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Fused oligomers of a macrocycle with dynamic figure eight chirality

Research Project

Project/Area Number 15K17818
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionHokkaido University

Principal Investigator

Katoono Ryo  北海道大学, 理学研究院, 助教 (60432142)

Research Collaborator TANAKA Yuki  
KAWAI Shunsuke  
KUSAKA Keiichi  
OBARA Yudai  
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords動的キラリティ / マクロサイクル / テレフタルアミド / 縮環多量体 / 縮環オリゴマー / 動的8の字キラリティ / 縮環型オリゴマー
Outline of Final Research Achievements

I have newly designed a series of fused oligomers of macrocycles with dynamic figure eight chirality. Dynamic features in solution of these fused oligomers were investigated through NMR, UV and CD spectroscopy.
For fused oligomers, the barrier to dynamic interconversion between two helical conformations with M- or P-helicity followed a specific pattern similar to that of the original unit of a macrocycle. Complexation and chiroptical properties were dependent on the molecular shape, that is a manner of fusion. We found a new perspective on "chiral amplification". In a fused trimer or a tetramer, the helical-sense preference increased with the number of units. These finding was brought about by quantitative observation of the helical-sense preferences through NMR spectroscopy in solution.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (19 results)

All 2018 2017 2016 2015

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Open Access: 4 results) Presentation (12 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Supramolecular chiroptical switching of helical-sense preferences through the two-way intramolecular transmission of a single chiral source2018

    • Author(s)
      Katoono Ryo、Kusaka Keiichi、Tanaka Yuki、Fujiwara Kenshu、Suzuki Takanori
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 16 Issue: 7 Pages: 1167-1171

    • DOI

      10.1039/c7ob03057f

    • NAID

      120006558997

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enhanced circular dichroism at elevated temperatures through complexation-induced transformation of a three-layer cyclophane with dualistic dynamic helicity2018

    • Author(s)
      Katoono Ryo、Obara Yudai、Fujiwara Kenshu、Suzuki Takanori
    • Journal Title

      Chemical Science

      Volume: 9 Issue: 8 Pages: 2222-2229

    • DOI

      10.1039/c7sc05242a

    • NAID

      120006473606

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Dynamic or undynamic chirality generated by helical arrangement of a shape-persistent ring and rod doubly bridged in a molecule2018

    • Author(s)
      Katoono Ryo、Obara Yudai、Kusaka Keiichi、Suzuki Takanori
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 7 Pages: 735-738

    • DOI

      10.1039/c7cc09485j

    • NAID

      120006549167

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Planar chiral desymmetrization of a two-layered cyclophane and control of dynamic helicity through the arrangement of two nonstereogenic centers2016

    • Author(s)
      Ryo Katoono* and Takanori Suzuki
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 5 Pages: 1029-1031

    • DOI

      10.1039/c5cc09069e

    • NAID

      120005866833

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Dynamic helical cyclophanes with two quadruply-bridged planes arranged in an “obverse and/or reverse” relation2016

    • Author(s)
      R. Katoono, S. Kawai, T. Suzuki
    • Journal Title

      Chem. Sci

      Volume: 7 Issue: 5 Pages: 3240-3247

    • DOI

      10.1039/c5sc04673d

    • NAID

      120006220021

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Dynamic Figure Eight Chirality: Multifarious Inversions of a Helical2015

    • Author(s)
      Ryo Katoono,* Yuki Tanaka, Keiichi Kusaka, Kenshu Fujiwara, and Takanori Suzuki
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 80 Issue: 15 Pages: 7613-7625

    • DOI

      10.1021/acs.joc.5b01206

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Controllability of dynamic double helices: quantitative analysis of the inversion of a screw-sense preference upon complexation2015

    • Author(s)
      Ryo Katoono,* Shunsuke Kawai, Kenshu Fujiwara and Takanori Suzuki
    • Journal Title

      Chemical Science

      Volume: 6 Issue: 11 Pages: 6592-6600

    • DOI

      10.1039/c5sc02614h

    • NAID

      120005676278

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 1,3,5-トリス(フェニルエチニル)ベンゼンをテンプレートとする大環状分子の合成と錯形成誘起キロプティカル特性2018

    • Author(s)
      上遠野亮・河合駿佑・石垣侑祐・鈴木孝紀
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 動的な8の字キラリティを有するマクロサイクルの縮環多量体における超分子キラリティ(1):o-フェニレンエチニレン骨格を足場とする縮環二量体2018

    • Author(s)
      上遠野亮・青木洸則・石垣侑祐・鈴木孝紀
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 動的な8の字キラリティを有するマクロサイクルの縮環多量体における超分子キラリティ(2): o-フェニレンエチニレン骨格を足場とする縮環三量体2018

    • Author(s)
      上遠野亮・坂本和生・石垣侑祐・鈴木孝紀
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 動的な8の字キラリティを有するマクロサイクルの縮環多量体における超分子キラリティ(3):ヘキサキス(フェニルエチニル)ベンゼンを足場とする縮環四量体2018

    • Author(s)
      上遠野亮・小原優大・齊藤将生・石垣侑祐・鈴木孝紀
    • Organizer
      日本化学会 第98春季年会 (2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] フェニルアセチレンマクロサイクル(PAM)の分子集合と架橋により創り 出されるヘリカルキラリティ2017

    • Author(s)
      上遠野亮・小原優大・河合駿佑・日下慶一・石垣侑祐・鈴木孝紀
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] A New Approach to Controlling a Helical-Sense Preference of Dynamic Helicity2017

    • Author(s)
      Ryo Katoono, Yusuke Ishigaki, Takanori Suzuki
    • Organizer
      Chirality2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] キラリティ伝達によらない動的らせん性制御2016

    • Author(s)
      上遠野亮 ・石垣 侑祐 ・鈴木孝紀
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島大学(広島県・広島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Presentation] 三層構造を有するシクロファンの錯形成誘起CDにおける特異な温度依存性2016

    • Author(s)
      上遠野亮 ・小原優大・石垣 侑祐 ・鈴木孝紀
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島大学(広島県・広島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Presentation] Phenylacetylene Macrocycle (PAM) を利用した キラリティ創出2016

    • Author(s)
      上遠野亮・日下慶一・鈴木孝紀
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学 京田辺キャンパス(京都)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] 動的な8の字型キラリティを有するマクロサイクルの縮環型二量体: 設計、合成および超分子キラリティ2015

    • Author(s)
      上遠野亮・河合駿佑・工藤隆晃・梅澤優・藤原憲秀・鈴木孝紀
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学(松山)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 二つのm-フェニレンエチニレンスペーサーを有するテレフタルアミドマクロサイクルにおける動的なキロプティカル特性2015

    • Author(s)
      上遠野亮・日下慶一・藤原憲秀・鈴木孝紀
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学(松山)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] テレフタルアミドを利用した動的な三環性分子プロペラのキロプティカル特性2015

    • Author(s)
      上遠野亮・工藤隆晃・藤原憲秀・鈴木孝紀
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学(松山)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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