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Development of color-change indicators using inclusion complex formation

Research Project

Project/Area Number 04453096
Research Category

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

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

Principal Investigator

UENO Akihiko  Tokyo Institute of Tecnnology, 生命理工学部, 教授 (50091658)

Co-Investigator(Kenkyū-buntansha) IKEDA Hiroshi  Tokyo Institute of Technology, 生命理工学部, 技官 (70201910)
NAKAMURA Asao  Tokyo Institute of Technology, 生命理工学部, 助手 (50155818)
IKEDA Tsukasa  Tokyo Institute of Technology, 生命理工学部, 助手 (40151295)
Project Period (FY) 1992 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥7,000,000 (Direct Cost: ¥7,000,000)
Fiscal Year 1994: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1993: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1992: ¥2,900,000 (Direct Cost: ¥2,900,000)
Keywordscyclodextrin / color change / indicator / inclusion complex / host-guest / steroid / molecular recognition / p-nitrophenol / p-ニトロフェノール / 分子認識 / センサー / サーモクロミズム / 電荷移動錯体 / 包接化合物 / 超分子 / 包接 / メチルレッド / pH指示薬 / 錯体
Research Abstract

Cyclodextrins (CDs) are spectroscopically inert, but they can be converted into spectroscopically active compounds by modification with cheomophores. In this study, we prepared several dye-modified CDs to construct color-change indicators for molecules.
We found that the chromophore-modified CDs change the location of the chromophore from their own hydrophobic cavity to the outside water environment upon guest accommodation. This environmental change around the chromophore moiety usually causes perturbation in its spectroscopic property. On this basis, methyl-red modified CD changes color from yellow to red upon guest binding in acidic media. On the other hand, p-nitrophenol-modified alpha-CD and beta-CD undergo guest-induced color (yellow)-to-colorless change under neutral pH conditions. Futhermore, we prepared phenolphthalein-modified beta-CD,which also undergoes color (purple)-to-colorless change upon guest binding. All these hosts exhibit different affinities for guest species, and consequently they can be used as color-change indicators for molecules.

Report

(4 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • 1992 Annual Research Report
  • Research Products

    (32 results)

All Other

All Publications (32 results)

  • [Publications] Kita Hamasaki: "Fluorescent Sensors of Molecular Recognition.Modified Cyclodextrins Capable of Exhibiting Guest-Responsive TICT Fluorescence" J.Am.Chem.Soc.115. 5035-5040 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo Kuwabara: "A Novel Color-Change Indicator for Molecules.Guest-induced Color-to-Colorless Change of p-nitrophenol-modified beta-Cyciodextrin" Chem.Lett. 2081-2084 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo Kuwabara: "Supramolecular Thermochromism of a Dye-appended beta-Cyclodextrin" J.Chem.Soc.,Chem.Commun.689-690 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Keita Hamasaki: "Molecular Recognition Indicators of Modified Cyclodextrins Using Intramolecular Charge Transfer Fluorescence" Bull.Chem.Soc.Jpn.67. 516-523 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Yong Wang: "Dansyl-beta-Cyclodextrins as Fluorescent Sensors Responsive to Organic Compounds" Bull.Chem.Soc.Jpn.7. 1598-1607 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo Kuwabara: "Inclusion Complexes and Guest-induced Color Changes of pH-Indic ator-Modified beta-Cyclodex-trins" J.Phys.Chem.98. 6297-6303 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tesuo Kuwabara: "Inclusion Complexes and Guest-induced Color Changes of pH-Indicator-modified beta-Cyclodextrin" J.Phys.Chem. 98. 6297-6303 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Yong Wang: "Dansyl-beta-Cyclodextrins as Fluorescent Sensors responsive to Organic Compounds" Bull.Chem.Soc.Jpn.67. 1598-1607 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Fumio Hamada: "Dansyl-modified gamma-Cyclodextrin as a Fluorescent Sensor for Molecular Recognition" J.Inclusion Phenomena and Molecular Recognition. 15. 273-279 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Keita Hamasaki: "Molecular Recognition Indicators of Modified Cyclodextrins Using Twisted Intra-molecular Charge Transfer Fluorescence" Bull.Chem.Soc.Jpn.67. 516-523 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo Kuwabara: "Supramolecular Thermochromism of a Dye-appended beta-Cyclodextrin" J.Chem.Soc., Chem.Commun.689-690 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Yong Wang: "Synthesis of a Cyclodextrin Heterodimer Having alpha- and beta-Cyclodextrin Units and Its Cooperative and Site-Specific Binding" Chem.Lett.167-170 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Akihiko Ueno: "Fluorescent Sensors and Color-Change Indicators for Molecules" Advanced Materials. 5. 132-134

