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2009 Fiscal Year Final Research Report

Design of Novel Stereoisomers by Using Narrow Space in π-System Rigid Frameworks

Research Project

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Project/Area Number 19550054
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOkayama University of Science

Principal Investigator

TOYOTA Shinji  Okayama University of Science, 理学部, 教授 (80207646)

Co-Investigator(Renkei-kenkyūsha) IWANAGA Tetsuo  岡山理科大学, 理学部, 助教 (40454805)
WAKAMATSU Kan  岡山理科大学, 理学部, 准教授 (60271425)
Project Period (FY) 2007 – 2009
Keywords立体異性体 / パイ系化合物 / 分子設計 / 構造有機化学
Research Abstract

We designed rigid cyclic compounds consisting of anthracene units and acetylene (or diacetylene) linkers as new π-conjugated compounds. Substituents were introduced at inner congested positions, and we isolated some novel stereoisomers (diastereomers and enantiomers) based on the steric hindrance between the ring framework and the intraannular substituents. The structures and dynamic behavior of these isomers were investigated by X-ray analysis, NMR spectra, and DFT calculations. We propose a new concept of stereochemistry through this molecular design.

  • Research Products

    (14 results)

All 2010 2009 2008 2007 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (6 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers XVI. Influence of Conformation of 9, 10-Anthrylene Rotors on Structures and Self-Association Properties of Macrocyclic Arylene-Alkynylene Oligomers2010

    • Author(s)
      K. Miyamoto, T. Iwanaga, S. Toyota
    • Journal Title

      Chem. Lett. 39(3)

      Pages: 288-290

    • Peer Reviewed
  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers XIII. Synthesis, Structures, and Spectroscopic Properties of All Possible 1,8-Anthrylene Cyclic Tetramers with Acetylene and Diacetylene Linkers2009

    • Author(s)
      S. Toyota, H. Miyahara, M. Goichi, S. Yamasaki, T. Iwanaga
    • Journal Title

      Bull. Chem. Soc. Jpn. 82(8)

      Pages: 931-945

    • Peer Reviewed
  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers XII. Enantiopure 1, 8-Anthrylene Dimer with Acetylene Linkers and an Intraannular Alkyl Group2009

    • Author(s)
      S. Toyota, H. Onishi, K. Wakamatsu, T. Iwanaga
    • Journal Title

      Chem. Lett. 38(4)

      Pages: 350-351

    • Peer Reviewed
  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers XI. Stereogenic Motif Consisting of Rigid Ring and Intraannular Chains: Isolation and Structures of Stereoisomers of 9-Alkyl-1, 8-anthrylene-butadiynylene Cyclic Dimers2009

    • Author(s)
      S. Toyota, H. Onishi, Y. Kawai, T. Morimoto, H. Miyahara, T. Iwanaga, K. Wakamatsu
    • Journal Title

      Org. Lett. 11(2)

      Pages: 321-324

    • Peer Reviewed
  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers X. Synthesis, Structures, and Properties of 1,8-Anthrylene-Alkynylene Cyclic Trimers2008

    • Author(s)
      S. Toyota, H. Miyahara, M. Goichi, K. Wakamatsu, T. Iwanaga
    • Journal Title

      Bull. Chem. Soc. Jpn. 81(9)

      Pages: 1147-1157

    • Peer Reviewed
  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers VII. Newπ-Conjugated System with Rigid Framework of 1,8-Anthrylene-Ethynylene Cyclic Dimer and its Monoanthraquinone Analogue2007

    • Author(s)
      S. Toyota, M. Kurokawa, M. Araki, K. Nakamura, T. Iwanaga
    • Journal Title

      Org. Lett. 9(18)

      Pages: 3655-3658

    • Peer Reviewed
  • [Presentation] アントラセン―アセチレンオリゴマーの化学:構造の多様化と立体化学2009

    • Author(s)
      豊田真司
    • Organizer
      日本化学会西日本大会2009
    • Place of Presentation
      松山(依頼講演)
    • Year and Date
      2009-11-07
  • [Presentation] アントラセンを組み込んだm-フェニレンーエチニレン大環状オリゴマーの合成と性質2009

    • Author(s)
      宮本和明・岩永哲夫・豊田真司
    • Organizer
      第20回基礎有機化学討論会
    • Place of Presentation
      桐生
    • Year and Date
      2009-09-28
  • [Presentation] Self-association Behavior of Anthracene-Anthraquinone Cyclic Dimers with Various Side Chains2009

    • Author(s)
      T. Iwanaga, K. Miyamoto, S. Toyota
    • Organizer
      13th International Symposium on Novel Aromatics
    • Place of Presentation
      Luxembourg
    • Year and Date
      2009-07-20
  • [Presentation] 内側にアルキル基を持つアントラセン-アセチレン環状二量体の構造と立体化学2009

    • Author(s)
      大西宏幸・岩永哲夫・豊田真司
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-28
  • [Presentation] 内側アルキル基をもつ1,8-アントラセン-アセチレン環状二量体の合成と立体異性体の単離2008

    • Author(s)
      豊田真司・大西宏幸・宮本和明・岩永哲夫・田原一邦・奥畑智・戸部義人
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      吹田
    • Year and Date
      2008-10-04
  • [Presentation] 内側アルキル基をもつ1,8-アントラセン-アセチレン環状二量体の合成と立体異性体の単離2008

    • Author(s)
      大西宏幸・川合良浩・森本高彰・豊田真司・岩永哲夫
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-27
  • [Book] Product Class 19: Naphthalenes, Anthracenes, 9H-Fluorenes, and Other Acenes, Science of Synthesis Vol 45b(ed. J. S. Siegel, Y. Tobe.)2010

    • Author(s)
      S. Toyota, T. Iwanaga
    • Total Pages
      745-854
    • Publisher
      George Thieme Verlag KG
  • [Remarks] 受賞BCSJ賞,S. Toyota, H. Miyahara, M. Goichi, S. Yamasaki, T. Iwanaga, 2009年8月

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Published: 2011-06-18   Modified: 2016-04-21  

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