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Development of New Fluorine-containing Ferroelectric Liquid Crystals

Research Project

Project/Area Number 06555277
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

NAKAI Takeshi  Tokyo Inst.Tech., Fac.Eng., Prof., 工学部, 教授 (90016717)

Co-Investigator(Kenkyū-buntansha) YOSHIZAWA Atsushi  Japan Energy Coorporation Petroleum Products Lab., Senior Researcher, 石油研究所, 研究員
Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥5,800,000 (Direct Cost: ¥5,800,000)
Fiscal Year 1995: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1994: ¥4,500,000 (Direct Cost: ¥4,500,000)
KeywordsFerroelectric Liquid Crystal / Fluorine Compound / Claisen Rearrangment / Asymmetric Synthesis / Spontaneous / Optically Active Compound / Liquid Crystal / 応答時間
Research Abstract

The purposes of this project are to develop a new and efficient synthetic method for optically active organofluorine compounds and, by using these as chiral building blocks, to develop new types of ferroelectric liquid crystals.
First, the Tokyo Inst.Tech.group has developed the new, silyl triflate-mediated procedure for the Claisen rearrangement and successfully applied this Claisen procedure to asymmetric synthesis of alpha-fluoro-alpha-methyl and alpha-fluoro-alpha-trifluoromethyl carboxylic acid derivatives. Of particular interest is that the senses of asymmetric transmission observed with the fluorinated substrates are opposite to those observed with the non-fluorinated counterparts. Second, the Japan Energy Co.group has prepared a variety of liquid crystals by using the optically active fluorine compounds as the chiral building blocks and evaluated their functional properties as ferroelectric LC's. Notable findings are : (I) the fluorinated liquid crystals provide a larger degree of the spontaneous polarization than the non-fluorinated counterparts in general, (2) Liquid crystal with the alpha-fluoro-alpha-methyl chiral center show a greater spontaneous polarization than the liquid crystals with alpha-fluoro-alpha-CF_3 chiral center, and (3) The liquid crystal with a pyrimidine ring in the core part and alpha-fluoro-alpha-methyl ester moiety in the chiral part is shown to provide a greater than 400 nC/cm^2 of spontaneous polarization.

Report

(3 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] 中井 武: "Stereochemical Control in the Silyl Triflate-Mediated Claisen Rearrangement of Allylic Esters" Tetrahedron Lett.(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 中井 武: "Claisen Rearrangement of α-(F-alkyl) enol Ethers Prepared via Wittig Olefination of Allyl Perfluoroalkanoates" Tetrahedron Lett.35. 2907-2910 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 中井 武: "Claisen Rearrangement of Fluorinated Enol Ethers : New Entries to α-Monofluoro and α,α-Difluro Acids" Journal of Fluorine Chemistry. 54. 68 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 吉沢 篤: "New Chiral Dopants Based on the 2-Fluoro-2-methylalkoxy Tail for Use in Ferroelectric Liquid Crystal Mixtures" Mol.Cryst.& Liq.Cryst.263. 217-222 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 吉沢 篤: "Decreasein Apparent Viscosity in Electric Fields in Chiral Smectic Liquid Crystals" Ferroelectrics. 147. 395-409 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 吉沢 篤: ":New Ferroelectric Liquid Crystals Having 2-Fluoro-2-Methyl Alkanoyloxy Group" Mol.Cryst.& Liq.Cryst.199. 129-140 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takeshi Nakai: "Stereochemical Control in the Silyl Triflate-Mediated Claisen Rearrangementof Allylic Esters" Tetrahedron Lett.37, (in press). (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takeshi Nakai: "Claisen Rearrangementof alpha- (F-alkyl) enol Ethers Prepared via Wittig Olefination of Allyl Perfluoroalkanoates" Tetrahedron Lett.35, [18]. 2907-2910 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Takeshi Nakai: "Claisen Rearrangementof Fluorinated Enol Ethers : New Entries to alpha-Monofluoro and alpha, alpha-Difluro Acids" Journal of Fluorine Chemistry. 54. 68 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Atsushi Yoshizawa: "New Chiral Dopants Based on the 2-Fluoro-2-methylalkoxy Tail for Use in Ferroelectric Liquid Crystal Mixtures" Mol.Cryst.& Liq.Cryst.263. 217-222 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Atsushi Yoshizawa: "Decrease in Apparent Viscosity in Electric Fields in Chiral Smectic Liquid Crystals" Ferroelectrics. 147. 395-409 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Atsushi Yoshizawa: "New Ferroelectric Liquid Crystals Having 2-Fluoro-2-Methyl Alkanoyloxy Group" Mol.Cryst.& Liq.Cryst.199. 129-140 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 中井 武: "Stereochemical Control in the Silyl Triflate-Mediated Claisen Rearrangement of Allylic Esters" Tetrahedron Letters. 印刷中

    • Related Report
      1995 Annual Research Report
  • [Publications] 中井 武: "Unique Radical Addition Reactions onto Perflouro-enol Esters" Tetrahedron Letters. 36. 6091-6094 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 吉沢 篤: "New Chiral Dopants Based on the 2-Fluoro-2-methylalkoxy Tail For Use in Ferroelectric Liquid Crystal Mixtures" Mol. Cryst. &Liq. Cryst.268. 675 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 吉沢 篤: "Interlayer Correlation in Semectic Phases Induced by Chiral Twin Molecules" Mol. Cryst. &Liq. Cryst.260. 403 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 吉沢 篤: "Helical Structures Induced by Laterally-connected Chiral Twin Molecules" Liq. Cryst tals. 18. 775 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 吉沢 篤: "液晶の構造と物性" 工業材料. 43. 482 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] 中井武: "Claisen Rearrangement of α- (F-alkyl) enol Ethers Prepared via Wittig Olefination of Alkyl Prefluoroalkanoates." Tetrahedron Letters. 35. 2907-2910 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 中井武: "Claisen Rearrangements of Fluorinated Enol Ethers : New Entries to α-Monofluoro and α,α-Difluro Acids" Journal of Fluorine Chemistry. 54. 68 (1992)

    • Related Report
      1994 Annual Research Report
  • [Publications] 吉沢篤: "Decrease in Apparent Viscocity in Electric Fields in Chiral Smectic Liquid Crystals" Ferroelectrics. 147. 395-409 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 吉沢篤: "New Ferroelectric Liquid Crystals Having 2-Fluoro-2-Methyl Alkanoyloxy Group" Mol.Cryst.Liq.Cryst.199. 129-140 (1991)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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