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Tetsuo Kuwabara: "Inclusion Complexes and Guest-Induced Color Changes of PH-Indicatior-Modified β-Cyclodextrins" J.Phys.Chem.98. 6297-6303 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Yong Wang: "Dansyl-β-Cyclodextrins as Fluorescent Sensors Responsive to Organic Compounds" Bill.Chem.Soc.Jpn.67. 1598-1607 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Fumio Hamada: "Dansyl-Modified γ-Cyclodextrin as a Fluorescent Sensor for Molecular Recognition" Journal of Inclusion Phenomena and Molecular Recognition. 15. 273-279 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] Keita Hamasaki: "Molecular Recognition Indicators of Modified Cyclodertrins Using Twisted Intramolecular Charge Transfer Fluorescence" Bull.Chom.Soc.Jpn.67. 516-523 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Tetsuo Kuwabara: "Supramolecular Thermochromism of a Dye-appended β-Cyclodoxtrin" J.Chem.Soc,Chem.Commun.689-690 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Yong Wang: "Synthosis of a Cyclodextrin Heterodimen Having α- and β-Cyclodoxtrin Units and Its Cooperative and Site-Spocific Binding" Chem.Lett.167-170 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Keita Hamasaki: "Fluorescent Sensors of Molecular Recognition.Modified Cyclodextrins Capable of Exhibiting Gues-Responsive Twistal Intrumolecular Charge Transfer Fluorescence" J.Am.Chem.Soc.115. 5035-5040 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yong Wang: "Fluorescein Matified β-Cyclodextrin as a Charge-Changeable Receptor" Tetrahedron Lett.34. 4971-4974 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Tetsuo Kuwabara: "A Novel Color-Change Indicator for Molecules.Guest-induced Color-to-Colorless Change of p-Nitrophenol-Modified β-Cyclodextrin" Chem.Lett.2081-2084 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yong Wang: "Synthesis of a Cyclodextrin Heterodimer Having α- and β-Cyclodextrins and Its Cooperative and Sice-Specific Binding" Chem.Lett.167-170 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Tetsuo Kuwabara: "Supramolecular Thermochronism of a Dye appended β-Cyclodextrin" J.Chem.Soc.,Chem.Commun.(発表予定). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Keita Hamasaki: "Molecular Recognition Indicators of Modified Cyclodextrins Using Twisted Intramolecular Charge Transfer Fluorescence" Buel.Chem.Soc.Jpn.67. 516-523 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] 上野 昭彦: "超分子の科学" 産業図書, 166 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Iwao Suzuki: "Detection of Organic Compounds by Dual Fluorescence of Bis(1-Pyrenecarbonyl)-γ-cyclodextrins" Chemistry Letters. 269-272 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akihiko Ueno: "A Modified Cyclodextrin as a Guest responsive Colour-Change Indicator" Nature. 356. 136-137 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Yong Wang: "Syntheses and Molecular Recognition Abilities of6-O-,2-O-,and 3-O-Dansyl-γ-Cyclodextrins" Chemistry Letters. 863-866 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akihiko Ueno: "Host-Guest Sensors of 6A,6B-,6A,6C-,6A,6D-,and 6A,6E-Bis(2-naphthylsulfenyl)-γ-cyclodextrins for Detecting Organic Compounds by Fluorescence Enhancement" Analytical Chemistry. 64. 1154-1157 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akihiko Ueno: "Detection of Organic Compounds by Guest-Responsive Circular Dichroism Variations of Ferrocene-appended Cyclodextrins" Analytical Chemistry. 64. 1650-1655 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akihiko Ueno: "Detection of Organic Compounds by Guest-Responsive Monomer and Excimer Fluorescence of 6A,6B-,6A,6C-,and 6A,6D-Bis(2-naphthylsulfonyl)-β-Cyclodextrins" Analytical Chemistry. 64. 2562-2565 (1992)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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