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Selective Synthesis and Application of Novel Liquid-Crystalline Diaryldiacetylenes

Research Project

Project/Area Number 09450334
Research Category

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

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

KITAMURA Tsugio  KYUSHU UNIVERSITY, Faculty of Engineering, Ass.Prof., 大学院・工学研究院, 助教授 (00153122)

Co-Investigator(Kenkyū-buntansha) NAGATA Kensuke  KYUSHU UNIVERSITY, Faculty of Engineering, Research Ass., 大学院・工学研究院, 助手 (40264080)
TANIGUCHI Yuki  KYUSHU UNIVERSITY, Faculty of Engineering, Research Ass., 大学院・工学研究院, 助手 (50217139)
FUJIWARA Yuzo  KYUSHU UNIVERSITY, Faculty of Engineering, Prof., 大学院・工学研究院, 教授 (10029481)
Project Period (FY) 1997 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥12,300,000 (Direct Cost: ¥12,300,000)
Fiscal Year 2000: ¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1999: ¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1998: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1997: ¥3,800,000 (Direct Cost: ¥3,800,000)
KeywordsDiaryldiacetylene / Liquid Crystals / Thiophenes / Ferroelectric Liquid Crystals / Enynes / Diethynylethenes / Tetraethynylethenes / Charge-Transfer Complex / ジエチニルエテン / テトラエチニルエテン / ジアリールアセチレン / アルキニルヨードニウム塩 / アルキニルベンゾトリアゾール / エンイン誘導体 / エンジイン誘導体 / ジアリールジアセチン / L-4-ジアリフレ-1-フチン-3-イン / L1-ビス(アリールエチニル)エテン / チオフェン誘導体 / キラルジアリールジアセチレン / キラルスメクチックC相
Research Abstract

(1) Selective Synthesis of Diaryldiacetylenes and Evaluation of Liquid Crystalline Properties
Arylethynyliodonium salts with long alkyl groups were prepared easily prepared by reaction of arylacetylenes and hydorxy(tosyloxy)iodobenzene. The reaction of the arylethynyliodonium salts with alkynylcopper reagents selectively provided diaryldiacetylenic compounds that exhibited liquid-crystalline properties. Liquid-crystalline thiophene derivatives were also synthesized from the diaryldiacelenes. Furthermore, chiral (S)-(2-methylbutoxy)phenylethynyliodonium tosylate was synthesized first and applied to chiral diaryldiacetylenic compounds by the reaction with arylethynylcopper reagents, affording chiral diaryldiacetylenic ferroelectric liquid crystals.
(2) Synthesis of Liquid-Crystalline Enynes
Synthesis of 1,4-diaryl-1-buten-3-ynes were synthesized by the palladium-catalyzed coupling reaction of arylacetylenes with styryl bromides having long alkyl groups. Thus prepared enyne derivatives showed smectic and nematic phases in a wide range of temperature.
(3) Synthesis of 1,1 -Diethynylethenes and Tetraethynylethenes
1,1 -Diethynylethenes and tetraethynylethenes have the structure that the π electronic system is delocalized on the molecular plane. 1,1 -Bis(arylethynyl)ethenes and tetrakis(4-decyloxyphenylethynyl)ethene were prepared but did not show mesogenic properties. The new charge-transfer complexes with trinitrofluorenone were obtained.

Report

(5 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (29 results)

All Other

All Publications (29 results)

