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Creation of pi-conjugated anthracene compounds with novel cyclic structures

Research Project

Project/Area Number 26410060
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Institute of Technology (2015-2016)
Okayama University of Science (2014)

Principal Investigator

TOYOTA SHINJI  東京工業大学, 理学院, 教授 (80207646)

Co-Investigator(Renkei-kenkyūsha) IWANAGA Tetsuo  岡山理科大学, 理学部, 講師 (40454805)
WAKAMATSU Kan  岡山理科大学, 理学部, 准教授 (60271425)
Research Collaborator INOUE Masataka  
OKI Tomohiro  
SAIBARA Toyoaki  
IKEDA Hiroshi  
YAMAMOTO Yuta  
NAGAOKA Maiko  
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsパイ共役系 / アントラセン / 環状構造 / アセチレン / ビニレン / 理論計算 / クロスカップリング / ひずみエネルギー / クロスカップリング反応 / NMR / DFT計算 / 動的挙動
Outline of Final Research Achievements

To create pi-conjugated anthracene compounds with novel cyclic structures, cyclic oligomers having acetylene or vinylene linkers were studied.
For compounds with rigid cyclic structures, anthracene cyclic dimers with inside alkyl groups were synthesized to evaluate the flexibility of the alkyl groups and the molecular strain. For vinylene-bridged compounds, anthracene cyclic dimers to tetramers were synthesized by repeated cross couplings. For face-to-face type macrocyclic compounds, structures of macrocyclic compounds with diacetylene linkers were investigated. Features of this anthracene-based molecular design are revealed from the relation between molecular structures of properties of the above cyclic compounds.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (27 results)

All 2017 2016 2015 2014 Other

All Journal Article (10 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 10 results,  Acknowledgement Compliant: 9 results) Presentation (14 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results) Remarks (3 results)

  • [Journal Article] Synthesis, structures, and properties of 2,5-dianthrylthiophene derivatives2017

    • Author(s)
      S. Toyota, M. Nishiuchi, T. Iwata, T. Yamauchi, T. Iwanaga, M. Hasegawa
    • Journal Title

      Can. J. Chem.

      Volume: 95 Issue: 3 Pages: 286-291

    • DOI

      10.1139/cjc-2016-0391

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 1,8-anthracene-ethenylene cyclic dimers and related compounds: effects of linkers on their structures, electronic properties, and dynamic behavior2017

    • Author(s)
      M. Inoue, T. Iwanaga, S. Toyota
    • Journal Title

      Asian J. Org. Chem.

      Volume: 印刷中 Issue: 5 Pages: 566-574

    • DOI

      10.1002/ajoc.201700046

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Planar Anthracene-Acetylene Frameworks as Stereogenic Motif2017

    • Author(s)
      S. Toyta, H. Ikeda, T. Iwanaga
    • Journal Title

      ChemPlusChem

      Volume: 印刷中 Issue: 7 Pages: 957-966

    • DOI

      10.1002/cplu.201600646

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Macrocyclic 2,7-Anthrylene Oligomers2016

    • Author(s)
      Y. Yamamoto, M. Inoue, K. Wakamatsu, T. Iwanaga
    • Journal Title

      Chem. Asian J.

      Volume: 11 Issue: 9 Pages: 1370-1375

    • DOI

      10.1002/asia.201600230

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] On-Surface Chirality of Self-Assembled Molecular Network of Fan-Blade-Shaped Anthracene-Acetylene Macrocycle with a Long Alkyl Chain2015

    • Author(s)
      T. Tsuya, K. Iritani, K. Tahara, Y. Tobe, T. Iwanaga, S. Toyota
    • Journal Title

      Chemistry - a European Journal

      Volume: 21 Issue: 14 Pages: 5520-5527

    • DOI

      10.1002/chem.201405638

    • Related Report
      2015 Research-status Report 2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structures, Dynamic Behavior, and Spectroscopic Properties of 1,8-Anthrylene-Ethenylene Cyclic Dimers and Their Substituent Effects2015

    • Author(s)
      M. Inoue, T. Iwanaga, S. Toyota
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 88 Issue: 11 Pages: 1591-1602

    • DOI

      10.1246/bcsj.20150245

    • NAID

      130005108569

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An Enantiopure 5,5’-Bitetracene2015

    • Author(s)
      S. Toyota, R. Miyaji, Y. Yamamoto, M. Inoue, K. Wakamatsu, T. Iwanaga
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 35 Issue: 35 Pages: 7648-7651

    • DOI

      10.1002/ejoc.201501135

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Effective Synthesis of Ethynylanthracene Derivatives and Their Applications to Oligomer Synthesis2015

    • Author(s)
      豊田真司,岩永哲夫
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 73 Issue: 4 Pages: 328-338

    • DOI

      10.5059/yukigoseikyokaishi.73.328

    • NAID

      130005070685

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Extended π-Conjugated Compounds with 9,10-Bis(phenylethynyl)anthracene Units2015

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

      Bulletin of Chemical Society of Japan

      Volume: 88 Issue: 1 Pages: 192-199

    • DOI

      10.1246/bcsj.20140279

    • NAID

      130004693813

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Theoretical Evaluation of Molecular Strain and Interactions in Anthracene–Acetylene Cyclic Oligomers by Homodesmotic Reaction Method2015

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

      Bulletin of Chemical Society of Japan

      Volume: 88 Issue: 2 Pages: 283-291

    • DOI

      10.1246/bcsj.20140294

    • NAID

      130004703937

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 1,8-アントラセン-ビニレン大環状オリゴマーの合成と構造2017

    • Author(s)
      井上真隆・岩永哲夫・豊田真司
    • Organizer
      日本化学会第96春季年会(2017)
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 1,8-アントリレンユニットを直接連結した鎖状オリゴマーの合成と構造2017

    • Author(s)
      西原豊顕・岩永哲夫・豊田真司
    • Organizer
      日本化学会第96春季年会(2017)
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 直線形アントラセン-ジアセチレンオリゴマーの合成と分光学的性質2017

    • Author(s)
      長岡麻衣子・鶴巻英治・豊田真司
    • Organizer
      日本化学会第96春季年会(2017)
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 9,10-ジメシチルアントラセン誘導体とベンザインの反応2017

    • Author(s)
      関川周司・鶴巻英治・豊田真司
    • Organizer
      日本化学会第96春季年会(2017)
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 9,10-ジフェニルアントラセンの酸化反応によるルビセン誘導体の合成2017

    • Author(s)
      河村昌彦・鶴巻英治・豊田真司
    • Organizer
      日本化学会第96春季年会(2017)
    • Place of Presentation
      横浜
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 隣接した多数のトリプチセンユニットをもつ大環状化合物の合成と構造2016

    • Author(s)
      河畑健太・岩永哲夫・豊田真司
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] ビニレンリンカーで連結した1,8-アントラセン環状三量体の合成2016

    • Author(s)
      井上 真隆・岩永 哲夫・豊田 真司
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      京田辺
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] Construction of chiral structures from anthracene units and acetylene linkers2015

    • Author(s)
      S. Toyota
    • Organizer
      The 2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-17
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemistry of Anthracene-Acetylene Oligomers2015

    • Author(s)
      S. Toyota
    • Organizer
      the 10th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Kaohsiung, Taiwan
    • Year and Date
      2015-11-03
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 3D and 2D Stereochemistry of Anthracene-Acetylene Cyclic Dimers2015

    • Author(s)
      S. Toyota, T. Iwanaga
    • Organizer
      16th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      2015-07-07
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 内側にイソプロピル基を導入したアントラセンーアセチレン環状二量体の合成2014

    • Author(s)
      田原秋桜美,岩永哲夫,豊田真司
    • Organizer
      第8回有機π電子系シンポジウム
    • Place of Presentation
      ホテル龍登園(佐賀)
    • Year and Date
      2014-11-21 – 2014-11-22
    • Related Report
      2014 Research-status Report
  • [Presentation] Strained Macrocyclic Framework of Anthracene-Diacetylene Cyclic Trimers and Pentamers2014

    • Author(s)
      T. Iwanaga, M. Yoshikawa, S. Toyota
    • Organizer
      International Symposium on the Synthesis and Application of Curved Organic π-Molecules and Materials
    • Place of Presentation
      京都大学(京都)
    • Year and Date
      2014-10-19 – 2014-10-21
    • Related Report
      2014 Research-status Report
  • [Presentation] ビニレン架橋アントラセン環状二量体の構造と性質2014

    • Author(s)
      井上真隆,岩永哲夫,豊田真司
    • Organizer
      第4回化学フェスタ2014
    • Place of Presentation
      タワーホール深堀(東京)
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] 様々なリンカーで連結した1,8-アントラセン環状二量体の合成と構造2014

    • Author(s)
      井上真隆,岩永哲夫,豊田真司
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学(仙台)
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Remarks] 東京工業大学理学院化学系 豊田研究室

    • URL

      http://www.chemistry.titech.ac.jp/~toyota/

    • Related Report
      2016 Annual Research Report
  • [Remarks] 東京工業大学理学院化学系 豊田研究室

    • URL

      http://www.chem.titech.ac.jp/~toyota/

    • Related Report
      2015 Research-status Report
  • [Remarks] 岡山理科大学 理学部化学科 物理有機化学研究室

    • URL

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

    • Related Report
      2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

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