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On-surface synthesis and investigation of electronic structure of higher acenes and their metal complexes

Research Project

Project/Area Number 18K19118
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 35:Polymers, organic materials, and related fields
Research InstitutionNara Institute of Science and Technology

Principal Investigator

Yamada Hiroko  奈良先端科学技術大学院大学, 先端科学技術研究科, 教授 (20372724)

Project Period (FY) 2018-06-29 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2019: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2018: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywordsアセン / ノナセン / グラフェンナノリボン / 走査型プローブ顕微鏡 / 原子間力顕微鏡 / 開殻構造 / 高次アセン / 走査型トンネル顕微鏡 / 金複合体 / 前駆体法 / 光反応 / 走査型プローブ顕微鏡(STM) / ノンコンタクト原子間力顕微鏡(nc-AFM) / AFM / STM / 金属錯体 / 前駆体
Outline of Final Research Achievements

Acene is a compound with a structure of linearly-fused benzene rings. It has attracted much attention as organic semiconductor materials, but synthesis and derivatization of pentacene (N = 5: N is a number of benzene rings) and longer is difficult because they are less soluble in organic solvents and are unstable for oxidation. We were successful to prepare bis-alpha-diketone precursor of nonacene. The precursor was vacuum-deposited on Au(111) surface and converted to nonacene by photoirradiation under ultra-high-vacuum. The electronic structure of nonacene and heptacene was investigated by STM and nc-AFM measurements. The comparison of experimentally obtained energy gap with computed values suggested nonacene and heptacene have singlet open-shell structure on Au(111).

Academic Significance and Societal Importance of the Research Achievements

1965年に予測された半導体の集積度に関する「ムーアの法則」が2017年に終焉を迎えたと宣言され、ポストシリコン材料としてナノカーボン材料への期待は高く、グラフェン・カーボンナノチューブ・グラフェンナノリボン(GNR)の合成開発が盛んである。しかし、長さ・幅の規定されたGNR、特にジグザグエッジナノリボン(ZGNR)は、導電性を持つと予測されるもののエッジがラジカル性を帯びるため不安定で、単離が困難である。アセンはGNRの部分構造であるとともにボトムアップ合成のユニットとしても注目されており、その電子構造の解明は学術的にも、応用の上からも重要な知見となる。

Report

(3 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Research Products

    (21 results)

All 2020 2019 2018 Other

All Int'l Joint Research (3 results) Journal Article (2 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 2 results,  Open Access: 1 results) Presentation (14 results) (of which Int'l Joint Research: 11 results,  Invited: 11 results) Remarks (2 results)

  • [Int'l Joint Research] EMPA/University of Bern(スイス)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Max Plank Institue of Polymer Research(ドイツ)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] EMPA(スイス)

    • Related Report
      2018 Research-status Report
  • [Journal Article] Overcoming Steric Hindrance in Aryl‐Aryl Homocoupling via On‐Surface Copolymerization2019

    • Author(s)
      Jose I. Urgel, Marco Di Giovannantonio, Guido Gandus, Qiang Chen, Xunshan Liu, Hironobu Hayashi, Pascal Ruffieux, Silvio Decurtins, Akimitsu Narita, Daniele Passerone, Hiroko Yamada, Shi‐Xia Liu, Klaus Mullen, Carlo A. Pignedoli, Roman Fasel
    • Journal Title

      ChemPhysChem

      Volume: 20 Issue: 18 Pages: 2360-2366

    • DOI

      10.1002/cphc.201900283

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] On-surface light-induced generation of higher acenes and elucidation of their open-shell character2019

    • Author(s)
      Urgel Jose I.、Mishra Shantanu、Hayashi Hironobu、Wilhelm Jan、Pignedoli Carlo A.、Di Giovannantonio Marco、Widmer Roland、Yamashita Masataka、Hieda Nao、Ruffieux Pascal、Yamada Hiroko、Fasel Roman
    • Journal Title

      Nature Communications

      Volume: 10 Issue: 1 Pages: 861-861

    • DOI

      10.1038/s41467-019-08650-y

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] On-Surface Synthesis of Large Acenes and Graphene Nanoribbons2020

    • Author(s)
      Hiroko Yamada
    • Organizer
      The 3rd Symposium for The Core Research Clusters for Materials Science and Spintronics
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] On-surface light-induced generation of higher acenes2019

    • Author(s)
      Hiroko Yamada
    • Organizer
      ICMAT2019 10th International Conference on Materials for Advanced Technologies
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] On-surface light-induced synthesis of higher acenes from alpha-diketone-type precursors2019

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      14th International Symposium on Functional pi-Electron Systems
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] On-Surface Synthesis of Large Acenes and Graphene Nanoribbons2019

    • Author(s)
      Hiroko Yamada
    • Organizer
      11h Conference in CEMES, France
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] On-Surface Synthesis of Large Acenes and Graphene Nanoribbons2019

    • Author(s)
      Hiroko Yamada
    • Organizer
      Conference in Strasbourg University
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] On-Surface Synthesis of Large Acenes and Graphene Nanoribbons2019

    • Author(s)
      Hiroko Yamada
    • Organizer
      Conference in Bordeaux University
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] On-Surface Synthesis of Large Acenes and Graphene Nanoribbons2019

    • Author(s)
      Hiroko Yamada
    • Organizer
      Conference in Renne University
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] On-surface synthesis of higher acenes by precursor approach2019

    • Author(s)
      Hironobu Hayashi
    • Organizer
      Lecture in BUCH
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of pi-Extended Aromatic Materials Using Precursor Approach2019

    • Author(s)
      山田 容子
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] 前駆体法による機能性材料開発2018

    • Author(s)
      山田 容子
    • Organizer
      ハリス理化学研究所イブニングセミナー
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] Visible-light-induced photodecarbonylation of a-diketone-type large acene precursors on Au(111) surface2018

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      第55回フラーレン・ナノチューブ・グラフェン学会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis and Characterization of Large Acenes and Porphyrin(2.1.2.1) Nanobelt2018

    • Author(s)
      Hiroko Yamada
    • Organizer
      The third international symposium on the synthesis and application of curved organic pi-molecules & materials(Curo-pi-3)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Precursor Approach for On-Surface Synthesis2018

    • Author(s)
      Hiroko Yamada, Hironobu Hayashi
    • Organizer
      International workshop On-Surface Synthesis (OSS18)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] On-Surface Synthesis of Self-Assembled Graphene Nanoribbon from Partially Fluorinated Precursors2018

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      International workshop On-Surface Synthesis (OSS18)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Remarks]

    • URL

      https://mswebs.naist.jp/LABs/env_photo_greenmat/publication.html

    • Related Report
      2019 Annual Research Report
  • [Remarks] 奈良先端科学技術大学院大学先端科学技術研究科

    • URL

      http://mswebs.naist.jp/LABs/env_photo_greenmat/publication.html

    • Related Report
      2018 Research-status Report

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Published: 2018-07-25   Modified: 2021-02-19  

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