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2006 Fiscal Year Final Research Report Summary

Construction of novel supramolecular systems with molecular functions based on curved conjugated compounds

Research Project

Project/Area Number 16350073
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

KAWASE Takeshi  Osaka University, Graduate School of Science, Department of Chemistry, Associate professor, 大学院理学研究科, 助教授 (10201443)

Project Period (FY) 2004 – 2006
KeywordsOrganic Chemistry / Supramolecular Chemistry / Nanotube / Molecular Recognition / Functional Materials / Fullerenes
Research Abstract

The author and co-workers have prepared carbon nanorings (CNR), possessing belt-shaped conjugated systems, and the CNRs with appropriate cavity sizes form considerably stable inclusion complexes with fullerenes. In the period of this grant, we have studied the host properties of the CNRs to construct new supramolecular systems with novel molecular functions.
1) Formation of ring-in-ring complexes with the CNRs has been examined. The complex composed of highly strained CNRs is more stable than that composed of low strained CNRs and exhibits large entropy effect. Thus, the complexation behavior is similar to general properties of fullerene complexes. The results provide the evidence that the electrostatic interaction plays important role in the attractive force between curved conjugated systems.
2) For the sake of the purification of carbon nanotubes, we examined the structural modification of CNRs. Thus, the CNR (Φ=1.75 nm) possessing eight hexyloxy groups solubilized a part of single-walled carbon nanotubes in organic solvents.
3) New pseudo-rotaxane systems were constructed from CNRs as a rotor and C70 derivatives as an axis.
4) For the preparation of model compounds of arm-chair type (7,7)-and (8,8)carbon nanotube (carbon nanobelts), we prepared a macrocyclic cyclophane as a promising intermediate. A hexabenzocoronene synthesis would be applicable to the final step.
5) We have found that Grubbs' reagent (2^<nd> generation) catalyzed olefin-metathesis reaction of 6,6'-divinylbinaphthol derivatives to give Corresponding cyclic oligomers. The ring sizes of the products were dependent upon the substituents on the hydroxyl groups of binaphthol units. The results indicate the efficiency of the catalyst for construction of macrocyclic conjugate systems.

  • Research Products

    (34 results)

All 2007 2006 2005 2004

All Journal Article (34 results)

  • [Journal Article] Cyclic [5]Paraphenyleneacetylene : Synthesis, Properties and Formation of a Ring-in-Ring Complex Showing Considerably Large Association Constant and Entropy Effect2007

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew. Chem. Int. Ed. 46・7

      Pages: 1086-1088

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 1,1,4,4-Tetra(2-furyl, 2-thienyl, and 2-selenienyl)butatrienes; Synthesis, Properties, and Molecular Structures2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Bull. Chem. Soc., Jpn 80・2

      Pages: 349-357

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Photochemical and Redox Switching in a Ring-closed Isomer of Thioindigo-Extended Quinone2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 36・3

      Pages: 386-387

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 5H,13H-5,13a-[1',2']Benzenocyclopenta[rst]pentaphen-13-one : A New Triptycene Derivative with a Strained Structure2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 36・4

      Pages: 540-541

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis and Properties of 1,3-Thiazole Extended p-Terphenoquinone : a New sp2 Nitrogen Atom-Containing Terquinone Derivative2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Bull. Chem. Soc., Jpn 80(印刷中)

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Cyclic [5]Paraphenyleneacetylene : Synthesis, Properties and Formation of a Ring-in-Ring Complex Showing Considerably Large Association Constant and Entropy Effect2007

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew.Chem.Int.Ed. 46-7

      Pages: 1086-1088

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 1,1,4,4-Tetra(2-furyl, 2-thienyl, and 2-selenienyl)butatrienes; Synthesis, Properties, and Molecular Structure2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Bull.Chem.Soc.Jpn 80-2

      Pages: 349-357

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Photochemical and Redox Switching in a Ring-closed Isomer of Thioindigo-Extended Quinone2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 36-3

      Pages: 386-387

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 5H,13H-5,13a-[1^1,2^1]Benzenocyclopenta[rst]pentaphen-13-one : A New Triptycene Derivative with a Strained Structure2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 36-4

      Pages: 540-541

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis and Properties of 1,3-Thiazole Extended p-Terphenoquinone : a New sp2 Nitrogen Atom-Containing Terquinone Derivative2007

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Bull.Chem.Soc. Jpn, 80(in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 7,7-Dipyridyl-2,6-di-tert-butyl-p-quinone Methides : Synthesis, Complexation with Silver(I) Ion, and Oxidation to their Pyridine N-Oxide2006

    • Author(s)
      Kouzou Matsumoto
    • Journal Title

      Chemistry Lett. 35・1

      Pages: 74-75

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Complexation of Carbon Nanorings with Fullerenes2006

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Pure & Appl. Chem. 77・4

      Pages: 831-839

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Three-dimensional Coordiination Polymer of Silver(I) with Bridging Ligand Hexakis(4- pyridyl)[3]radialene2006

