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Understanding the electronic state of graphene at the molecular level and elucidation of new functions

Research Project

Project/Area Number 26288016
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

Kubo Takashi  大阪大学, 理学(系)研究科(研究院), 教授 (60324745)

Co-Investigator(Kenkyū-buntansha) 中野 雅由  大阪大学, 基礎工学研究科, 教授 (80252568)
鎌田 賢司  国立研究開発法人産業技術総合研究所, その他部局等, 研究員 (90356816)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000)
Fiscal Year 2016: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2015: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2014: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Keywordsグラフェン / 二次元ポリマー / 芳香族化合物 / 三回対称 / ディラック点 / エッジ状態 / 芳香族分子 / 電子スピン / 二次元構造
Outline of Final Research Achievements

We understand two major electronic features of graphene, "edge state" and "Dirac point" at the molecular level using chemically synthesized model molecules and elucidate the unique electronic properties derived from its characteristic electronic structure. For the study of the edge state, we succeeded in developing a reaction to form the main skeleton by combining aromatic rings and acetylene and finally filling the cob region to form zigzag edges. Regarding the Dirac point, attempts were made to synthesize new two-dimensional symmetric molecules and two-dimensional integration, and actually succeeded in forming a two-dimensional honeycomb lattice. Furthermore, we investigated the rate of the electron transfer reaction occurring between the three blades, and obtained information serving as a clue to determine the electron transfer rate in the stack.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (44 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (3 results) Journal Article (22 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 22 results,  Acknowledgement Compliant: 9 results) Presentation (16 results) (of which Int'l Joint Research: 10 results,  Invited: 8 results) Book (2 results) Remarks (1 results)

  • [Int'l Joint Research] Aalto University(Finland)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] Polish Academy of Sciences(Poland)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] Georgetown University(米国)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Synthesis, crystal structure, and photophysical properties of 2,9-disubstituted peropyrene derivatives2017

    • Author(s)
      K. Uchida, T. Kubo, D. Yamanaka, A. Furube, H. Matsuzaki, R. Nishii, Y. Sakagami, A. Abulikemu, K. Kamada
    • Journal Title

      Can. J. Chem.

      Volume: - Issue: 4 Pages: 432-444

    • DOI

      10.1139/cjc-2016-0569

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Syntheses of Partially Brominated Derivatives of Tetra-2-thienylmethane for Three-Dimensionally Extended π-Electron Systems2017

    • Author(s)
      K. Matsumoto, T. Suzuki, Y. Hirao, H. Kurata, T. Kubo
    • Journal Title

      Heterocycles

      Volume: 95 Issue: 1 Pages: 615-623

    • DOI

      10.3987/com-16-s(s)44

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Anthroxyl-based biradical: toward the construction of highly stable multi-spin systems2017

    • Author(s)
      Yasukazu Hirao, Akihito Konishia, Takashi Kubo
    • Journal Title

      Org. Chem. Front.

      Volume: 印刷中 Issue: 5 Pages: 828-838

    • DOI

      10.1039/c7qo00130d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Direct quantitative measurement of the C=O- - -H-C bond by atomic force microscopy2017

    • Author(s)
      S. Kawai, T. Nishiuchi, T. Kodama, P. Spijker, R. Pawlak, T. Meier, J. Tracey, T. Kubo, E. Meyer, A. S. Foster
    • Journal Title

      Science Advances

      Volume: 印刷中

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Elucidation of Intramolecular Through‐Space Electronic Communication in Propeller‐Shaped Molecule2017

    • Author(s)
      Takuya Kodama, Yasukazu Hirao, Tomohiko Nishiuch, Takashi Kubo
    • Journal Title

      ChemPlusChem

      Volume: 印刷中 Issue: 7 Pages: 1006-1009

    • DOI

      10.1002/cplu.201700045

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Structure and Properties of Thiophene and Bithiophene Derivatives Incorporated Quinone Methides as Possible: New Overcrowded Extended Quinonoid π-Systems2016

    • Author(s)
      H. Kurata, T. Inoue, T. Suzuki, Y. Hirao, K. Matsumoto, T. Kubo
    • Journal Title

      Synlett

      Volume: 27 Issue: 14 Pages: 2133-2139

    • DOI

      10.1055/s-0035-1561475

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stealth fast photoswitching of negative photochromic naphthalene-bridged phenoxyl-imidazolyl radical complexes2016

    • Author(s)
      Katsuya Mutoh, Yoichi Kobayashi, Yasukazu Hirao, Takashi Kubo and Jiro Abe
    • Journal Title

      Chemical Communications

      Volume: 印刷中 Issue: 41 Pages: 6797-6800

    • DOI

      10.1039/c6cc01534d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Non-planar butterfly-shaped π-expanded pyrrolopyrroles2016

    • Author(s)
      M. Krzeszewski, T. Kodama, E. M. Espinoza, V. I. Vullev, T. Kubo, D. T. Gryko
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 46 Pages: 16478-16488

