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Expansion of Host Cavities by Mechanical Forces

Research Project

Project/Area Number 15K13665
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionYamagata University

Principal Investigator

MURASE TAKASHI  山形大学, 理学部, 准教授 (70508184)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsシクロアルカン / 環化反応 / 疎水効果 / ロタキサン / 分子認識
Outline of Final Research Achievements

Threading long alkyl chains into cycloalkanes has been attempted to form hydrocarbon rotaxanes. However, the conventional statistical approaches provided a negligible amount of rotaxanes due to the absence of attractive interactions between the ring and axis components. In this study, we prepare C3n macrocycles bearing six polar functional groups to use solvophobic effects in a polar media.
Parent C3n macrocycles (n = 8-11) were prepared from diethyl malonate and α,ω-dibromoalkane. A precise control of the reactant concentration (3 mM) was demanded in the successive intermolecular alkylation-intramolecular ring closing process. Then, the lateral ester groups were hydrolyzed. We attempted to synthesize cycloalkane-based rotaxanes by suspending an axle component in a H2O/CH3CN solution of C27 macrocycle. The resulting solution was refluxed for 10 days. Microwave irradiation was also applied to promote the reaction. However, rotaxane formation was not observed.

Report

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

    (12 results)

All 2017 2016 2015

All Journal Article (6 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 1 results) Presentation (6 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Azahelicenes from the Oxidative Photocyclization of Boron Hydroxamate Complexes2017

    • Author(s)
      T. Murase, T. Suto, H. Suzuki
    • Journal Title

      Chem. Asian J.

      Volume: 12 Issue: 7 Pages: 726-729

    • DOI

      10.1002/asia.201700096

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Effect of the Ag Ion Insertion on Electron Transport through Au Ion Wires2016

    • Author(s)
      S. Fujii, S. Kanae, M. Iwane, T. Nishino, T. Osuga, T. Murase, M. Fujita, M. Kiguchi
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 7 Pages: 764-766

    • DOI

      10.1246/cl.160286

    • NAID

      130005253025

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tuning of Charge Transport Properties of Stacks of Aromatic Molecules2016

    • Author(s)
      藤井慎太郎・小本祐貴・多田朋史・大須賀孝史・村瀬隆史・藤田誠・木口学
    • Journal Title

      Hyomen Kagaku

      Volume: 37 Issue: 8 Pages: 342-347

    • DOI

      10.1380/jsssj.37.342

    • NAID

      130005405081

    • ISSN
      0388-5321, 1881-4743
    • Related Report
      2016 Annual Research Report
  • [Journal Article] Cavity-Directed Chromism of Phthalein Dyes2015

    • Author(s)
      H. Takezawa, S. Akiba, T. Murase, M. Fujita
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 22 Pages: 7043-7046

    • DOI

      10.1021/jacs.5b03618

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cavity-Promoted Diels-Alder Reactions of Unsubstituted Naphthalene: Fine Reactivity Tuning by Cavity Shrinkage2015

    • Author(s)
      Y. Fang, T. Murase, M. Fujita
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 8 Pages: 1095-1097

    • DOI

      10.1246/cl.150351

    • NAID

      130005092597

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-Step Synthesis of [16]Helicene2015

    • Author(s)
      K. Mori, T. Murase, M. Fujita
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 54 Issue: 23 Pages: 6847-6851

    • DOI

      10.1002/anie.201502436

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis and Properties of Macrocyclic Alkanes with Six Functional Side Chains2017

    • Author(s)
      Yoshinori Kurata, Noriyo Seya, Takashi Murase
    • 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)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of [16]Helicene by Multiple Photocyclization: Influence of the Precursor Sequences2017

    • Author(s)
      Wataru Araki, Takashi Murase
    • 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)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Photocyclization of Terminally-Polyfluorinated Stilbene Derivatives toward [7]Helicenes2017

    • Author(s)
      Chikako Matsuda, Takashi Murase
    • 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)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] One-step synthesis of [16]helicene by multiple photocyclization2015

    • Author(s)
      Takashi Murase
    • Organizer
      Pacifichem2015
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2015-12-18
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] [16]ヘリセンの合成2015

    • Author(s)
      村瀬 隆史・森 一晋・藤田 誠
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学(城北キャンパス)(愛媛)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] [16]Helicene: Helical Folding by Multiple Photocyclization2015

    • Author(s)
      Takashi Murase
    • Organizer
      平成27年度化学系学協会東北大会
    • Place of Presentation
      弘前大学(文京キャンパス)(青森)
    • Year and Date
      2015-09-12
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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