5, 6-二氟苯并呋喃：新的核结构用于液晶分子设计

李建; 车昭毅; 莫玲超; 胡明刚; 邓登; 杜渭松; 高嫒嫒

doi:10.37188/YJYXS20203510.1000

您当前的位置：

首页 >

文章列表页 >

5, 6-二氟苯并呋喃：新的核结构用于液晶分子设计

材料物理 | 更新时间：2020-09-28

- 5, 6-二氟苯并呋喃：新的核结构用于液晶分子设计
- 5, 6-Difluoro-benzofuran:A new core structure for the design of liquid crystal compound
- 液晶与显示 2020年35卷第10期页码：1000-1005
- 作者机构：
  
  1.氟氮化工资源高效开发与利用国家重点实验室, 陕西西安 710065
  2.西安近代化学研究所, 陕西西安 710065
  3.西安彩晶光电科技股份有限公司, 陕西西安 710065
- 作者简介：
  
  [ "李建(1975-), 男, 陕西汉中人, 硕士, 研究员, 2002年于西安近代化学研究所获得硕士学位, 主要从事液晶材料分子设计与合成、性能及器件应用研究。E-mail:204lijian@163.com" ]
- 基金信息：
  
  陕西省重点研发计划(2019ZDLGY04-06)
- DOI：10.37188/YJYXS20203510.1000
  中图分类号： O621;O753.2
- 收稿日期：2020-03-18，
  
  修回日期：2020-06-08，
  
  录用日期：2020-6-8，
  
  纸质出版日期：2020-10-05
- 稿件说明：
移动端阅览
李建, 车昭毅, 莫玲超, 等. 5, 6-二氟苯并呋喃：新的核结构用于液晶分子设计[J]. 液晶与显示, 2020,35(10):1000-1005.

Jian LI, Zhao-yi CHE, Ling-chao MO, et al. 5, 6-Difluoro-benzofuran:A new core structure for the design of liquid crystal compound[J]. Chinese journal of liquid crystals and displays, 2020, 35(10): 1000-1005.
李建, 车昭毅, 莫玲超, 等. 5, 6-二氟苯并呋喃：新的核结构用于液晶分子设计[J]. 液晶与显示, 2020,35(10):1000-1005. DOI： 10.37188/YJYXS20203510.1000.

Jian LI, Zhao-yi CHE, Ling-chao MO, et al. 5, 6-Difluoro-benzofuran:A new core structure for the design of liquid crystal compound[J]. Chinese journal of liquid crystals and displays, 2020, 35(10): 1000-1005. DOI： 10.37188/YJYXS20203510.1000.

摘要

含稠杂环液晶是当前液晶分子结构设计与开发的重要方向。本文采用环己基取代的乙炔与邻碘代苯酚衍生物经过钯催化偶联-关环反应合成出新型具有5，6-二氟取代苯并呋喃环结构的液晶化合物，总收率达到54%。采用

HNMR、MS对其结构进行了表征，采用DSC和POM对其热性能进行了测试，发现该化合物熔点为118℃，清亮点为202℃，向列相液晶温区84℃。物理性能测试表明，该类液晶化合物的双折射率约为0.13，介电各向异性达到12.6，旋转粘度为420 mP·s。与类似的3，4-二氟苯类液晶化合物相比，含5，6-二氟取代苯并呋喃环的液晶分子双折射率增大65%，介电常数值增大97%，清亮点增加63%。5，6-二氟取代苯并呋喃作为一种新的含氟砌块，综合性能表现突出，在液晶显示领域有良好的应用前景。

Abstract

At present

liquid crystal with fused heterocyclic ring is an important direction of molecular structure design and development. In this paper

a new liquid crystal compound with 5

6-difluorobenzofuran ring structure was synthesized via palladium catalyzed coupling reaction and ring closing reaction of cyclohexyl substituted acetylene and

-iodophenol derivative. The total yield was 54%. Its structure was characterized by

H NMR and MS

and its phase transition temperatures were tested by DSC and POM. It is found that the melting point and the clear point of the compound is 118℃ and 202℃ respectively

and the nematic temperature range is 84℃. The physical properties test shows that the birefringence is about 0.13

the dielectric anisotropy is 12.6 and the rotational viscosity is 420 mPa·s. Compared with the similar 3

4-difluorobenzene liquid crystal compound

the birefringence of the compound containing 5

6-difluorobenzofuran ring increases by 65%

the dielectric constant increases by 97%

and the clear point increases by 66%. As a new kind of fluorine-containing building block

6-difluorobenzofuran has outstanding comprehensive performance and good application prospect in the field of liquid crystal display.

关键词

Keywords

references

P KIRSCH , M BREMER . Nematic liquid crystals for active matrix displays:molecular design and synthesis . Angewandte Chemie International Edition , 2000 . 39 ( 23 ): 4216 - 4235 . http://onlinelibrary.wiley.com/doi/10.1002/chin.200106250/full http://onlinelibrary.wiley.com/doi/10.1002/chin.200106250/full .

