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Construction of novel unsaturated cyclophanes with π-cavitand structure

Research Project

Project/Area Number 14540501
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Metropolitan University

Principal Investigator

KUWATANI Yoshiyuki  Tokyo Metropolitan University, Graduate School of Science, Research Associate, 大学院・理学研究科, 助手 (00234625)

Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2004: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2003: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2002: ¥1,200,000 (Direct Cost: ¥1,200,000)
Keywordsunsaturated cyclophanes / π-conjugated hydrocarbons / cavitands / macrocyclic compounds / deltaphane / theoretical calculations / supramolecular chemistry / 分子ピンセット / ホストゲスト化学 / 芳香族性
Research Abstract

In this research, design and synthesis of novel unsaturated cyclophanes with caged structure was planned in order to investigate the unique electronic structure and to examine the possibility of the supramolecular chemistry based on the cavity surrounded with π-electrons.
Hexabenzo[24]annulene, which is a macrocyclic benzannulene composed of six o-phenylenes and six cis-ethylene bridges, was probed to adopt a ‘self-filled' structure, where three alternate arene rings were located inside of the cavity. This energy-minimum structure was observed at low temperature in the solution as well as in the solid state. The preference of the conformer was ascribed to the cyclic concurrent CH-π interaction among the inside three benzene rings.
Theoretical calculations for unsaturated deltaphanes, which was designed here, suggested the unique electronic properties : the compounds should have low reduction potential and the corresponding anions should have fully delocalized structure. Therefore, many methodologies for the synthesis of the. compounds were examined. Although the synthesis was not achieved, effective synthetic methods for the related compounds have been developed. These method will be applied for many other structurally interesting compounds.
These results will provide new aspects for the research of new carbon conjugated systems including fullerenes, which are expected to be unique materials in nanotechnology applications.

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (40 results)

All 2005 2004 2003 2002 Other

All Journal Article (30 results) Publications (10 results)

  • [Journal Article] Belt shaped unsaturated cyclophanes : Synthesis and properties of benzannulenes composed of cis-stilbene unit2005

    • Author(s)
      Y.Kuwatani
    • Journal Title

      New Trend in Structural Organic Chemistry

      Pages: 155-176

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Bis(ethylenedioxy)-1,4,5,8-tetraselenanaphthalene : The First Example of Tetraselenanaphthalene.2005

    • Author(s)
      R.Watanabe, Y.Miyake, Y.Kuwatani, M.Iyoda
    • Journal Title

      Chem.Lett. 34巻・1号

      Pages: 68-69

    • NAID

      10014218055

    • Related Report
      2004 Annual Research Report
  • [Journal Article] All-Z-Hexabenzo[24]annulene with a triangular benzene cluster substructure.2004

    • Author(s)
      Y.Kuwatani, J.Igarashi, M.Iyoda
    • Journal Title

      Tetrahedron Lett. 45巻

      Pages: 359-362

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Aggregation of star-shaped tris(tetrathiafulvalenylethynyl)benzene in solution and in the solid state.2004

    • Author(s)
      M.Hasegawa, J.Takano, H.Enozawa, Y.Kuwatani, M.Iyoda
    • Journal Title

      Tetrahedron Lett. 45巻

      Pages: 4109-4112

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Copper-Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives.2004

    • Author(s)
      M.Iyoda, S.Sirinintasak, Y.Nishiyama, A.Vorasingha, F.Sultana, K.Nakao, Y.Kuwatani, H.Matsuyama, M.Yoshida, Y.Miyake
    • Journal Title

      Synthesis

      Pages: 1527-1531

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Mono-and bis(tetrathiafulvaleno)hexadehydro[12]annulenes.2004

    • Author(s)
      K.Hara, M.Hasegawa, Y.Kuwatani, H.Enozawa, M.Iyoda
    • Journal Title

      Chem. Commun.

      Pages: 2042-2043

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Novel π-Expanded Radialene Macrocycles with Inner Cavity.2004

    • Author(s)
      M.Iyoda, Y.Kuwatani, S.Yamagata, N.Nakamura, M.Todaka, G.Yamamoto
    • Journal Title

      Org. Lett. 6巻

      Pages: 4667-4670

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] All-Z-Hexabenzo[24]annulene with a triangular benzene cluster substructure.2004

    • Author(s)
      Y.Kuwatani, J.Igarashi, M.Iyoda
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 359-362

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Aggregation of star-shaped tris(tetrathiafulvalenylethynyl)benzene in solution and in the solid state.2004

    • Author(s)
      M.Hasegawa, J.Takano, H.Enozawa, Y.Kuwatani, M.Iyoda
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 4109-4112

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Mono- and bis(tetrathiafulvaleno)hexadehvdro[12]annulenes.2004

    • Author(s)
      K.Hara, M.Hasegawa, Y.Kuwatani, H.Enozawa, M.Iyoda
    • Journal Title

      Chem.Commun.

