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Construction of Self-Assembled Unsymmetrical Nanocapsule Space Ditected to Molecular Devices

Research Project

Project/Area Number 17350067
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

KOBAYASHI Kenji  Shizuoka University, Graduate School of Science and Technology, Professor (40225503)

Co-Investigator(Kenkyū-buntansha) YAMANAKA Masamichi  Shizuoka University, Faculty of Science, Assistant Professor (10377715)
Project Period (FY) 2005 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥15,040,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥840,000)
Fiscal Year 2007: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2006: ¥4,500,000 (Direct Cost: ¥4,500,000)
Fiscal Year 2005: ¥6,900,000 (Direct Cost: ¥6,900,000)
KeywordsMolecular Self-Assembly / Capsule / Unsymmetrical Nano-Space / Supramolecule / Host-Guest / Molecular Recognition / Encapsulation / Control of Orientation / ホスト-ゲスト
Research Abstract

We studied on the construction and elucidation of functions of unsymmetrical molecular capsules self-assembled by hydrogen bonds or metal-coordinations. Our findings in this study are as follows.
(1) We synthesized bowl-shaped cavitands 1〜7 with hydrogen-bonding sites or metal-coordination sites. We found that 1 and 3, 4 and 5, and 4, 6, and Pd(dppp)(OTf)_2, self-assemble into hydrogen-bonded heterocapsules 1・3 and 4・5, and metal-coordination heterocapsule 4・6・4[Pd(dppp)]^(8+), respectively.
(2) We found that these heterocapsules encapsulate unsymmetrical guests with high orientational selectivity what is called "orientational isomerism".
(3) The structural and/or electronic environments of one half-capsule unit of the heterocapsule are different from those of the other half-capsule unit. We found that the delicate balance among electrostatic potential repulsion between the lone pair of the carbonyl oxygen atom of a guest and the aromatic cavity of a cavitand, attractive CH-πinteraction, or attractive CH-halogen (halogen-π) interaction in a heterocapsule-guest assembly influences the orientational isomeric selectivity of unsymmetrical guests within heterocapsule.
(4) Fine and/or drastic tuning of capsule space has been attained by alteration of the hydrogen-bonding linker and/or hemispherical cavitand, respectively.

Report

(4 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • 2005 Annual Research Report
  • Research Products

    (33 results)

All 2008 2007 2006 2005 Other

All Journal Article (24 results) (of which Peer Reviewed: 9 results) Presentation (5 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Orientational Isomerism Controlled by the Difference in Electronic Environments of a Self-Assembling Heterodimeric Capsule.2007

    • Author(s)
      K. Kobayashi, 他6名
    • Journal Title

      The Journal of Organic Chemistry 72

      Pages: 3242-3246

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Orientational Isomerism Controlled by the Difference in Electronic Environments of a Self-Assembling Heterodimeric Capsule2007

    • Author(s)
      K. Kobayashi,* R. Kitagawa, Y. Yamada, M. Yamanaka, T. Suematsu, Y. Sei, K. Yamaguchi
    • Journal Title

      The Journal of Organic Chemistry 72

      Pages: 3242-3246

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Orientational Isomerism Controlled by the Difference in Electronic Environments of a Self-Assembling Heterodimeric Capsule2007

    • Author(s)
      K. Kobayashi, 他6名
    • Journal Title

      The Journal of Organic Chemistry 72

      Pages: 3242-3246

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Formation of Self-Assembling Homo or Hetero Cavitand Cage via Metal Coordination Based on Thermodynamic or Kinetic Control.2006

    • Author(s)
      M. Yamanaka, 他4名
    • Journal Title

      Journal of the American Chemical Society 128

      Pages: 1531-1539

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Growth of Anthracene Derivative Thin Films with a π-Stacking Structure.2006

    • Author(s)
      H. Sasaki, 他5名
    • Journal Title

      Applied Physics Letters 88

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis and Cofacial π-Stacked Packing Arrangement of 6,13-Bis(alkylthio)pentacene.2006

    • Author(s)
      K. Kobayashi, 他4名
    • Journal Title

      Organic Letters 8

      Pages: 2385-2388

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Interfacial Electronic States of an Anthracene Derivative Deposited on a SiO_2/Si Substrate.2006