P KIRSCH , M BREMER , A TAUGERBECK , 等 . Difluorooxymethylene-bridged liquid crystals:a novel synthesis based on the oxidative alkoxydifluorodesulfuration of dithianylium salts . Angewandte Chemie International Edition , 2001 . 40 ( 8 ): 1480 - 1484 . DOI: 10.1002/1521-3773(20010417)40:8<1480::AID-ANIE1480>3.0.CO;2-M http://doi.org/10.1002/1521-3773(20010417)40:8<1480::AID-ANIE1480>3.0.CO;2-M .

J LI , M G HU , J L LI , 等 . Highly fluorinated liquid crystals with wide nematic phase interval and good solubility . Liquid Crystals , 2014 . 41 ( 12 ): 1783 - 1790 . DOI: 10.1080/02678292.2014.950617 http://doi.org/10.1080/02678292.2014.950617 .

M BREMER , P KIRSCH , M KLASEN-MEMMER , 等 . The TV in your pocket:development of liquid-crystal materials for the new millennium . Angewandte Chemie International Edition , 2013 . 52 ( 34 ): 8880 - 8896 . DOI: 10.1002/anie.201300903 http://doi.org/10.1002/anie.201300903 .

P KIRSCH , M BREMER . Understanding fluorine effects in liquid crystals . ChemPhysChem , 2010 . 11 ( 2 ): 357 - 360 . DOI: 10.1002/cphc.200900745 http://doi.org/10.1002/cphc.200900745 .

P KIRSCH , W BINDER , A HAHN , 等 . Super-fluorinated liquid crystals:towards the limits of polarity . European Journal of Organic Chemistry , 2008 . 2008 ( 20 ): 3479 - 3487 . DOI: 10.1002/ejoc.200800149 http://doi.org/10.1002/ejoc.200800149 .

K ARAKI , T YAMAMOTO , R TANAKA , 等 . Stereoselective synthesis and physicochemical properties of liquid-crystal compounds possessing a trans -2, 5-disubstituted tetrahydropyran ring with negative dielectric anisotropy . Chemistry:A European Journal , 2015 . 21 ( 6 ): 2458 - 2466 . DOI: 10.1002/chem.201405495 http://doi.org/10.1002/chem.201405495 .

莫玲超 , 李建 , 郭兆琦 , 等 . 新型吡啶环液晶化合物的合成及性能 . 应用化学 , 2016 . 33 ( 5 ): 542 - 548 . http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=yyhx201605006 http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=yyhx201605006 .

L C MO , J LI , Z Q GUO , 等 . Synthesis and properties of novel liquid crystal compounds containing pyridine ring . Chinese Journal of Applied Chemistry , 2016 . 33 ( 5 ): 542 - 548 . http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=yyhx201605006 http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=yyhx201605006 .

P KIRSCH , D MAILLARD . A convenient synthetic route to tetrahydropyran-based liquid crystals . European Journal of Organic Chemistry , 2006 . 2006 ( 15 ): 3326 - 3331 . DOI: 10.1002/ejoc.200600160 http://doi.org/10.1002/ejoc.200600160 .

M R FRIEDMAN , K J TOYNE , J W GOODBY , 等 . The synthesis and transition temperatures of 2-(4-alkyl-and 4-alkoxy-phenyl)-5-cyano-1-benzofurans and related diaryl-1-benzofurans-an assessment of how deviations from linearity and conformational effects in a core unit affect mesogenicity . Journal of Materials Chemistry , 2001 . 11 ( 11 ): 2759 - 2772 . DOI: 10.1039/b102837p http://doi.org/10.1039/b102837p .

张芳苗 , 员国良 , 张晶梅 , 等 . 苯并呋喃类液晶的合成 . 液晶与显示 , 2010 . 25 ( 1 ): 5 - 10 . http://cjlcd.lightpublishing.cn/thesisDetails?columnId=1689069&Fpath=&index=-1&l=zh http://cjlcd.lightpublishing.cn/thesisDetails?columnId=1689069&Fpath=&index=-1&l=zh .

F M ZHANG , G L YUAN , J M ZHANG , 等 . Synthesis of benzofuran liquid crystals . Chinese Journal of Liquid Crystals and Displays , 2010 . 25 ( 1 ): 5 - 10 . http://cjlcd.lightpublishing.cn/thesisDetails?columnId=1689069&Fpath=&index=-1&l=zh http://cjlcd.lightpublishing.cn/thesisDetails?columnId=1689069&Fpath=&index=-1&l=zh .

MARKUS K, EIKE P, ATSUTAKA M, et al . Benzofuran and benzothiophene derivatives, useful as components of liquid crystal media for electro-optical display devices are new: Germany, DE102004053279A[P]. 2005-06-23.

N G KUNDU , M PAL , J S MAHANTY , 等 . Palladium-catalysed heteroannulation with acetylenic compounds:synthesis of benzofurans . Journal of the Chemical Society, Perkin Transactions 1 , 1997 . ( 19 ): 2815 - 2820 . DOI: 10.1039/a703305b http://doi.org/10.1039/a703305b .

浏览量

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

新型乙烯桥键含氟液晶化合物的合成及性能研究

含氟液晶的性能、应用与合成进展

低阈值TFT液晶材料物理性能研究

非手性β-甲基丁基多联苯异硫氰酸酯液晶合成及高频介电性能

反式环己基（三）联苯类液晶化合物微波介电性能分析