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Extended Pyrazinacenes as a New Class of Near-Infrared Emissive Materials for Potential Bioimaging Applications

Research Project

Project/Area Number 21K05044
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionShibaura Institute of Technology

Principal Investigator

RICHARDS GARY  芝浦工業大学, 工学部, 准教授 (00708620)

Co-Investigator(Kenkyū-buntansha) 堀 顕子  芝浦工業大学, 工学部, 教授 (90433713)
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: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2022: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2021: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
KeywordsPyrazinacenes / Near Infrared / Fluorescence / Cellular Imaging / Bioimaging / Acenes / Azaacenes / Near Infrared Emitters / REDOX / Cellular imaging / Near infrared absorption
Outline of Research at the Start

Chromophore-based bioimaging techniques rely on the availability of dyes that are emissive in regions of the electromagnetic spectrum not obscured by absorptive processes of biomolecules or water. Thus, dyes emitting in the near-infrared transparency window region of tissues from 650 to 900 nm are useful for imaging. This project aims to develop a new class of highly efficient near infra-red emitting materials based on extended pyrazinacenes - molecules built with linearly fused pyrazine units.

Outline of Final Research Achievements

An extended pyrazinacenes consisting of 7 rectilinearly fused pyrazine units appended with hydrophilic triethylene glycol groups was synthesised. The synthesis of the compound and its purification was optimized. The compound was used in cellular imaging studies in the near-infrared region. Interestingly, this new fluorescent dye can distinguish DNA and RNA cellular structures by simply changing excitation and observation wavelengths.
Redox-active pyrazinacenes consisting of four or five fused pyrazine rings appended with electron-donating triphenylamine groups were synthesized. These compounds exhibit redox-coupled fluorescence switching between visible and near infrared or shortwave infrared regions. We are now developing related compounds as new types of probes for biological and cellular redox states.

Academic Significance and Societal Importance of the Research Achievements

細胞イメージングは、生物学、医学、薬学研究において非常に重要な分野である。近赤外領域に活性を持つ蛍光分子を用いることで、細胞を傷つけることなく、長期間にわたって細胞のプロセスを研究することが可能になる。近赤外領域に活性を持つ蛍光色素の多くは、蛍光量子収率の低さや光退色という問題を抱えている。本研究では、これらの問題を克服する新しいタイプの近赤外蛍光分子の開発を目指す。

Report

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

    (18 results)

All 2024 2023 2022 2021

All Journal Article (5 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 5 results,  Open Access: 1 results) Presentation (12 results) (of which Int'l Joint Research: 4 results,  Invited: 4 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Protic Processes in an Extended Pyrazinacene: The Case of Dihydrotetradecaazaheptacene2024

    • Author(s)
      Cador A、Kahlal Samia、Richards Gary J.、Halet Jean-Francois、Hill Jonathan P.
    • Journal Title

      Molecules

      Volume: 29 Issue: 10 Pages: 2407-2407

    • DOI

      10.3390/molecules29102407

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Pyrazinacenes as a New Class of Highly Fluorescent REDOX Active Chromophores2023

    • Author(s)
      RICHARDS Gary J.、AOKI Keita、AKIBAYASHI Daiki、TAMBOLI Majid、HILL Jonathan P.、HORI Akiko
    • Journal Title

      Journal of the Japan Society of Colour Material

      Volume: 96 Issue: 4 Pages: 131-136

    • DOI

      10.4011/shikizai.96.131

    • ISSN
      0010-180X, 1883-2199
    • Year and Date
      2023-04-20
    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Mechanical Manipulation of Archimedean Spirals of an Achiral Pyrazinacene for Chiral Assemblies2022

    • Author(s)
      Mondal Pramita、Manna Gouranga、Kamilya Tapas、Das Mrinmay、Ariga Katsuhiko、Richards Gary J.、Hill Jonathan P.、Acharya Somobrata
    • Journal Title

      Advanced Materials Interfaces

      Volume: 9 Issue: 22 Pages: 2200209-2200209

    • DOI

      10.1002/admi.202200209

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Pyrazinacene luminescence enhancement by heat-activated surface adsorption and de-aggregation in a saponite colloidal system2022

    • Author(s)
      Monika SUTEKOVA, Martinc BARLOG, Timea S. BARANYAIOVA, Robert KLEMENT, Gary J. RICHARDS, Jonathan P. HILL, Jan LABUTA, Juraj BUJDAK
    • Journal Title

      Applied Clay Science

      Volume: 218 Pages: 106413-106413

    • DOI

      10.1016/j.clay.2022.106413

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] The Pyrazinacenes2021

    • Author(s)
      Gary J. RICHARDS, Jonathan P. HILL
    • Journal Title

      Accounts of Chemical Research

      Volume: 54 Issue: 16 Pages: 3228-3240

    • DOI

      10.1021/acs.accounts.1c00315

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Extended Pyrazinacenes: Highly Fluorescent NIR Chromophores for Bioimaging Applications2024