    • DOI

      10.1002/chem.201603282

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Quantum Master Equation Approach to Singlet Fission Dynamics of Realistic/Artificial Pentacene Dimer Models: Relative Relaxation Factor Analysis2016

    • Author(s)
      M. Nakano, S. Ito, T. Nagami, Y. Kitagawa, and T. Kubo
    • Journal Title

      J. Phys. Chem. C

      Volume: 120 Issue: 40 Pages: 22803-22815

    • DOI

      10.1021/acs.jpcc.6b06402

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Biphenalenylidene: Isolation and Characterization of the Reactive Intermediate on the Decomposition Pathway of Phenalenyl Radical2016

    • Author(s)
      K. Uchida, S. Ito, M. Nakano,* M. Abe,* and T. Kubo
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 7 Pages: 2399-2410

    • DOI

      10.1021/jacs.5b13033

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Fluxional σ-Bonds of the 2,5,8-Trimethylphenalenyl Dimer: Direct Observation of the Sixfold σ-Bond Shift via a π-Dimer2016

    • Author(s)
      K. Uchida, Z. Mou, M. Kertesz, T. Kubo
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 13 Pages: 4665-4672

    • DOI

      10.1021/jacs.6b01791

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Intramolecular Interaction, Photoisomerization, and Mechanical C-C Bond Dissociation of 1,2-di(9-anthryl)benzene and Its Photoisomer: A Fundamental Moiety of Anthracene-Based pi-Cluster Molecules2016

    • Author(s)
      T. Nishiuchi, S. Uno, Y. Hirao, T. Kubo
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 5 Pages: 2106-2112

    • DOI

      10.1021/acs.joc.6b00134

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stable Delocalized Singlet Biradical Hydrocarbon for Organic Field-Effect Transistors2016

    • Author(s)
      H. Koike, M. Chikamatsu, R. Azumi, J. Tsutsumi, K. Ogawa, W. Yamane, T. Nishiuchi, T. Kubo, T. Hasegawa, K. Kanai
    • Journal Title

      Adv. Funct. Mater.

      Volume: 26 Issue: 2 Pages: 277-283

    • DOI

      10.1002/adfm.201503650

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Nickel(II) Cage Complex with μ2-Cl Bridging2016

    • Author(s)
      T. Kubo, K. Matsumoto, N. Kitayama, Y. Hirao, H. Kurata
    • Journal Title

      Heterocycles

      Volume: in press Issue: 1 Pages: 406-406

    • DOI

      10.3987/com-15-s(t)21

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hetero-π-Dimers of Phenalenyls2015

    • Author(s)
      Z. Mou, T. Kubo, M. Kertesz
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 50 Pages: 18230-18236

    • DOI

      10.1002/chem.201503409

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis, Molecular Structure, and Morphological Properties of Dendritic Tetra-2-Thienylmethane2015

    • Author(s)
      K. Matsumoto, S. Kugo, T. Suzuki, D. Takajo, A. Inaba, Y. Hirao, H. Kurata, T. Kubo
    • Journal Title

      Heterocycles

      Volume: 91 Issue: 12 Pages: 2343-2353

    • DOI

      10.3987/com-15-13337

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A facile synthesis of trinaphtho[3.3.3]propellane and its pi-extension and the formation of a two-dimensional honeycomb molecular assembly2015

    • Author(s)
      Takashi Kubo, Shogo Miyazaki, Takuya Kodama, Mitsuya Aoba, Yasukazu Hirao and Hiroyuki Kurata
    • Journal Title

      Chem. Comm.

      Volume: 51 Issue: 18 Pages: 3801-3803

    • DOI

      10.1039/c4cc09883h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Recent Progress in Quinoidal Singlet Biradical Molecules2014

    • Author(s)
      Takashi Kubo
    • Journal Title

      Chem. Lett., 44

      Volume: 44 Issue: 2 Pages: 111-122

    • DOI

      10.1246/cl.140997

    • NAID

      130004712951

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Anthenes: model systems for understanding the edge state of graphene nanoribbons2014

    • Author(s)
      Konishi, A.; Hirao, Y.; Kurata, H.; Kubo, T.; Nakano, M.; Kamada, K.
    • Journal Title

      Pure Appl. Chem.

      Volume: 86 Issue: 4 Pages: 497-505

    • DOI

      10.1515/pac-2013-0811

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] グラフェンナノリボンを指向したアンテン類の合成と磁気的性質2014

    • Author(s)
      久保孝史
    • Journal Title

      化学工業

      Volume: 65 Pages: 105-110

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Evidence of σ- and π-Dimerization in a Series of Phenalenyls2014

    • Author(s)
      Zhongyu Mou, Kazuyuki Uchida, Takashi Kubo, and Miklos Kertesz
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 52 Pages: 18009-18022

    • DOI

      10.1021/ja509243p

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of New Stable Fluorenyl-Based Radicals2014

    • Author(s)
      Yi Tian, Kazuyuki Uchida, Hiroyuki Kurata, Yasukazu Hirao, Tomohiko Nishiuchi, and Takashi Kubo
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 36 Pages: 12784-12793

    • DOI

      10.1021/ja507005c

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Presentation] Elucidation of the Through-Space Spin Delocalization Mode of Phenalenyl-Fused [3.3.3]Propellane2017

    • Author(s)
      T. Kodama, Y. Hirao, T. Nishiuchi, T. Kubo
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis and Characterization of Stable Fluorenyl-Based Hydrocarbon Radicals2016

    • Author(s)
      T. Kubo
    • Organizer
      The 11th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-11)
    • Place of Presentation
      Fusion Hall, KAIST, Korea
    • Year and Date
      2016-10-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] o-キノジメタン含有ビスフェナレニル「シグマレン」の合成と量子化学計算2016

    • Author(s)
      佐原慶亮・西内智彦・平尾泰一・久保孝史
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] Investigation of the dimerization behavior of phenalenyl radicals2016

    • Author(s)
      T. Kubo
    • Organizer
      Osaka City University International Conference (OCUIC2016)
    • Place of Presentation
      大阪市立大学
    • Year and Date
      2016-08-31
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Syntheses and Properties of Triperyleno/Trifluorantheno [3.3.3]propellane Aimed at Construction of Two-Dimensional Honeycomb Electronic Structure2016

    • Author(s)
      T. Kodama, Y. Hirao, T. Nishiuchi, T. Kubo
    • Organizer
      The 2nd International Sympnsium on Synthetic Two-Dimensional Polymers
    • Place of Presentation
      東大寺文化センター
    • Year and Date
      2016-06-02
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Self-Association Behaviors of Phenalenyl Radicals2016

    • Author(s)
      T. Kubo , M. Kertesz
    • Organizer
      The 70th Fujhara Seminer
    • Place of Presentation
      THE LUIGANS Spa & Resort, Fukuoka, Japan
    • Year and Date
      2016-04-17
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Properties of Through-Space Conjugated Phenalenyl Radical2016

    • Author(s)
      T. Kodama, T. Kubo
    • Organizer
      Workshop on New π-Electronic Systems: Theory and Experiments
    • Place of Presentation
      大阪大学
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Novel fluorenyl-based hydrocarbon radicals2015

    • Author(s)
      Takashi Kubo
    • Organizer
      Pacifichem2015
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Revisiting the chemistry of the phenalenyls.2015

    • Author(s)
      Takashi Kubo
    • Organizer
      250th ACS National Meeting & Exposition
    • Place of Presentation
      Boston, USA
    • Year and Date
      2015-08-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Experimental Study on Association Mode of Phenalenyl Radicals2015

    • Author(s)
      Takashi Kubo
    • Organizer
      7th Pacific Symposium on Radical Chemistry
    • Place of Presentation
      Singapore
    • Year and Date
      2015-07-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Studies on Self-Association Mode of Phenalenyl Radicals2015

    • Author(s)
      Takashi Kubo
    • 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] New Aspects of Association of Phenalenyl Radicals2015

    • Author(s)
      Takashi Kubo
    • Organizer
      "Gordon Research Conferences (Physical Organic Chemistry)"
    • Place of Presentation
      Holderness, USA
    • Year and Date
      2015-06-21
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] フェナレルラジカルの会合挙動に関する実験的考察2015

    • Author(s)
      久保孝史
    • Organizer
      第18回 理論化学討論会
    • Place of Presentation
      大阪大学会館
    • Year and Date
      2015-05-20
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] フルオレニルを基盤とする新規炭化水素ラジカル2014

    • Author(s)
      田一、内田一幸、蔵田浩之、西内智彦、平尾泰一、○久保孝史1
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] フェナレニルラジカルの会合様式に関する研究2014

    • Author(s)
      内田一幸、平尾泰一、西内智彦、○久保孝史
    • Organizer
      第12回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      東京工業大学
    • Year and Date
      2014-05-30 – 2014-06-01
    • Related Report
      2014 Annual Research Report
  • [Presentation] Investigating the dimerizations of phenalenyl radicals2014

    • Author(s)
      Kubo, T.
    • Organizer
      The International Symposium on Reactive Intermediates and Unusual Molecules
    • Place of Presentation
      Hiroshima, Japan
    • Year and Date
      2014-04-01 – 2014-04-06
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Book] Organic Redox Systems2015

    • Author(s)
      Takashi Kubo (Ed. Tohru Nishinaga)
    • Total Pages
      596
    • Publisher
      Wiley
    • Related Report
      2015 Annual Research Report
  • [Book] Chemical Sceience of π-Electon Systems2015

    • Author(s)
      Takashi Kubo (Eds. Takeshi Akasaka, Atsuhiro Osuka, Shunichi Fukuzumi, Hideki Kandori, Yoshio Aso)
    • Total Pages
      777
    • Publisher
      Springer
    • Related Report
      2015 Annual Research Report
  • [Remarks] 研究室ホームページ

    • URL

      http://www.chem.sci.osaka-u.ac.jp/lab/kubo/

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2022-01-27  

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