• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Chemistry of Boron-Containing pi-Electron Materials

Research Project

Project/Area Number 18H05261
Research Category

Grant-in-Aid for Scientific Research (S)

Allocation TypeSingle-year Grants
Review Section Broad Section E
Research InstitutionNagoya University

Principal Investigator

Yamaguchi Shigehiro  名古屋大学, 物質科学国際研究センター(WPI), 教授 (60260618)

Project Period (FY) 2018-06-11 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥193,700,000 (Direct Cost: ¥149,000,000、Indirect Cost: ¥44,700,000)
Fiscal Year 2022: ¥29,900,000 (Direct Cost: ¥23,000,000、Indirect Cost: ¥6,900,000)
Fiscal Year 2021: ¥34,580,000 (Direct Cost: ¥26,600,000、Indirect Cost: ¥7,980,000)
Fiscal Year 2020: ¥37,960,000 (Direct Cost: ¥29,200,000、Indirect Cost: ¥8,760,000)
Fiscal Year 2019: ¥39,910,000 (Direct Cost: ¥30,700,000、Indirect Cost: ¥9,210,000)
Fiscal Year 2018: ¥51,350,000 (Direct Cost: ¥39,500,000、Indirect Cost: ¥11,850,000)
Keywordsホウ素 / π電子系 / 近赤外蛍光 / 超分子ポリマー / ラジカル / Lewis酸性 / 有機EL / 蛍光イメージング / 蛍光 / パイ電子系 / 近赤外色素 / 有機電界発光素子 / ルイス酸性 / 超分子重合 / 半導体 / 超分子 / 有機半導体 / 安定性
Outline of Final Research Achievements

Among various main-group elements, boron is particularly a useful element to create pi-conjugated skeletons with unusual electronic structures. In this study, we developed various types of optoelectronic functional molecules by pursuing the characteristic features of boron. So far, we have shown that the triarylborane skeleton can be stabilized without steric protection by constraining the structure in a planar fashion. By taking this design strategy one-step further, we developed near-infrared fluorescent materials and luminescent stable organic radicals. We also in-depth studied the complex formation between the planarized boron-containing π-electron systems and Lewis bases in both ground and excited states, and achieved controlling over the supramolecular polymerization processes. Furthermore, we applied the boron π-electron systems to organic electroluminescent devices and fluorescence imaging to demonstrate their potential utilities in these aspects.

Academic Significance and Societal Importance of the Research Achievements

物質の特性・機能を決める特定元素の役割を理解し,有効活用することは物質科学の根源であり,挑戦し続けるべき課題である.本研究では,構造固定化の概念を分子設計指針に据え,ホウ素を含む一連の機能性材料の開発を達成した.秀逸な近赤外蛍光材料の開発やホウ素安定化ラジカルの有機発光性材料としての有用性を実証しただけでなく,ホウ素のLewis酸性を活用した分子の集合化の制御の仕方や,蛍光イメージングなどの生物学ツールとしての潜在性を示し,機能性材料を指向した有機ホウ素化学ひいては典型元素化学に重要な方向性を示した.

Assessment Rating
Ex-post Assessment Comments (Rating)

A: In light of the aim of introducing the research area into the research categories, expected outcomes of research have been produced.

Assessment Rating
Interim Assessment Comments (Rating)

A: In light of the aim of introducing the research area into the research categories, the expected progress has been made in research.

Report

(8 results)
  • 2023 Ex-post Assessment (Comments) ( PDF )
  • 2022 Final Research Report ( PDF )
  • 2020 Abstract (Interim Assessment) ( PDF )   Interim Assessment (Comments) ( PDF )
  • 2019 Annual Research Report
  • 2018 Abstract ( PDF )   Comments on the Screening Results ( PDF )   Annual Research Report
  • Research Products

    (35 results)

All 2020 2019 2018 Other

All Int'l Joint Research (2 results) Journal Article (7 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 7 results,  Open Access: 2 results) Presentation (26 results) (of which Int'l Joint Research: 20 results,  Invited: 15 results)

