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Creation of Paramagnetic Endofullerenes by Organic Synthesis

Research Project

Project/Area Number 24655027
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

MURATA Yasujiro  京都大学, 化学研究所, 教授 (40314273)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機合成 / 常磁性 / 内包フラーレン / フラーレン / 開口フラーレン / 窒素分子 / 酸素分子 / 水分子 / 硫黄
Research Abstract

The reaction of a tetraketo-open-cage C60 derivative with elemental sulfur in the presence of tetrakis(dimethylamino)ethylene afforded novel open C60 derivatives containing sulfur atom(s) in the rim of the orifice and the first example of an open C59S derivative. The single crystal X-ray analyses clearly determined these structures and demonstrated that a water molecule was encapsulated inside the cages. The orifice sizes were found to be large enough to insert N2 and O2 molecule inside the molecule. On the other hand, we conducted the X-ray diffraction study of He@C60 and the clear observation of a single helium atom inside C60. In addition, the close packing of a helium atom and a nitrogen atom inside fullerenes is realized using two stepwise insertion techniques, that is, molecular surgery to synthesize the fullerenes encapsulating a helium atom, followed by nitrogen radio-frequency plasma methods to generate the fullerenes encapsulating both helium and nitrogen atoms.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (49 results)

All 2014 2013 2012 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (28 results) (of which Invited: 1 results) Book (4 results) Remarks (1 results)

  • [Journal Article] Catalytic Stereodivergent Functionalization of H2@C602014

    • Author(s)
      Maroto, E. E.; Izquierdo, M.; Filippone, S.; Murata, M.; Murata, Y.; Komatsu, K.; Martin, N.
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 6 Pages: 740-742

    • DOI

      10.1039/c3cc46999a

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] “A Cubic Dipole Lattice of Water Molecules Trapped Inside Carbon Cages”2014

    • Author(s)
      S.Aoyagi
    • Journal Title

      Chem.Commun.

      Volume: 50 Issue: 5 Pages: 524-526

    • DOI

      10.1039/c3cc46683c

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Paramagnet Enhanced Nuclear Spin Relaxation in H_2O@Open-C_<60> and H_2@Open-C_<60>2013

    • Author(s)
      Li, Y.; Lei, X.; Chen, J. Y.-C.; Murata, Y.; Turro, N. J.; Lawler
    • Journal Title

      R. G. Org. Lett.

      Volume: 15 Issue: 18 Pages: 4746-4749

    • DOI

      10.1021/ol402111x

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nuclear Magnetic Resonance of Hydrogen Molecules Trapped inside C_<70> Fullerene Cages2013

    • Author(s)
      Mamone, S.; Concistre, M.; Heinmaa, I.; Carravetta, M.; Kuprov, I.; Wall, G.; Denning, M.; Lei, X.; Chen, J. Y.-C.; Li, Y.; Murata, Y.; Turro, N. J.; Levitt
    • Journal Title

      M. H. ChemPhysChem

      Volume: 14 Issue: 13 Pages: 3121-3130

    • DOI

      10.1002/cphc.201300269

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nuclear Spin Isomers of Guest Molecules in H_2@C_<60>, H_2O@C_<60> and Other Endofullerenes2013

    • Author(s)
      Chen, J. Y.-C.; Li, Y.; Frunzi, M.; Lei, X.; Murata, Y.; Lawler, R.G.; Turro, N. J. Phil
    • Journal Title

      Trans. R. Soc.

      Volume: 371,20120429 Issue: 1998 Pages: 16-16

    • DOI

      10.1098/rsta.2012.0429

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Assessment of Fullerene Derivatives as Rolling Journals in a Finite Carbon Nanotube Bearing2013

    • Author(s)
      Hitosugi, S.; Iizuka, R.; Yamasaki, T.; Zhang, R.; Murata, Y.; Isobe, H.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 13 Pages: 3199-3201

    • DOI

      10.1021/ol400982r

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and X-Ray Structure of Endohedral Fullerene C60 Dimer Encapsulating a Water Molecule in Each C60 Cage2013

    • Author(s)
      Zhang, R.; Murata, M.; Wakamiya, A.; Murata, Y.
    • Journal Title

      Chem. Lett.