      Pages: 2042-2043

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Novel π-Expanded Radialene Macrocycles with Inner Cavity.2004

    • Author(s)
      M.Iyoda, Y.Kuwatani, S.Yamagata, N.Nakamura, M.Todaka, G.Yamamoto
    • Journal Title

      Org.Lett. 6

      Pages: 4667-4670

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Novel -Expanded Radialene Macrocycles with Inner Cavity.2004

    • Author(s)
      M.Iyoda, Y.Kuwatani, S.Yamagata, N.Nakamura, M.Todaka, G.Yamamoto
    • Journal Title

      Org.Lett. 6巻・25号

      Pages: 4667-4670

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Mono- and bis(tetrathiafulvaleno)hexadehydro[12]annulenes.2004

    • Author(s)
      K.Hara, M.Hasegawa, Y.Kuwatani, H.Enozawa, M.Iyoda
    • Journal Title

      Chem.Commun. 18号

      Pages: 2042-2043

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Copper-Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives.2004

    • Author(s)
      M.Iyoda, et al.
    • Journal Title

      Synthesis 9号

      Pages: 1527-1531

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Aggregation of star-shaped tris(tetrathiafulvalenylethynyl)benzene in solution and in the solid state.2004

    • Author(s)
      M.Hasegawa, J.Takano, H.Enozawa, Y.Kuwatani, M.Iyoda
    • Journal Title

      Tetrahedron Lett. 45巻・21号

      Pages: 4109-4112

    • Related Report
      2004 Annual Research Report
  • [Journal Article] All-Z-Hexabenzo[24]annulene with a triangular benzene cluster substructure.2004

    • Author(s)
      Y.Kuwatani, J.Igarashi, M.Iyoda
    • Journal Title

      Tetrahedron Lett. 45巻・2号

      Pages: 359-362

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Unconventional TTF-based molecular magnets.2003

    • Author(s)
      T.Enoki, H.Yamazaki, K.Okabe, K.Enomoto, T.Kato, A.Miyazaki, E.Ogura, Y.Kuwatani, M.Iyoda
    • Journal Title

      Synth. Met. 133-134巻

      Pages: 501-503

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Ferromagnetic interaction and metallic conductivity of radical ion salts (DIEDO)_2M(mnt)_2(M=Ni, Pt).2003

    • Author(s)
      J.Nishijo, E.Ogura, J.Yamaura, A.Miyazaki, T.Enoki, T.Takano, Y.Kuwatani, M.Iyoda
    • Journal Title

      Synth. Met. 133-134巻

      Pages: 539-541

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A twin-rotor system created on a [4]radialne frame.2003

    • Author(s)
      Y.Kuwatani, G.Yamamoto, M.Iyoda
    • Journal Title

      Org. Lett. 5巻

      Pages: 3371-3374

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Unconventional TTF-based molecular magnets.2003

    • Author(s)
      T.Enoki, H.Yamazaki, K.Okabe, K.Enomoto, T.Kato, A.Miyazaki, E.Ogura, Y.Kuwatani, M.Iyoda
    • Journal Title

      Synth.Met. 133-134

      Pages: 501-503

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Ferromagnetic interaction and metallic conductivity of radical ion salts (DIEDO_2,M(mnt)_2 (M=Ni,Pt).2003

    • Author(s)
      J.Nishijo, E.Ogura, J.Yamaura, A.Miyazaki, T.Enoki, T.Takano, Y.Kuwatani, M.Iyoda
    • Journal Title

      Synth.Met. 133-134

      Pages: 539-541

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A twin-rotor system created on a [4]radialene frame.2003

    • Author(s)
      Y.Kuwatani, G.Yamamoto, M.Iyoda
    • Journal Title

      Org.Lett. 5

      Pages: 3371-3374

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Intramolecular Charge Transfer Interaction in the Radical Cations and Dications of Conjugated Tetrathiafulvalene Dimers.2002

    • Author(s)
      M.Iyoda, M.Hasegawa, J.Takano, K.Hara, Y.Kuwatani
    • Journal Title

      Chem. Lett.