  • [Int'l Joint Research] University of Wuerzburg(ドイツ)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Eindhoven University of Technology(オランダ)

    • Related Report
      2019 Annual Research Report
  • [Journal Article] The Effect of Branching on the One‐ and Two‐Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging2019

    • Author(s)
      Griesbeck Stefanie、Michail Evripidis、Rauch Florian、Ogasawara Hiroaki、Wang Chenguang、Sato Yoshikatsu、Edkins Robert M.、Zhang Zuolun、Taki Masayasu、Lambert Christoph、Yamaguchi Shigehiro、Marder Todd B.
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 57 Pages: 13164-13175

    • DOI

      10.1002/chem.201902461

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Near-infrared fluorescein dyes containing a tricoordinate boron atom2019

    • Author(s)
      Ando Naoki、Soutome Hiroki、Yamaguchi Shigehiro
    • Journal Title

      Chemical Science

      Volume: 10 Issue: 33 Pages: 7816-7821

    • DOI

      10.1039/c9sc02314c

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Planarized B,N-phenylated dibenzoazaborine with a carbazole substructure: electronic impact of the structural constraint2019

    • Author(s)
      Ando Mikinori、Sakai Mika、Ando Naoki、Hirai Masato、Yamaguchi Shigehiro
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 17 Issue: 22 Pages: 5500-5504

    • DOI

      10.1039/c9ob00934e

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells2019

    • Author(s)
      Griesbeck Stefanie、Michail Evripidis、Wang Chenguang、Ogasawara Hiroaki、Lorenzen Sabine、Gerstner Lukas、Zang Theresa、Nitsch J?rn、Sato Yoshikatsu、Bertermann R?diger、Taki Masayasu、Lambert Christoph、Yamaguchi Shigehiro、Marder Todd B.
    • Journal Title

      Chemical Science

      Volume: 10 Issue: 20 Pages: 5405-5422

    • DOI

      10.1039/c9sc00793h

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Structurally Constrained Boron-, Nitrogen-, Silicon-, and Phosphorus-Centered Polycyclic π-Conjugated Systems2019

    • Author(s)
      Hirai Masato、Tanaka Naoki、Sakai Mika、Yamaguchi Shigehiro
    • Journal Title

      Chemical Reviews

      Volume: - Issue: 14 Pages: 8291-8331

    • DOI

      10.1021/acs.chemrev.8b00637

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Optimization of Aqueous Stability versus π‐Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live‐Cell Fluorescence Imaging2019

    • Author(s)
      Griesbeck Stefanie、Ferger Matthias、Czernetzi Corinna、Wang Chenguang、Bertermann R?diger、Friedrich Alexandra、Haehnel Martin、Sieh Daniel、Taki Masayasu、Yamaguchi Shigehiro、Marder Todd B.
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 32 Pages: 7679-7688

    • DOI

      10.1002/chem.201900723

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Donor-π-Acceptor Type Unsymmetrical Triarylborane-Based Fluorophores: Synthesis, Fluorescence Properties, and Photostability2018

    • Author(s)
      Ito Masato、Ito Emi、Hirai Masato、Yamaguchi Shigehiro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 15 Pages: 8449-8456

    • DOI

      10.1021/acs.joc.8b01015

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] Main-group π-materials for organic electronics and bioimaging2020

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      17th European Workshop on Phosphorus Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main-group π-materials for organic electronics and bioimaging2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      2019 Russell Lecture, Queen’s University, Canada
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main-Group Strategy toward Functional pi-Materials2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      The 4th PKU-WuXi AppTec Symposium of Organic Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main-Group Approach toward Functional pi-Electon Materials2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      8th SolTech Workshop
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Planarized Boron-Containing pi-Electron Materials2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      The 2nd International Conference on Boron Chemistry (ICBC-2)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main Group Strategy toward Functional pi-Electron Materials2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      The 6th EOC Symposium, Nankai University
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main Group Strategy toward Functional pi-Electron Materials2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      International C-H Functionalization Workshop, KAIST, Korea
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main Group Strategy for Functional pi-Electron Materials2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      NU-UoE JD and JSPS Core-to-Core Joint-Workshop
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main Group-Containing pi-Electron Materials with Structural Constraint2019