      Volume: 42 Issue: 8 Pages: 879-881

    • DOI

      10.1246/cl.130358

    • NAID

      10031189282

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Expansion of Orifices of Open C60 Derivatives and Formation of an Open C59S Derivative by Reaction with Sulfur2013

    • Author(s)
      Futagoishi, T.; Murata, M.; Wakamiya, A.; Sasamori, T.; Murata, Y.
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 11 Pages: 2750-2753

    • DOI

      10.1021/ol401083c

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and photovoltaic properties of acceptor materials based on the dimerization of fullerene C_60 for use in efficient polymer solar cells2013

    • Author(s)
      森中裕太
    • Journal Title

      Chemical Communications

      Volume: (印刷中) Issue: 35 Pages: 3670-3672

    • DOI

      10.1039/c3cc41084f

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] X-ray observation of a helium atom and placing a nitrogen atom inside He@C_60 and He@C_702013

    • Author(s)
      森中裕太
    • Journal Title

      Nature Communications

      Volume: 4 Issue: 1 Pages: 1554-1554

    • DOI

      10.1038/ncomms2574

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Recognition of Hydrogen Isotopomers by an Open-Cage Fullerene2013

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

      Phil. Trans. R. Soc. A

      Volume: 371 Issue: 1998 Pages: 20110629-20110629

    • DOI

      10.1098/rsta.2011.0629

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Isomer Count, and Nuclear Spin Relaxation of H2O@Open-C60 Nitroxide Derivatives2012

    • Author(s)
      Li, Y.; Lei, X.; Lawler, R. G.; Murata, Y.; Komatsu, K.; Turro, N. J.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 15 Pages: 3822-3825

    • DOI

      10.1021/ol3013155

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Quantum Rotation of Ortho and Para-water Encapsulated in a Fullerene Cage, Beduz, C.; Carravetta2012

    • Author(s)
      Beduz, C.; Carravetta, M.; Chen, J. Y.-C.; Concistre, M.; Denning, M.; Frunzi, M.; Horsewill, A. J.; Johannessen, O. G.; Lawler, R.; Lei, X.; Levitt, M. H.; Li, Y.; Mamone, S.; Murata, Y.; Nagel, U.; Nishida, T.; Ollivier, J.; Rols, S.; Room, T.; Sarker, R.; Turro, N. J.; Yang, Y
    • Journal Title

      Proc. Natl. Acad. Sci. USA

      Volume: 109 Issue: 32 Pages: 12894-12898

    • DOI

      10.1073/pnas.1210790109

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Planarized Triarylboranes : Stabilization by Structural Constraint and Their Plane-to-Bowl Conversion2012

    • Author(s)
      Zhiguo Zhou, Atsushi Wakamiya, Tomokatsu Kushida, Shigehiro Yamaguchi
    • Journal Title

      Journal of The American Chemical Society

      Volume: 134 Issue: 10 Pages: 4529-4532

    • DOI

      10.1021/ja211944q

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Comparison of Nuclear Spin Relaxation of H2O@C60 and H2@C60 and Their Nitroxide Derivatives2012

    • Author(s)
      Li, Y.; Chen, J.; Lei, X.; Lawler, R.; Murata, Y.; Komatsu, K.; Turro, N.
    • Journal Title

      J. Phys. Chem. Lett.

      Volume: 3 Issue: 9 Pages: 1165-1168

    • DOI

      10.1021/jz3002794

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Inelastic Neutron Scattering Investigations of the Quantum Molecular Dynamics of a H2 Molecule Entrapped inside a Fullerene Cage2012

    • Author(s)
      Horsewill, A. J.; Levitt, M. H.; Murata, Y.; Komatsu, K.; Turro, N. J. et al.,
    • Journal Title

      Phys. Rev. B

      Volume: 85 Issue: 20 Pages: 205440-205440

    • DOI

      10.1103/physrevb.85.205440

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] X-ray Structure and Reaction of a Precursor for Endohedral C_<59>N2014

    • Author(s)
      Yoshifumi Hashikawa, 他
    • Organizer
      Institute for Chemical Research International Symposium 2014
    • Place of Presentation
      Obaku Plaza, Kyoto University, Uji, Japan
    • Year and Date
      2014-10-12
    • Related Report
      2013 Final Research Report
  • [Presentation] フラーレンC_<60>のケトラクタム誘導体における開口部拡大反応2014