    • Author(s)
      RICHARDS Gary J.
    • Organizer
      Catalysis and Sensing for Our Environment (CASE2024)
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] Donor-Appended Pyrazinacenes - Switching Absorption and Fluorescence from Visible to Near Infrared Region Through a Simple REDOX Process.2024

    • Author(s)
      RICHARDS, Gary J.; AOKI Keita; KANEHISA Kou; NAKADA Kazushi; NAKAMURA; HILL Jonathan P.; HORI Akiko
    • Organizer
      104th Chemical Society of Japan Annual Meeting
    • Related Report
      2023 Annual Research Report
  • [Presentation] Revealing RNA Secrets: Extended Pyrazinacene Shines Light on Spatial Heterogeneities of Photodamaged Cells2023

    • Author(s)
      SUTRISNO Linawati; RICHARDS Gary J.; MATSUMOTO Michio; UTO Koichiro; TAKI Masayasu; YAMAGUCHI Shigehiro; HILL Jonathan, P.; ARIGA Katsuhiko
    • Organizer
      MANA International Symposium 2023
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pyrazinacenes - REDOX Switchable Near-Infrared Absorption and Efficient Fluorescence in Highly Nitrogenated Acene Analogues2023

    • Author(s)
      RICHARDS Gary J.; AOKI Keita; AKIBAYASHI Daiki; TAMBOLI Majid; NAKADA; HILL Jonathan; HORI Akiko
    • Organizer
      22nd European Symposium of Organic Chemistry
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Triphenylamine Donor Appended Pyrazinacenes - Their Synthesis and Spectroscopic Properties2023

    • Author(s)
      NAKADA Kazushi; AOKI Keita; HASHIMOTO K.; TAJIMA T.; HORI Akiko, RICHARDS Gary J.
    • Organizer
      22nd European Symposium of Organic Chemistry
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pyrazinacenes appended with electron-rich substituents and their REDOX dependant photophysical properties2022

    • Author(s)
      Gary James RICHARDS, Keita AOKI, Daiki AKIBAYASHI, Majid TAMBOLI, Akiko HORI
    • Organizer
      Symposium of Host Guest and Supramolecular Chemistry (SHGSC) 2022
    • Related Report
      2022 Research-status Report
  • [Presentation] Pyrazinacenes as a new class of highly fluorescent REDOX active chromophores2022

    • Author(s)
      Gary James RICHARDS, Keita AOKI, Daiki AKIBAYASHI, Majid TAMBOLI, Jonathan HILL, Akiko HORI
    • Organizer
      The 95th Japan Society of Colour Material Anniversary Conference
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] Redox-Dependent Photophysical and On-Surface Self-Assembling Properties of Pyrazinacenes2022

    • Author(s)
      Gary James RICHARDS
    • Organizer
      Division of Colloid and Interface Sciences Summer Symposium
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] Decaazapentacenes appended with electron-rich triphenylamine and phenanthrene units - their redox-coupled photophysical and self-assembling properties.2022

    • Author(s)
      Gary J. RICHARDS, Majid TAMBOLI, Keita AOKI, Jonathan P. HILL, Akiko HORI
    • Organizer
      102nd Chemical Society of Japan Annual Meeting
    • Related Report
      2021 Research-status Report
  • [Presentation] Synthesis and physical properties of octaazatetracene derivatives with bulky triphenylamine2022

    • Author(s)
      Keita AOKI, Tomoki JITSUKATA, Akiko HORI, Jonathan P. HILL, Gary J. RICHARDS
    • Organizer
      102nd Chemical Society of Japan Annual Meeting
    • Related Report
      2021 Research-status Report
  • [Presentation] The Pyrazinacenes2022

    • Author(s)
      Jonathan P. HILL, Gary J. RICHARDS, David MIKLIK
    • Organizer
      Aromatic Heterocycles: A wonderful pool of organic materials
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] Photoredox Photophysical Properties, Liquid Crystalline Behaviour and Activity of Phenanthrene-Terminated Pyrazinacenes2021

    • Author(s)
      Gary J. RICHARDS, Jonathan P. Hill, Akiko HORI
    • Organizer
      Pacifichem 2020
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Patent(Industrial Property Rights)] Novel near-infrared emitting materials for real-time fluorescence imaging2023

    • Inventor(s)
      L. SUSTRINO; G. J. RICHARDS
    • Industrial Property Rights Holder
      L. SUSTRINO; G. J. RICHARDS
    • Industrial Property Rights Type
      特許
    • Filing Date
      2023
    • Related Report
      2023 Annual Research Report

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

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