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      14th International Symposium on Functional π-Electron Systems
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ホウ素安定化発光性ラジカルの有機電界発光素子への応用2019

    • Author(s)
      伊藤正人,Xie Yongfa,安藤直紀,櫛田知克,白井秀典,早乙女広樹,田畑顕一,宮田康生,北弘志,山口茂弘
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 平面固定フェニルジチエニルボランからなるπ電子系の合成と光物性2019

    • Author(s)
      坂井美佳,平井正人,森正義,安藤直紀,山口茂弘
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 極性溶媒中で高効率発光を示すD-A-A型近赤外蛍光色素の開発2019

    • Author(s)
      杉原圭亮,Thomas Baumgartner,山口茂弘
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ベンジル位水素をもたないアリール基が置換したジチエニルボランの光反応2019

    • Author(s)
      鍛治田浩史,安藤直紀,山口茂弘
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ボラフルオレン骨格をもつ平面固定ホウ素π電子系の合成と物性2019

    • Author(s)
      安藤直紀,山口茂弘
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Emissive Radicals Stabilized by a Boron Atom at a Distant Position2019

    • Author(s)
      Masato Ito, Shunsuke Shirai, Yongfa Xie, Naoki Ando, Hiroki Soutome, Shigehiro Yamaguchi
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] CH/π Interaction-driven Self-assembly of Biphenylanthracene-based Amphiphiles in Aqueous Media2019

    • Author(s)
      Hiroki Narita, Tsuyoshi Nishikawa, Soichiro Ogi, Shigehiro Yamaguchi
    • Organizer
      18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] The Structural Effects of the Red Fluorescent Radicals Stabilized by a Boron Atom at a Distant Position2019

    • Author(s)
      Masato Ito, Shunsuke Shirai, Yongfa Xie, Naoki Ando, Hiroki Soutome, Shigehiro Yamaguchi
    • Organizer
      ITbM-GTR Pre-ISNA Symposium “Toward Advanced Functions form New pi-Skeletons”
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis, Derivatization and Photophysical Properties of Planarized Phenyldithienylborane2019

    • Author(s)
      Mika Sakai, Masato Hirai, Masayoshi Mori, Naoki Ando, Shigehiro Yamaguchi
    • Organizer
      ITbM-GTR Pre-ISNA Symposium "Toward Advanced Functions form New pi-Skeletons"
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Photoreaction of Dithienylborane Stabilized by Bis(trimethylsilyl)phenyl Group2019

    • Author(s)
      Hirofumi Kajita, Naoki Ando, and Shigehiro Yamaguchi
    • Organizer
      ITbM-GTR Pre-ISNA Symposium "Toward Advanced Functions form New pi-Skeletons"
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Properties of Planarized B, N-Embedded Polycyclic Compounds with a Carbazole Substructure2019

    • Author(s)
      Mika Sakai, Mikinori Ando, Masato Hirai, Shigehiro Yamaguchi
    • Organizer
      14th International Symposium on Functional π-Electron Systems
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Phosphorus-Containing Fluorophores for Bioimaging2018

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      ACS National Meeting
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photostable and Near IR Phosphorus Fluorophores for Bioimaging2018

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      22nd International Conference on Phosphorus Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Planarized Boron-Containing pi-Electron Materials2018

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      BORAM XVI
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main-Group Strategy for NIR and Photostable Fluorescent Dyes2018

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      The Chinese University of Hong Kong
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Main-Group Strategy for New pi-Electron Materials2018

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      GRC Hybrid Electronic and Photonic Materials and Phenomena
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Main-Group Strategy toward NIR and Photostable Fluorescent Dyes for Bioimaging2018

    • Author(s)
      Shigehiro Yamaguchi
    • Organizer
      Burgenstock Conference 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited

URL: 

Published: 2018-06-12   Modified: 2024-03-28  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi