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Material applications with heteroatom containing pi-conjugated molecules

Research Project

Project/Area Number 19H02702
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionKyoto University

Principal Investigator

Hiroto Satoru  京都大学, 人間・環境学研究科, 准教授 (30547427)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2021: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2020: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2019: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Keywordsヘリセン / 極性結晶 / 近赤外発光 / 積層制御 / ラジカルカチオン / 自発分極 / 金錯体 / 非線形光学効果 / アザヘリセン / アザバッキーボウル / ビラジカル / バッキーボウル / 有機半導体 / 固体発光
Outline of Research at the Start

最近、平面ではなく曲面構造をもつπ共役分子が次々と合成され、注目されている。しかしながら、その機能性についてはまだ未開拓である。そこで、本研究では、曲面という構造に着目した曲面π共役分子ならではの新たな機能の創出を目指す。特に、酸化・還元という電気化学刺激応答性や導電性など電気を活用した次世代の有機分子材料の開発に繋がる機能創出を目指し、曲面π共役分子の有用性を示す。

Outline of Final Research Achievements

The aim of this study was to control the structure and electronic state of curved π-conjugated molecules containing nitrogen elements by installing or modifying substituents, and to create new functions using the unique properties of curved π-conjugated molecules. As a result, control of the stacking structure of bowl-shaped molecules and control of structural and photochemical properties by substituents on twisted molecules were achieved. In particular, they developed a selective substituent conversion reaction of azahelicenes and succeeded in creating unprecedented functions such as near-infrared emission and spontaneous polarization based on this reaction.

Academic Significance and Societal Importance of the Research Achievements

本研究ではこれまで使い道が不透明であった曲面π共役分子の材料展開における重要な知見を与える。特に、三次元構造と分子間相互作用を巧みに活用した固体中での積層構造の制御は、有機半導体だけでなく強誘電体や焦電体などこれまで有機材料にあまり活躍の場がなかった材料分野への応用可能性を広げるものである。さらに、発光性のらせん分子の創出や分子設計における知見は生体内におけるらせん化合物、DNAやRNAとの親和性を期待するものであり、遺伝子を用いた薬剤や生体中における物質の動きの可視化など生体応用への応用展開を伺う重要な知見となる。

Report

(4 results)
  • 2022 Final Research Report ( PDF )
  • 2021 Annual Research Report
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • Research Products

    (10 results)

All 2022 2021 2020 2019

All Journal Article (5 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results) Presentation (5 results) (of which Int'l Joint Research: 3 results,  Invited: 3 results)

  • [Journal Article] A Strategy for Polar Crystals with Dipolar Heterohelicenes2022

    • Author(s)
      Hiroto Satoru、Wakita Mana、Chujo Moeko
    • Journal Title

      Chemistry ? An Asian Journal

      Volume: 17 Issue: 22

    • DOI

      10.1002/asia.202200808

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Heteroatoms in bowl-shaped polycyclic aromatic hydrocarbons: Synthesis and structures2021

    • Author(s)
      Satoru Hiroto
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 6 Pages: 1146-1155

    • DOI

      10.1246/cl.200965

    • NAID

      130008053375

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Helical Pitch Dependent Optical Properties of π-Extended Aza[5]helicene Radical Cations2020

    • Author(s)
      Satoru Hiroto
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 93 Issue: 11 Pages: 1334-1339

    • DOI

      10.1246/bcsj.20200181

    • NAID

      130007939764

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Amplified Heavy-Atom Free Phosphorescence from Meta-Dimethoxy Difluoroboron β-Diketonate Charge-Transfer Materials2019

    • Author(s)
      C. DeRosa, S. Hiroto, C. L. Fraser
    • Journal Title

      J. Phys. Chem. C

      Volume: 123 Issue: 33 Pages: 20488-20496

    • DOI

      10.1021/acs.jpcc.9b05736

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Regioselective Desilylation of a pi-Extended Aza[5]helicene Web of Science2019

    • Author(s)
      Ushiyama, Ayako; Shinokubo, Hiroshi; Hiroto, Satoru
    • Journal Title

      Chem. Lett.

      Volume: 48 Issue: 9 Pages: 1069-1069

    • DOI

      10.1246/cl.190369

    • NAID

      130007703012

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] 非対称アザヘリセンの合成とその物性解明2022

    • Author(s)
      福元政彦、廣戸 聡
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 分極したヘリセンによる自発分極結晶の創出2022

    • Author(s)
      廣戸 聡・脇田真奈・中條 萌絵子
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Electrochemistry of three-dimensional porphyrins and related compounds2019

    • Author(s)
      Satoru Hiroto
    • Organizer
      235th ECS Meeting
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Regioselective functionalizations and properties of π-extended aza[5]helicenes2019

    • Author(s)
      Satoru Hiroto
    • Organizer
      the 12th Japan-Taiwan Bilateral Symposium on“Architecture of Functional Organic Molecules
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and redox switching properties of nitrogen-containing three-dimensional π-conjugated molecules2019

    • Author(s)
      Satoru Hiroto
    • Organizer
      IUPAC 15th International Conference on Novel Materials and their Synthesis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited

URL: 

Published: 2019-04-18   Modified: 2024-01-30  

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