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Design and Functionality of Near-Infrared Organic Materials with Intermediate Open-Shell Character

Research Project

Project/Area Number 21K05215
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 InstitutionOsaka Metropolitan University (2022-2023)
Osaka Prefecture University (2021)

Principal Investigator

Maeda Takeshi  大阪公立大学, 大学院工学研究科, 准教授 (90507956)

Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2023: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2022: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2021: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords近赤外 / 機能性色素 / 中間ジラジカル性 / 二光子吸収 / 反強磁性相互作用 / 中間開殻性 / ジラジカロイド / 励起子相互作用 / ポリメチン色素 / 開殻性 / 磁気的双安定性
Outline of Research at the Start

多くの物質に対して透明である近赤外光を吸収する有機材料は,近赤外テクノロジーによる技術革新に不可欠である.本研究では開殻分子に向けた分子設計を巧みに適用した近赤外有機材料の新機軸設計法を確立し,堅牢な近赤外有機材料群を創製することを目的とする.得られる分子群は近赤外光吸収能のみならず電子スピンに起因した分子磁性を示す.これら物性に関わる材料応用を指向して,分子レベルの研究を分子集積系へと発展させ,集積構造が光学特性,分子磁性,有機半導体特性に及ぼす効果を明らかにする.これら分子レベルと分子集積レベルでの階層的研究から,開殻性に基づく近赤外有機材料の学理を構築し,その有効性と制限を明らかにする.

Outline of Final Research Achievements

Robust near-infrared absorbing organic materials are essential for advancing technologies that utilize near-infrared light. In this study, we focused on polymethine dyes composed of an oxocarbon skeleton and chalcogenopyrylium, investigating their electronic structures and physical properties to enhance their functionality. Our findings indicate that these dyes exhibit intermediate diradical properties due to the presence of an open-shell singlet state, where two unpaired electrons have a singlet electron configuration. Additionally, we observed that the contribution of the open-shell singlet state increases with the atomic number of the chalcogen element. These dyes also display paramagnetic properties due to the unpaired electrons and demonstrate excellent light absorption capabilities beyond 1000 nm.

Academic Significance and Societal Importance of the Research Achievements

これまでに多様な近赤外線吸収有機色素が報告されているが,それらは閉殻構造の分子と認識されてきた.本研究では,近赤外線吸収有機色素の一種であるポリメチン色素が中間ジラジカル性を持つことを初めて明らかにした.中間ジラジカル性という概念は多環芳香族化合物などの特定の分子に適用されきたが,本研究は,その概念を有機色素にまで拡張しており,学術的に意義深い.また,近赤外線吸収有機色素の正確な電子状態を明示できたことは,近赤外吸収有機材料の設計新機軸の確立に貢献するものと考えられ,情報通信,生体深部の可視化,非侵襲性治療に利活用される近赤外吸収有機材料の創製につながると期待でき,社会的に意義深い.

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • 2021 Research-status Report
  • Research Products

    (38 results)

All 2024 2023 2022 2021 Other

All Int'l Joint Research (2 results) Journal Article (6 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 6 results,  Open Access: 2 results) Presentation (27 results) (of which Int'l Joint Research: 10 results,  Invited: 2 results) Remarks (3 results)

  • [Int'l Joint Research] CSIR-NIIST(インド)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] CSIR-NIIST(インド)

    • Related Report
      2021 Research-status Report
  • [Journal Article] Development of Intramolecular Exciton-Coupled Bis-Squaraine Dyes for Application to Near-Infrared Organic Photodetectors2024

    • Author(s)
      Ryuhei Sawada, Reiji Hama, Saki Kinoshita, Takeshi Maeda, , Naoya Suzuki, Shigeyuki Yagi
    • Journal Title

      Journal of the Japan Society of Colour Material

      Volume: 97 Pages: 1-9

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One‐Photon and Two‐Photon Absorption Properties of Multi‐Branched Squaraine Dyes Comprised of Triphenylamine Cores and Ethynylene Linkers2023