    • Author(s)
      橋川祥史, 他
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Final Research Report
  • [Presentation] ケトラクタム構造をもつ新しい開口C_<60>誘導体の合成2014

    • Author(s)
      橋川祥史, 他
    • Organizer
      第45回フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Place of Presentation
      東京大学伊藤謝恩ホール
    • Related Report
      2013 Final Research Report
  • [Presentation] 巨大開口部をもつC60誘導体の合成と小分子内包体のX線構造2014

    • Author(s)
      二子石師、村田理尚、若宮淳志、村田靖次郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 13員環C70誘導体における開口部の構造変換2014

    • Author(s)
      張鋭、村田理尚、若宮淳志、村田靖次郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] フラーレンC60のケトラクタム誘導体における開口部拡大反応2014

    • Author(s)
      橋川祥史、村田理尚、若宮淳志、村田靖次郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] Recent Progress on the Synthesis and Reaction of Novel Endofullerenes2013

    • Author(s)
      Yasujiro Murata
    • Organizer
      A Life in Science : A Meeting on Endofullerene Molecular Systems in Memory of Nicholas J. Turro
    • Place of Presentation
      Department of Chemistry, Columbia University, New York, USA
    • Year and Date
      2013-05-12
    • Related Report
      2013 Final Research Report
  • [Presentation] 水内包フラーレンC_60の二量化とX線構造2013

    • Author(s)
      張鋭, 他
    • Organizer
      第9回有機元素化学セミナー
    • Place of Presentation
      京都大学宇治キャンパスきはだホール
    • Related Report
      2013 Final Research Report
  • [Presentation] Organic Synthesis of Endohedral Fullerenes and Their Reactions2013

    • Author(s)
      Yasujiro Murata
    • Organizer
      5th International Symposium on Emergence of Highly Elavoratedπ-Space and Its Function
    • Place of Presentation
      Okazaki Conference Center, Higashiokazaki, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] Novel Endohedral Fullerenes : Synthesis and Reactions2013

    • Author(s)
      Yasujiro Murata
    • Organizer
      The Third Symposium on "Carbon Nanoforms"
    • Place of Presentation
      Madrid Institute for Advanced Studies in Nanoscience, Madrid, Spain
    • Related Report
      2013 Final Research Report
  • [Presentation] 水分子内包フラーレンの結晶構造と誘電的性質2013

    • Author(s)
      青柳忍, 他
    • Organizer
      本物理学会2013年秋期大会
    • Place of Presentation
      徳島大学
    • Related Report
      2013 Final Research Report
  • [Presentation] 硫黄挿入反応を利用した新規開口C_<60>誘導体の合成と小分子内包体のX線構造2013

    • Author(s)
      二子石師, 他
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学目白キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] H_2O@C_<60>の固体反応ならびに[2+2]型二量体のX線構造2013

    • Author(s)
      張鋭, 他
    • Organizer
      第45回フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Place of Presentation
      大阪大学
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis and Reactions of Novel Endohedral Fullerenes2013

    • Author(s)
      Yasujiro Murata, 他
    • Organizer
      15th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Taipei, Taiwan
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] ヘリウム原子と窒素原子を内包したフラーレンの発生2013

    • Author(s)
      村田靖次郎, 他
    • Organizer
      新学術領域研究「高次π空間の創発と機能開発」第9回公開シンポジウム
    • Place of Presentation
      シーサイドホテル舞子ビラ神戸、神戸
    • Related Report
      2013 Final Research Report
  • [Presentation] ヘリウム内包フラーレンの有機合成ならびに2つの異種原子を内包したフラーレンの発生2013

    • Author(s)
      森中裕太, 他
    • Organizer
      第44回フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Place of Presentation
      東京大学伊藤国際学術研究センター謝恩ホール
    • Related Report
      2013 Final Research Report
  • [Presentation] Organic Synthesis of Endohedral Fullerenes and Their Reactions2013

    • Author(s)
      Yasujiro Murata
    • Organizer
      5th International Symposium on Emergence of Highly Elavorated pi-Space and Its Function
    • Place of Presentation
      Higashiokazaki, Japan
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ヘリウム原子内包フラーレンの有機合成と新規異種原子内包フラーレンの発生2013

