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On-surface Synthesis of Graphene Nanoribbon with Self-Assembled Monolayer Method

Research Project

Project/Area Number 15K17843
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionNara Institute of Science and Technology

Principal Investigator

Hayashi Hironobu  奈良先端科学技術大学院大学, 物質創成科学研究科, 特任助教 (00736936)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsグラフェンナノリボン / 化学吸着 / エッジ修飾 / 前駆体法 / ナノファイバー / 基板上合成 / 単分子膜
Outline of Final Research Achievements

Graphene nanoribbons (GNRs) have drawn much attention as promising materials for next generation nanoelectronic devices. Here, we report the synthesis of the simplest model compounds toward developing a bottom-up synthesis of GNRs with a self-assembled monolayer (SAM) method. The binding units for the SAM method were introduced at two termini of the central aromatic core of the model compounds, which was not only for preparing a monolayer of model compounds but also for binding a gold surface ideally. Cyclic voltammograms of gold electrodes modified with the model compounds implied that annealing the substrates at 300 degree led to cyclodehydrogenation. In addition, we have successfully synthesized precursor molecules for edge-functionalized GNR and low band gap GNR. Furthermore, theoretical analysis revealed the key intermediate states during cyclodehydrogenation for synthesizing edge-functionalized GNRs.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (24 results)

All 2017 2016 2015 Other

All Int'l Joint Research (1 results) Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Acknowledgement Compliant: 6 results,  Open Access: 3 results) Presentation (12 results) (of which Int'l Joint Research: 5 results,  Invited: 1 results) Book (1 results) Patent(Industrial Property Rights) (2 results)

  • [Int'l Joint Research] EMPA(Switzerland)

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Experimental and Theoretical Investigations of Surface-Assisted Graphene Nanoribbon Synthesis Featuring Carbon-Fluorine Bond Cleavage2017

    • Author(s)
      Hironobu Hayashi, Junichi Yamaguchi, Hideyuki Jippo, Ryunosuke Hayashi, Naoki Aratani, Mari Ohfuchi, Shintaro Sato, Hiroko Yamada
    • Journal Title

      ACS Nano

      Volume: 印刷中 Issue: 6 Pages: 6204-6210

    • DOI

      10.1021/acsnano.7b02316

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Semiconducting Self-assembled Nanofibers Prepared from Photostable Octafluorinated Bisanthene Derivatives2017

    • Author(s)
      H. Hayashi, N. Aratani, H. Yamada
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Issue: 29 Pages: 7000-7008

    • DOI

      10.1002/chem.201700080

    • NAID

      120006369666

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue2017

    • Author(s)
      A. Matsumoto, M. Suzuki, H. Hayashi, D. Kuzuhara, J. Yuasa, T. Kawai, N. Aratani, H. Yamada
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 90 Issue: 6 Pages: 667-677

    • DOI

      10.1246/bcsj.20160337

    • NAID

      130006770647

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Fullerene-linked tetrabenzoporphyrins for solution-processed organic photovoltaics: flexible vs. rigid linkers2016

    • Author(s)
      Y. Tamura, D. Kuzuhara, M. Suzuki, H. Hayashi, N. Aratani, H. Yamada
    • Journal Title

      J. Mater. Chem. A

      Volume: 4 Issue: 40 Pages: 15333-15342

    • DOI

      10.1039/c6ta06599f

    • NAID

      120006334972

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Bisanthra-thianthrene: synthesis, structure and oxidation properties2016

    • Author(s)
      M. Yamashita, H. Hayashi, M. Suzuki, D. Kuzuhara, J. Yuasa, T. Kawai, N. Aratani, H. Yamada
    • Journal Title

      RSC Adv.