    • Author(s)
      Tay V. Nguyen, Takeshi Maeda, Tetsuya Matsuyama, Naoya Suzuki, Hiroyuki Nakazumi, Shigeyuki Yagi, Ayyappanpillai Ajayaghosh
    • Journal Title

      ChemPhotoChem

      Volume: 7 Issue: 11

    • DOI

      10.1002/cptc.202300152

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Squaraine Appended with Benzodipyrrole for Fluorescent Sensing of Methanol: Exciton Coupling Controls Photophysical Properties2023

    • Author(s)
      Ryuhei Sawada, Chinju Govind, Takeshi Maeda, Naoya Suzuki, Shigeyuki Yagi, Venugopal Karunakaran, Ayyappanpillai Ajayaghosh
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 18 Issue: 24

    • DOI

      10.1002/asia.202300868

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Unveiling a new aspect of oxocarbons: open-shell character of 4- and 5-membered oxocarbon derivatives showing near-infrared absorption2023

    • Author(s)
      Takeshi Maeda, Taishi Oka, Daisuke Sakamaki, Hideki, Fujiwara, Naoya Suzuki, Shigeyuki Yagi, Tatsuki Konishi, Kenji Kamada
    • Journal Title

      Chemical Science

      Volume: 14 Issue: 8 Pages: 1978-1985

    • DOI

      10.1039/d2sc06612b

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and photophysical properties of photostable 1,8-naphthalimide dyes incorporating benzotriazole-based UV absorbers2022

    • Author(s)
      Toshiyuki Uesaka, Tomoyuki Ishitani, Takahito Shimeno, Naoya Suzuki, Shigeyuki Yagi, Takeshi Maeda
    • Journal Title

      RSC Advances

      Volume: 12 Issue: 27 Pages: 17350-17361

    • DOI

      10.1039/d2ra02028a

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis, Photophysical and Electrochemical Properties of Bis‐Squaraine Dyes Fused on Isomeric Benzodipyrrole Central Units2022

    • Author(s)
      Ryuhei Sawada, Takeshi Maeda, Yuya Oda, Shigeyuki Yagi, Venugopal Karunakaran, Hideki Fujiwara, Ayyappanpillai Ajayaghosh
    • Journal Title

      Chemistry - An Asian Journal

      Volume: - Issue: 13

    • DOI

      10.1002/asia.202200227

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] ベンゼン縮環インドレニンからなるC2v対称スクアレン色素の結晶性薄膜の作製と近赤外光検出器への展開2024

    • Author(s)
      濱 玲史、前田 壮志、鈴木 直弥、八木 繁幸、藤原 秀紀
    • Organizer
      日本化学会 第104春季年会 (2024)
    • Related Report
      2023 Annual Research Report
  • [Presentation] チオフラビリウム骨格からなる中間開殻性クロコナイン色素の相転移が磁気特性に及ぼす効果2024

    • Author(s)
      小野 皓平、岡 大志、前田 壮志、酒巻 大輔、藤原 秀紀、鈴木 直弥、小玉 晋太朗、八木 繁幸
    • Organizer
      日本化学会 第104春季年会 (2024)
    • Related Report
      2023 Annual Research Report
  • [Presentation] Intermediate Open-Shell Character of Near-Infrared Absorbing Oxocarbon Derivatives2023

    • Author(s)
      T. Maeda, T. Oka, T. Ohno, D. Sakamaki, H. Fujiwara, N. Suzuki, S. Yagi, T. Konishi, K. Kamada
    • Organizer
      15th International Symposium on Functional π Electron Systems
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Intermediate Open-Shell Character of Near-Infrared Absorbing Polymethine Dyes Derived from Oxocarbons2023

    • Author(s)
      T. Maeda, T. Oka, T. Ohno, D. Sakamaki, H. Fujiwara, N. Suzuki, S. Yagi, T. Konishi, K. Kamada
    • Organizer
      11th East Asia Symposium on Functional Dyes and Advanced Materials
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Optical and Electrochemical Properties of C2v-Symmetric Bissquaraine Dyes Fused on Benzodipyrrole Central Units2023

    • Author(s)
      R. Sawada, S. Kinoshita, N. Suzuki, S. Kodama, T. Maeda, S. Yagi
    • Organizer
      11th East Asia Symposium on Functional Dyes and Advanced Materials
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Effects of Intermediate Diradical Character on cis-trans Isomerization of Near-Infrared Absorbing Squaraine Dyes2023

    • Author(s)
      T. Oka, T. Maeda, N. Suzuki, S. Kodama, D. Sakamaki, H. Fujiwara, S. Yagi
    • Organizer
      11th East Asia Symposium on Functional Dyes and Advanced Materials
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Properties of Intramolecular Hydrogen-Bonded Squaraine Dyes and Their Application to Near-Infrared Photodetectors2023

    • Author(s)
      R. Hama, T. Maeda, N. Suzuki, S. Kodama, S. Yagi
    • Organizer
      11th East Asia Symposium on Functional Dyes and Advanced Materials
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 近赤外吸収スクアレン色素の中間ジラジカル性がシス-トランス異性化に及ぼす効果2023

    • Author(s)
      岡大志,前田壮志,鈴木直弥,小玉晋太朗,酒巻大輔,藤原秀紀,八木繁幸
    • Organizer
      第33回基礎有機化学討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 分子内水素結合を有するC2v対称スクアレン色素の合成と光学特性2023

    • Author(s)
      濵 玲史・前田壮志・鈴木直弥・小玉晋太朗・八木繁幸
    • Organizer
      第33回基礎有機化学討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 種々の複素環からなる近赤外吸収クロコナイン色素の中間開殻性2023

    • Author(s)
      前田壮志,岡 大志,大野友彰,酒巻大輔,藤原秀紀,鈴木直弥,八木繁幸
    • Organizer
      2023 年度色材研究発表会
    • Related Report
      2023 Annual Research Report
  • [Presentation] フェニル置換カルコゲノピリリウム骨格からなるクロコナイン色素の中間開殻性評価2023

    • Author(s)
      岡大志,前田壮志,酒巻大輔,鈴木直弥,八木繁幸,藤原秀紀
    • Organizer
      日本化学会 第103春季年会(2023)
    • Related Report
      2022 Research-status Report
  • [Presentation] 近赤外吸収クロコナイン色素の複素環成分が中間開殻性に及ぼす効果2023

    • Author(s)
      大野友彰,岡大志,前田壮志,酒巻大輔,鈴木直弥,八木繁幸,藤原秀紀
    • Organizer
      日本化学会 第103春季年会(2023)
    • Related Report
      2022 Research-status Report
  • [Presentation] インダンジオン骨格を有するスクアレン色素の合成と有機近赤外フォトディテクターへの応用2022

    • Author(s)
      前田壮志, 田中大気, 八木繁幸, 藤原秀紀
    • Organizer
      第 32 回基礎有機化学討論会
    • Related Report
      2022 Research-status Report
  • [Presentation] Experimental Evaluation of Intermediate Open Shell Character in Near-Infrared Absorbing Croconaine Dyes2022

    • Author(s)
      T. Maeda, T. Oka, D. Sakamaki, H. Fujiwara, N. Suzuki, S. Yagi, T. Konishi, K. Kamada
    • Organizer
      95th JSCM Anniversary Conference
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] Intermediate Open-Shell Character of Near-Infrared Absorbing Croconaine Dyes Consisting of Alkoxy-Substituted Flavylium Skeletons2022

    • Author(s)
      Tomoaki Ohno, Takeshi Maeda, Daisuke Sakamaki, Hideki Fujiwara, Shigeyuki Yagi
    • Organizer
      95th JSCM Anniversary Conference
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] 光熱変換特性を示す液晶性色素の開発とリライタブル材料への応用2022

