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Development of Calixarene Derivatives Having Molecular Recognition Ability and Catalytic Ability

Research Project

Project/Area Number 05555242
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionUniversity of Osaka Prefecture

Principal Investigator

MIZUNO Kazuhiko (1994)  University of Osaka Prefecture, College of Engineering, Associate Professor, 工学部, 助教授 (10109879)

大辻 吉男 (1993)  大阪府立大学, 工学部, 教授 (20081341)

Co-Investigator(Kenkyū-buntansha) MORITA Yutaka  Dainichiseika Color & Chemicals Mfg.Co.Ltd., Consultant, 中央研究所, 顧問
NOMURA Eisaku  Industrial Technology Center of Wakayama Prefecture, Researcher, 精密化学担当, 研究員
TANIGUCHI Hisaji  Industrial Technology Center of Wakayama Prefecture, Chief Researcher, 精密化学担当, 主任研究員
OTSUJI Yoshio  University of Osaka Prefecture, Emeritus Professor, 名誉教授 (20081341)
水野 一彦  大阪府立大学, 工学部, 助手 (10109879)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥6,100,000 (Direct Cost: ¥6,100,000)
Fiscal Year 1994: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1993: ¥4,000,000 (Direct Cost: ¥4,000,000)
KeywordsCalixarene / Heavy metal ion capturing / Alkali-metal ion extraction / Esterification / Dichlorocarbene / Permanganate oxidation / Hydroboration / ジエン-ヨウ素錯体 / チタン錯体 / 包接化合物 / 分子認識 / 触媒機能 / 金属イオン抽出能 / クロモトロピック特性 / 酸化反応
Research Abstract

The synthesis and properties of calixarene derivatives have been studied with the intention of developing materials having a high molecular recognition ability and a high catalytic ability. The results obtained are summarized below.
1. Calix[4]quinone and calix[4]hydroquinone were synthesized starting with p-H-calix[4]arene, and their conformational properties were elucidated.
2. p-Phenylazocalix[4]and[6]arenes exhibited the high ability of capturing heavy metal ions such as Ag^+, Hg^+, and Hg^<2+>. They also exhibited a chromotropic property.
3. The p-t-butylcalix[6]arene derivative bearing 3,6,9-trioxadecyl group at six phenolic oxygens showed the high ability of capturing K^+ion. By utilizing this ability, new esterification reaction and dichlorocarbene generation reaction were developed.
4. The above calixarene derivative served as catalysts for the KMnO_4oxidation of alkenes, alkynes, and primary alcohols to yield carboxylic acids and also for the oxidation of secondary alcohols to ketones.
5. The above calixarene derivatives also exhibited the ability of including diene-iodine complexes.Moreover, the calixarene derivative enhanced the reactivity and selectivity in the Ti-complex catalyzed hydroboration of isolated dienes with NaBH_4.
6. The method for technical production of p-t-butylcalix[6]arene was established.

Report

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

    (9 results)

All Other

All Publications (9 results)

  • [Publications] Eisaku Nomura, Hisaji Taniguchi, Kouichi Kawaguchii, and Yoshio Otsuji: "Catalytic Ability of Flexible Octopus-Type Calix[6]arene in Ester-Forming Reaction and Its Structural Properties" J.Org.Chem. 58. 4709-4715 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Eisaku Nomura, Hisaji Taniguchi, and Yoshio Otsuji: "Binding Properties of p-(Phenylazo)calixarenes for Metal Ions" Bull.Chem.Soc.Jpn. 66. 3797-3801 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Hisaji Taniguchi, Eisaku Nomura, and Tooru Hinomoto: "The Determination of the Conformation of p-tert-Butylcalix[6]arene Derivative in Solution by Means of Simplified "Up-Down" Conformation of Calix[6]arenes" Report of the Industrial Technology Center of Wakayama Prefecture. 16-18 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Eisaku Nomura and Hisaji Taniguchi: "Solvent Effects on Temperature-dependent NMR Spectra of p-Phenyl-azocalix[6]arene : Behavior of Intramolecular Hydrogen Bonding and Conformation of the Calixarenes" Report of the Industrial Technology Center of Wakayama Prefecture. 19-21 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Eisaku Nomura, Hisaji Taniguchi, and Yoshio Otsuji: "Calixarene-Catalyzed Permanganate Oxidation of Organic Compounds" Bull.Chem.Soc.Jpn. 67. 309-311 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Eisaku Nomura, Hisaji Taniguchi, and Yoshio Otsuji: "Calixarene-Catalyzed Generation of Dichlorocarbene and Its Application to Organic Reactions : The Catalytic Action of Octopus-type Calix[6]arene" Bull.Chem.Soc.Jpn. 67. 792-799 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Eisaku Nomura and Hisaji Taniguchi: "Ion Binding and Chromotropic Properties of Calixarene Derivatives Bearing Azo Groups" Dyestuffs & Chemicals. 39. 94-102 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Eisaku Nomura, Hisaji Taniguchi, Kouichi Kawaguchi, and Yoshio Otsuji: "Catalytic Ability of Octopus-type Calix[6]arene on Ether-Forming Reaction and Its Structural Properties" Report of the Industrial Technology Center of Wakayama Prefecture. 1-3 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Eisaku Nomura, Hisaji Taniguchi, and Yoshio Otsuji: "Organic Reaction Catalyzed Octopus-type Calix[6]arene" Report of the Industrial Technology Center of Wakayama Prefecture. 4-6 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary

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Published: 1993-04-01   Modified: 2016-04-21  

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