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

Research Project

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
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2007: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords立体異性体 / パイ系化合物 / 分子設計 / 構造有機化学 / 剛直環構造 / アセチレン / アントラセン / カップリング反応 / キラル / 分子構造 / 立体障害 / 自己会合 / X線構造解析
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.

Report

(4 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (38 results)

All 2010 2009 2008 2007 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (19 results) Book (3 results) Remarks (2 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

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers XV. Synthesis, Structures, and Dynamic Behavior of Chiral Anthrylene-Ethynylene Cyclic Tetramers and Related Derivatives and Resolution of Enantiomer2010

    • Author(s)
      T.Ishikawa, S.Toyota, 他
    • Journal Title

      Bulletin of the Chemical Society of Japan 83

      Pages: 220-232

    • NAID

      10027172419

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [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, S.Toyota, 他
    • Journal Title

      Chemistry Letters 39

      Pages: 288-290

    • Related Report
      2009 Annual Research Report
    • 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

    • NAID

      10025126789

    • Related Report
      2009 Final Research Report
    • 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

    • Related Report
      2009 Final Research Report
    • 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

    • Related Report
      2009 Final Research Report
    • 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, 他
    • Journal Title

      Chemistry Letters 38

      Pages: 350-351

    • Related Report
      2009 Annual Research Report
    • 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, 他
    • Journal Title

      Bulletin of the Chemical Society of Japan 82

      Pages: 931-945

    • NAID

      10025126789

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemistry of Anthracene-Acetylene Oligomers XIV. Convenient Synthesis of Anthrylethynes by Double Elimination Reaction from Aldehydes and Sulfones2009

    • Author(s)
      S.Toyota, 他
    • Journal Title

      Bulletin of the Chemical Society of Japan 82

      Pages: 1287-1291

    • NAID

      10025864754

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 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
    • Journal Title

      Organic Letters 11

      Pages: 321-324

    • Related Report
      2008 Annual Research Report
    • 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

    • NAID

      10022019437

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Structures, and Properties of 1, 8-Anthrylene-Alkynylene Cyclic Trimers2008

    • Author(s)
      S. Toyota
    • Journal Title

      Bull. Chem. Soc. Jpn. 81

      Pages: 1147-1157

    • Related Report
      2008 Annual Research Report
    • 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

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Newπ-Conjugated System with Rigid Framework of 1,8-Anthrylene-Ethynylene Cyclic Dimer and its Monoanthraquinone Analogue2007

    • Author(s)
      S. Toyota
    • Journal Title

      Organic Letters 9

      Pages: 3655-3658

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis and Properties of Cyclic 9, 10-Bis(phenylethynyl)anthracene Oligomers with Diacetylene Linkers2009

    • Author(s)
      宮本和明・豊田真司, 他
    • Organizer
      12th Kyushu International Symposium on Physical Organic Chemistry
    • Place of Presentation
      九州大学(福岡)
    • Year and Date
      2009-12-16
    • Related Report
      2009 Annual Research Report
  • [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
    • Related Report
      2009 Final Research Report
  • [Presentation] アセチレンリンカーで連結した1, 8-アントリレン大環状オリゴマーの構造と分光学的性質2009

    • Author(s)
      原田紘明・豊田真司, 他
    • Organizer
      日本化学会西日本大会2009
    • Place of Presentation
      愛媛大学(松山)
    • Year and Date
      2009-11-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] アントラセンの1,8位と1,5位をアセチレンで連結した環状オリゴマーの合成と電子スペクトル2009

    • Author(s)
      石川丈晴・豊田真司
    • Organizer
      日本化学会西日本大会2009
    • Place of Presentation
      愛媛大学(松山)
    • Year and Date
      2009-11-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] 9-トリプチシル基を利用した平歯車型分子の設計2009

    • Author(s)
      豊田真司・岩永哲夫, 他
    • Organizer
      日本化学会西日本大会2009
    • Place of Presentation
      愛媛大学(松山)
    • Year and Date
      2009-11-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] アントラセン-アントラキノン環状二量体の構造と自己会合に及ぼす置換基効果2009

