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Synthesis and dynamic function of helical substances at the oligomer, molecular aggregate, and molecular assembly levels

Research Project

Project/Area Number 17H03050
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTohoku University

Principal Investigator

YAMAGUCHI MASAHIKO  東北大学, 薬学研究科, 教授 (30158117)

Co-Investigator(Kenkyū-buntansha) 谷井 沙織  東北大学, 薬学研究科, 助教 (20792295)
有澤 美枝子  東北大学, 薬学研究科, 准教授 (50302162)
Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥17,940,000 (Direct Cost: ¥13,800,000、Indirect Cost: ¥4,140,000)
Fiscal Year 2019: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2018: ¥6,110,000 (Direct Cost: ¥4,700,000、Indirect Cost: ¥1,410,000)
Fiscal Year 2017: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Keywordsラセン分子 / ヘリセン / 二重ラセン / 構造変化 / 自己組織化 / 非平衡 / 不均一系 / オリゴマー / 触媒設計 / 反応 / 分子会合反応制御 / 不均一反応場 / 動的機能
Outline of Final Research Achievements

Employing chiral helical organic molecules, bottom up studies on synthesis and functions of diverse organic substances have been conducted, which range between small molecules, molecular complex of oligomer molecules, and self-assembly materials. At small molecular level, chiral recognition in the inhibition of enzyme activity was observed. At the molecular complex of oligomer molecules, inverse thermoresponse phenomenon was found, and lyotropic liquid crystal and monodomain anisotropic films were synthesized. At self-assembly level, notable phenomena in chiral symmetry breaking phenomenon were found. These are novel material phenomena, not known before. Transition metal catalyzed synthesis of heteroatom compounds, which can be used in the study of helical substances, was also conducted.

Academic Significance and Societal Importance of the Research Achievements

本研究はキラルなラセン構造に着目して,小分子,オリゴマー分子,分子会合体,分子集合体の順に物質階層 ボトムアップを行なう合成方法論と不均一溶液系における動的機能の探索を目的とした.ラセン物質の新しい構 造と機能を解明したとともに,分子レベルとバルクレベル物質を関連させる新しい学術分野と機能発現の開拓 を行なった.とくに, 1)機械的的刺激応答, 2)熱応答, 3)可逆的異方性繊維構築, 4)遷移金属触媒反応の成果をあげた.

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (25 results)

All 2019 2018 2017

All Journal Article (15 results) (of which Peer Reviewed: 15 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (10 results) (of which Invited: 2 results)

  • [Journal Article] Proximate stochastic chiral symmetry breaking is mechanically tunable: formation of enantiomeric hetero-double-helices and aggregates from racemic oxymethylenehelicene oligomers2019

    • Author(s)
      Tsukasa Sawato, Nozomi Saito and Masahiko Yamaguchi
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 21 Issue: 45 Pages: 25406-25414

    • DOI

      10.1039/c9cp04299g

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation and dissociation of synthetic hetero-double-helix complex in aqueous solutions: significant effect of water content on dynamics of structural change2019

    • Author(s)
      Tsukasa Sawato, Ryosuke Yuzawa, Higashi Kobayashi, Nozomi Saito and Masahiko Yamaguchi
    • Journal Title

      RSC Advances

      Volume: 9 Issue: 50 Pages: 29456-29462

    • DOI

      10.1039/c9ra06073a

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Rhodium-Catalyzed Synthesis of Organosulfur Compounds using Sulfur2019

    • Author(s)
      Mieko Arisawa and Masahiko Yamaguchi
    • Journal Title

      Synlett

      Volume: 30 Issue: 14 Pages: 1621-1631

    • DOI

      10.1055/s-0037-1611867

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical Systems Involving Two Competitive Self-Catalytic Reactions2019

    • Author(s)
      Sawato Tsukasa、Saito Nozomi、Yamaguchi Masahiko
    • Journal Title

      ACS Omega

      Volume: 4 Issue: 3 Pages: 5879-5899

    • DOI

      10.1021/acsomega.9b00133

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Acid-catalyzed synthesis of condensed polycyclic diaryl ethers from arenols2019

    • Author(s)
      Saori Tanii, Mieko Arisawa, Masahiko Yamaguchi
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 93 Pages: 14078-14080

    • DOI

      10.1039/c9cc07172e

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical CD oscillation and chemical resonance phenomena in a competitive self-catalytic reaction system: a single temperature oscillation induces CD oscillations twice2019

    • Author(s)
      Sawato Tsukasa、Shinozaki Yasuhiro、Saito Nozomi、Yamaguchi Masahiko
    • Journal Title

      Chemical Science

      Volume: 10 Issue: 6 Pages: 1735-1740

    • DOI

      10.1039/c8sc03109f

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Long-range Anisotropic Structural Films and Fibers Formed from Lyotropic Liquid Crystal Gels Containing Hetero-double-helices with C16 Terminal Groups2018

    • Author(s)
      N. Saito, H. Kobayashi, K. Kanie and M. Yamaguchi
    • Journal Title

      Langumuir

      Volume: accepted Issue: 14 Pages: 5075-5080

    • DOI

      10.1021/acs.langmuir.7b04385

    • Related Report
      2019 Annual Research Report 2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Self-Assembly of Chiral Cylindrical Molecular Complexes: Functional Heterogeneous Liquid-Solid Materials Formed by Helicene Oligomers2018

