Synthesis and properties of the tetrahydropyrane liquid crystal compound containing CF<sub>2</sub>O bridge

Xiao-yu TAN; Hui-qiang TIAN; Jie WANG; Xiong DAI; Li-long GAO

doi:10.3788/YJYXS20173209.0701

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Synthesis and properties of the tetrahydropyrane liquid crystal compound containing CF₂O bridge

Material Science | 更新时间：2020-07-07

- Synthesis and properties of the tetrahydropyrane liquid crystal compound containing CF₂O bridge
- Chinese Journal of Liquid Crystals and Displays Vol. 32, Issue 9, Pages: 701-707(2017)
- 作者机构：
  
  1.北京八亿时空液晶科技股份有限公司, 北京 102205
  2.液晶材料分析及应用技术北京市重点实验室, 北京 102205
- 作者简介：
- 基金信息：
- DOI：10.3788/YJYXS20173209.0701
  CLC： O753+.2;O625.21
- Received：14 April 2017，
  
  Accepted：12 May 2017，
  
  Published：05 September 2017
- 稿件说明：
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Xiao-yu TAN, Hui-qiang TIAN, Jie WANG, et al. Synthesis and properties of the tetrahydropyrane liquid crystal compound containing CF₂O bridge[J]. Chinese journal of liquid crystals and displays, 2017, 32(9): 701-707.
DOI：

Xiao-yu TAN, Hui-qiang TIAN, Jie WANG, et al. Synthesis and properties of the tetrahydropyrane liquid crystal compound containing CF₂O bridge[J]. Chinese journal of liquid crystals and displays, 2017, 32(9): 701-707. DOI： 10.3788/YJYXS20173209.0701.

摘要

以对二溴苯、5-烷基-四氢吡喃-2-酮和3，4，5-三氟-2-甲基苯酚为原料，经过丁基锂反应、脱羟基、Suzuki和Williamson等共5步反应最终合成2[4'[二氟(3，4，5-三氟2-甲基苯氧基)甲基]-3'，5'-二氟-[1，1'联苯]

-4-基]-5-烷基四氢吡喃类液晶化合物。反应中考察了温度、溶剂、催化剂和原料比对反应收率的影响。其中脱羟基反应滴加温度-70℃~-80℃，原料羟基化合物：三乙基硅烷：三氟化硼乙醚的摩尔比为1：1.5：2.5；Suzuki反应选用四（三苯基磷）钯反应收率最高；3，4，5-三氟-2-甲基苯酚的Williamson醚化最优条件为在DMSO与水的混合溶剂中醚化6 h。纯化后目标产物气相色谱纯度≥ 99.5%，总收率约为35.6%，结构经

HNMR及GC-MS确证。该化合物添加到液晶的基础配方中，能增加介电各向异性（△

），降低阈值电压。

Abstract

2[4'[difluoro(3

5trifluoro2methylphenoxy)methyl]-3'

5'difluoro[1

1'biphenyl]

-4yl]-5alkyltetrahydropyran derivatives was synthesized via butyl lithium

dehydroxylation

Suzuki and Williamson reaction (five steps'reaction) by employing 1

4-Dibromo-benzene

5-alkyl-tetrahydro-pyran-2-one and 3

5-Trifluoro-2-methyl-phenol as starting materials. The effects of reaction temperature

solvent

catalyst and material ratio on the yield were investigated. The optimum reaction conditions for the Dehydroxylation reaction

the mole ratio of hydroxyl compounds

triethylsilane and boron trifluoride diethyl ether is 1:1.5:2.5 under the drop-temperature at -70~-80℃. For the Suzuki reaction

(beta-4)-platinum was the best catalysts. The optimum reaction condition for Williamson etherification of 3

5-Trifluoro-2-methyl-phenol were 6 h in DMSO-water mixed solvent. After purification processing

the total yield was 35.6% with the purity was 99.5% (GC)

the structure was characterized by

H NMR and GC-MS.The addition of the compound into the basic formula of liquid crystal

could improve the dielectric anisotropy (△

)

and could reduce threshold voltage as well.

关键词

Keywords

references

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Synthesis and properties of the tetrahydropyrane liquid crystal compound containing CF2O bridge

DOI：10.3788/YJYXS20173209.0701

摘要

Abstract

关键词

Keywords

references

Synthesis and properties of the tetrahydropyrane liquid crystal compound containing CF₂O bridge