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Preparation of Box-shaped Cyclophane Compounds Recognizing Endocrine Disruptors and their Immobilization

Research Project

Project/Area Number 11650900
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKyushu Institute of Technology

Principal Investigator

TSUGE Akihiko  Kyushu Institute of Technology, Department of Chemistry, Associate Professor, 物質工学科・応用化学, 助教授 (80179986)

Co-Investigator(Kenkyū-buntansha) MORIGUCHI Tetsuji  Kyushu Institute of Technology, Department of Chemistry, Research Assistant, 物質工学科・応用化学, 教務職員 (40243985)
Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2000: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1999: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsEndocrine disrupters / Cyclophane / Host-guest chemistry / Polyion complex / 内分泌撹物質 / ホストーゲスト化学
Research Abstract

Complexation of macrocyclic cyclophane compounds with guest molecules in water has always attracted a major interest since it can mimic the molecular recognition which is a basic process in biological systems. Although modified cyclodextrins have been extensively investigated in terms of inclusion, recognition, and catalysis in aqueous media, versatility of their structure is limited. On the contrary water-soluble calixarenes and cyclophanes have a great advantage of molecular design. On the other hand it has been reported that the chemical compounds known as endocrine disrupters could have an unexpected influence on human beings. Thus, novel cyclophans consisting of fluorene, naphthalene, anthracene or pyrene component which could exhibit a binding ability against some kinds of endocrine disrupters have been proposed. We have shown the facile synthetic methods of such macrocyclic cyclophanes containing fluorene, naphthalene, anthracene or pyrene component. In order to recognize the en … More docrine disrupters weak intermolecular interactions such as CH-π interaction, π-π interaction, hydrogen bondings and so on could be very important. We have clarified the conformational properties of these cyclophanes, indicating that the ring inversion is highly dependent on their molecular structures, especially the inner substituents and the length of the bridging part. Hydrogen bondings also play a decisive role on the conformation. Some cyclophanes exhibit a very interesting properties by switching an intramolecular hydrogen bonding to an intermolecular one. During this process crystal structure changes. In the cyclophanes having the fluorene component fluorescence energy transfer is observed, depending the rigidity of the molecule and the orientation of two aromatic components. The cyclophanes consisting of anthracene or pyrene unit exhibit a unique CH-π interaction between the amino group and the aromatic unit, which has an influence on the conformation. Now we are developing the desired system using the knowledge of weak interactions obtained here. Less

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (31 results)

All Other

All Publications (31 results)

