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新しい二重蛍光現象を利用した微視的粘度・圧力センサーの開発

Research Project

Project/Area Number 06650990
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionOsaka University

Principal Investigator

INOUE Yoshihisa  Osaka University, Molecular Chemistry, Professor, 工学部, 教授 (30112543)

Project Period (FY) 1994 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1995: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1994: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsPhotochemistry / Dual Fluorescence / Rotational Relaxation / Aromatic Carboxylic Esters / Viscosity Sensor / Pressure Sensor / 粘度効果 / 圧力効果
Research Abstract

Fluorescence behavior of a variety of newly synthesized aromatic carboxylic esters and amides has been examined in order to reveal the detailed mechanism of novel dual fluorescence induced by steric hindrance between the adjacent bulky ester or amide groups. The results obtained by this research may be summarized as follows :
1) First, a wide variety of novel benzenecarboxylic esters and amides possessing bulky alkyl groups were synthesized.
2) Fluorescence behavior of these highly congested esters and amides was examined by means of fluorimeter, single photon counting technique, and fluorescence anisotropy measurement. We found that the esters exhibit dual fluorescence in the region 330-390 nm, while the amides do not fluoresce at all, and also that the steric hindrance between the adiacent bulky ester groups causes the dual fluorescence arising from the rotational barrier.
3) The dual fluorescence behavior found was found to be useful as a microviscosity sensor, for example, in micelles, since the relative intensity of dual fluorescence peaks does not depend on solvent polarity but only on solvent viscosity. The same compounds were also demonstrated to be good in situ pressure sensors between the range of 1-5000 atm.
4) Quite interestingly, the alkyl benzenepolycarboxylates and amides carrying chiral alkyl groups were employed as chiral sensitizer in enantiodifferentiating geometrical photoisomerizations of cycloalkenes to give good to excellent optical yields.

Report

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

    (33 results)

All Other

All Publications (33 results)

