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Study on design, construction and functionality of novel supramolecular structures composed of belt-shaped conjugated systems

Research Project

Project/Area Number 14340197
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

KAWASE Takeshi  Osaka University, Graduate School of Science, 大学院・理学研究科, 助教授 (10201443)

Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥12,800,000 (Direct Cost: ¥12,800,000)
Fiscal Year 2003: ¥5,000,000 (Direct Cost: ¥5,000,000)
Fiscal Year 2002: ¥7,800,000 (Direct Cost: ¥7,800,000)
KeywordsSupramolecule / Fullerenes / Belt-shaped conjugated systems / Complexation / Supramolecular interaction / 分子間相互作用 / カーボンナノチューブ / ロタキサン
Research Abstract

New carbon allotropes having a carved conjugated system such as fullerenes and carbon nanotubes have been extensively studied from physical and chemical viewpoints. However, the supramolecular properties of the hollow of these materials have not been known well. We have recently synthesized a series of [n]CPPAs (cyclic paraphenylacetylenes) la-d (n = 6〜9) as relatively stable compounds. These compounds have smooth belt-shaped structure similar to a cut piece of carbon nanotube, and thus may be termed "carbon nanorings". They can be regarded as good model compounds for investigating the supramolecular properties of inner space of carved conjugated systems.
In the period of this grant, we have found interesting host properties of CPPAs as the following.
1)The belt-shaped π-conjugated [6]-and [8]CPPA exhibit nanosizecl cavities, and act as host molecules in crystalline inclusion complexes with hexamethylbenzene and toluene, respectively. The concave side of the cavities appears to possess a negative electronic potential.
2)Unusually stable complexes are formed between [6]CPPA and fullerenes (either C60 or bis(ethoxy-carbonyl)methanofullerene), Crystallographic analysis reveals that; a major driving force for the formation of such complexes is the existence of a novel concave-convex π-π interaction.
3)Carbon nanorings are structurally tuned to optimize their complexation with fullerenes (C_<60> and C_<70>). The affinity of carbon nanorings with fullerenes correlates with the width of the contact area. As the intence fluorescence emission of the CPPA host is quenched by the complexation of a fullerene, this effect can be used as a basis of a fullerene sensor.
4)Multi-inclusion structure, reminiscent of Russian Matrioshka dolls, have been constructed in nonpolar organic solvents from carbon nanorings and a C_<60> molecule. A study of these structures show there is a substantial difference between the electronic properties of planar and curved conjugated systems.

Report

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

    (35 results)

All Other

All Publications (35 results)

