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Formation of Double Helix on Gold Surfaces and Development of Stimulus-Responsive Functional Materials Using Synthetic Helicene Oligomers

Research Project

Project/Area Number 26860005
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionInstitute for Molecular Science

Principal Investigator

YAMAMOTO Koji  分子科学研究所, 協奏分子システム研究センター, 特別協力研究員 (80725557)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords外部刺激応答性 / 酸応答性 / 可逆的電子移動反応 / 安定ラジカル / 三次元パイ電子骨格 / 電子ドナー / スリットバタフライ骨格 / バタフライ骨格 / ヘリセン / ヒドラジン / ビアクリジン / ラジカル / 不均化反応
Outline of Final Research Achievements

Novel molecular skeletons possessing reversible response to external stimulus have been developed for the purpose of the development of functional solid surfaces.
The novel biacridine derivatives (TBA) undergo reversible electron transfer disproportionation reaction regulated by acidification/neutralization. In addition, novel 3D π-conjugated cyclobisazaanthracenes consisting of butterfly-shaped azaanthracene derivatives (dimethylacridine, phenothiazine, and acridone) featuring a slit structure were formed via one-step cyclodimerization of dibromoazaanthracene derivatives. Furthermore, closing the slit via N-N bond formation afforded hydrazinobisanthenes, containing an embedded hydrazine structure in a fully fused bisanthene skeleton with a flexible 3D butterfly or 2D plane structure depending on the nature of the heterocycle. Hydrazinobisanthenes exhibited strong electron donor character.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (16 results)

All 2016 2015 2014 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 3 results,  Open Access: 1 results) Presentation (11 results) (of which Int'l Joint Research: 2 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Synthesis of three-dimensional butterfly slit-cyclobisazaanthracenes and hydrazinobisanthenes via one-step cyclodimerization and their properties2016

    • Author(s)
      Koji Yamamoto, Shuhei Higashibayashi
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 2 Pages: 663-671

    • DOI

      10.1002/chem.201504144

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acid-regulated electron transfer disproportionation of a non-substituted tetramethyl-biacridine derivative2015

    • Author(s)
      Koji Yamamoto, Toshikazu Nakamura, Shuhei Higashibayashi
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 9 Pages: 1229-1231

    • DOI

      10.1246/cl.150498

    • NAID

      130005096898

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acid/Base-Regulated Reversible Electron Transfer Disproportionation of N-N linked Bicarbazole and Biacridine Derivatives2015

    • Author(s)
      Palash Pandit,† Koji Yamamoto,† (†: equally contributed) Toshikazu Nakamura, Katsuyuki Nishimura, Yuki Kurashige, Takeshi Yanai, Go Nakamura, Shigeyuki Masaoka, Ko Furukawa, Yumi Yakiyama, Masaki Kawano and Shuhei Higashibayashi
    • Journal Title

      Chemical Science

      Volume: 印刷中 Issue: 7 Pages: 4160-4173

    • DOI

      10.1039/c5sc00946d

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Butterfly-Shaped Slit-Cyclobisazaanthracenes and Hydrazinobisanthenes2016

    • Author(s)
      Koji Yamamoto, Shuhei Higashibayashi
    • Organizer
      2nd International Symposium on pi-System Figuration
    • Place of Presentation
      埼玉県浦和市 浦和コミュニティセンター
    • Year and Date
      2016-04-14
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 剛直なスリットバタフライ型シクロビスアザアントラセン類と柔軟なヒドラジノビスアンテン類の合成2016

    • Author(s)
      山本浩司,東林修平
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都府京田辺市 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
  • [Presentation] ヒドラジノヘリセン型ビアクリジン誘導体の酸塩基刺激による可逆的電子移動不均化反応2015

    • Author(s)
      山本浩司,Palash Pandit,中村敏和,西村勝之,倉重佑輝,柳井毅,中村豪,正岡重行,古川貢,燒山佑美,河野正規,東林修平
    • Organizer
      第2回パイ造形科学若手研究会
    • Place of Presentation
      大阪府池田市 不死王閣
    • Year and Date
      2015-11-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] 三次元スリットシクロビスアザアントラセン類と三次元,二次元ヒドラジノビスアンテン類の合成と性質2015