      Volume: 6 Issue: 74 Pages: 70700-70703

    • DOI

      10.1039/c6ra13036d

    • NAID

      120006334976

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Aromaticity Relocation in Perylene Derivatives upon Two-electron Oxidation to Form Anthracene and Phenanthrene2016

    • Author(s)
      A. Matsumoto, M. Suzuki, H. Hayashi, D. Kuzuhara, J. Yuasa, T. Kawai, N. Aratani, H. Yamada
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 41 Pages: 14462-14466

    • DOI

      10.1002/chem.201602188

    • NAID

      120006334985

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] An electron-deficient tetrathiafulvalene-conjugated bistetracene2015

    • Author(s)
      M. Yamashita, H. Hayashi, N. Aratani*, H. Yamada*
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 24 Pages: 3804-3808

    • DOI

      10.1016/j.tetlet.2015.04.080

    • NAID

      120006334960

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indolizino[5,6-b]quinoxaline Derivatives: Intramolecular Charge Transfer Characters and NIR Fluorescence2015

    • Author(s)
      Mitsuru Kojima, Hironobu Hayashi, Tatsuya Aotake, Shinya Ikeda, Mitsuharu Suzuki, Naoki Aratani, Daiki Kuzuhara, Hiroko Yamada
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 10 Issue: 11 Pages: 2337-2341

    • DOI

      10.1002/asia.201500597

    • NAID

      120006334980

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Graphene nanoribbon synthesis associated with a dissociation of carbon-fluorine bonds2017

    • Author(s)
      Hironobu Hayashi, Junichi Yamaguchi, Hideyuki Jippo, Shintaro Sato, Hiroko Yamada
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 自己組織化単分子膜の鎖長がアントラセン二量体の金表面への吸着に与える影響2017

    • Author(s)
      坂倉 光洋・林 宏暢・山田 容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 光変換型ヘプタセン前駆体の合成2017

    • Author(s)
      稗田 奈央・林 宏暢・山田 容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 多量体化を目指したTIPSペンタセン誘導体の合成と物性評価2017

    • Author(s)
      川野 倖暉・林 宏暢・山田 容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] On-surface reaction of fluorinated precursor molecule for graphene nanoribbon2017

    • Author(s)
      Hironobu Hayashi
    • Organizer
      Mini-symposium on functional p-molecules
    • Place of Presentation
      奈良先端科学技術大学院大学(奈良県生駒市)
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Self-assembled nanofibers of fluorinated bisanthene derivatives2016

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      The 51th fullerenes-nanotubes-graphene general symposium
    • Place of Presentation
      北海道立道民活動センター かでる2・7(北海道札幌市)
    • Year and Date
      2016-09-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis and Physical Properties of Model Compounds of Graphene Nanoribbon2016

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      8th international conference on Molecular Electronics
    • Place of Presentation
      Paris, France
    • Year and Date
      2016-08-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of model compounds toward graphene nanoribbon synthesis through a bottom-up approach2016

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      The 2nd international symposium on synthetic two-dimensional polymers
    • Place of Presentation
      Todaiji Temple Cultural Center (Nara, Japan)
    • Year and Date
      2016-06-02
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ボトムアップ式グラフェンナノリボン作製を目指した前駆体分子の合成2016

    • Author(s)
      林竜之輔、林宏暢、山田容子
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis and Electronic Properties of Fluorine-Functionalized Condensed Acene Derivatives2015

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学・松山大学(愛媛県松山市)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthesis of Acene for Badgap Modulated Graphene Nanoribbon2015

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      ISNA16
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      2015-07-05
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Acene for Graphene Nanoribbon with Different Bandage2015

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      NT15
    • Place of Presentation
      名古屋大学(愛知県名古屋市)
    • Year and Date
      2015-06-29
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Book] 有機合成化学協会誌2015

    • Author(s)
      林宏暢、鈴木充朗、葛原大軌、荒谷直樹、山田容子
    • Total Pages
      13
    • Publisher
      公益社団法人 有機合成化学協会
    • Related Report
      2015 Research-status Report
  • [Patent(Industrial Property Rights)] 高次アセン誘導体及び高次アセン誘導体の製造方法2016

    • Inventor(s)
      林宏暢、山下正貴、山田容子
    • Industrial Property Rights Holder
      林宏暢、山下正貴、山田容子
    • Industrial Property Rights Type
      特許
    • Filing Date
      2016-11-29
    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] グラフェンナノリボン前駆体製造法2015

    • Inventor(s)
      林宏暢、山田容子
    • Industrial Property Rights Holder
      林宏暢、山田容子
    • Industrial Property Rights Type
      特許
    • Filing Date
      2015-09-18
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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