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Toward the realization of higher-order response system exhibiting expandability/fissionability of the extremely elongated C-C single bond

Research Project

Project/Area Number 16H06591
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Functional solid state chemistry
Research InstitutionHokkaido University

Principal Investigator

Ishigaki Yusuke  北海道大学, 理学研究院, 助教 (60776475)

Project Period (FY) 2016-08-26 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords長い結合 / 高歪み炭化水素 / X線結晶構造解析 / DFT計算 / ラマン分光法 / 分子内コア-シェル構造 / Scissor効果 / 超結合 / 構造有機化学 / クロミズム系 / dyrex系
Outline of Final Research Achievements

The C-C single bond length of 1.791(3) angstrom has been considered the longest value among neutral organic compounds. Expandability/fissionability of such a long bond in crystals plays an important role for construction of response system. Toward the realization of higher-order response system, further longer C-C bond could work efficiently due to large expandability of the weakened bond. Therefore, we have designed a compound with a bond length beyond 1.8 angstrom.
In this study, a highly strained hydrocarbon, which has the longest C-C single bond with a bond length of 1.806(2) angstrom, has been synthesized based on the intramolecular "core-shell strategy": the weak C-C bond (core) is protected by the shape-persistent sp2 carbon framework (shell). We proposed to term the C-C bond with a bond length of 1.8-2.0 angstrom "hyper covalent bond".

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • Research Products

    (21 results)

All 2018 2017 2016

All Journal Article (7 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 7 results,  Acknowledgement Compliant: 4 results,  Open Access: 3 results) Presentation (14 results) (of which Int'l Joint Research: 5 results,  Invited: 1 results)

  • [Journal Article] Longest C-C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8A2018

    • Author(s)
      Ishigaki Yusuke、Shimajiri Takuya、Takeda Takashi、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Chem

      Volume: 2018 Issue: 4 Pages: 795-806

    • DOI

      10.1016/j.chempr.2018.01.011

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Narrower HOMO-LUMO gap attained by conformational switching through peripheral polyarylation in 1,4,5,8-tetraaza-9,10-anthraquinodimethanes2018

    • Author(s)
      Suzuki Takanori、Ishigaki Yusuke、Sugawara Kazuma、Umezawa Yu、Katoono Ryo、Shimoyama Atsushi、Manabe Yoshiyuki、Fukase Koichi、Fukushima Takanori
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 18 Pages: 2239-2244

    • DOI

      10.1016/j.tet.2018.03.041

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselecive Encapsulation for a Triarylmethylium o,o-Dimer by Natural gamma-Cyclodextrin: Origin of Chiral Recogntion For the Acially Chiral Dicationic Guest2017

    • Author(s)
      T. Suzuki, J. P. Cerón-Carrasco, H. Tamaoki, Y. Ishigaki, R. Katoono, T. Fukushima, H. Pérez-Sánchez,
    • Journal Title

      Heterocycles

      Volume: - Issue: 6 Pages: 1123-1123

    • DOI

      10.3987/com-17-13674

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] 9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units: A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior2017

    • Author(s)
      Ishigaki Yusuke、Hayashi Yuki、Sugawara Kazuma、Shimajiri Takuya、Nojo Wataru、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Molecules

      Volume: 22 Issue: 11 Pages: 1900-1900

    • DOI

      10.3390/molecules22111900

    • NAID

      120006383818

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] xidative Desulfurization of Electron-Donating 5,5,7,7-Tetraaryl-5,7-dihydrodibenzo[c,e]thiepins and the Related Heterocycles: Generation of Dicationic Dyes upon Two-Electron Oxidation2017

    • Author(s)
      T. Suzuki, T. Kuroda, H. Tamaoki, S. Higasa, T. Nehira, R. Katoono, Y. Ishigaki, K. Fujiwara, T. Fukushima, H. Yamada
    • Journal Title

      Heterocycles

      Volume: 95(2), Issue: 2 Pages: 816-829

    • DOI

      10.3987/com-16-s(s)50

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Organic Molecular Layer with High Electrochemical Bistability: Synthesis, Structure, and Properties of a Dynamic Redox System with Lipoate Units for Binding to Au(111),2017

    • Author(s)
      E. Ohta, H. Uehara, Y. Han, K. Wada, H. Noguchi, R. Katoono, Y. Ishigaki, H. Ikeda, K. Uosaki, T. Suzuki
    • Journal Title

      ChemPlusChem

      Volume: - Issue: 7 Pages: 1043-1047

    • DOI

      10.1002/cplu.201600649

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Bis(diarylethenyl)thiophenes, -bithiophenes, and -terthiophenes: A New Series of Electrochromic Systems that Exhibit a Fluorescence Response2016

    • Author(s)
      Y. Ishigaki, H. Kawai, R. Katoono, K. Fujiwara, H. Higuchi, H. Kikuchi, T. Suzuki
    • Journal Title

      Can. J. Chem.

      Volume: 95(3) Issue: 3 Pages: 243-252

    • DOI

      10.1139/cjc-2016-0222

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] テトラアリールアントラキノジメタン型電子供与体の構築とメカノフルオロクロミズム2018

    • Author(s)
      石垣侑祐, 菅原一真, 島尻拓哉, 上遠野亮, 鈴木孝紀
    • Organizer
      化学系学協会北海道支部2018年冬季研究発表会(札幌)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 2つのジベンゾシクロヘプタトリエンを有する高歪み炭化水素の酸化還元応答挙動2018

    • Author(s)
      石垣侑祐, 林裕貴, 菅原一真, 島尻拓哉, 能條航, 上遠野亮, 鈴木孝紀
    • Organizer
      化学系学協会北海道支部2018年冬季研究発表会(札幌)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Longest C-C single bond among neutral hydrocarbons with a bond length beyond 1.8 Å based on the intramolecular core-shell strategy2018

    • Author(s)
      石垣侑祐, 島尻拓哉, 上遠野亮, 鈴木孝紀
    • Organizer
      日本化学会第98春季年会(船橋)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 1.80 Åを超えるC-C単結合:実験値と理論値の比較2017

    • Author(s)
      石垣 侑祐・島尻 拓哉・内村 康人・上遠野 亮・鈴木 孝紀
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ジベンゾシクロヘプタトリエンがスピロ縮環したジヒドロピラシレン誘導体:1.8 Åを超えるC-C単結合2017

    • Author(s)
      石垣 侑祐・島尻 拓哉・上遠野 亮・鈴木 孝紀
    • Organizer
      化学系学協会北海道支部2017年冬季研究発表会
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Year and Date
      2017-01-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] フッ化アレーン骨格を有する共役ジエン型電子供与体の構築と酸化還元挙動2017

    • Author(s)
      石垣 侑祐・杉本 佳亮・ 石割 文崇・上遠野 亮・福島 孝典・鈴木 孝紀
    • Organizer
      化学系学協会北海道支部2017年冬季研究発表会
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Year and Date
      2017-01-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] A Novel Redox System Based on Perfluoroarenes: Toward Advanced Response Systems Assembled by SNAr Reaction2017

    • Author(s)
      Y. Ishigaki, K. Sugimoto, H. Tamaoki, R. Katoono, T. Suzuki
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (Stony Brook, USA)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] スピロ縮環型ジヒドロフェナントレン誘導体:立体障害に基づく炭素-炭素単結合の伸長2017

    • Author(s)
      石垣侑祐, 林裕貴, 菅原一真, 島尻拓哉, 上遠野亮, 鈴木孝紀
    • Organizer
      第28回基礎有機化学討論会(福岡)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 極度に伸長したC-C単結合を有するジスピロジベンゾシクロヘプタトリエン誘導体の合成/構造/性質2017

    • Author(s)
      石垣侑祐, 島尻拓哉, 上遠野亮, 鈴木孝紀
    • Organizer
      第28回基礎有機化学討論会(福岡)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Highly Strained Caged Hydrocarbons with an Ultralong C-C Single Bond2017

    • Author(s)
      Y. Ishigaki, T. Shimajiri, R. Katoono, T. Suzuki
    • Organizer
      The 5th International Symposium on AMBITIOUS LEADER’S PROGRAM Fostering Future Leaders to Open New Frontiers in Materials Science (Sapporo)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly strained aromatic hydrocarbons with a bond length of C-C single bond beyond 1.8 Å2017

    • Author(s)
      Y. Ishigaki, T. Shimajiri, R. Katoono, T. Suzuki
    • Organizer
      The 18th RIES-HOKUDAI International Symposium (Sapporo)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A Novel Electrochromic System with Perfluoroarenes: Conjugated Diene-type Electron Donor and Its Dication2017

    • Author(s)
      Y. Ishigaki, K. Sugimoto, R. Katoono, T. Suzuki
    • Organizer
      The 18th RIES-HOKUDAI International Symposium (Sapporo)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ジベンゾシクロヘプタトリエン骨格を有する高歪み炭化水素の特異な性質2017

    • Author(s)
      石垣侑祐
    • Organizer
      2017PHyM若手フォーラム(仙台)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] A Novel Electrochromic Systems Based on Bis(diarylethenyl)-thiophene Framework Exhibiting a Fluorescence Response2016

    • Author(s)
      Y. Ishigaki, R. Katoono, T. Suzuki
    • Organizer
      The 10th International Symposium on Integrated Synthesis
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫県淡路市)
    • Year and Date
      2016-11-18
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research

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Published: 2016-09-02   Modified: 2019-03-29  

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