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Synthesis of Tailor-Made Nanocarbons and Their Application to Devices

Research Project

Project/Area Number 23241032
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Nanostructural science
Research InstitutionKyoto University

Principal Investigator

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

Co-Investigator(Renkei-kenkyūsha) MURATA Michihisa  京都大学, 化学研究所, 助教 (30447932)
WAKAMIYA Atsushi  京都大学, 化学研究所, 准教授 (60362224)
Project Period (FY) 2011-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥48,880,000 (Direct Cost: ¥37,600,000、Indirect Cost: ¥11,280,000)
Fiscal Year 2015: ¥8,970,000 (Direct Cost: ¥6,900,000、Indirect Cost: ¥2,070,000)
Fiscal Year 2014: ¥8,970,000 (Direct Cost: ¥6,900,000、Indirect Cost: ¥2,070,000)
Fiscal Year 2013: ¥8,970,000 (Direct Cost: ¥6,900,000、Indirect Cost: ¥2,070,000)
Fiscal Year 2012: ¥8,970,000 (Direct Cost: ¥6,900,000、Indirect Cost: ¥2,070,000)
Fiscal Year 2011: ¥13,000,000 (Direct Cost: ¥10,000,000、Indirect Cost: ¥3,000,000)
Keywordsフラーレン / C60 / C70 / 内包フラーレン / 開口フラーレン / 固体物性 / 小分子 / 水 / 水素 / アザフラーレン / 有機合成 / 核磁気共鳴 / 緩和時間 / ヘテロフラーレン / X線結晶解析 / 酸化還元特性 / 有機薄膜太陽電池デバイス / エネルギー移動
Outline of Final Research Achievements

The synthetic methods to create a large opening on fullerenes have been developped. A water molecule was encapsulated into the open-cage C60 derivative, and the opening was completely restored to afford H2O@C60 in a macro-scopic scale under the mild reaction conditions. To reallize an encapsulation of a large molecule, efficient way to create a larger opening was found by the reaction with nucleophilic oxidants, which was also applied to a precursor of azafullerenes, in which one of the carbon atoms in fullerene cages is replaced with a nitrogen atom. As another method to enlarge the opening, a sulfur atom was introduced on the rim of the openings. When this reaction was applied to an open-cage C60 derivative, a new open-cage C59S derivative was obtained in addition to the expected compound having a larger opening. Furthermore, when this reaction was applied to an open-cage C70 derivative, another new reaction was found to afford an open-cage C69S derivative.

Report

(6 results)
  • 2016 Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (45 results)

All 2016 2015 2014 2013 2012

All Journal Article (20 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 20 results,  Acknowledgement Compliant: 6 results,  Open Access: 3 results) Presentation (21 results) (of which Int'l Joint Research: 3 results,  Invited: 4 results) Book (4 results)

  • [Journal Article] Synthesis and Properties of Endohedral Aza[60]fullerenes: H2O@C59N and H2@C59N as Their Dimers and Monomers2016

    • Author(s)
      Hashikawa, Y.; Michihisa, M.; Wakiamiya, A.; Murata, Y.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 12 Pages: 4096-4104

    • DOI

      10.1021/jacs.5b12795

    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] H2O Entrapped inside Fullerene Cages: Potential Probe for Evaluation of Bond Polarization2016

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

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 42 Pages: 13109-13113

    • DOI

      10.1002/anie.201607040

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of a Distinct Water Dimer inside Fullerene C702016

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

      Nat. Chem.

      Volume: 8 Issue: 5 Pages: 435-441

    • DOI

      10.1038/nchem.2464

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Trapping N2 and CO2 on the Sub-Nano Scale in Confined Internal Spaces of Open-Cage C60 Derivatives: Isolation and Structural Characterization of Host-Guest Complexes2015

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

      Angew. Chem. Int. Ed.

