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Investigations on Synthesis and Properties of as-Indacene and its Congeners

Research Project

Project/Area Number 15K13643
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

Tobe Yoshito  大阪大学, 基礎工学研究科, 教授 (60127264)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords開殻性一重項分子 / ジラジカル / 反芳香族性 / インダセン
Outline of Final Research Achievements

(1) As a model study for the synthesis of as-indacene derivatives, an entirely new synthetic route to s-indacene derivatives was successfully developed.t Because this method is applicable to the synthesis of as-indacene derivatives, it has became feasible to achieve the synthesis of the final target.
(2) In order to synthesize as-indacenes fused by thiophene rings, an o-quinodimethane type isomer was successfully generated, giving a dimer derived by 4+4 cycloaddition of the reactive intermediate. Attempts to kinetically stabilize the system by introducing bulky substituents failed to isolate the desired product, indicating the limit of kinetic stability of this system. In addition, two dihydro-o-quinodimethane type derivatives were synthesized and their photophysical properties were investigated.

Report

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

    (5 results)

All 2017 2016 Other

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (2 results) (of which Invited: 2 results) Remarks (2 results)

  • [Journal Article] Fluoreno[2,3-b]fluorene vs Indeno[2,1-b]fluorene: Unusual Relationship between the Number of π Electrons and Excitation Energy in m-Quinodimethane-Type Singlet Diradicaloids2017

    • Author(s)
      Hirokazu Miyoshi, Masahito Miki, Shintaro Hirano, Akihiro Shimizu, Ryohei Kishi, Kotaro Fukuda, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Ichiro Hisaki, Masayoshi Nakano, Yoshito Tobe
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 3 Pages: 1380-1388

    • DOI

      10.1021/acs.joc.6b02500

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] 新奇な電子状態をもつ開殻性一重項分子の合成、構造と物性2017

    • Author(s)
      戸部義人
    • Organizer
      新学術領域研究「高次複合光応答分子システムの開拓と学理の構築」第5回公開シンポジウム
    • Place of Presentation
      大阪大学基礎工学国際棟(豊中市・大阪府)
    • Year and Date
      2017-01-20
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Indenofluorene Motifs in Singlet Diradicaloids and Tetraradicaloids2016

    • Author(s)
      Yoshito Tobe
    • Organizer
      The 70th Fujiwara Seminar
    • Place of Presentation
      THE LUIGANS Spa & Resort(福岡県・福岡市)
    • Year and Date
      2016-04-17
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Remarks] 大阪大学大学院基礎工学研究科・物質創成専攻・未来物質領域・新物質創成講座・機能分子創製グループ

    • URL

      http://www.supra.chem.es.osaka-u.ac.jp/publications/

    • Related Report
      2016 Annual Research Report
  • [Remarks] 大阪大学大学院基礎工学研究科・物質創成専攻・未来物質領域・新物質創製講座・機能分子創製グループ

    • URL

      http://www.supra.chem.es.osaka-u.ac.jp/publications/

    • Related Report
      2015 Research-status Report

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

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