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Development of functional dyes for near infrared region

Research Project

Project/Area Number 16K05826
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Analytical chemistry
Research InstitutionNagahama Institute of Bio-Science and Technology

Principal Investigator

Shin-ichi Sasaki  長浜バイオ大学, バイオサイエンス学部, 教授 (50317294)

Research Collaborator TAMIAKI hitoshi  
SUZUKI koji  
IKEUCHI toshitaka  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords近赤外 / クロロフィル / 発光 / バイオセンシング / 光合成 / 色素 / エネルギー移動 / 自己会合 / 太陽電池 / ナノ粒子 / 有機化学 / 超分子化学 / 分子認識 / 分析科学
Outline of Final Research Achievements

To develop functional dyes in the Near-Infrared (NIR) region, several chlorophyll derivatives were designed and synthesized. 1) A series of chlorins were employed for fluorescent organic nanoparticles with Pluronic F127 as the encapsulation matrix, and successfully used for cancer cell imaging. 2) The chemiluminescence of coelenterazine, Renilla reniformis luciferase, was largely red-shifted to NIR region by intramolecular energy transfer in coelenterazine/chlorin conjugate. 3) Chlorin-indoline dyad having an excellent light absorption ability over the whole visible range was synthesized, and applied as photocatalyst for hydrogen evolution.

Academic Significance and Societal Importance of the Research Achievements

光による医療診断への応用を目的として発光プローブを開発する際には、「生体の光学的窓」と呼ばれる近赤外(NIR)領域の波長利用が望まれる。本研究ではクロロフィル誘導体を合成し、NIR領域でのがん細胞イメージング蛍光色素として活用できることを示し、またクロロフィルと結合させることでウミシイタケの発光基質セレンテラジンの発光ピークの長波長にも成功した。これらの分子設計は天然色素の活用例として学術的意義があり、また開発したNIR領域の機能性色素はバイオセンシングの分野に大きなインパクトを与えるものと期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (21 results)

All 2019 2018 2017 2016

All Journal Article (13 results) (of which Int'l Joint Research: 10 results,  Peer Reviewed: 13 results,  Acknowledgement Compliant: 3 results) Presentation (8 results) (of which Int'l Joint Research: 5 results)

  • [Journal Article] Effects of cyclic tetrapyrrole rings of aggregate-forming chlorophyll derivatives as hole-transporting materials on performance of perovskite solar cells2018

    • Author(s)
      M. Li, N. Li, W. Hu, S. Sasaki, K. Sakai, T. Ikeuchi, T. Miyasaka, H. Tamiaki, G. Chen, X.-F. Wang
    • Journal Title

      ACS Appl. Energy Mater.

      Volume: 1 Issue: 1 Pages: 9-16

    • DOI

      10.1021/acsaem.7b00018

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Biosupramolecular bacteriochlorin aggregates as hole-transporters for perovskite solar cells2018

    • Author(s)
      M. Li, S. Sasaki, Y. Sanehira, T. Miyasaka, H. Tamiaki, T. Ikeuchi, G. Chen, X.-F. Wang
    • Journal Title

      J. Photochem. Photobiol. A: Chem.

      Volume: 353 Pages: 639-644

    • DOI

      10.1016/j.jphotochem.2017.08.051

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Azide- and Dye-Conjugated Coelenterazine Analogues for a Multiplex Molecular Imaging Platform2018

    • Author(s)
      Ryo Nishihara, Emi Hoshino, Yoshiki Kakudate, Satoshi Kishigami, Naoko Iwasawa, Shin-ichi Sasaki, Takahiro Nakajima, Moritoshi Sato, Shigeru Nishiyama, Daniel Citterio, Koji Suzuki, Sung Bae Kim
    • Journal Title

      Bioconjugate Chemistry (ACS)

      Volume: 印刷中 Issue: 6 Pages: 1922-1931

    • DOI

      10.1021/acs.bioconjchem.8b00188

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enhancement of performance in chlorophyll-based bulk-heterojunction organic-inorganic solar cells upon aggregate management via solvent engineering2018

    • Author(s)
      Zhao Wenjie、Sasaki Shin-ichi、Tamiaki Hitoshi、Sanehira Yoshitaka、Wei Yingjin、Chen Gang、Wang Xiao-Feng
    • Journal Title

