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Design and control of dynamic propeller chirality based on terephthalamides

Research Project

Project/Area Number 25810017
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(系)研究科(研究院), 助教 (60432142)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords分子プロペラ / 動的キラリティ / 動的らせん性 / テレフタルアミド / ホスト-ゲスト / 立体特異的構造変化 / らせん性反転 / 面不斉
Outline of Final Research Achievements

We have designed and synthesized dynamic molecules with propeller chirality based on a terephthalamide skeleton. The two amide groups in a terephthalamide unit acted as a binding site for caputuring a ditopic guest through the formation of hydrogen bonds, and contributed to creation of chiroptical signals when the guest was chiral, or a chiral auxiliary was attached to the terephthalamide unit(s).
We have demonstrated chiroptical signals based on dynamic molecular propellers.
In a complexed state, a particular sense of dynamic propeller chirality was predominantly favored over the other, and exhibited chiroptical signals.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (18 results)

All 2015 2014 2013 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (12 results) (of which Invited: 1 results) Book (1 results)

  • [Journal Article] 1.A foldable cyclic oligomer: chiroptical modulation through molecular folding upon complexation and a change in temperature2014

    • Author(s)
      Katoono, R.; Tanaka, Y.; Fujiwara, K.; Suzuki, T.
    • Journal Title

      J. Org. Chem.

      Volume: 79(21) Issue: 21 Pages: 10218-10225

    • DOI

      10.1021/jo501883m

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiroptical molecular propeller based on hexakis(phenylethyl)benzene through the complexation-induced intramolecular transmission of local point chirality2014

    • Author(s)
      Ryo Katoono, Keiichi Kusaka, Shunsuke Kawai, Yuki Tanaka, Keisuke Hanada, Tatsuo Nehira, Kenshu Fujiwara, Takanori Suzuki
    • Journal Title

      Prganic and Biomolecular Chemistry

      Volume: 12 Issue: 47 Pages: 9532-9538

    • DOI

      10.1039/c4ob01601g

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 3.Controlled Dynamic Helicity of a Folded Macrocycle Based on a Bisterephthalamide with a Twofold Z-Shaped Structure2014

    • Author(s)
      Katoono, R.; Kusaka, K.; Fujiwara, K.; Suzuki, T.
    • Journal Title

      Chem. Asian J.

      Volume: 9(11) Issue: 11 Pages: 3182-3187

    • DOI

      10.1002/asia.201402658

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Complexation-induced inversion of helicity by an organic guest in a dynamic molecular propeller based on a tristerephtalamide host with a two-layer structure2014

    • Author(s)
      R. Katoono, K. Fujiwara, T. Suzuki
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 41 Pages: 5438-5440

    • DOI

      10.1039/c4cc00323c

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] C3-symmetric chiroptical molecular propeller based on hexakis(phenylethynyl)benzene with a threefold terephthalamide: stereospecific propeller generation through the cooperative transmission of point chiralities on the host and guest upon complexation2013

    • Author(s)
      R. Katoono, H. Kawai, M. Ohkita, K. Fujiwara, T. Suzuki
    • Journal Title

      Chemical Communications

      Volume: 49 Issue: 88 Pages: 10352-10354

    • DOI

      10.1039/c3cc43571g

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 四架橋二層構造を有するテレフタルアミド誘導体の合成とキロプティカル特性2015

    • Author(s)
      上遠野亮・藤原憲秀・鈴木孝紀
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] テレフタルアミドマクロサイクルを利用した動的二重らせん構造の構築とらせん性制御2015

    • Author(s)
      上遠野亮・河合駿佑・藤原憲秀・鈴木孝紀
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 動的な8の字型キラリティ: 環状テレフタルアミド誘導体の動的構造およびらせん性制御2015

    • Author(s)
      上遠野亮・田中優貴・藤原憲秀・鈴木孝紀
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] テレフタルアミドに基づく三環性分子プロペラの合成と錯形成挙動2015

    • Author(s)
      上遠野亮・工藤隆晃・藤原憲秀・鈴木孝紀
    • Organizer
      化学系学協会北海道支部2015年冬季研究発表会
    • Place of Presentation
      札幌
    • Year and Date
      2015-01-27 – 2015-01-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] テレフタルアミドをモチーフとした動的らせん分子の設計とキラリティセンシング2014

    • Author(s)
      上遠野亮
    • Organizer
      2014高分子・ハイブリッド材料研究センター若手フォーラム
    • Place of Presentation
      仙台
    • Year and Date
      2014-12-12
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Z字型スペーサーを有する折りたたまれた環状ビステレフタルアミド誘導体における動的らせん性の超分子的制御2014

    • Author(s)
      上遠野亮・日下慶一・藤原憲秀・鈴木孝紀
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 動的な8の字型キラリティを有する環状テレフタルアミド誘導体の合成、構造およびキラリティ制御2014

    • Author(s)
      上遠野亮・田中優貴・藤原憲秀・鈴木孝紀
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] トリス(テレフタルアミド)ホストによる動的らせん性の創出とキラリティセンシング

    • Author(s)
      上遠野亮
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学、豊島区
    • Related Report
      2013 Research-status Report
  • [Presentation] 環状トリス(テレフタルアミド)ホストの分子折りたたみによる動的らせん性の創出とキラリティセンシング

    • Author(s)
      上遠野亮
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学、豊島区
    • Related Report
      2013 Research-status Report
  • [Presentation] 階層構造を有するテレフタルアミド誘導体の動的不斉に基づくメソ様配座と キラリティセンシング

    • Author(s)
      上遠野亮
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、名古屋市
    • Related Report
      2013 Research-status Report
  • [Presentation] マクロサイクルを利用した動的らせん性の創出(1):二環状ビス(テレフタルアミド)ホストの動的二重らせん構造とキラリティセンシング

    • Author(s)
      上遠野亮
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、名古屋市
    • Related Report
      2013 Research-status Report
  • [Presentation] マクロサイクルを利用した動的らせん性の創出(2):環状トリス(テレフタルアミド)ホストの分子折りたたみによる立体特異的シグナリング

    • Author(s)
      上遠野亮
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、名古屋市
    • Related Report
      2013 Research-status Report
  • [Book] 5.Ch.14 Design of chirality-sensing systems based on supramolecular transmission of chirality, In "Synergy in Supramolecular Chemistry" ed. by T. Nabeshima2014

    • Author(s)
      R. Katoono
    • Publisher
      CRC press
    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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