    • Author(s)
      Saito Nozomi、Yamaguchi Masahiko
    • Journal Title

      Molecules

      Volume: 23 Issue: 2 Pages: 277-277

    • DOI

      10.3390/molecules23020277

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Rhodium-Catalyzed Isomerization and Alkyne Exchange Reactions of 1,4-Dithiins via the 1,2-Ethenedithiolato Rhodium Complex2018

    • Author(s)
      Mieko Arisawa*, Kyosuke Sawahata, Takuya Ichikawa, and Masahiko Yamaguchi*
    • Journal Title

      Organometallics

      Volume: 37 Issue: 18 Pages: 3174-3180

    • DOI

      10.1021/acs.organomet.8b00498

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Synthesis of Dialkyl(Heteroaryl)Phosphine Sulfides by Phosphinylation of Heteroaryl Sulfides2018

    • Author(s)
      Mieko Arisawa*, Takeru Tazawa, Wataru Ichinose, Haruki Kobayashi, and Masahiko Yamaguchi*
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 360 Issue: 18 Pages: 3488-3491

    • DOI

      10.1002/adsc.201800630

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Method for the Synthesis of C-N-Linked Bi(heteroaryl)s Using Heteroaryl Ethers and N‐Benzoyl Heteroarenes2018

    • Author(s)
      Saori Tanii, Mieko Arisawa*, Takaya Tougo, Masahiko Yamaguchi*
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 7 Pages: 1756-1759

    • DOI

      10.1021/acs.orglett.8b00245

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Optically active iodohelicene derivatives exhibit histamine N-methyl transferase inhibitory activity2018

    • Author(s)
      Ichinose Wataru、Sawato Tsukasa、Kitano Haruna、Shinozaki Yasuhiro、Arisawa Mieko、Saito Nozomi、Yoshikawa Takeo、Yamaguchi Masahiko
    • Journal Title

      The Journal of Antibiotics

      Volume: - Issue: 6 Pages: 476-481

    • DOI

      10.1038/s41429-018-0118-z

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Inverse thermoresponse of a water-soluble helicene oligomer in aqueous-organic mixed solvent systems2017

    • Author(s)
      Saito Nozomi、Kobayashi Higashi、Yamaguchi Masahiko
    • Journal Title

      Tetrahedron

      Volume: 73 Issue: 42 Pages: 6047-6051

    • DOI

      10.1016/j.tet.2017.08.046

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical braking exhibited by ethynylhelicene (M)-nonamer in solution: Competitive reaction system of self-catalysis to form double- helix and approach towards equilibrium to form random-coil2017

    • Author(s)
      Tsukasa Sawato; Atsushi Yagi; Mieko Arisawa; Masahiko Yamaguchi
    • Journal Title

      Tetradron

      Volume: 73 Issue: 19 Pages: 2801-2805

    • DOI

      10.1016/j.tet.2017.03.083

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Mechanical Stirring Induces Heteroaggregate Formation and Self-assembly of Pseudoenantiomeric Oxymethylene Helicene Oligomers in Solution2017

    • Author(s)
      Tsukasa Sawato, Nozomi Saito, Masanori Shigeno, Masahiko Yamaguchi
    • Journal Title

      ChemistrySelect

      Volume: 2 Issue: 6 Pages: 2205-2211

    • DOI

      10.1002/slct.201700303

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 化学反応とは何か2019

    • Author(s)
      山口 雅彦
    • Organizer
      新学術領域「精密制御反応場」第7回公開シンポジウム 於:仙台
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Chiral Symmetry Breaking Exhibited by Aminomethylene and Oxymethylene Helicene Oligomers2018

    • Author(s)
      Masahiko Yamaguchi
    • Organizer
      6th Symposium on Foldamer 2018, University of Bordeaux
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] ビシクロヘキシルを有するエチニルヘリセンオリゴマーの合成とリオトロピック液晶ゲル形成2018

    • Author(s)
      齋藤 望、湯澤 玲介、山口 雅彦
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] C16アルキル末端を有するエチニルヘリセンオリゴマーによる長距離単一ドメインの異方的自己組織体形成2018

    • Author(s)
      齋藤 望、小林 東史、山口 雅彦
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 複素環スルフィドのホスフィニル化による複素環ジアルキルホスフィン誘導体のロジウム触媒合成2018

    • Author(s)
      有澤 美枝子、田沢 健、山口 雅彦
    • Organizer
      日本化学会第98回春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジスルフィドのロジウム触媒的チオリン酸エステル化反応2018

    • Author(s)
      有澤 美枝子、福本 昂平、山口 雅彦
    • Organizer
      日本化学会第98回春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ペンタフェニルシクロペンタホスフィンPhP基のジスルフィドへのロジウム触媒挿入反応2018

    • Author(s)
      有澤 美枝子、澤畑 恭佑、山田 朋貴、山口 雅彦
    • Organizer
      日本化学会第98回春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 複素環エーテルとN-ベンゾイル複素環化合物のC-N結合生成によるビス複素環化合物の触媒的合成法の開発2018

    • Author(s)
      谷井 沙織、有澤 美枝子、山口 雅彦
    • Organizer
      日本化学会第98回春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 1,4-ジチインのロジウム触媒的異性化反応とアルキン交換反応2017

    • Author(s)
      有澤 美枝子、澤畑 恭佑、市川 拓哉、山口雅彦
    • Organizer
      化学系学協会東北大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 複素環チオ基交換を伴うロジウム触媒的非対称ビス複素環スルフィドの合成反応2017

    • Author(s)
      田沢 健、有澤 美枝子、山口 雅彦
    • Organizer
      第28回万有仙台シンポジウム
    • Related Report
      2017 Annual Research Report

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Published: 2017-04-28   Modified: 2021-02-19  

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