  • [Publications] T.Kitamura et al.: "A New Route to Chiral Diarydiacetylenic Liquid Crystals, Preparation of lodonium Salts Bearing Chiral Alkynyl Ligands and Utility for Chiral Alkynyl Iranster Agents"J.Am.Chem.Soc.. 119. 619-620 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Transformation of Liquid-Crystalline Diaryldiacetylenes to Liquid-Crystalline 2,5-Diarylthiophenes"Mol.Cryst.Lig.Cryst.. 293. 239-245 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Aromatic C-H Insertion of β-Phenoxyalkylidenecarbenes Generated by Reaction of Alkynyl(p-phenylene) bisiodonium Ditrifluormethanesulfonate (Ditriflates) with Phenoxide Anions"J.Chem.Soc.Perkin Trans.2. 1511-1515 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Alkynylbenzotriazoles by Direct Alkynylation of Benzotriazole Using Alkynyliodonium Salts"Tetrahedron Lett.. 39. 3787-3790 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Novel Heteroaromatic C-H Insertion of Alkylidenecarbenes. A New Entry to Furopyridine Synthesis"Tetrahedron Lett.. 39. 5375-5376 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "(Phenyl)[3-(trimethylsilyl)-2-naphthyl]iodonium Triflate as a New Precursor of 2,3-Didehydronaphthalene"J.Org.Chem,. 63. 8579-8581 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Synthesis of Liquid-Crystalline Enynes by Palladium-Catalyzed Cross-Coupling Reaction"Chem.Lett.. 1271-1272 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Synthesis and Reactions of Hypervalent Iodine-Benzyne Precursor Possessing an Ester Group"Synlett. 731-732 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Oligomerization of (Diacetoxyiodo) benzene with Trifluoromethanesulfonic Acid. Preparation and Structure of Hypervalent Iodine Oligomers"Org.Lett.. 1. 253-256 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "A New and Efficient Hypervalent Iodine-Benzyne Precursor (Phenyl)[ο-(trimethylsilyl)phenyl]iodonium Triflate. Generation, Trapping Reaction, and Nature of Benzyne"J.Am.Chem.Soc.. 121. 11674-11679 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "A Convenient Synthesis of New 1-Alkynyl-1H-benzotriazoles by Reaction of Alkynyl(phenyl)iodonium Tosylates with Benzotriazole Ion"Heterocycles. 52. 303-312 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "A New Route to Chiral Diaryldiacetylenic Liquid Crystals. Preparation of Iodonium Salts Bearing Chiral Alkynyl Ligands and Utility for Chiral Alkynyl Transfer Agents"J.Am.Chem.Soc.. Vol.119. 619-620 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Transformation of Liquid-Crystalline Diaryldiacetylenes to Liquid-Crystalline 2,5-Diarylthiophenes"Mol.Cryst.Liq.Cryst.. Vol.293. 239-245 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Aromatic C-H Insertion of β-Phenoxyalkylidenecarbenes Generated by Reaction of Alkynyl(p-phenylene)bisiodonium Ditrifluoromethanesulfonate (Ditriflates) with Phenoxide Anions"J.Chem.Soc.Perkin Trans.. 2. 1511-1515 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Alkynylbenzotriazoles by Direct Alkynylation of Benzotriazole Using Alkynyliodonium Salts"Tetrahedron Lett.. Vol.39. 3787-3790 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Novel Heteroaromatic C-H Insertion of Alkylidenecarbenes. A New Entry to Furopyridine Synthesis"Tetrahedron Lett.. Vol.39. 5375-5376 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "(Phenyl)[3-(trimethylsilyl)-2-naphthyl]iodonium Triflate as a New Precursor of 2,3-Didehydronaphthalene"J.Org.Chem.. Vol.63. 8579-8581 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Synthesis of Liquid-Crystalline Enynes by Palladium-Catalyzed Cross-Coupling Reaction"Chem.Lett.. 1271-1272 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T,Kitamura et al.: "Synthesis and Reactions of Hypervalent Iodine-Benzyne Precursor Possessing an Ester Group"Synlett. 731-732 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "Oligomerization of (Diacetoxyiodo)benzene with Trifluoromethanesulfonic Acid. Preparation and Structure of Hypervalent Iodine Oligomers"Org.Lett.. Vol.1. 253-256 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "A New and Efficient Hypervalent Iodine-Benzyne Precursor, (Phenyl)[o-(trimethylsilyl)phenyl]iodonium Triflate. Generation, Trapping Reaction, and Nature of Benzyne"J.Am.Chem.Soc.. Vol.121. 11674-11679 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Kitamura et al.: "A Convenient Synthesis of New 1-Alkynyl-1H-benzotriazoles by Reaction of Alkynyl(phenyl)iodonium Tosylates with Benzotriazole Ion"Heterocycles. Vol.52. 303-312 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tsugio Kitamura et al.: "Synthesis of a New Hypervalent Iodine Compound, [2-(Hydroxydimethylsilyl) phenyl](phenyl) iodonium Triflate as a Convennient Approach to Benzyne"Tetrahedron Letters. 41. 6611-6614 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 北村 二雄: "A Convenient Synthesis of New 1-Alkynyl-1H-bengotriag otes by Reaction of Alkymyl(phenyl)inodinum Salts with Bengotriagde Ion"Heterocycles. 52巻・1号. 303-312 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] 北村二雄: "Alkyal benzotriazoles by Direct Alkynylation of Benzotriazole Using ALKnyliodonium Salts" Tetrahedron Letters. 39巻. 3738-3790 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 北村二雄: "Synthesis of Liguid-Crystalline Enynes by Palladium-Catalyzed Cross-Coupling Reaction" Chemestry Letters. 1271-1274 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 北村 二雄: "Recent Progress in the Use of Hypervalent Iodine Peagents in Organic Synthesis.A Review" Organic Preparations and Procedures International. 29巻. 409-458 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 北村 二雄: "A New Route to Chiral Diaryldiacetylenic Liquid Crystals.Preparation of Iodonium Salts Bearing Chiral Alkynyl Ligands and Utility for Chiral Alkynyl Transfer Agents" Journal of American Chemical Society. 119巻. 619-620 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 北村 二雄: "Transformation of Liquid-Crystalline Diaryldiacatylenes to Liquid-Crystalline 2,5-Diarylthiophenes" Molecular Crystals and Liquid Crystals. 293巻. 239-245 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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