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Development of NIR-photoredox reactions for functionalization of organic materials

Research Project

Project/Area Number 18K19071
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionKanazawa University

Principal Investigator

Furuyama Taniyuki  金沢大学, 物質化学系, 准教授 (30584528)

Project Period (FY) 2018-06-29 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Keywords近赤外光 / アザポルフィリン / フォトレドックス反応 / 光物理特性 / 可視光材料
Outline of Final Research Achievements

In developing new materials, the direct conversion of materials that absorb visible light is a powerful strategy. On the other hand, it is difficult to apply visible-light-absorbing materials to visible-light mediated organic photoredox reactions, which has attracted much attention because the absorption of catalysts competes for substrates. In this study, we investigated the NIR-light mediated organic reactions toward a selective activation of catalysts. By using fine-tuned azaporphyrin-based photocatalyst, trifluoromethylation and dehydrogenative coupling reactions could be developed. Furthermore, these reactions can be applied to the direct conversion of visible light materials. Therefore, these NIR-mediated photoreactions are new tools for the development of novel materials.

Academic Significance and Societal Importance of the Research Achievements

深赤色-近赤外光は可視光と比べてエネルギーが低いため、有機合成反応に用いることが本質的に困難とされている。さらに、触媒設計にあたってはこれらの光を強く吸収すると同時に、酸化還元電位や励起状態の性質を制御する必要があるため、長波長の光を用いる有機合成反応は挑戦的な課題であった。本研究では精密な物性制御が可能なアザポルフィリン類を適切に設計することでこの問題を克服し、従来不可能とされてきた可視光材料の光を用いた直接変換を実現した。本手法は新材料の開発にあたり新たな概念・手段を提供すると位置付けられる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (20 results)

All 2021 2020 2019 2018 Other

All Journal Article (9 results) (of which Peer Reviewed: 6 results,  Open Access: 3 results) Presentation (9 results) (of which Int'l Joint Research: 4 results,  Invited: 5 results) Remarks (2 results)

  • [Journal Article] 近赤外ケイ素フタロシアニンの近赤外光線力学療法への応用2021

    • Author(s)
      石井孝知、古山渓行
    • Journal Title

      マテリアルステージ

      Volume: 2020 Pages: 80-84

    • Related Report
      2020 Annual Research Report
  • [Journal Article] Temperature-dependent changes in the molecular orientation and visible color of phthalocyanine films2020

    • Author(s)
      Furuyama Taniyuki、Uchiyama Shiori、Chikamatsu Tatsuki、Horikawa Takafumi、Maeda Hajime、Segi Masahito、Takahashi Hiromi、Taima Tetsuya
    • Journal Title

      RSC Advances

      Volume: 10 Issue: 52 Pages: 31348-31354

    • DOI

      10.1039/d0ra06273a

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of Low-symmetry Ball-shaped Ruthenium Complexes and Fine-tuning of Their Optical Properties in the Visible and NIR Region2020

    • Author(s)
      Ishikawa Sari、Shimasaki Fumika、Maeda Hajime、Segi Masahito、Furuyama Taniyuki
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 11 Pages: 1394-1398

    • DOI

      10.1246/cl.200557

    • NAID

      130007936947

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 近赤外光を活用できる有機金属錯体の合成技術2020

    • Author(s)
      古山渓行
    • Journal Title

      オプトロニクス

      Volume: 485 Pages: 134-139

    • Related Report
      2019 Research-status Report
    • Open Access
  • [Journal Article] Cationic axial ligands on sulfur substituted silicon(iv) phthalocyanines: improved hydrophilicity and exceptionally red-shifted absorption into the NIR region2019

    • Author(s)
      Furuyama Taniyuki、Ishii Takashi、Ieda Naoya、Maeda Hajime、Segi Masahito、Uchiyama Masanobu、Nakagawa Hidehiko
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 51 Pages: 7311-7314

    • DOI

      10.1039/c9cc03022k

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Chemoselective Synthesis of Aryloxy-Substituted Phthalocyanines2019