    • Author(s)
      山本浩司,東林修平
    • Organizer
      第2回パイ造形科学若手研究会
    • Place of Presentation
      大阪府池田市 不死王閣
    • Year and Date
      2015-11-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] 三次元スリットシクロビスアザアセン類と三次元,二次元ヒドラジノペリアセン類の合成2015

    • Author(s)
      山本浩司,東林修平
    • Organizer
      第108回有機合成シンポジウム
    • Place of Presentation
      東京都新宿区 早稲田大学国際会議場
    • Year and Date
      2015-11-05
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヒドラジノヘリセン型ビアクリジン誘導体の酸塩基刺激による可逆的電子移動不均化反応2015

    • Author(s)
      山本浩司,Palash Pandit,中村敏和,西村勝之,倉重佑輝,柳井毅,中村豪,正岡重行,古川貢,燒山佑美,河野正規,東林修平
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛県松山市 愛媛大学城北キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 三次元スリットシクロビスアザアントラセン類と三次元または二次元ヒドラジノビスアンテン類の合成と性質2015

    • Author(s)
      山本浩司,東林修平
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛県松山市 愛媛大学城北キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Acid/Base-Regulated Reversible Electron Transfer Disproportionation of N-N Linked Biacridine Derivatives2015

    • Author(s)
      Koji Yamamoto, Palash Pandit, Toshikazu Nakamura, Yuki Kurashige, Takeshi Yanai, Go Nakamura, Shigeyuki Masaoka, and Shuhei Higashibayashi
    • Organizer
      16th International Symposium on Novel Aromatic Compounds (ISNA16)
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      2015-07-05 – 2015-07-10
    • Related Report
      2014 Research-status Report
  • [Presentation] Acid-Base-Regulated Reversible Electron Transfer Disproportionation of N-N Linked Biacridine Derivatives2015

    • Author(s)
      Koji Yamamoto, Palash Pandit, Toshikazu Nakamura, Yuki Kurashige, Takeshi Yanai, Go Nakamura, Shigeyuki Masaoka, Shuhei Higashibayashi
    • Organizer
      16th International Symposium on Novel Aromatic Compounds (ISNA16)
    • Place of Presentation
      Universidad Complutense de Madrid, Madrid, Spain
    • Year and Date
      2015-07-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] N-N結合を有するヘリセン型新規ビアクリジン誘導体の酸塩基刺激による可逆的電子移動反応2015

    • Author(s)
      山本浩司,Palash Pandit,中村敏和,西村勝之,倉重佑輝,柳井毅,中村豪,正岡重行,古川貢,燒山佑美,河野正規,東林修平
    • Organizer
      パイ造形科学第2回公開シンポジウム
    • Place of Presentation
      大阪府大阪市 大阪市中央公会堂
    • Year and Date
      2015-06-08
    • Related Report
      2015 Annual Research Report
  • [Presentation] 酸応答性ビアクリジン誘導体2015

    • Author(s)
      山本 浩司,P. PANDIT,中村 敏和,倉重 佑輝,柳井 毅,中村 豪,正岡 重行, 東林 修平
    • Organizer
      日本化学会 第95春季年会
    • Place of Presentation
      千葉県船橋市習志野台 日本大学 理工学部船橋キャンパス/薬学部
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Remarks] 高効率に電子を受け渡すらせん型有機分子を発見~弱い酸刺激でも反応し、塩基で中和すれば元通り~

    • URL

      http://www.jst.go.jp/pr/announce/20150522-2/index.html

    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] 4,4',10,10'-ビジヒドロアクリジン類及びその製造方法2014

    • Inventor(s)
      東林修平、山本浩司
    • Industrial Property Rights Holder
      自然科学研究機構
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-226660
    • Filing Date
      2014-11-07
    • Related Report
      2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2017-05-10  

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