    • Author(s)
      森中裕太、佐藤悟、若宮淳志、二川秀史、溝呂木直美、田辺史行、村田理尚、小松紘一、古川貢、加藤立久、永瀬茂、赤阪健、村田靖次郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 13員環開口部をもつ水内包C70誘導体の合成と性質2013

    • Author(s)
      張鋭、村田理尚、村田靖次郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 硫黄挿入を鍵反応としたフラーレンC60への巨大開口部の構築と小分子の内包2013

    • Author(s)
      二子石師、村田理尚、村田靖次郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学 びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 小分子内包フラーレンの有機合成2012

    • Author(s)
      村田靖次郎, 他
    • Organizer
      奈良先端未来開拓コロキウム2012~分子、超分子から分子技術の時代へ~
    • Place of Presentation
      学際融合領域研究棟1号館1階「交流・カンファレンスルーム」、奈良先端科学技術大学院大学、奈良
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis and Photophysical Properties of Azafullerenes Directly Connected to an Organic Dye2012

    • Author(s)
      Yasujiro Murata, 他
    • Organizer
      4th International Symposium on Emergence of Highly Elaboratedπ-Space and Its Function
    • Place of Presentation
      Hamanako Royal Hotel, Hamamatsu, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis and Photovoltaic Properties of Dumbbell-Shaped Fullerene Derivatives2012

    • Author(s)
      Michihisa Murata, 他
    • Organizer
      The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Rihga Royal Hotel Kyoto, Kyoto, Japan
    • Related Report
      2013 Final Research Report
  • [Presentation] ダンベル型フラーレン誘導体 : 有機薄膜太陽電池のモルフォロジー制御2012

    • Author(s)
      村田理尚, 他
    • Organizer
      23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ、京都
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of Endohedral Fullerene C_<60> Encapsulating a Single Molecule of Water2012

    • Author(s)
      Kei Kurotobi, 他
    • Organizer
      第43回フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Place of Presentation
      東北大学百周年記念会館川内萩ホール
    • Related Report
      2013 Final Research Report
  • [Presentation] 17員環開口部をもつ新規フラーレン誘導体の合成と性質2012

    • Author(s)
      村田靖次郎, 他
    • Organizer
      新学術領域研究「高次π空間の創発と機能開発」第8回公開シンポジウム
    • Place of Presentation
      ホテルアローレ、加賀
    • Related Report
      2013 Final Research Report
  • [Presentation] ダンベル型フラーレン誘導体の合成と光電変換特性2012

    • Author(s)
      村田理尚, 他
    • Organizer
      日本学術振興会産学協力研究委員会第9回「次世代の太陽光発電システム」シンポジウム
    • Place of Presentation
      京都テルサ
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of Endohedral C_<60> Encapsulating a Water Molecule2012

    • Author(s)
      Yasujiro Murata, 他
    • Organizer
      The 10th International Conference on Heteroatom Chemistry (ICHAC-10)
    • Place of Presentation
      Obaku Plaza, Kyoto University, Kyoto, Japan
    • Related Report
      2013 Final Research Report
  • [Book] Organic Synthesis of Endohedral Fullerenes Encapsulating Helium, Dihydrogen, and Water2013

    • Author(s)
      Murata, M.; Murata, Y.; Komatsu, K. Organic Nanomaterials, Torres, T., Bottari, G. Eds
    • Publisher
      Wiley-Blackwell, Oxford
    • Related Report
      2013 Final Research Report
  • [Book] CSJカレントレビュー「未来材料を創出するπ電子系の科学」2013

    • Author(s)
      村田靖次郎
    • Publisher
      化学同人
    • Related Report
      2013 Final Research Report
  • [Book] 高次π空間の創発と機能開発2013

    • Author(s)
      村田靖次郎
    • Publisher
      シーエムシー出版
    • Related Report
      2013 Final Research Report
  • [Book] Organic Nanomaterials2013

    • Author(s)
      Murata, M.; Murata, Y.; Komatsu, K.
    • Total Pages
      16
    • Publisher
      Wiley-Blackwell, Oxford
    • Related Report
      2013 Annual Research Report
  • [Remarks]

    • URL

      http://www.scl.kyoto-u.ac.jp/~kouzou/index.html

    • Related Report
      2013 Final Research Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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