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2000 Fiscal Year Final Research Report Summary

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
KeywordsEndocrine disrupters / Cyclophane / Host-guest chemistry / Polyion complex
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

  • Research Products

    (19 results)

All Other

All Publications (19 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2002-03-26  

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