    • Author(s)
      H. Sasaki, 他5名
    • Journal Title

      Solid State Communications 139

      Pages: 153-156

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Tunable Capsule Space: Self-Assembly of Hemispherical Cavitands with Hydrogen-Bondine Linkers.2006

    • Author(s)
      M. Yamanaka, 他3名
    • Journal Title

      The Journal of Organic Chemistry 71

      Pages: 8800-8806

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Selective Formation of Self-Assembling Homo or Hetero Cavitand Cage via Metal Coordination Based on Thermodynamic or Kinetic Control2006

    • Author(s)
      M. Yamanaka, Y. Yamada, Y. Sci, K. Yamaguchi, K. Kobayashi*
    • Journal Title

      Journal of the American Chemical Society 128

      Pages: 1531-1539

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Growth of Anthracene Derivative Thin Films with a π-Stacking Structure2006

    • Author(s)
      H. Sasaki, Y. Wakayama, T. Chikyow, E. Barrena, H. Dosch, K. Kobayashi
    • Journal Title

      Applied Physics Letters 88

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis and Cofacial π-Stacked Packing Arrangement of 6,13-Bis(alkylthio)pentacene2006

    • Author(s)
      K. Kobayashi,* R. Shimaoka, M. Kawahata, M. Yamanaka, K. Yamaguchi
    • Journal Title

      Organic Letters 8

      Pages: 2385-2388

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Interfacial Electronic States of an Anthracene Derivative Deposited on a SiO2/Si Substrate2006

    • Author(s)
      H. Sasaki, Y. Wakayama, T. Chikyow, M. Imamura, A. Tanaka, K. Kobavashi
    • Journal Title

      Solid State Communications 139

      Pages: 153-156

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Tunable Capsule Space : Self-Assembly of Hemispherical Cavitands with Hydrogen-Bonding Linkers2006

    • Author(s)
      M. Yamanaka, K. Ishii, Y. Yamada, K. Kobayashi*
    • Journal Title

      The Journal of Organic Chemistry 71

      Pages: 8800-8806

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Growth of Anthracene Derivative Thin Films with a π-Stacking Structure.2006

    • Author(s)
      H.Sasaki, Y.Wakayama, T.Chikyow, E.Barrena, H.Dosch, K.Kobayashi
    • Journal Title

      Applied Physics Letters 88・

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis and Cofacial π-Stacked Packing Arrangement of 6,13-Bis(alkylthio)pentacene.2006

    • Author(s)
      K.Kobayashi, R.Shimaoka, M.Kawahata, M.Yamanaka, K.Yamaguchi
    • Journal Title

      Organic Letters 8・11

      Pages: 2385-2388

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Interfacial Electronic States of an Anthracene Derivative Deposited on a SiO_2/Si Substrate.2006

    • Author(s)
      H.Sasaki, Y.Wakayama, T.Chikyow, M.Imamura, A.Tanaka, K.Kobayashi
    • Journal Title

      Solid State Communications 139・

      Pages: 153-156

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Tunable Capsule Space : Self-Assembly of Hemispherical Cavitands with Hydrogen-Bonding Linkers.2006

    • Author(s)
      M.Yamanaka, K.Ishii, Y.Yamada, K.Kobayashi
    • Journal Title

      The Journal of Organic Chemistry 71・23

      Pages: 8800-8806

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Selective Formation of Self-Assembling Homo or Hetero Cavitand Cage via Metal Coordination Based on Thermodynamic or Kinetic Control.2006

    • Author(s)
      M.Yamanaka, Y.Yamada, Y.Sei, K.Yamaguchi, K.Kobayashi
    • Journal Title

      Journal of the American Chemical Society 128・5

      Pages: 1531-1539

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Orientational Isomerism and Binding Ability of Nonsymmetrical Guests Encapsulated in a Self-Assembling Heterodimeric Capsule.2005

    • Author(s)
      K. Kobayashi, 他2名
    • Journal Title

      Chemistry-A European Journal 11

      Pages: 4725-4734

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Control of Face-to-Face π-π Stacked Packing Arrangement of Anthracene Rings via Chalcogen-Chalcogen Interaction: 9,10-Bis(methylchalcogeno)anthracenes.2005