  • [Publications] T.Kawase: "Moius Aromatic Hydrocarbon : Theoretical and Synthetic Challenges Toward Nonplanar but Fully Conjugated Systems"Angew.Chem.Int.Ed.. 43(in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "2,6-Di-tert-butyl-4-(3,3-diarylpropadienylidene)-2,5-cyclohexadien-1-ones, the first stable p-quinopropadienes"Eur.J.Org.Chem.. (in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Onion-Type Complexation Based on Carbon Nanorings and a Buckminsterfullerene"Angew.Chem.Int.Ed.. 43. 1722-1724 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Complexation of Carbon Nanorings with Fullerenes. Novel Supramolecular Dynamics and Structural Tuning for a Fullerene Sensor"Angew.Chem.Int.Ed.. 42. 5579-5600 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Thermal Rearrangement of 2,5-Bis(dicyanomethylene)bicyclo[4.2.0]oct-7-ene and 2,5-Bis(dicyanomethylene)bicyclo[4.2.0]octa-3,7-diene. Unexpected"Bull.Chem.Soc., Jpn. 76. 1793-1799 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Kurata: "Synthesis, Structure and Properties of a Dibenzo-ortho-terphenoquinone. The first o-Terphenoquinone Derivative"Chemistry Lett.. 32. 538-539 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Kurata: "Novel Monocation, Dication, and Dianion of a Cage Molecule, Trithienylmethanophane"Chemistry Lett.. 32. 422-423 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Utsumi: "[2.0.2.0]Metacyclophane-1,15-diynes : A Potential Fragment of Double-Helical Conjugated Systems"Chemistry Lett.. 32. 412-413 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Complexation of a Carbon Nanoring with Fullerenes"Angew.Chem.Int.Ed.. 42. 1624-1628 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "All-Hydrocarbon Inclusion Complexes of Carbon Nanorings, Cyclic [6]- and [8]Paraphenylacetylenes"Angew.Chem.Int.Ed.. 42. 1621-1624 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "7,7-Dicyano-8,8-bis[4-(N,N-dimethylamino)phenyl]-meta-xylylenes : The First Stable Zwitterionic Metaxylylene Derivatives"Chemistry Lett.. 32. 322-323 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Moius Aromatic Hydrocarbon, Theoretical and Synthetic Challenges Toward Nonplanar but Fully Conjugated Systems"Angew.Chem.Int.Ed.. 43 (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "2,6-Di-tert-butyl-4-(3,3-diarylpropadienylidene)-2,5-cyclohexadi en-1-ones, the first stable p-quinopropadienes"Eur.J.Org.Chem.. (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Onion-Type Complexation Based on Carbon Nanorings and a Buckminsterfullerene"Angew.Chem.Int.Ed.. 43. 1722-124 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Complexation of Carbon Nanorings with Fullerenes. Novel Supramolecular Dynamics and Structural Tuning for a Fullerene Sensor"Angew.Chem.Int.Ed.. 42. 5597-5600 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Thermal Rearrangement of 2,5-Bis(dicyanomethylene)bicyclo[4.2.0]oct-7-ene and 2,5-Bis(dicyanomethylene)bicyclo[4.2.0]octa-3,7-diene.Unexpected Formation of 2,6-Bis(dicyanomethylene)bicyclo[3.3.0]octa-l(5)-ene, New Electron Acceptors"Bull.Chem.Soc.. 76. 1793-1799 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Kurata: "Synthesis, Structure and Properties of a Dibenzo-ortho-terphenoquinone.The first o-Terphenoquinone Derivative"Chemistry Lett.. 32. 538-539 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Kurata: "Novel Monocation, Dication, and Dianion of a Cage Molecule, Trithienylmethanophane"Chemistry Lett.. 32. 422-423 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Utsumi: "[2.0.2.0]Metacyclophane-l,15-diynes : A Potential Fragment of Double-Helical Conjugated Systems"Chemistry Lett.. 32. 412-413 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "Complexation of a Carbon Nanoring with Fullefenes"Angew.Chem.Int.Ed.. 42. 1621-1624 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "All-Hydrocarbon Inclusion Complexes of Carbon Nanorings, Cyclic [6]-and [8]Paraphenylacetylenes"Angew.Chem.Int.Ed.. 42. 1621-1624 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "7,7-Dicyano-8,8-bis[4-(N, N-dimethylamino)phenyl]-meta-xylylenes : The First Stable Zwitterionic Metaxylylene Derivatives"Chemistry Lett.. 32. 322-323 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Kawase: "7,7-Dicyano-8,8-bis[4-(N, N-dimethylamino)phenyl]-meta-xylylenes : The First Stable Zwitterionic Metaxylylene Derivatives"Chemistry Lett.. 32. 322-323 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kawase: "All-Hydrocarbon Inclusion Complexes of Carbon Nanorings, Cyclic [6]- and [8]Paraphenylacetylenes"Angew.Chem.Int.Ed.. 42. 1621-1624 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kawase: "Complexation of a Carbon Nanoring with Fullerenes"Angew.Chem.Int.Ed.. 42. 1624-1628 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Utsumi: "[2.0.2.0]Metacyclophane-1,15-diynes : A Potential Fragment of Double-Helica Conjugated Systems"Chemistry Lett.. 32. 412-413 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Kurata: "Novel Monocation, Dication, and Dianion of a Cage Molecule, Trithienylmethanophane"Chemistry Lett.. 32. 422-423 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Kurata: "Synthesis, Structure and Properties of a Dibenzo-ortho-terphenoquinone. The first o-Terphenoquinone Derivative"Chemistry Lett.. 32. 538-539 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kawase: "Thermal Rearrangement of 2,5-Bis(dicyanomethylene)bicyclo[4.2.0]oct-7-ene 2,5-Bis(dicyanomethylene)bicyclo[4.2.0]octa-3,7-diene"Bull.Chem.Soc., Jpn.. 76. 1793-1799 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kawase: "Complexation of Carbon Nanorings with Fullerenes. Novel Supramolecular Dynamics and Structural Tuning for a Fullerene Sensor"Angew.Chem.Int.Ed.. 42. 5597-5600 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kawase: "Onion-Type Complexation Based on Carbon Nanorings and a Buckminsterfullerene"Angew.Chem.Int.Ed.. 43(in press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Kawase: "7,7-Dicyano-8,8-bis[4-(N, N-dimethylamino)phenyl]-meta-xylylenes : The First Stable Zwitterionic Metaxylylene Derivatives"Chemistry Lett.. 32・4(in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Kawase: "All-Hydrocarbon Inclusion Complex of Carbon Nanorings, Cyclic [6]-and [8]Paraphenylacetylenes"Angew. Chem. Int. Ed.. 42(in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Kawase: "Complexation of Carbon Nanoring with Fullerenes"Angew. Chem. Int. Ed.. 42(in press). (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Utsumi: "[2.0.2.0]Metacyclophane-1,15-diynes : A Potential Fragment of Double-Helical Conjugated Systems"Chemistry Lett.. 32(in press). (2003)

    • Related Report
      2002 Annual Research Report

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

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