)cyclohexyldifluoromethoxy)bromobenzene (3CCBr-1)

[0088] Trans-4-(trans-4-n-propylcyclohexyl) cyclohexyl carboxylic acid 3CCA (6.2200g, 0.0240mol) (structure is ), toluene (12.0 mL), isooctane (12.0 mL) and 1,3-propanedithiol (2.4 mL, 0.0240 mol) were added to a dry 250 mL three-neck round bottom flask. The mixture was stirred at 50°C for 1 hour, and trifluoromethanesulfonic acid (2.0 mL, 0.0240 mol) was slowly added dropwise (0.5 h) to the reaction solution using a dropping funnel. Heat to 102-105°C, reflux and separate water for about 4 hours. After the water was separated, the solvent was distilled off under reduced pressure, and 20.0 mL of the dichloromethane solution after dewatering was added to obtain the disulfide salt (3CCB) in dichloromethane solution. The entire r...

Embodiment 2

[0097] The synthesis of 2-[4-(trans-4-(trans-4-n-propylcyclohexyl)cyclohexyldifluoromethoxy)phenyl]-5-methylbenzoxazole (5b) includes the following steps :

[0098] (1) Synthesis of 1-(4-(4-(trans-4-n-propylcyclohexyl)cyclohexyldifluoromethoxy)bromobenzene (3CCBr-1)

[0099] The same as in Example 1.

[0100] (2) Synthesis of 2-[4-(trans-4-(trans-4-n-propylcyclohexyl)cyclohexyldifluoromethoxy)phenyl]-5-methylbenzoxazole (5b)

[0101] The product in (1) 3CCBr-1 (0.0950g, 0.0002mol), 5-methylbenzoxazole (0.0319, 0.00024mol), Pd(OAc) 2 (0.0025g, 0.005%mol), NiXantphos (0.0110g, 0.01%mol) and NatOBu (0.0480g, 0.0005mol) were dissolved in THF, heated to 65°C, and reacted for 12h. After cooling, it was filtered, extracted with ethyl acetate (30.0 mL) three times, washed, and dried over anhydrous sodium sulfate. Finally, column chromatography was performed with petroleum ether: ethyl acetate (V:V=50:1) to obtain a white solid with a yield of 78%.

[0102] The structural characterization dat...

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Abstract

The invention discloses a difluoromethoxy liquid crystal compound containing benzoxazole heterocycle as well as a synthesis method and application thereof. The compound has a structure as shown in formula 1, wherein n is 3 or 5, m is 1 or 2, R1, R2, R3 and R4 are H or F, and R5 is H or CH3. The synthesis method of the difluoromethoxy liquid crystal compound containing oxazole heterocycle is simpleand feasible, the raw materials are simple and easy to obtain, and the yield is high; the compound has the advantages of wide mesomorphic phase temperature range, high thermal stability, moderate refractive index and the like; and in addition, the liquid crystal compound provided by the invention can adjust the mesomorphic phase transition temperature, viscosity, refractive index and other physical properties of the product by adopting different terminal oxazole heterocyclic substituent groups and fluorine substitution positions, and has the advantages of simple and convenient adjustment.

Description

Technical field [0001] The invention belongs to the field of liquid crystal materials, and specifically relates to a difluoromethoxy liquid crystal compound containing a benzoxazole heterocycle, a synthesis method and application thereof. Such compounds can effectively control their physical and liquid crystal properties by changing the substituent groups on the terminal benzoxazole heterocyclic phenyl group and the substitution position of the fluorine atom. Background technique [0002] In recent decades, with the discovery of the photoelectric effect of liquid crystal materials, the field of liquid crystal materials has developed rapidly. At present, liquid crystal materials have been widely used in electronic products such as computer screens, electronic watches, mobile phones, calculators, and have become indispensable materials for the display industry. [0003] The introduction of strongly electronegative fluorine atoms in the fluorine-containing liquid crystal is beneficia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/34C07D263/57
CPCC07D263/57C09K19/3486C09K2019/0466
Inventor 曾卓熊丽罗忠峰张梅
Owner SOUTH CHINA NORMAL UNIVERSITY
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