      Volume: 54 Issue: 49 Pages: 14791-14794

    • DOI

      10.1002/anie.201507785

    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Hole-Transporting Materials with a Two-Dimensionally Expanded π-System around an Azulene Core for Efficient Perovskite Solar Cells2015

    • Author(s)
      H. Nishimura, N. Ishida, A. Shimazaki, A. Wakamiya, A. Saeki, L. T. Scott, and Y. Murata
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 50 Pages: 15656-15659

    • DOI

      10.1021/jacs.5b11008

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Purely organic electroluminescent material realizing 100% conversion from electricity to light2015

    • Author(s)
      Hironori Kaji, Hajime Suzuki, Tatsuya Fukushima, Katsuyuki Shizu, Katsuaki Suzuki, Shosei Kubo, Takeshi Komino, Hajime Oiwa, Furitsu Suzuki, Atsushi Wakamiya, Yasujiro Murata, and Chihaya Adachi
    • Journal Title

      Nature Communications

      Volume: 6 Issue: 1 Pages: 84761-8

    • DOI

      10.1038/ncomms9476

    • NAID

      120005663313

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Enantiospecific cis-trans Isomerization in Chiral Fulleropyrrolidines: H-Bonding Assistance in the Carbanion Stabilization in H2O@C602015

    • Author(s)
      Maroto, E. E.; Mateos, J.; Garcia-Borras, M.; Osuna, S.; Filippone, S.; Herranz, M. A.; Murata, Y.; Sola, M.; Martin, N.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 3 Pages: 1190-1197

    • DOI

      10.1021/ja5108854

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [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
    • Peer Reviewed
  • [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 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Interaction of H2@C60 and Nitroxide through Conformationally Constrained Peptide Bridges2014

    • Author(s)
      Garbuio, L.; Li, Y.; Antonello, S.; Gascon, J. A.; Lawler, R. G.; Lei, X.; Murata, Y.; Turro, N. J.; Maran, F.
    • Journal Title

      Photochem. Photobiol.

      Volume: 90 Issue: 2 Pages: 439-447

    • DOI

      10.1111/php.12191

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reproducible Fabrication of Highly Efficient Perovskite-based Solar Cells: X-ray Crystallographic Studies on the Formation of CH3NH3PbI3 Layers2014

    • Author(s)
      Wakamiya, A.; Endo, M.; Sasamori, T.; Tokitoh, N.; Ogomi, Y.; Hayase, S.; Murata, Y.
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 11 Pages: 711-713

    • DOI

      10.1021/ol501113y

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and Structure of an Open-Cage Thiafullerene C69S: Reactivity Differences of an Open-Cage C70 Tetraketone Relative to Its C60 Analogue.2014

    • Author(s)
      Zhang Rui, Futagoishi Tsukasa, Murata Michihisa, Wakamiya Atsushi, Murata Yasujiro
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 23 Pages: 8193-8196

    • DOI

      10.1021/ja504054s

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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
      2012 Annual Research Report 2011 Annual 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
      2012 Annual Research Report 2011 Annual 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
      2012 Annual 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
      2012 Annual 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
      2012 Annual 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
      2012 Annual 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
      2012 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
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] アザフラーレンC59Nに内包された水分子の動的挙動2016

    • 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96回春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
  • [Presentation] 開口フラーレンC60誘導体の閉環反応に関する研究2016

    • 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96回春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2014 Annual Research Report
  • [Presentation] Open-cage Fullerenes toward Endofullerenes and Heterofullerenes2015

    • Author(s)
      Yasujiro Murata
    • Organizer
      The 2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 炭素π共役系分子錯体の非平衡単分子界面科学2015

    • Author(s)
      村田靖次郎
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀、東京
    • Year and Date
      2015-10-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] 内包アザフラーレンの合成および内包分子の核磁気緩和2015

    • Author(s)
      橋川祥史、村田理尚、若宮淳志、村田靖次郎
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学・松山大学
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Open-Cage Fullerenes: Fascinating Host Molecules for Small Molecules and Rational Precursors for Endofullerenes and Heterofullerenes2015

    • Author(s)
      Yasujiro Murata, Tsukasa Futagoishi, Rui Zhang, Yoshifumi Hashikawa, Michihisa Murata, and Atsushi Wakamiya
    • Organizer
      16th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      2015-07-05
    • Related Report
      2015 Annual Research Report 2014 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of H2@C59N and H2O@C59N Dimers2015