  • [Publications] M. Yasuda,G. Kuwamura,T. Nakazono,K. Shima,Y. Inoue,N. Yamasaki and A. Tai: "Highly Twisted tert-Butoxycarbonyl Groups in Benzenepolycarboxylate. The Origin of Steric Hindrance-Induced Dual Fluorescence" Bull. Chem. Soc. Jpn.67. 505-510 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 井上佳久: "不斉反応におけるエントロピーの役割-温度による生成物キラリティーの逆転" 生産と技術. 46. 43-46 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A. Tai,T. Kikukawa,T. Sugimura,Y. Inoue,S. Abe,T. Osawa and T. Harada: "An Improved Asymmetrically-Modified Nickel Catalyst Prepared from Ultrasonicated Raney Nickel" Bull. Chem. Soc. Jpn.67. 2473-2477 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 井上佳久: "光増感反応で不斉合成に迫る" 有機合成化学協会誌. 53. 348-357 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y. Inoue: "Vital Role of Entropy in Asymmetric Photochemistry" Kokagaku (Photochemistry). 19. 29-33 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H. Tsuneishi,T. Hakushi,A. Tai and Y. Inoue :"Enantiodifferentiating Photoisomerization of 1-Methylcyclooctene Sensitized by Chiral Alkyl Benzenecarboxylates : Steric Effects upon Stereodifferentiation" J. Chem. Soc.,Perkin Trans. 2. 1995. 2057-2062 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y. Inoue,F. Dong,K. Yamamoto,L. -H. Tong,H. Tsuneishi,T. Hakushi and A. Tai: "Inclusion-Enhanced Opticaland E/Z Ratio in Enantiodifferentiating Photoisomerization of Cyclooctene Included and Sensitized by β-Cyclodextrin Monobenzoate" J. Am. Chem. Soc.117. 11033-11034 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y. Inoue,H. Tsuneishi,T. Hakushi,and A. Tai(分担執筆): "“PhotochemicalKey Steps in OrganicSynthesis" (edited by J. Mattay and A. G. Griesbeck)" VCH Verlag (Weinheim,Germany), 350 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] 井上佳久(分担執筆): "光と化学の事典(本多健一、飛田満彦編)" 丸善, 600 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Yasuda, G.Kuwamura, T.Nakazono, K.Shima, Y.Inoue, N.Yamasaki and A.Tai: "Highly Twisted tert-Butoxycarbonyl Groups in Benzenepolycarboxylate. The Origin of Steric Hindrance-Induced Dual Fluorescence" Bull.Chem.Soc.Jpn.67. 505-510 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Inoue: "Role of Entropy in Asymmetric Chemistry. Temperature-Switching of Product Chirality" Product.Technol.46. 43-46 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] A.Tai, T.Kikukawa, T.Sugimura, Y.Inoue, S.Abe, T.Osawa and T.Harada: "An Improved Asymmetrically-Modified Nickel Catalyst Prepared from Ultrasonicated Raney Nickel" Bull.Chem.Soc.Jpn.67. 2473-2477 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Inoue: "Asymmetric Synthesis Through Photosensitization : State of the Art" J.Synth.Org.Chem.Jpn.53. 348-357 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Inoue: "Vital Role of Entropy in Asymmetric Photochemistry" Kokagaku (Photochem.). 19. 29-33 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] H.Tsuneishi, T.Hakushi, A.Tai and Y.Inoue: "Enantio-differentiating Photoisomerization of 1-Methylcyclooctene Sensitized by Chiral Alkyl Benzenecarboxylates : Steric Effects upon Stereodifferentiation" J.Chem.Soc., Perkin Trans.2. 2057-2062 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Inoue, F.Dong, K.Yamamoto, L.-H.Tong, H.Tsuneishi, T.Hakushi and A.Tai: "Inclusion-Enhanced Optical and E/Z Ratio in Enantiodifferentiating Photoisomerization of Cyclooctene Included and Sensitized by beta-Cyclodextrin Monobenzoate" J.Am.Chem.Soc.117. 11033-11034 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Inoue, H.Tsuneishi, T.Hakushi, and A.Tai: "Photochemical Key Step in Organic Synthesis" (edited by J.Mattay and A.G.Griesbeck). VCH Verlag (Weinheim, Germary), 350 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Y.Inoue: "Dictionary of Light and Chemistry" (edited by K.Honda and M.Tobita). Maruzen (Tokyo), 600 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] M.Yasuda,G.Kuwamura,T.Nakazono,K.Shima,Y.Inoue,N.Yamasaki and A.Tai: "Highly Twisted tert-Butoxycarbonyl Groups in Benzenepolycarboxylate. The Origin of Steric Hindrance-Induced Dual Fluorescence" Bull.Chem.Soc.Jpn.67. 505-510 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] 井上佳久: "不斉反応におけるエントロピーの役割-温度による生成物キラリティーの逆転" 生産と技術. 46. 43-46 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Tai,T.Kikukawa,T.Sugimura,Y.Inoue,S.Abe,T.Osawa and T.Harada: "An Improved Asymmetrically-Modified Nickel Catalyst Prepared from Ultrasonicated Raney Nickel" Bull.Chem.Soc.Jpn.67. 2473-2477 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] 井上佳久: "光増感反応で不斉合成に迫る" 有機合成化学協会誌. 53. 348-357 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Inoue: "Vital Role of Entropy in Asymmetric Photochemistry" Kokagaku (Photochemistry). 19. 29-33 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Tsuneishi,T.Hakushi,A.Tai and Y.Inoue:"Enantiodifferentiating Photoisomerization of 1-Methylcyclooctene Sensitized by Chiral Alkyl Benzenecarboxylates : Steric Effects upon Stereodifferentiation" J.Chem.Soc., Perkin Trans.2. 1995. 2057-2062 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Inoue,F.Dong,K.Yamamoto,L.-H. Tong,H.Tsuneishi,T.Hakushi and A.Tai: "Inclusion-Enhanced Opticaland E/Z Ratio in Enantiodifferentiating Photoisomerization of Cyclooctene Included and Sensitized by β-Cyclodextrin Monobenzoate" J.Am.Chem.Soc.117. 11033-11034 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Inoue,H.Tsuneishi,T.Hakushi,and A.Tai (分担執筆): "“PhotochemicalKey Steps in Organic Synthesis" (edited by J.Mattay and A.G.Griesbeck)" VCH Verlag (Weinheim,Germany), 350 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] 井上佳久(分担執筆): "光と化学の事典(本多健一,飛田満彦編)" 丸善, 600 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Yasuda,G.Kuwamura,T.Nakazono,K.Shima,Y.Inoue,N.Yamasaki and A.Tai: "Highly Twisted tert-Butoxycarbonyl Groups in Benzenepolycarboxylate.The Origin of Steric Hindrance-Induced Dual Flurescence" Bull.Chem.Soc.Jpn.67. 505-510 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 井上佳久: "不斉反応におけるエントロピーの役割-温度による生成物キラリティーの逆転" 生産と技術. 46. 43-46 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] A.Tai,T.Kikukawa,T.Sugimura,Y.Inoue,S.Abe,T.Osawa and T.Harada: "An Improved Asymmetrically-Modified Nickel Catalyst Prepared from Ultrasonicated Raney Nickel" Bull.Chem.Soc.Jpn.67. 2473-2477 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 井上佳久: "光増感反応で不斉合成に迫る" 有機合成化学協会誌. 53(5月号). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y.Inoue,H.Tsuneishi,T.Hakushi,and A.Tai(分担執筆): "“Photochemical Key Steps in Organic Synthesis"(edited by J.Mattay and A.G.Griesbeck)" VCH Verlag(Weinheim,Germany), 350 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 井上佳久(分担執筆): "光と化学の事典(本多健一、飛田光満彦編)" 丸善, 600 (1996)

    • Related Report
      1994 Annual Research Report

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

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