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Organic Synthesis of Novel Endohedral Fullerenes by the Method of Molecular Surgery

Research Project

Project/Area Number 19020067
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionFukui University of Technology

Principal Investigator

KOMATSU Koichi  Fukui University of Technology, 工学部, 教授 (70026243)

Co-Investigator(Kenkyū-buntansha) MURATA Yasujiro  京都大学, 化学研究所, 教授 (40314273)
MURATA Michihisa  京都大学, 化学研究所, 助教 (30447932)
Project Period (FY) 2007 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2008: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2007: ¥1,500,000 (Direct Cost: ¥1,500,000)
Keywords合成有機化学 / 水素内包フラーレン / 開口フラーレン / 温度可変NMR / フラーレンC70 / [4+2]付加反応 / ネオン / ヘリウム内包フラーレン / NMR / カチオン / アニオン / 低磁場シフト / ヒドラジン
Research Abstract

炭素原子のみからなる球状の分子であるフラーレンの内部空間に小原子や分子を入れた「内包フラーレン」を、従来用いられてきた効率の低い物理的手段ではなく、「分子手術法」とよぶ有機化学的手法によって合成した。すなわち、フラーレン分子C60およびC70について、有機化学反応によってまず骨格に開口部を設け、それを適当なサイズに拡大した後に、ヘリウム、水素、重水素などを内部に入れ、最後に開口部を閉じることによって、これらの化学種を含んだ内包フラーレンを合成することに初めて成功した。

Report

(3 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • Research Products

    (44 results)

All 2009 2008 2007 2006 Other

All Journal Article (20 results) (of which Peer Reviewed: 20 results) Presentation (18 results) Book (5 results) Remarks (1 results)

  • [Journal Article] Synthesis and Reaction of Fullerene C70 Encapsulating Two Molecules of H22008

    • Author(s)
      M. Murata, S. Maeda, Y. Morinaka, Y. Murata, and K. Komatsu
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 15800-15801

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Demonstration of a Chemical Transformation Inside a Fullerene. The Reversible Conversion of the Allotropes of H2@C60.2008

    • Author(s)
      N. J. Turro, A. A. Marti, J. Y. -C. Chen, S. Jockusch, R. G. Lawler, M. Ruzzi, E. Sartori, S-C. Chuang, K. Komatsu and Y. Murata,
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 10506-10507

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] NMR Studies on Monofunctionalized Fullerenyl Cation and Anion Encapsulating a H2 Molecule.2008

    • Author(s)
      M. Murata, Y, Ochi, T. Kitagawa, K. Komatsu, and Y. Murata
    • Journal Title

      Chem. Asian J. 3

      Pages: 1336-1342

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Encapsulation and Dynamic Behavior of Two H2 Molecules in an Open-Cage C70.2008

    • Author(s)
      Y. Murata, S. Maeda, M. Murata, and K. Komatsu.
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 6702-6703

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Paramagnet Enhanced Nuclear Relaxation of H2 in Organic Solvents and in H2@C60.2008

    • Author(s)
      E. Sartori, M. Ruzzi, N. J. Turro, K. Komatsu, Y. Murata, R. G. Lawler, and A. L. Buchachenko
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 2221-2225

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Internal Magnetic Fields of Dianions of Fullerene C60 and Its Cage-Opened Derivatives Studied by Encapsulated H2 as an NMR Probe.2008

    • Author(s)
      M. Murata, Y. Ochi, F. Tanabe, K. Komatsu, and Y. Murata, Angew.
    • Journal Title

      em. Int. Ed. 47

      Pages: 2039-2041

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Encapsulation and Dynamic Behavior of Two H_2 Molecules in an Open-Cage C_<70>2008

    • Author(s)
      Y. Murata
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 6702-6703

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Demonstration of a Chemical Transformation Inside a Fullerene. The Reversible Conversion of the Allotropes of H_2@C_<60>2008

    • Author(s)
      N. J. Turro
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 10506-10507

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Reaction of Fullerene C<70> Encapsulating Two Molecules of H_22008

    • Author(s)
      M. Murata
    • Journal Title

      Journal of the American Chemical Society 130

      Pages: 15800-15801

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Can H2 Inside C60 Communicate with the Outside World?2007

    • Author(s)
      J. Lopez-Gejo, A. A. Marti, M. Ruzzi, S. Jockusch, K. Komatsu, Y. Murata, and N. J. Turro,
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 14554-14555

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Synthesis of Open-Cage Fullerene Derivatives Having 16-Membered-Ring Orifices.2007

    • Author(s)
      M. M. Roubelakis, Y. Murata, K. Komatsu, and M. Orfanopoulos
    • Journal Title

      J. Org. Chem. 72

      Pages: 7042-7045

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] An Orifice-Size Index for Open-Cage Fullerenes.2007

    • Author(s)
      S-C. Chuang, Y. Murata, M. Murata, and K. Komatsu
    • Journal Title

      J. Org. Chem. 72

      Pages: 6447-6453

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] The Outside Knows the Difference Inside : Trapping Helium by Immediate Reduction of Orifice Size of an Open-Cage Fullerene and the Effect of Encapsulated Helium and Hydrogen upon the NMR of Proton Directly Attached to the Outside2007

    • Author(s)
      S-C. Chuang, Y. Murata, M. Murata, and K. Komatsu
    • Journal Title

      Chem. Commun.