    • Author(s)
      前田壮志,高野将史,八木繁幸,大越研人
    • Organizer
      第31回ポリマー材料フォーラム
    • Related Report
      2022 Research-status Report
  • [Presentation] Unveiling Open-Shell Character of Near-Infrared Absorbing Polymethine Dyes2022

    • Author(s)
      T. Maeda, T. Oka, D. Sakamaki, H. Fujiwara, N. Suzuki, S. Yagi, T. Konishi, K. Kamada
    • Organizer
      11th Singapore International Chemistry Conference
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] The Open-Shell Character of Croconaine Dyes Showing Near-Infrared Absorption over 800 nm2022

    • Author(s)
      T. Maeda, T. Oka, D. Sakamaki, H. Fujiwara, S. Yagi
    • Organizer
      International CREST-CPL Conference 2022
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Evaluation of Optical and Electrochemical Properties of Bis-Squaraine Dyes2022

    • Author(s)
      R. Sawada, T. Maeda, S. Yagi
    • Organizer
      International CREST-CPL Conference 2022
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] オキソカーボン中心骨格を持つ近赤外吸収ポリメチン色素のジラジカル特性2022

    • Author(s)
      岡大志,前田壮志,酒巻大輔,藤原秀紀,八木繁幸,小西龍生,鎌田賢司
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] 対称型スクアレン発色団からなるビススクアレン色素の光学および電気化学特性2022

    • Author(s)
      澤田隆平,前田壮志,八木繁幸
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] 液晶性スクアレン色素の光熱変換特性2021

    • Author(s)
      前田壮志,高野将史,八木繁幸,大越研人
    • Organizer
      第70回高分子学会年次大会
    • Related Report
      2021 Research-status Report
  • [Presentation] スクアレンおよびクロコナイン色素の中間的な開殻性2021

    • Author(s)
      岡大志,前田壮志,酒巻大輔,八木繁幸,藤原秀紀
    • Organizer
      2021年度色材研究発表会
    • Related Report
      2021 Research-status Report
  • [Presentation] スクアレン発色団が融合した構造を持つ色素の光学特性と電気化学特性評価2021

    • Author(s)
      澤田隆平,前田壮志,八木繁幸
    • Organizer
      2021年度色材研究発表会
    • Related Report
      2021 Research-status Report
  • [Presentation] フラビリウム骨格とオキソカーボン酸残基からなる近赤外吸収色素の開殻性評価2021

    • Author(s)
      大野友彰,岡 大志,前田壮志,酒巻大輔,藤原秀紀,八木繁幸
    • Organizer
      2021年度色材研究発表会
    • Related Report
      2021 Research-status Report
  • [Presentation] オキソカーボン酸を中心骨格に持つ近赤外吸収ポリメチン色素の中間的な開殻性2021

    • Author(s)
      岡大志,前田壮志,酒巻大輔,藤原秀紀,八木繁幸
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] フラビリウム骨格とオキソカーボン酸残基からなるポリメチン色素の開殻性評価2021

    • Author(s)
      大野友彰,岡大志,前田壮志,酒巻大輔,藤原秀紀,八木繁幸
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Remarks] 大阪公立大学研究者詳細

    • URL

      https://kyoiku-kenkyudb.omu.ac.jp/html/100001915_ja.html

    • Related Report
      2023 Annual Research Report
  • [Remarks] 大阪公立大学大学院工学研究科物質化学生命系専攻応用化学分野有機機能化学研究グループ

    • URL

      http://www2.chem.osakafu-u.ac.jp/ohka/ohka6/index.html

    • Related Report
      2023 Annual Research Report 2022 Research-status Report
  • [Remarks] 大阪公立大学 最新の研究成果

    • URL

      https://www.omu.ac.jp/info/research_news/entry-04477.html

    • Related Report
      2022 Research-status Report

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Published: 2021-04-28   Modified: 2025-01-30  

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