5, 6-Difluoro-benzofuran:A new core structure for the design of liquid crystal compound

Jian LI; Zhao-yi CHE; Ling-chao MO; Ming-gang HU; Deng DENG; Wei-song DU; Ai-ai GAO

doi:10.37188/YJYXS20203510.1000

您当前的位置：

首页 >

文章列表页 >

5, 6-Difluoro-benzofuran:A new core structure for the design of liquid crystal compound

Material Physics | 更新时间：2020-09-28

- 5, 6-Difluoro-benzofuran:A new core structure for the design of liquid crystal compound
- Chinese Journal of Liquid Crystals and Displays Vol. 35, Issue 10, Pages: 1000-1005(2020)
- 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：
- 基金信息：
  
  Key Research and Development Program of Shaanxi(2019ZDLGY04-06)
- DOI：10.37188/YJYXS20203510.1000
  CLC： O621;O753.2
- Received：18 March 2020，
  
  Revised：08 June 2020，
  
  Accepted：08 June 2020，
  
  Published：05 October 2020
- 稿件说明：
移动端阅览
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：

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 .

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Synthesis and properties of novel fluorinated liquid crystal compounds with vinyl linking group

Fluorinated liquid crystal properties, application and synthetic progress

Physical Properties of TFT Liquid Crystals with Low Threshold Voltage

Synthesis of liquid crystals of non-chiral β-methylbutyl polybiphenyl isothiocyanate and high-frequency dielectric properties

Analysis for the dielectric properties of trans-cyclohexyl（tri）biphenyl liquid crystal compounds in microwave frequency bands

Related Author

LI Jian

LI Juan-li

HU Ming-gang

GAN Ning

AN Zhong-wei

GAO Ai-ai

ZHENG Yuan-yang

DU Wei-song

Related Institution

Research Division of Optoelectronic Materials, Xi'an Modern Chemistry Research Institute

西安彩晶光电科技股份有限公司

Optical and Electrical Material Department,Xian Modern Chemistry Research Institute, Xian 710065,China,E-mail: lijl208@sohu.

School of Electronic Science and Engineering， University of Electronic Science and Technology

Department of Chemistry and Environmental Engineering， Wuhan Polytechnic University

AI问答

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China 130033 Postal code：130033
Tel：0431-86176059 Email：yjxs@ciomp.ac.cn
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