    • Author(s)
      K. Kobayashi, 他3名
    • Journal Title

      Chemistry of Materials 17

      Pages: 6666-6673

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Orientational Isomerism and Binding Ability of Nonsymmetrical Guests Encapsulated in a Self-Assembling Heterodimeric Capsule2005

    • Author(s)
      K. Kobavashi,* K. Ishii, M. Yamanaka
    • Journal Title

      Chemistry -A European Journal 11

      Pages: 4725-4734

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Control of Face-to-Face π-π Stacked Packing Arrangement of Anthracene Rings via Chalcogen-Chalcogen Interaction : 9,10-Bis(methylchalcogeno)anthracenes2005

    • Author(s)
      K. Kobavashi,* H. Masu, A. Shuto, K. Yamaguchi
    • Journal Title

      Chemistry of Materials 17

      Pages: 6666-6673

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Orientational Isomerism and Binding Ability of Nonsymmetrical Guests Encapsulated in a Self-Assembling Heterodimeric Capsule.2005

    • Author(s)
      K.Kobayashi, K.Ishii, M.Yamanaka
    • Journal Title

      Chemistry - A European Journal 11・16

      Pages: 4725-4734

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Control of Face-to-Face π-π Stacked Packing Arrangement of Anthracene Rings via Chalcogen-Chalcogen Interaction : 9,10-Bis(methylchalcogeno)anthracenes.2005

    • Author(s)
      K.Kobayashi, H.Masu, A.Shuto, K.Yamaguchi
    • Journal Title

      Chemistry of Materials 17・26

      Pages: 6666-6673

    • Related Report
      2005 Annual Research Report
  • [Presentation] 水素結合に基づくヘテロダイマーカプセルのゲスト包接挙動2007

    • Author(s)
      小林 健二, 他3名
    • Organizer
      第2回ホスト-ゲスト化学シンポジウム
    • Place of Presentation
      大阪市立大学(大阪市)
    • Year and Date
      2007-05-24
    • Related Report
      2007 Annual Research Report
  • [Presentation] Unsymmetrical Nanospace: Self-Assembling Heterodimeric Capsule.2006

    • Author(s)
      K. Kobayashi, 他2名
    • Organizer
      The First Joint International Symposium on Macrocyclic and Supramolecular Chemistry
    • Place of Presentation
      Victoria, British Columbia, Canada
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Unsymmetrical Nanospace: Orientational Isomerism of Unsymmetrical Guests Encapsulated in Self-Assembling Heterodimeric Capsules.2006

    • Author(s)
      K. Kobayashi
    • Organizer
      The 232nd ACS Conference
    • Place of Presentation
      San Francisco, California, USA
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Unsymmetrical Nanospace : Self-Assembling Heterodimeric Capsule2006

    • Author(s)
      Kenji, Kobayshi,*Yoshifumi Yamada, Masamichi, Yamanaka
    • Organizer
      The First Joint International Symposium on Macrocyclic and Supramolecular Chemistry
    • Place of Presentation
      Victoria, British Columbia, Canada
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Unsymmetrical Nanospace : Orientational Isomerism of Unsymmetrical Guests Encapsulated in Self-Assembling Heterodimeric Capsules2006

    • Author(s)
      K. Kobayashi
    • Organizer
      The 232nd ACS Conference
    • Place of Presentation
      San Francisco, California. USA
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Remarks] 「研究成果報告書概要(和文)」より

    • URL

      http://www.ipc.shizuoka.ac.jp/~skkobay/welcome.htm

    • Related Report
      2007 Final Research Report Summary
  • [Remarks]

    • URL

      http://www.ipc.shizuoka.ac.jp/~skkobay/welcome.htm

    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] 特許権2008

    • Inventor(s)
      小林健二、今村悟、茂岩統之
    • Industrial Property Rights Holder
      静岡大学三菱化学
    • Industrial Property Number
      2008-027758
    • Filing Date
      2008-02-07
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 特許権2005

    • Inventor(s)
      小林健二、茂岩統之、前田修一
    • Industrial Property Rights Holder
      静岡大学三菱化学
    • Industrial Property Number
      2005-375151
    • Filing Date
      2005-12-27
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2005-04-01   Modified: 2016-04-21  

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