• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of Functional Materials Based on Efficient Synthesis of PAHs Containing Pentagonal Rings

Research Project

Project/Area Number 16H04111
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOsaka Institute of Technology

Principal Investigator

Murata Michihisa  大阪工業大学, 工学部, 准教授 (30447932)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2018: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2016: ¥10,010,000 (Direct Cost: ¥7,700,000、Indirect Cost: ¥2,310,000)
Keywords多環芳香族炭化水素 / 固体発光 / 芳香族性 / カーボン物質 / 単結晶X線構造解析 / 酸化的クロスカップリング / インターカレーション / X線構造解析 / Scholl反応 / 反応機構 / Scholl 反応 / 反応機構解析 / 固体発光特性 / 円偏光発光特性 / X線結晶構造解析
Outline of Final Research Achievements

Polycyclic aromatic hydrocarbons (PAHs) that contain fully unsaturated pentagonal ring(s), the so-called CP-PAHs, have attracted substantial interest due to their unusual properties such as high electron affinity and reactivity. In this project, we demonstrated the facile synthesis of a dithieno-fused CP-PAH that contains a pyracylene moiety from a twofold Scholl cyclization. The results of a combined experimental and theoretical approach revealed a strong contribution of antiaromatic character to the electronic structure of this dithieno-fused CP-PAH. Furthermore, we found the twofold Scholl cyclization of a 5,11-dinaphthyltetracene derivative, which affords a twisted PAH that contains fully unsaturated pentagonal and hexagonal rings. This reaction should proceed via dication intermediates, which stands in stark contrast to the previously reported mechanisms that involve radical cation or arenium ion intermediates.

Academic Significance and Societal Importance of the Research Achievements

本研究では,電子受容性の多環芳香族化合物に関して,実験および計算化学の両アプローチから検討を実施し,酸化的C-Hカップリング反応を用いる手法により5員環構造を含む一連のCP-PAH類を効率的に合成できることを実証した。また,長くPAH類の合成に多用されてきた酸化的C-H カップリング反応が,テトラセン誘導体の二重環化反応においては,これまで提唱されていないジカチオン中間体を経る反応機構で進行することを初めて示した。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (15 results)

All 2019 2018 2017

All Journal Article (4 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 4 results) Presentation (11 results) (of which Int'l Joint Research: 1 results,  Invited: 5 results)

  • [Journal Article] Near- and Mid-IR Gas-Phase Absorption Spectra of H2@C60+-He2018

    • Author(s)
      Strelnikov Dmitry V.、 Jasik Juraj、Gerlich Dieter、Murata Michihisa、Murata Yasujiro、Komatsu Koichi、Roithova Jana
    • Journal Title

      The Journal of Physical Chemistry A

      Volume: 122 Issue: 41 Pages: 8162-8166

    • DOI

      10.1021/acs.jpca.8b06222

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Unsymmetric Twofold Scholl Cyclization of a 5,11-Dinaphthyltetracene: Selective Formation of Pentagonal and Hexagonal Rings via Dicationic Intermediates2017

    • Author(s)
      Chaolumen, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 印刷中 Issue: 18 Pages: 5082-5086

    • DOI

      10.1002/anie.201701054

    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cycloaddition of Benzyne to Naphthalene-fused Tetracene with a Twisted π-Surface2017

    • Author(s)
      Chaolumen, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata
    • Journal Title

      Chem. Lett.

      Volume: 46 Issue: 4 Pages: 591-593

    • DOI

      10.1246/cl.161170

    • NAID

      130005549094

    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dithieno-Fused Polycyclic Aromatic Hydrocarbon with a Pyracylene Moiety: Strong Antiaromatic Contribution to the Electronic Structure2017

    • Author(s)
      Chaolumen, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 4 Pages: 826-829

    • DOI

      10.1021/acs.orglett.6b03819

    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] 酸化的脱水素型クロスカップリングによるチエノ縮環テトラセンの合成2019

    • Author(s)
      都合真弘,村岡 雅弘,村田 理尚
    • Organizer
      日本化学会 第99春季年会 (2019)
    • Related Report
      2018 Annual Research Report
  • [Presentation] ニッケル配位高分子の汎用的合成法の開発と熱電変換特性2019

    • Author(s)
      上田和樹,當山奈菜,奥美華,村岡雅弘,村田 理尚
    • Organizer
      日本化学会 第99春季年会 (2019)
    • Related Report
      2018 Annual Research Report
  • [Presentation] π共役テトラチオール誘導体の汎用的合成法の開発と配位高分子の創出2018

    • Author(s)
      當山奈菜,上田和樹,奥美華,村岡雅弘,村田理尚
    • Organizer
      第38回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Related Report
      2018 Annual Research Report
  • [Presentation] 配位高分子の界面制御によるフレキシブル熱電材料の創製に関する研究2018

    • Author(s)
      上田和樹,當山奈菜,奥美華,村岡雅弘,村田理尚
    • Organizer
      日本油化学会第57回年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 親水性基を導入した配位高分子の合成と熱電変換特性2018

    • Author(s)
      當山奈菜,上田和樹,奥美華,村岡雅弘,村田理尚
    • Organizer
      日本油化学会第57回年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] フレキシブル熱電デバイスのための配位高分子の創製2018

    • Author(s)
      村田理尚
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] A Straightforward Oxidative Cross-Coupling Route to Thieno-Fused Polycyclic Aromatic Hydrocarbons2018

    • Author(s)
      Masahiro Togo, Hideharu Tanaka, Masahiro Muraoka, and Michihisa Murata
    • Organizer
      13th International Symposium on Organic Reactions (ISOR-13)
    • Related Report
      2018 Annual Research Report
  • [Presentation] Efficient Syntheses and Properties of Two- and Three-Dimensional π-Conjugated Molecules and Metal Complexes2017

    • Author(s)
      M. Murata
    • Organizer
      IUMRS-ICAM2017
    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 有機熱電材料に向けた取り組みと2D、3Dπ電子系の合理的合成2017

    • Author(s)
      村田 理尚
    • Organizer
      阪大産研ナノテクセンター若手セミナー
    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Invited
  • [Presentation] 次元性の制御された機能性π共役物質の合成研究2017

    • Author(s)
      村田理尚
    • Organizer
      第52回有機反応若手の会
    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Invited
  • [Presentation] 拡張π電子系の制御合成と熱電変換材料の創出2017

    • Author(s)
      村田理尚
    • Organizer
      第37回有機合成若手セミナー 明日の有機合成を担う人のために
    • Related Report
      2017 Annual Research Report 2016 Annual Research Report
    • Invited

URL: 

Published: 2016-04-21   Modified: 2020-03-30  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi