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Study for the Appearance of Mesogenic Property Induced by Sigmatropic Rearrangement

Research Project

Project/Area Number 08454226
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 機能・物性・材料
Research InstitutionKyushu University

Principal Investigator

MORI Akira  Kyushu University, Institute of Advanced Material Study, Professor, 機能物質科学研究所, 教授 (70038602)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥7,900,000 (Direct Cost: ¥7,900,000)
Fiscal Year 1997: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 1996: ¥6,200,000 (Direct Cost: ¥6,200,000)
KeywordsMonocyclic Troponoid Liquid Crystals / [1,9] Sigmatropic Rearrangement / Virtual Smectic A Phase / Fluorinated Alkyl Side Chain / 側方カルボニル基 / スメクチックA相 / シグマトロピー転移 / トロポノイド液晶
Research Abstract

Previously, we have prepared monocyclic troponoid liquid crystals, 2-acyloxy-5-alkoxytrpones (1) , which showed monotropic smectic A phases. We could observe an acyl group at C-2 could migrate to the neighboring carbonyl group in liquid crystalline states. I called this migration [1,9] sigmatropic rearrangement.
In this project, I jntended that dynamic molecular rearrangement would induce the exhibition of the mesogenic properties. When we prepared 5-acyloxy-2-alkoxytropones (2) , in which the substituents on C-2 and C-5 of 1 were replaced, 2 were not mesogenic. We could determine, however, virtual transition temperatures by extrapolation of the binary phase diagram between 2 and the reference compounds, which has a smectic A phase. The virtual transition temperatures were similar to the transition tenperatures of 1, but their melting points were higher than 1. Therefore, we could conclude that [1,9] sigmatropy reduced melting points.
Next, in order to prepare monocyclic troponoid liquid crystals with higher thermal stability, we introduced fluorine atoms into the alkyl chains to synthesis enantiotropic liquid crystals with monocyclic troponoids. Furthermore, we extended to prepare enantiotropic liquid crystals with 2,5-dialkoxytropone structure with fluorine atoms in the side chains.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] Akira Mori et al.: "Mesogenic Propeties of Tricyclic 3,5-Di(4-alkoxybenzoyloxy)tropones.Increasing Smectic Thermal Stabilities by the Lateral Polar Carbonyl Group" Chemistry Letters. 699-700 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori et al.: "New Troponoid Liquid Crystalline Compounds,5-Alkoxy-2-(4-alkoxybenzoylamino)tropones" Chemistry Letters. 509-510 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori et al.: "Preparation of Sigmatropic 2-Acyloxy-5-perfluoroalkoxytropones:New Monocyclic Troponoid Liquid Crystals with an Enantiotropic Smectic A Phase" Chemistry Letters. 1009-1010 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori et al.: "Preparation of Troponoid Liquid Crystals with a Flexible Oxymethylene Linking Unit" Journal of Materials Chemisty. 8. 595-597 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori, Hisashi Taya, Minoru Uchida, and Hitoshi Takeshita: "Properties of Tricyclic 2,5-Di (4-alkoxy-benzoyloxy) tropones. Increasing Smectic Thermal Stabilities by the Lateral Polar Carbonyl Group" Chemistry Letters. 699-700 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori, Ken Hirayama, Nobuo Kao, Hitoshi Takeshita, and Seiji Ujiie: "New Troponoid Liquid Crystalline Compounds, 5-Alkoxy-2- (4-alkoxybenzoylamino) tropones" Chemistry Letters. 509-510 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori, Shinji Takematsu, and Hitoshi Takeshita: "Preparation of Sigmatropic 2-Acyloxy-5-perfluoro-alkoxytropones : New Monocyclic Troponoid Liquid Crystals with an Enantiotropic Smectic A Phase" Chemistry Letters. 1009-1010 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori, Hisashi Taya, Hitoshi Takeshita, and Seiji Ujiie: "Preparation of Troponoid Liquid Crystals with a Flexible Oxymethylene Linking Unit" Journal of Materials Chemistry. 8. 595-597 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Akira Mori et al.: "Mesogenic Properties of Tricyclic 3,5-Di(4-alkoxybenzoyloxy)tropones.Increasing Smectic Thermal Stabilities by the Lateral Polar Carbonyl Group" Chemistry Letters. 699-700 (1996)

    • Related Report
      1997 Annual Research Report
  • [Publications] Akira Mori et al.: "New Troponoid Liquid Crystalline Compounds,5-Alkoxy-2-(4-alkoxybenzoylamino)tropones" Chemistry Letters. 509-510 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Akira Mori et al.: "Preparation of Sigmatropic 2-Acyloxy-5-perfluoroalkoxytropones:New Monocyclic Troponoid Liquid Crystals with an Enantiotropic Smectic A Phase" Chemistry Letters. 1009-1010 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Akira Mori et al.: "Preparation of Troponoid Liquid Crystals with a Flexible Oxymethylene Linking Unit" Journal of Materials Chemistry. 8(in press). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Akira Mori,et al.: "Mesogenic Properties of Tricyclic 3,5-Di(4-alkoxybenzoyloxy)tropone.Increasing Smectic Thrmal Stabilities by the Lateral Polar Carbonyl Group" Chemistry Letters. 699-700 (1996)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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