    • Author(s)
      Yoshifumi Hashikawa, Michihisa Murata, Atsushi Wakamiya, and Yasujiro Murata
    • Organizer
      16th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      2015-07-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ペロブスカイト型太陽電池の高効率化のための新規正孔輸送性材料開発2015

    • Author(s)
      西村秀隆、丸山直樹、遠藤克、若宮淳志、Lawrence T. Scott、村田靖次郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] 開口部をもつチアフラーレンC69SならびにオキサフラーレンC69O誘導体の合成とX線構造2014

    • Author(s)
      張鋭、二子石師、村田理尚、若宮淳志、村田靖次郎
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部市文化会館文化ホール
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] Synthesis and X-ray Structure of Open-Cage Thiafullerene C69S and Oxafullerene C69O Derivatives2014

    • Author(s)
      Rui Zhang, Tsukasa Futagoishi, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata
    • Organizer
      International Symposium on the Synthesis and Application of Curved Organic Pi-Molecules and Materials
    • Place of Presentation
      Kyoto University
    • Year and Date
      2014-10-19 – 2014-10-21
    • Related Report
      2013 Annual Research Report
  • [Presentation] フラーレン骨格の化学変換による小分子内包体の合成2014

    • Author(s)
      村田靖次郎
    • Organizer
      第63回高分子討論会
    • Place of Presentation
      長崎大学
    • Year and Date
      2014-09-24 – 2014-09-26
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 準平面型構造を鍵骨格に用いた正孔輸送性材料の開発2014

    • Author(s)
      西村秀隆、遠藤克、若宮淳志、Scott, L. T.、村田靖次郎
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内北キャンパス
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2013 Annual Research Report
  • [Presentation] ケトラクタム構造をもつ新しい開口C60誘導体の合成2014

    • Author(s)
      橋川祥史、村田理尚、若宮淳志、村田靖次郎
    • 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
    • Related Report
      2012 Annual 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
      2012 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Reactions of Novel Endohedral Fullerenes2013

    • Author(s)
      Yasujiro Murata, Yuta Morinaka, Tsukasa Futagoishi,Rui Zhang, Michihisa Murata, Atsushi Wakamiya
    • Organizer
      15th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Taipei, Taiwan
    • Related Report
      2012 Annual Research Report
    • Invited
  • [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、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
      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
      2011 Annual Research Report
  • [Presentation] フラーレンC70における開口部構築と水分子の内包2013

    • Author(s)
      張鋭、村田理尚、村田靖次郎
    • 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
      2011 Annual Research Report
  • [Presentation] 含硫黄開口部をもつC60誘導体の合成と窒素分子内包体のX線構造2013

    • Author(s)
      二子石師、村田理尚、村田靖次郎
    • 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
      2011 Annual 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、登政博、森中裕太、若宮淳志、佐川尚、吉川暹、村田靖次郎
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ、京都
    • Related Report
      2012 Annual 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、登 政博、若宮 淳志、佐川 尚、吉川 暹、村田 靖次郎
    • 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、京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of Endohedral C60 Encapsulating a Water Molecule2012

    • Author(s)
      Yasujiro Murata, Kei Kurotobi, Tomoko Nishida
    • Organizer
      The 10th International Conference on Heteroatom Chemistry
    • Place of Presentation
      Kyoto University
    • Related Report
      2012 Annual Research Report
  • [Book] Open-Cage Fullerene Derivatives: Synthesis, Reactions, and Encapsulation of a Small Molecule2015

    • Author(s)
      Murata, Y.
    • Total Pages
      14
    • Publisher
      Springer, Japan
    • Related Report
      2014 Annual Research Report
  • [Book] 高次π空間の創発と機能開発2013

    • Author(s)
      村田靖次郎
    • Total Pages
      4
    • Publisher
      シーエムシー出版
    • Related Report
      2012 Annual 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
    • Total Pages
      7
    • Publisher
      化学同人
    • Related Report
      2012 Annual Research Report
  • [Book] Organic Nanomaterials2013

    • Author(s)
      Murata, M.; Murata, Y.; Komatsu, K.
    • Total Pages
      16
    • Publisher
      Wiley-Blackwell
    • Related Report
      2012 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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