    • Author(s)
      宮本和明・岩永哲夫・豊田真司
    • Organizer
      日本化学会西日本大会2009
    • Place of Presentation
      愛媛大学(松山)
    • Year and Date
      2009-11-06
    • Related Report
      2009 Annual Research Report
  • [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
      愛媛大学(松山)
    • Year and Date
      2009-11-06
    • Related Report
      2009 Annual Research Report
  • [Presentation] 内側にアルコキシ基を持つ1,8-アントラセン-アセチレン環状二量体の合成と構造2009

    • Author(s)
      津屋卓也・豊田真司
    • Organizer
      第20回基礎有機化学討論会
    • Place of Presentation
      群馬大学(桐生)
    • Year and Date
      2009-09-30
    • Related Report
      2009 Annual Research Report
  • [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
      群馬大学(桐生)
    • Year and Date
      2009-09-29
    • Related Report
      2009 Annual Research Report
  • [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
    • Related Report
      2009 Final Research Report
  • [Presentation] アントラセン環状オリゴマーの動的挙動と分光学的性質に及ぼすアセチレンリンカーの位置と長さの効果2009

    • Author(s)
      石川丈晴・豊田真司
    • Organizer
      第20回基礎有機化学討論会
    • Place of Presentation
      群馬大学(桐生)
    • Year and Date
      2009-09-28
    • Related Report
      2009 Annual Research Report
  • [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
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] Stereogenic Motif Consisting of Rigid Ring and Intraannular Chains : Isolation of Stereoisomers of Anthracene-Acetylene Cyclic Dimers2009

    • Author(s)
      豊田真司, 他
    • Organizer
      13th International Symposium on Novel Aromatics
    • Place of Presentation
      Luxembourg
    • Year and Date
      2009-07-20
    • Related Report
      2009 Annual Research Report
  • [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
    • Related Report
      2009 Final Research Report
  • [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
    • Related Report
      2009 Final Research Report
  • [Presentation] アントラセン-アセチレンオリゴマーの化学-環状二量体の合成, 構造および立体化学2008

    • Author(s)
      豊田真司
    • Organizer
      第19回基礎有機化学討論会
    • Place of Presentation
      吹田
    • Year and Date
      2008-10-04
    • Related Report
      2008 Annual Research Report
  • [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
    • Related Report
      2009 Final Research Report
  • [Presentation] アントラセンとアントラキノンをアセチレンで連結した平面環状化合物の合成と性質2007

    • Author(s)
      宮本 和明
    • Organizer
      2007年日本化学会西日本大会
    • Place of Presentation
      岡山
    • Year and Date
      2007-11-10
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis and Isolation of Stereoisomers of 1,8-Anthrylene-Butadiynylene Cylcic Dimers with Intraannular Alkyl Groups2007

    • Author(s)
      S. Toyota
    • Organizer
      12th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路
    • Related Report
      2007 Annual Research Report
  • [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
    • Publisher
      George Thieme Verlag KG
    • Related Report
      2009 Final Research Report
  • [Book] Science of Synthesis : Houben-Weyl methods of molecular transformation Vol 45b, Chap.45.192010

    • Author(s)
      S.Toyota, T.Iwanaga
    • Total Pages
      110
    • Publisher
      George Thieme Verlag KG
    • Related Report
      2009 Annual Research Report
  • [Book] Science of Synthesis : Houben-Weyl methods of molecular transformation Vol 45b, Chap.45.202010

    • Author(s)
      S.Toyota
    • Total Pages
      29
    • Publisher
      George Thieme Verlag KG
    • Related Report
      2009 Annual Research Report
  • [Remarks] 受賞BCSJ賞,S. Toyota, H. Miyahara, M. Goichi, S. Yamasaki, T. Iwanaga, 2009年8月

    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://butuyu2.chem.ous.ac.jp/

    • Related Report
      2009 Annual Research Report

URL: 

Published: 2007-04-01   Modified: 2016-04-21  

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