      Pages: 590-591

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] π-d Interaction-Based Molecular Magnets in TTF-Type Salts2002

    • Author(s)
      A.Miyazaki, M.Enomoto, J.Nishijo, K.Enomoto, T.Enoki, E.Ogura, T.Takano, Y.Kuwatani, M.Iyoda
    • Journal Title

      Mol. Cryst. Liq. Cryst. 376巻

      Pages: 535-542

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Conducting Molecular Magnets Based on TTF-Derivatives.2002

    • Author(s)
      A.Miyazaki, K.Enomoto, K.Okabe, H.Yamazaki, J.Nishijo, T.Enoki, E.Ogura, K.Ugawa, Y.Kuwatani, M.Iyoda
    • Journal Title

      J. Solid State Chem. 168巻

      Pages: 547-562

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Conducting Molecular Magnets Based on TTF-Derivatives.2002

    • Author(s)
      M.Iyoda, K.Hara, E.Ogura, T.Takano, M.Hasegawa, M.Yoshida, Y.Kuwatani, H.Nishikawa, K.Kikuchi, I.Ikemoto, T.Mori
    • Journal Title

      J. Solid State Chem. 168巻

      Pages: 597-607

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Intramolecular Charge Transfer Interaction in the Radical Cations and Dications of Conjugated Tetrathiafulvalene Dimers.2002

    • Author(s)
      M.Iyoda, M.Hasegawa, J.Takano, K.Hara, Y.Kuwatani
    • Journal Title

      Chem.Lett.

      Pages: 590-591

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] π-d Interaction-Based Molecular Magnets in TTF-Type Salts2002

    • Author(s)
      A.Miyazaki, M.Enomoto, J.Nishijo, K.Enomoto, T.Enoki, E.Ogura, T.Takano, Y.Kuwatani, M.Iyoda
    • Journal Title

      Mol.Cryst.Liq.Cryst. 376

      Pages: 535-542

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Conducting Molecular Magnets Based on TTF-Derivatives.2002

    • Author(s)
      A.Miyazaki, K.Enomoto, K.Okabe, H.Yamazaki, J.Nishijo, T.Enoki, E.Ogura, K.Ugawa, Y.Kuwatani, M.Iyoda
    • Journal Title

      J.Solid State Chem. 168

      Pages: 547-562

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and Electroconductive Properties of Radical Salts Derived from Tetrathiafulvaalene Dimers2002

    • Author(s)
      M.Iyoda, K.Hara, E.Ogura, T.Takano, M.Hasegawa, M.Yoshida, Y.Kuwatani, H.Nishikawa, K.Kikuchi, I.Ikemoto, T.Mori
    • Journal Title

      J.Solid State Chem. 168

      Pages: 597-607

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Y.Kuwatani, J.Igarashi, M.Iyoda: "All-Z-Hexabenzo[24]annulene with a triangular benzene cluster substructure."Tetrahedron Lett.. 45. 359-362 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Kuwatani, G.Yamamoto, M.Iyoda: "A twin-rotor system created on a [4]radialene frame."Org.Lett.. 5. 3371-3374 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] J.Nishijo, E.Ogura, J.Yamaura, A.Miyazaki, T.Enoki, T.Takano, Y.Kuwatani, M.Iyoda: "Ferromagnetic interaction and metallic conductivity of radical ion salts (DIEDO)_2M(mnt)_2 (M=Ni, Pt)."Synth.Met.. 133-134. 539-542 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Enoki, H.Yamazaki, K.Okabe, K.Enomoto, T.Kato, A.Miyazaki, E.Ogura, Y.Kuwatani, M.Iyoda: "Unconventional TTF-based molecular magnets."Synth.Met.. 133-134. 501-503 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Enoki, H.Yamazaaki, J.Nishijo, A.Miyazaki, K.Ugawa, E.Ogura, Y.Kuwatani, M.Iyoda, Y.V.Sushko: "Novel Magnetism of EDO-TTFX_2 Salts (X=Br,I)"Synth.Met. 137. 1173-1174 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Hasegawa, J.Takano, H.Enozawa, Y.Kuwatani, M.Iyoda: "Aggregation of Star-Shaped Tris(tetrathiafulvalenylethynyl)benzene in Solution and in the Solid"Tetrahedron Lett.. (in press).

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Iyoda, M.Hasegawa, J.Takano, K.Hara, Y.Kuwatani: "Intramolecular Charge Transfer Interaction in the Radical Cations and Dications of Conjugated Tetrathiafulvalene Dimers"Chemistry Letters. 590-591 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] A.Miyazaki, M.Enomoto, J.Nishijo, K.Enomoto, T.Enoki, E.Ogura, T.Takano, Y.Kuwatani, M.Iyoda: "π-d Interaction-Based Molecular Magnets in TTF-Type Salts"Mol. Cryst. Liq. Cryst.. 376巻. 535-542 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Iyoda, K.Hara, E.Ogura, T.Takano, M.Hasegawa, M.Yoshida, Y.Kuwatani, H.Nishikawa, K.Kikuchi, I.Ikemoro, T.Mori: "Synthesis and Electroconductive Properties of Radical Salts Derived from Tetrathiafulvaalene Dimers"J. Solid State Chem.. 168巻. 597-607 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 伊与田正彦 編: "材料有機化学(先端材料のための新化学4)"朝倉書店. 230 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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