    • Author(s)
      Kouzou Matsumoto
    • Journal Title

      Crystal Growth & Design 6・5

      Pages: 1083-1085

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Carbon Nanorings and Their Complexing Abilities : Exploration of the Concave-Convex π-π Interaction2006

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Chemical Review 106・12

      Pages: 5250-5273

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 7,7-Dipyridy1-2,6-di-tert-butyl-p-quinone Methides : Synthesis, Complexation with Silver (I) Ion, and Oxidation to their Pyridine N-Oxide2006

    • Author(s)
      Kouzou Matsumoto
    • Journal Title

      Chemistry Lett. 35-1

      Pages: 74-75

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Complexation of Carbon Nanorings with Fullerenes2006

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Pure & Appl.Chem 77-1

      Pages: 831-839

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Three-dimensional Coordination Polymer of Silver (I) with Bridging Ligand Hexakis(4-pyridyl)[3]radialene2006

    • Author(s)
      Kouzou Matsumoto
    • Journal Title

      Crystal Growth & Design 6-5

      Pages: 1083-1085

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Carbon Nanorings and Their Corn016xing Abilities : Exploration of the Concave-Convex 7C-7c Interaction2006

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Chemical Review 106-12

      Pages: 5250-5273

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] A Hexapentaene Extended Quinocumulene Cyclotrimerized to a Tricyclobutabenzene Derivative2005

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew. Chem. Int. Ed. 44・2

      Pages: 316-319

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis of Tetrakis(2-furyl)methane2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 34・7

      Pages: 910-911

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Chiral Allenophane and Alleno-acetylenic Macrocycles : A New Field of Cyclophanes2005

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew. Chem. Int. Ed. 44・45

      Pages: 7334-7336

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Synthesis, Structure and Properties of a Cyclopent[fg]acenaphthylene-1,2-bis(p-quinone methide)s Derivative. An Extended Pyracyloquinone2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 34・12

      Pages: 1660-1661

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] A Hexapentaene Extended Quinocumulene Cyclotrimerized to a Tricyclobutabenzene, Derivative.2005

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew.Chem.Int.Ed. 44-2

      Pages: 316-319

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis of Tetrakis(2-furyl)methane2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 34-7

      Pages: 910-911

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Chiral Allenophane and Alleno-acetylenic Macrocycles : A New Field of Cyclophanes2005

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew.Chein.Int.Ed. 44-45

      Pages: 7334-7336

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Synthesis, Structure and Properties of a Cyclopent[fg]acenaphthylene- 1,2-bis(p-quinone methide)s Derivative. An Extended Pyracyloquinone2005

    • Author(s)
      Hiroyuki Kurata
    • Journal Title

      Chemistry Lett. 34-12

      Pages: 1660-1661

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] 2,6-Di-tert-butyl-4-(3,3-diarylpropadienylidene)-2,5-cyclohexadien-1-ones, the First Stable p-Quinopropadienes2004

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Eur. J. Org. Chem. 2004・6

      Pages: 3090-3096

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] [2.2](2,7)-Fluorenophanediene, [2.2.2](2,7)-Fluorenophanetriene, and Their Fluorenide Ions2004

    • Author(s)
      Kouzou Matsumoto
    • Journal Title

      Org. Biomol. Chem. 2・8

      Pages: 2323-2326

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Mobius Aromatic Hydrocarbons : Challenges for Theory and Synthesis2004

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew. Chem. Int. Ed. 43・34

      Pages: 4396-4398

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Supramolecular Dynamics of Cyclic [6]Paraphenyleneacetylene Complexes with [60]- and [70]Fullerene Derivatives : Electronic and Structural Effect to the Complexation2004

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew. Chem. Int. Ed. 43・38

      Pages: 5060-5062

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] 2,6-Di-tert-butyl-4-(3,3-diarylpropadienylidene)-2,5-cyclohexadien-l-ones the First Stable p-Quinopropadienes2004

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Eur.J.Org.Chem. 2004-6

      Pages: 3090-3096

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] [2.2](2,7)-Fluorenophanediene, [2.2.2](2,7)-Fluorenophanetriene, and Their Fluorenide Ions2004

    • Author(s)
      Kouzou Matsumoto
    • Journal Title

      Org.Biomol.Chem. 2004-2

      Pages: 2323-2326

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Mobius Aromatic Hydrocarbons : Challenges for Theory and Synthesis2004

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew.Chem.Int.Ed. 43-34

      Pages: 4396-4398

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Supramolecular Dynamics of Cyclic [6]Paraphenyleneacetylene Complexes with [60]-and [70]Fullerene Derivatives : Electronic and Structural Effect to the Complexation2004

    • Author(s)
      Takeshi Kawase
    • Journal Title

      Angew.Chem.Int.Ed. 43-38

      Pages: 5060-5062

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2008-05-27  

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