    • Author(s)
      Furuyama Taniyuki、Maeda Kazuya、Maeda Hajime、Segi Masahito
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 21 Pages: 14306-14312

    • DOI

      10.1021/acs.joc.9b02126

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-step synthesis of ball-shaped metal complexes with a main absorption band in the near-IR region2019

    • Author(s)
      Furuyama Taniyuki、Shimasaki Fumika、Saikawa Natsumi、Maeda Hajime、Segi Masahito
    • Journal Title

      Scientific Reports

      Volume: 9 Issue: 1 Pages: 16528-16528

    • DOI

      10.1038/s41598-019-53014-7

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Extremely Photostable Electron‐Deficient Phthalocyanines that Generate High Levels of Singlet Oxygen2019

    • Author(s)
      Furuyama Taniyuki、Miyaji Yusuke、Maeda Kazuya、Maeda Hajime、Segi Masahito
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 7 Pages: 1678-1682

    • DOI

      10.1002/chem.201805082

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] 典型元素を活用するフタロシアニン光材料の合成2019

    • Author(s)
      古山 渓行
    • Journal Title

      化学工業

      Volume: 70 Pages: 169-174

    • Related Report
      2018 Research-status Report
  • [Presentation] 精密有機合成技術に基づく近赤外色素材料の開発と応用2021

    • Author(s)
      古山渓行
    • Organizer
      金沢大学先端科学・イノベーション推進機構協力会 第16回金沢大学研究室見学会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 近赤外光を活用できる機能性色素の精密有機合成技術2020

    • Author(s)
      古山渓行
    • Organizer
      岡山大学次世代研究育成グループ講演会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Synthesis of ball-shaped metal complexes with a main absorption band in the near-IR region2019

    • Author(s)
      Taniyuki Furuyama, Fumika Shimasaki, Hajime Maeda, Masahito Segi
    • Organizer
      7th Geogian Bay International Conference on Bioinorganic Chemistry
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Near-Infrared Light Absorbing Hydrophilic Silicon(IV) Phthalocyanines2019

    • Author(s)
      Takashi Ishii, Naoya Ieda, Hajime Maeda, Masahito Segi, Hidehiko Nakagawa and Taniyuki Furuyama
    • Organizer
      7th Geogian Bay International Conference on Bioinorganic Chemistry
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 電気・光特性を自在に活用できる有機材料の開発2019

    • Author(s)
      古山渓行
    • Organizer
      2019年度電気化学会北陸支部春季(石川)大会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] A Light-stable Phthalocyanine with High Ability to Generate Singlet Oxygen2018

    • Author(s)
      Taniyuki Furuyama, Yusuke Miyaji, Hajime Maeda and Masahito Segi
    • Organizer
      10th International Conference on Porphyrins and Phthalocyanines (ICPP-10)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Versatile Synthesis of Functionalized Near-infrared Light-absorbing Phthalocyanines2018

    • Author(s)
      Takayuki Iwamoto, Hajime Maeda, Masahito Segi and Taniyuki Furuyama
    • Organizer
      10th International Conference on Porphyrins and Phthalocyanines (ICPP-10)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] ジシアノ部位をアクセプターとする固体発光材料の開発2018

    • Author(s)
      古山渓行・篠崎潤一・藤原亮一・前多 肇・千木昌人
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 元素の特性を利用した有機近赤外光材料の開発2018

    • Author(s)
      古山渓行
    • Organizer
      第3回有機若手ワークショップ
    • Related Report
      2018 Research-status Report
    • Invited
  • [Remarks] 金沢大学研究者情報

    • URL

      https://ridb.kanazawa-u.ac.jp/public/detail.php?id=4466&page=3&org2_cd=340400

    • Related Report
      2020 Annual Research Report
  • [Remarks] 金沢大学研究者情報

    • URL

      http://ridb.kanazawa-u.ac.jp/public/detail.php?id=4466&page=3&org2_cd=340400

    • Related Report
      2019 Research-status Report 2018 Research-status Report

URL: 

Published: 2018-07-25   Modified: 2022-01-27  

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