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DEVELOPMENT OF NEW ORGANIC NONLINEAR OPTICAL MATERIELS

Research Project

Project/Area Number 03555186
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

TANIGUCHI Hiroshi  KYUSHU UNIVERSITY, PROFESSOR (Fac.of Eng.), 工学部, 教授 (10037715)

Co-Investigator(Kenkyū-buntansha) KITAMURA Tsugio  KYUSHU UNIVERSITY, ASSOCIATE PROFESSOR (Fac.of Eng.), 工学部, 助教授 (00153122)
ISOMURA Kazuaki  KITAKYUSHU NATIONAL COLLEGE OF TECHNOLOGY, PROFESSOR, 化学工学科, 教授 (80037887)
Project Period (FY) 1991 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥15,300,000 (Direct Cost: ¥15,300,000)
Fiscal Year 1993: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1992: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1991: ¥11,300,000 (Direct Cost: ¥11,300,000)
KeywordsORGANIC OPTICAL MATERIAL / AMPHIPHILE HAVING HETEROCYCLE / STRUCTURE OF MONOLAYER / LANGMUIR-BLODGETT FILM / MOLECULAR ASSEMBLY / THEORY ON INTERMOLECULAR FORCE / MULTIPOLE-MULTIPOLE INTERACTION / LIQUID CRYSTAL / 液晶 / 複素環両親媒性化合物 / 分子間力の分子軌道 / 異積膜 / 分子集分体
Research Abstract

This investigation was performed to develop optically non-linear organic thin films from newly designed compounds having long and polar heterocyclic chromophores. The important results obtained by this study are as follow :
1. The amphiphiles having phenylpyrazine or phenylpyridazine chromophore were shown to be excellent amphiphiles to fabricate organic thin film by Langmuir-Blodgett (LB) technique. Comparison with related compounds suggested the excellence of pyrazine and pyridazine derivatives would be caused by electrostatic multipole-multipole interaction between these heterocycles in the layred structures. This consideration was supported by computer simulation based on 2-dimensional crystalline models. The molecular arrangement in the monolayr of a liquid crystalline material, alkoxyphenylpyrazine carbonitrile, could be observed by scanning tunneling microscope (STM) and the STM image was reproduced by same simulation, which revealed this simulation could be used as a guide line for the molecular design of compound to fabricate molecular assemblies.
2. By introduction of acryloxy group at the end of the hydrophobic alkyl chain of an amphiphile having pyrazine ring, Z-type LB film was obtained. The Z-type LB film mechanically strengthened by photopolymerization showed strong second harmonic generation. The amphiphiles having MeO-, NC-, N_3- at the end of alkyl group also gave Z-type LB film, which revealed that introducing polar group at the end of alkyl chain caused Z-type deposition which is favorable for monlinear optical activity.
3. Amphiphiles having acetylenic or diacetylenic linkage between two aromatic rings were also prepared. The LB-films of these compound were shown to be strong nonlinear optical material

Report

(4 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • 1991 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] H.Taniguchi,K.Isomura,S.Saito,K.Takehara: "Second-order Nonlinear Optical Langmuir-Blodgett Films of Pyrazine Derivatives" Thin Solid Films. 210/211. 163-165 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Taniguchi,K.Isomura,K.Takehara: "Theoreticaal Study on the Effect of Heterocycles Reinforcing the Layered Structures" Thin Solid Films. 210/211. 169-171 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Taniguchi,K.Isomura,M.Matsumoto: "キラル置換基を有する非対称ピラジンの強誘電性液晶" 日本化学会誌. 1213-1219 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Matsushige,H.Taniguchi,K.Isomura: "Scanning Tunneling Microscope Observation of a Polar Liquid Crystal and Its Computer Simulation" Jpn.J Appl.Phys.32. 1716-1721 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Taniguchi,K.Isomura,K.Takehara: "Z-Type Deposition of a Polymerizable Amphiphile to Fabricate Immobilized LB-Film Showing Strong SHG" Thin Solid Films. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] H.Taniguchi,K.Isomura,K.Takehara: "Effect of Elongation of π-Electron System on the Behaviors of Amphiphiles Containing Pyrazine Ring" Thin Solid Films. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masanao Era, Hisashi Kawafuji, Tetsuo Tsutsui, Shogo Saito, Kazuaki Isomura, Kenji Takehara, and Hiroshi Taniguchi: "Second-order Nonlinear Optical Langmuir-Blodgett Films of Pyrazine Derivatives" Thin Solid Films. Vol.210/211. 163-165 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kazuaki Isomura, Kenji Takehara, Tetsuro Fukuda, and Hiroshi Taniguchi: "Theoretical Study on the Effect of Heterocycles Reinforcing the Layred Structure" Thin Solid Films. Vol.210/211. 169-171 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masaru Matsumoto, Youichi Sano, Toshiyuki Nagaishi, Syunichi Yoshinaga, Kazuaki Isomura and Hiroshi Taniguchi: "Ferroelectric Liquid Crystallinity of Unsymmetrically Disubstituted Pyrazines with Chiral Substituents" Nippon Kagakukaishi. No.10. 1213-1219 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kazumi Matsusige, Seiji Taki, Hirotaka Okabe, Yasuo Takebayashi, Kouichi Hayashi, Yuji Yoshida, Toshihisa Horiuchi, Kazuhiro Hara, Kazuaki Isomura, Kenji Takehara, and Hiroshi Taniguchi: "Scanning Tunneling Microscope Observation of a Polar Liquid Crystal and its Computer Simulation" Jpn.J.Appl.Phys.Vol.32. 1716-1721 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kenji Takehara, Kazuaki Isomura, Goro Funakoshi, Kazuhiko Kobayashi, Hiroshi Taniguchi, Masanao Era, Tsutsui Tetsuo, and Shogo Saito: "Z-Type Deposition of a Polymerizable Amphiphile to Fabricate Immobilized LB-Film Showing Strong SHG" Thin Solid Films. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Kenji Takehara, Katsumi Takehara, Kazukai Isomura, and Hiroshi Taniguchi: "Effect of Elongation of pi-Electron System on the Behaviors of Amphiphiles Containing Pyrazine Ring" Thin Solid Films. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] 竹林 康夫: "STMによる極性有機分子の分子配列の直接観察" 九州大学工業集報. 66. 63-70 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Kazuaki ISOMURA: "Molecular Design of Polar Amphiphiles for Fabrication of LB Film Capable of Second Harmonic Generation" Chemistry of Functional Dyes. 2. 469-474 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Kazuaki ISOMURA: "Z-Type Deposition of Polar Amphiphiles Showing Strong SHG" Chemistry of Functional Dyes. 2. 490-493 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Kazuaki ISOMURA: "Second Harmonic Generation of the LB-Film Prepared from Newly Designed Amphiphiles Having Heterocycles" Chemistry of Functional Dyes. 2. 505-508 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Kazami MATSUSHIGE: "Scanning Tunneling Microscope Observation of a Polar Liguid Crystal and its Computer Simulation" Jpn.J.Appl.Phys. 32. 1716-1721 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Junzo UEMURA: "Raman Spectroscopic Study of Alternate Langmuir-Blodgett Films with Pyroelectric Efficiency" Bulletin of the Institute for Chemical Research,Kyoto University. 71. 120-126 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Kenji TAKEHARA: "UV Study on the Interaction of Amphiphilies Having Heterocyclic Chromophore" Thin Solid Films. 210/211. 124-126 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Kenji TAKEHARA: "Theoretical Study on the Effect of Heterocycles Reinforcing the Layered Structure" Thin Solid Films. 210/211. 169-171 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Masanao ERA: "Second-order nonlinear optical Langmuir-Blodgett films of pyrazine derivatives" Thin Soled Films. 210/211. 163-165 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Tsugio Kitamura: "Electrophilic Additions of Iodosylbenzene Activated by Trifluoromethanesulfonic Acid,[PhIO-TfOH],to Alkynes" Tetrahedron. 48. 7149-7156 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Tsugio Kitamura: "A Convenient Preparation of Diaryliodonium Triflates" Synthesis. 10. 945-946 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Tsugio Kitamura: "Novel Alkynyl-substituted(p-Phenylene)bisiodonium Ditriflates.Preparation and Reaction with Thiocyanate Ion" Chemistry Letters. 2241-2244 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Kenji TAKEHARA: "UV Study on the Interaction of Amphiphilies Having Heterocyclic Chromophore" Thin Solid Films. 207. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Kenji TAKEHARA: "Theoretical Study on the Effect of Heterocycles Reinforcing the Layered Structure" Thin Solid Films. 207. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Tsugio Kitamura: "Phenylthiolation of Arylviny Bromides by Photolysis." Joumal of Organic Chemistry. 56. 3739-3741 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Tsugio Kitamura: "Photolytic and Solvolytic Reactions of β-[o-(Aryloxy)phenyl]vinyl Bromides.Intramolecular Arylation of Vinyl Cations into Dibenzoxepins" Joumal of American Chemical Society. 113. 6240-6245 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Tsugio Kitamura: "Ipso Substitution of Triarylvinyl Cations by Alkoxide Anions" Joumal of American Chemical Society. 113. 7255-7261 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Tsugio Kitamura: "Selective Coupling Reactions of Alkynyl(phenyl)iodonium Tosylates with Alkynylcopper Reagents" J.Chem.Soc.,Perkin Transactions 1. 11. 2892-2893 (1991)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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