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Synthesis and Function Developpement of Radial Pi-Clusters Composed of Anthracene Units

Research Project

Project/Area Number 17K17849
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Organic chemistry
Research InstitutionOsaka University

Principal Investigator

Tomohiko Nishiuchi  大阪大学, 理学研究科, 助教 (10706774)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2017: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords放射状πクラスター / アントラセン / 光異性化 / エキシマ-発光 / エキシマー発光
Outline of Final Research Achievements

In this study, we planed to synthesize anthracene congested molecular structures, that is, pi-cluster mokecule, to explore fundermental properties, such as long-wavelength absorption, emission, electron donating property, or intramolecular photoisomerization behavior, in pi-congested aromatic molecules. Although one of the target molecules 1,2,3,4-tetra(9-anthryl)benzene could not be obtained in this reaserch period, we could synthesize a highly congested tri(9-anthryl)methyl (TAntM) radical and its cationic species. Due to the bulky three anthryl units, TAntM radical showed ultimate stability under ambient condition, resulting in facile silica-gel column purification as well as recrystallization under air. In addition, TantM radical shows wide range absorption reaching to 1000 nm and good redox properties.

Academic Significance and Societal Importance of the Research Achievements

TAntMラジカルの分子骨格は、以前にも合成が試みられたことがあるが達成されていなかった。本研究課題においてはその合成法を編み出すことに成功し、今後類似のπ電子密集型化合物の合成にも適用されることが期待される。
TAntMラジカルの物性において、近赤外吸収と安定な酸化還元特性はラジカル種のSOMOエネルギーの高さにアントラセン骨格のπ平面の広さが掛け合わされて得られた特徴であり、良い電子ドナーとしての利用が大いに期待できる。さらに驚異的な速度論的安定化は、アントラセン骨格を密に集積させたことで初めて得られるものであり、高反応性化学種の安定化手法の一つとして普及していくことが期待できる。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (5 results)

All 2019 2018

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

  • [Journal Article] Synthesis and Properties of a Highly Congested Tri(9-anthryl)methyl Radical2018

    • Author(s)
      Nishiuchi Tomohiko、Aibara Seito、Kubo Takashi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 50 Pages: 16516-16519

    • DOI

      10.1002/anie.201811314

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] 新奇アントラセン密集型分子、放射状πクラスター分子:酸化種の電子状態の考察2019

    • Author(s)
      清水和人・西内智彦・平尾泰一・久保孝史
    • Organizer
      日本化学会第99回春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] アントラセン骨格を基盤としたπクラスター分子の配列様式の違いによる物性の評価2018

    • Author(s)
      西内智彦・赤澤勇樹・木坂和貴・清水和人・平尾泰一・久保孝史
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 新奇アントラセン密集型分子、放射状πクラスター分子の合成と酸化種の電子状態2018

    • Author(s)
      清水和人・西内智彦・平尾泰一・久保孝史
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Tri(9-anthryl)methyl Species: Synthesis and Properties of The Highly Congested Novel Hydrocabons2018

    • Author(s)
      Tomohiko Nishiuchi
    • Organizer
      The 10th Singapore International Chemistry Conference (SICC-10)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited

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Published: 2017-04-28   Modified: 2020-03-30  

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