      Pages: 1751-1753

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Fine Tuning of the Orifice Size of an Open-Cage Fullerene by Placing Selenium in the Rim : Insertion/Release of Molecular Hydrogen.2007

    • Author(s)
      S-C. Chuang, Y. Murata, M. Murata, S. Mori, S. Maeda, F. Tanabe, and K. Komatsu
    • Journal Title

      Chem. Commun.

      Pages: 1278-1280

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Electrochemistry of an Open-Cage Fullerene Embedded in a Film of Hydrophobic Ammonium Ion on an Electrode2007

    • Author(s)
      K. Watanabe
    • Journal Title

      Journal of Physical Chemistry-C 111

      Pages: 6500-6504

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Orifice-Size Index for Open-Cage Fullerenes2007

    • Author(s)
      S-C. Chuang
    • Journal Title

      The Journal of Organic Chemistry 72

      Pages: 6447-6453

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Can H_2 Inside C_<60> Communicate with the Outside World?2007

    • Author(s)
      J.Lopez-Gejo
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 14554-14555

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nuclear Relaxation of H2 and H2@C60 in Organic Solvents.2006

    • Author(s)
      E. Sartori, M. Ruzzi, N. J. Turro, J. D. Decatur, D. C. Doetschman, R. G. Lawler, A. L. Buchachenko, Y. Murata, and K. Komatsu
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 14752-14753

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article]2006

    • Author(s)
      M. Murata, Y. Murata, and K. Komatsu
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 8024-8033

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cryogenic NMR Spectroscopy of Endohedral Hydrogen-Fullerene Complexes.2006

    • Author(s)
      M. Carravetta, O. G. Johannessen, M. H. Levitt, I. Heinmaa, R. Stern, A. Samoson, A. J. Horsewill, Y. Murata, and K. Komatsu
    • Journal Title

      J. Chem. Phys. 124

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Presentation] 2個の水素分子を内包したフラーレンC70 の[4+2]環化付加反応2009

    • Author(s)
      小松紘一(代表)
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-27
    • Related Report
      2008 Final Research Report
  • [Presentation] Generation of Ionic [60]Fullerene Derivatives Encapsulating Molecular Hydrogen2008

    • Author(s)
      小松紘一(代表)
    • Organizer
      Pacific Rim Meeting on Electrochemical and Solid-State Science
    • Place of Presentation
      Honolulu, U. S. A.
    • Year and Date
      2008-10-15
    • Related Report
      2008 Final Research Report
  • [Presentation] 二次元および三次元π共役系に新規構造を求めて2008

    • Author(s)
      小松紘一
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-10-05
    • Related Report
      2008 Annual Research Report
  • [Presentation] Synthesis of Endohedral Open-Cage Fullerenes and Studies on Non-Covalent Interaction between Encapsulated Species and Fullerene Cage.2008

    • Author(s)
      小松紘一(代表)
    • Organizer
      The 213th Electrochemical Society Meeting
    • Place of Presentation
      Phoenix, U. S. A.
    • Year and Date
      2008-05-20
    • Related Report
      2008 Final Research Report
  • [Presentation] ラクトン構造をもつ新しい開口フラーレンの合成と性質2008

    • Author(s)
      小松紘一(代表)
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-27
    • Related Report
      2008 Final Research Report
  • [Presentation] ビシクロ炭素骨格によって取囲まれたπ 電子系-ビシクロ[2.2.2]オクテンとビシクロ[2.1.1]ヘキセンの違い2007

    • Author(s)
      小松紘一
    • Organizer
      有機π電子系シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2007-12-08
    • Related Report
      2008 Final Research Report
  • [Presentation] Synthesis of Endohedral Open-Cage Fullerenes and Studies on Non-Covalent Interaction between Encapsulated Species and Fullerene Cage2007

    • Author(s)
      小松紘一(代表)
    • Organizer
      12th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路
    • Year and Date
      2007-07-24
    • Related Report
      2008 Final Research Report
  • [Presentation] Organic Chemistry of Fullerenes : Solid-State Reaction to Molecular Surgery2007

    • Author(s)
      小松紘一(代表)
    • Organizer
      The 15th European Symposium on Organic Chemistry
    • Place of Presentation
      Dublin, Ireland
    • Year and Date
      2007-07-09
    • Related Report
      2008 Final Research Report
  • [Presentation] Organic Chemistry of Fullerenes: Solid-State Reaction to Molecular Surgery(基調講演)2007

    • Author(s)
      小松 紘一
    • Organizer
      The 15th European Symposium on Organic Chemistry
    • Place of Presentation
      University College, Dublin, Ireland
    • Year and Date
      2007-07-09
    • Related Report
      2007 Annual Research Report
  • [Presentation] Fine Tuning of the Orifice Size : Synthesis and Properties of Selenium-Containing Open-Cage C602007

    • Author(s)
      小松紘一(代表)
    • Organizer
      The 211th Electrochemical Society Meeting
    • Place of Presentation
      Chicago, U. S. A.
    • Year and Date
      2007-05-14
    • Related Report
      2008 Final Research Report
  • [Presentation] Organic Synthesis of Endohedral Fullerenes by Molecular Surgery2006

    • Author(s)
      小松紘一
    • Organizer
      The 10th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2006-11-15
    • Related Report
      2008 Final Research Report
  • [Presentation] 有機化学によるフラーレンの構造変換-固体反応から分子手術まで2006

    • Author(s)
      小松紘一
    • Organizer
      有機合成化学協会中国四国支部特別講演会
    • Place of Presentation
      岡山
    • Year and Date
      2006-11-11
    • Related Report
      2008 Final Research Report
  • [Presentation] 分子を手術して内包フラーレンをつくる2006

    • Author(s)
      小松紘一
    • Organizer
      学術創成研究公開シンポジウム「物理と化学が生み出す未来物質」
    • Place of Presentation
      東京
    • Year and Date
      2006-11-04
    • Related Report
      2008 Final Research Report
  • [Presentation] 有機化学によるフラーレンの構造変換-固体反応から分子手術まで-2006

    • Author(s)
      小松紘一
    • Organizer
      機能物質化学セミナー
    • Place of Presentation
      相模
    • Year and Date
      2006-07-21
    • Related Report
      2008 Final Research Report
  • [Presentation] Organic Synthesis of Endohedral Fullerenes Encapsulating Hydrogen Molecule(s)2006

    • Author(s)
      小松紘一
    • Organizer
      Forum for Molecular Science
    • Place of Presentation
      西安
    • Year and Date
      2006-06-30
    • Related Report
      2008 Final Research Report
  • [Presentation] 炭素π共役系の極限的構造と物性に関する実験的研究2006

    • Author(s)
      小松紘一
    • Organizer
      日本化学会第86春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2006-03-28
    • Related Report
      2008 Final Research Report
  • [Presentation] 分子手術法による水素内包フラーレン類の新規合成2006

    • Author(s)
      小松紘一
    • Organizer
      東京工業大学21世紀COE公開シンポジウム「分子多様性の創出と機能開拓」
    • Place of Presentation
      東京
    • Year and Date
      2006-01-28
    • Related Report
      2008 Final Research Report
  • [Presentation] 新しい二次元および三次元π共役系の実現を目指して2006

    • Author(s)
      小松紘一
    • Organizer
      有機合成新春講演会
    • Place of Presentation
      大阪
    • Year and Date
      2006-01-25
    • Related Report
      2008 Final Research Report
  • [Book] ナノカーボンハンドブック2007

    • Author(s)
      小松紘一,村田理尚
    • Publisher
      エヌティーエス出版
    • Related Report
      2008 Final Research Report
  • [Book] Recent Developments in Carbocation and Onium Ion Chemistry2007

    • Author(s)
      K. Komatsu
    • Publisher
      ACS Symposium Series
    • Related Report
      2008 Final Research Report
  • [Book] ナノカーボンハンドブック2007

    • Author(s)
      小松 紘一
    • Total Pages
      5
    • Publisher
      エヌティーエス出版
    • Related Report
      2007 Annual Research Report
  • [Book] 化学:元素が彩る暮らしと未来2006

    • Author(s)
      小松紘一,クバプロ
    • Related Report
      2008 Final Research Report
  • [Book] Carbon-Rich Compounds‐From Molecules to Materials2006

    • Author(s)
      T. Kitagawa, Y. Murata, and K. Komatsu
    • Publisher
      Wiley-VCH Verlag
    • Related Report
      2008 Final Research Report
  • [Remarks] 平成21年1月5日付にて村田靖次郎が研究分担者を辞退し、代わって村田理尚が追加となった。

    • Related Report
      2008 Annual Research Report

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Published: 2007-04-01   Modified: 2018-03-28  

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