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Development of electric conductive and lustrous materials synergetically using halogen features

Research Project

Project/Area Number 20K05642
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionChiba University

Principal Investigator

MATSUMOTO Shoji  千葉大学, 大学院工学研究院, 准教授 (50302534)

Project Period (FY) 2020-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2022: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2021: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2020: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords電気伝導性 / ハロゲン結合 / ヨウ素 / チオアミジウム塩 / チアゾロイソキノリニウム塩 / チアゾリウム-3-オラート / ヒドロキシイミダゾピリジニウム / 双性イオン / チアゾリウム-3-オラート / ヒドロキシチアゾロピリジニウム / 対アニオン / 双性イオン化合物 / 電気伝導度 / 光沢
Outline of Research at the Start

本申請研究は,ハロゲン原子同士で構築されるハロゲン結合に注目し,σ-ホール形成と電気陰性度に由来する電子密度増加といったハロゲン元素の異なる特性を協同的に利用した電気伝導性光沢材料の開発を目的としている。ヨウ素置換基をもった双性イオン化合物とヨウ素分子やフッ素化合物との複合体化により電気伝導性の獲得を目指す。σ-ホール形成と電子密度増加というハロゲン元素が持つ別々の特性を同時に利用した機能性材料ではこれまで注目されていない視点となる。また,低分子による光沢発現についても検討し,低有機分子材料での高効率電気伝導性と光沢の獲得,さらに各種測定および計算化学的手法を用いた発現機構解明を行う。

Outline of Final Research Achievements

We synthesized thioamidium salts, thiazoloisoquinolinium salts, and thiazoium-3-olate bearing iodine atom. By investigation of their electric conductivity with or without iodine vapor, we found that all compounds showed the electric conductivity over 10 to the power of -9 S/cm under iodine vapor conditions. We revealed that the halogen-halogen interactions in the crystal structures were important to increase the electric conductivity. Unfortunately, we could not obtain the lustrous compounds with or without contacting iodine molecules. We also investigated the hydroxyimidazopyridinium zwitterions which was converted sulfur atom into nitrogen atom in the compound with lustrous color under the complexation of iodine molecules. Although the hydroxyimidazopyridinium compounds did not show the lustrous color, the compounds gave higher electric conductivity (10 to the power of -3 S/cm) than the compounds with sulfur atom (10 to the power of -6 S/cm) under iodine vapor conditions.

Academic Significance and Societal Importance of the Research Achievements

本研究は,ヨウ素の酸化能とハロゲン結合能を協同的に利用することで電気伝導性を達成しており,さらにハロゲン結合の変化が物理的性質に影響を与えたことを示した初めての事例である。このことで,ハロゲン結合が単なる結合様式の一種にとどまらず,物性変化へも強く関与することを示すことができた。また,多様な骨格へと研究を広げることで,非金属による電気伝導性材料開発への多くの知見が得られた。主にヨウ素について研究することで,日本由来の資源であるヨウ素の有効活用とポテンシャルについて発信することができた。

Report

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

    (12 results)

All 2022 2021

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (10 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results)

  • [Journal Article] Relationship between halogen-halogen interaction and electric conductivity in thiazolo[2,3-a]isoquinolin-7-ium triiodides2022

    • Author(s)
      Matsumoto Shoji、Sumida Ryuta、Akazome Motohiro
    • Journal Title

      Journal of Molecular Structure

      Volume: 1264 Pages: 133306-133306

    • DOI

      10.1016/j.molstruc.2022.133306

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemoselective Reduction of α,β-Unsaturated Carbonyl and Carboxylic Compounds by Hydrogen Iodide2021

    • Author(s)
      Matsumoto Shoji、Marumoto Hayato、Akazome Motohiro、Otani Yasuhiko、Kaiho Tatsuo
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 2 Pages: 590-599

    • DOI

      10.1246/bcsj.20200341

    • NAID

      130007995388

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Presentation] 2-フェニル-1H-イミダゾ[1,2-a]ピリジ-4-ニウム-3-オラートおよび誘導体のヨウ素による電気伝導性発現2022

    • Author(s)
      秋山陽菜・赤染元浩・松本祥治
    • Organizer
      第25回ヨウ学会シンポジウム
    • Related Report
      2022 Annual Research Report
  • [Presentation] Formation, Crystal Structure, and Electric Conductivity of 5-Iodobenzo[4,5]thiazolo[2,3-a]isoquinolin-7-ium Salts2022

    • Author(s)
      Kondo Satoshi, Akazome Motohiro, Matsumoto Shoji
    • Organizer
      5th International Symposium on Halogen Bonding (ISXB5)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Electric Conductivity of Iodinated Thiazolo[2,3-a]isoquinolinum Salts: Relationship Between Their Properties and Halogen-Halogen Interactions2022

    • Author(s)
      Matsumoto Shoji
    • Organizer
      International Congress on Pure & Applied Chemistry Kota Kinabalu, Sabah, Malaysia (ICPAC KK 2022)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Relationship between Electric Conductivity, Halogen-Halogen Interaction, and HOMO Energy in Iodinated Thiazolo[2,3-a]isoquinolinum Salts2022

    • Author(s)
      MATSUMOTO Shoji
    • Organizer
      2022 Symposium for the Promtion of Applied Research Collaboration in Asia (SPARCA 2022)
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Iodine-mediated Cyclization of o-(Arylethynyl)phenylthiazoles with Substituents on Aryl Ring to Form Thiazoloisoquinolium Salts2022

    • Author(s)
      KONDO Satoshi, AKAZOME Motohiro, MATSUMOTO Shoji
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] o-エチニルチオベンズアミド類のヨウ素による環状チオアミジウム塩形成における電子供与基の影響2021

    • Author(s)
      永松拓人・赤染元浩・松本祥治
    • Organizer
      第24回ヨウ学会シンポジウム
    • Related Report
      2021 Research-status Report
  • [Presentation] Crystal Structure and Electric Conductivity of Iodinated Thiazolo[2,3-a]isoquinolinum Salts2021

    • Author(s)
      MATSUMOTO Shoji, SUMIDA Ryuta, TAN Sia Er, AKAZOME Motohiro
    • Organizer
      2021 International Chemical Congress of Pacific Basin Societies (PACHIFICHEM 2021)
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] ヨウ化水素を用いたα,β-不飽和カルボニル化合物の選択的還元反応の反応機構2021

    • Author(s)
      丸本颯人・赤染元浩・海宝龍夫・松本祥治
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] Modified Synthesis of Iododihydropyrrole by Iodine-mediated Cyclization2021

    • Author(s)
      Ryohei Nakada, Motohiro Akazome, Shoji Matsumoto
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] Influence on Counter Anion of Cyclic Thioamidium Salts by Introduction Oxygen Functional Substituent in Iodine-mediated Cyclization of o-Ethynylthiobenzamide2021

    • Author(s)
      Takuto Nagamatsu, Motohiro Akazome, Shoji Matsumoto
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report

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Published: 2020-04-28   Modified: 2024-01-30  

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