  • [Publications] A.Tsuge et al: "Conformational and Intermolecular Hydrogen-Bonding Properties of Substituted Dithia [3.3] metacyclophanes"Chem.Lett.. 167-168 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Tsuge et al: "Specific transannular interaction in small-sized cyclophane systems"Recent Research Developments in Pure & Applied Chemistry. 3. 47-55 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Tsuge et al: "Evaluation of Transannular Interaction of [2.3] metacyclophane diazonium Tetrafluoroborate and its Dediazoniated Derivatives"J.Chem.Res.. 78-79 437-448 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Tsuge et al: "Synthesis of Small-sized Stilbenophanes and their Transannular Delocalization"J.Org.Chem.. 64. 7246-7248 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Tsuge et al: "Preparation, Conformation and Reaction of Medium-sized [1.n.n] Metacyclophanes"Chem.Lett.. 948-949 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A.Tsuge et al: "Intra- and Intermolecular Interaction in Substituted Dithia [3.3] metacyclophanes"J.Chem.Soc, Perkin Trans 2. (in press). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Moriguchi, T., Sakata, K., Tsuge, A.: "Conformational and Intramolecular Hydrogen-Bonding Properties of Substituted Dithia [3.3] metacyclophanes."Chem.Lett.. 167-168 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tsuge, A.: "Specific transannular interaction in small-sized cyclophane systems."Recent Research Developments in Pure & Applied Chemistry. 3. 47-55 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Moriguchi, T., Sakata, K., Tsuge, A.: "Evaluation of Transannular Interaction of [2.3] metacyclophanediazonium Tetrafluoroborate and its Dediazoniated Derivatives."J.Chem.Res.. 78-79. 437-448(M) (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Sakata, K., Wang, Z., Hashimoto, M., Tsuge, A., Tanoue, Y.: "Characterization, Spectroscopic Properties and Crystal Structure of a Tetraaza [14] annulene Manganese (III) Complex."Synth.React.Inorg.Met-Org.Chem.. 29. 265-277 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tsuge, O., Hatta, T., Fujiwara, T., Yokohari, T., Tsuge, A., Moriguchi, T.: "Diene-transmissive Hetero Diels-Alder Reaction of 1,5-Diphenyl-1,4-Pentadien-3-one."Heterocycles. 50. 661-666 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tsuge, A., Nishimoto, T., Uchida, T., Yasutake, M., Moriguchi, T., Sakata, K.: "Synthesis of Small-sized Stilbenophanes and their Transannular Delocalization."J.Org.Chem.. 64. 7246-7248 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Moriguchi, T., Sakata, K., Tsuge, A.: "Transannular Interactions and Reactions of the Dithia [3.3] metacyclophanediazonium Salts."J.Chem.Res(S).. 604-605. 2601-2609(M) (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tsuge, A., Takagi, N., Kakara, T., Moriguchi, T., Sakata, K.: "Preparation, Conformation and Reaction of Medium-sized [1.n.n] Metacyclophanes."Chem.Lett.. 948-949 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Moriguchi, Y., Uchiyama, K., Sakata, K., Tsuge, A.: "Synthesis, spectroscopic properties and X-ray crystal structures of tris (tfacacmetacyclophane)(bpy) europium (III) and piperidinium tetrakis (p-tolutfacac) europate (III) complexes."Polyhedron. 19. 785-790 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Wang, Z.Sakata, K.Hashimoto M.Moriguchi, T.Tsuge, A.: "Complexes of H2tmtaa, (Zn(tmtaa)L[L=PPh3, OPPh3 and CH3CN]) and Crystal Structure of Zn (tmtaa) OPPh3."Synth.React.Inorg.Met-Org.Chem.. 30. 73-87 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Moriguchi, T., Sakata, K., Tsuge, A.: "Intra-and Intermolecular Interaction in Substituted Dithia [3.3] metacyclophanes."J.Chem.Soc., Perkin Trans. 2. (in press). (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tsuge, A., Nishimoto, H, Moriguchi, T., Sakata, K.: "Unusual Chloromethylation of 3,6-Di (tert-butyl) fluorene."Org.Prep.Proc.Int.. (in press). (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tsuge, A., Fukumaru, Y., Taniguchi, R., Moriguchi, T., Sakata, K., Araki, K.: "Synthesis and Electrochemical Properties of Bis ([2.2]metacyclophane)bipyridinium."J.Chem.Res.. (in press). (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] A Tsuge et al: "Conformational and Intermolecular Hydrogen-Bonding Properties of Substituted Dithia [3.3] metacyclophanes"Chem.Lett.. 167-168 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Tsuge et al: "Specific Transannular Interaction in Small-sized Cyclophane Systems"Recent Research Development in Pure & Applied Chemistry. 3. 47-55 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Tsuge et al: "Evaluation of Transannular Interaction of [2.3]Metacyclophane-diazonium Tetrafluoroborate and its Dediazoniated Deriratives."J.Chem.Res.. 78-79,437-448 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Tsuge et al: "Synthesis of Small-sized Stilbenophanes and Their Transannular Delocalization"J.Ory.Chem.. 64. 7246-7248 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Tsuge et al: "Preparation, Conformation and Reaction of Medium-sized [1.n.n]Metacyclophanes"Chem.Lettt.. 948-949 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Tsuge et al: "Intra-and Intermolecular Interaction in Substituted Dithia[3.3]metacyclophanes"J.Chem.Soc,Perkin Trans 2. (in press). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.Tsuge et al: "Specific transannular interuction in small-sized cyclophone system"Recent Research Developments in Pure & Applied Chemistry. 3. 47-55 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] A.Tsuge et al: "Diene-Transmissive Hetero Diels-Alder Reaction of 1,5-Diphenyl-1,4-Pentadien-3-one."Heterocycles. 50. 661-666 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Sakata et al: "Characterization,Spectroscopic Properties and Crystal Structure of a Tetruaza[14] annulene Manganese(III) Complex"Synth.React.Inorg.Met-Org.Chem. 29. 265-277 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Moriguchi et al: "Conformational and Intramolecular Hydrogen-Bonding Properties of Substituted Dithia[3.3] metacyclophanes"Chem.Lett.. 167-168 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.Moriguchi et al: "Evaluation of Transannular Interaction of [2,3] Metacyclophane-diazonium Tetrafluoroborate and its Dediazoniated Derivatives"J.Chem.Res(S). 78-79 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] A.Tsuge et al: "Synthesis of Small-sized Stilbenophane and Their Transannular Delocalization"J.Org.Chem.. 64. 7246-7248 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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