      Organic Electronics

      Volume: 59 Pages: 419-426

    • DOI

      10.1016/j.orgel.2018.05.041

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Dyad Sensitizer of Chlorophyll with Indoline Dye for Panchromatic Photocatalytic Hydrogen Evolution2018

    • Author(s)
      Sun Yuan、Sun Yuliang、Dall’Agnese Chunxiang、Wang Xiao-Feng、Chen Gang、Kitao Osamu、Tamiaki Hitoshi、Sakai Kotowa、Ikeuchi Toshitaka、Sasaki Shin-ichi
    • Journal Title

      ACS Applied Energy Materials

      Volume: 1 Issue: 6 Pages: 2813-2820

    • DOI

      10.1021/acsaem.8b00380

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Bilayer Chlorophyll-Based Biosolar Cells Inspired from the Z-Scheme Process of Oxygenic Photosynthesis2018

    • Author(s)
      Duan Shengnan、Dall’Agnese Chunxiang、Chen Gang、Wang Xiao-Feng、Tamiaki Hitoshi、Yamamoto Yuya、Ikeuchi Toshitaka、Sasaki Shin-ichi
    • Journal Title

      ACS Energy Letters

      Volume: 3 Issue: 7 Pages: 1708-1712

    • DOI

      10.1021/acsenergylett.8b00797

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Pluronic micelle-encapsulated red-photoluminescent chlorophyll derivative for biocompatible cancer cell imaging2017

    • Author(s)
      Li Yue、Zhang Fengli、Wang Xiao-Feng、Chen Gang、Fu Xueqi、Tian Wenjing、Kitao Osamu、Tamiaki Hitoshi、Sasaki Shin-ichi
    • Journal Title

      Dyes and Pigments

      Volume: 136 Pages: 17-23

    • DOI

      10.1016/j.dyepig.2016.08.018

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Near-infrared absorption carboxylated chlorophyll- a derivatives for biocompatible dye-sensitized hydrogen evolution2017

    • Author(s)
      Sun Yuan、Wang Xiao-Feng、Chen Gang、Zhan Cong-Hong、Kitao Osamu、Tamiaki Hitoshi、Sasaki Shin-ichi
    • Journal Title

      International Journal of Hydrogen Energy

      Volume: 42 Issue: 24 Pages: 15731-15738

    • DOI

      10.1016/j.ijhydene.2017.04.265

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chlorophyll-Based Organic-Inorganic Heterojunction Solar Cells2017

    • Author(s)
      Li Yue、Zhao Wenjie、Li Mengzhen、Chen Gang、Wang Xiao-Feng、Fu Xueqi、Kitao Osamu、Tamiaki Hitoshi、Sakai Kotowa、Ikeuchi Toshitaka、Sasaki Shin-ichi
    • Journal Title

      Chemistry - A European Journal

      Volume: 23 Issue: 45 Pages: 10886-10892

    • DOI

      10.1002/chem.201701858

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Near-infrared absorption bacteriochlorophyll derivatives as biomaterial electron donor for organic solar cells2017

    • Author(s)
      Duan Shengnan、Chen Guo、Li Mengzhen、Chen Gang、Wang Xiao-Feng、Tamiaki Hitoshi、Sasaki Shin-ichi
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 347 Pages: 49-54

    • DOI

      10.1016/j.jphotochem.2017.07.014

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Visible and near-infrared spectra of chlorosomal zinc chlorin self-aggregates dependent on their peripheral substituents at the 8-position2016

    • Author(s)
      S. Matsubara, M. Kunieda, A. Wada, S. Sasaki, H. Tamiaki
    • Journal Title

      J. Photochem. Photobiol. A: Chem.

      Volume: 330 Pages: 195-199

    • DOI

      10.1016/j.jphotochem.2016.07.028

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Dopant-Free Zinc Chlorophyll Aggregates as Efficient Biocompatible Hole-Transporter for Perovskite Solar Cells2016

    • Author(s)
      Mengzhen Li, Yue Li, Shin-ichi Sasaki, Jiaxing Song, Chen Wang, Hitoshi Tamiaki, Wenjing Tian, Gang Chen, Tsutomu Miyasaka, and Xiao-Feng Wang
    • Journal Title

      ChemSusChem

      Volume: 9 Issue: 19 Pages: 2862-2869

    • DOI

      10.1002/cssc.201601069

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Rotational isomerization of 3-substituents in synthetic chlorophyll derivatives2016

    • Author(s)
      H. Tamiaki, K. Mizutani, S. Sasaki, T. Tatebe
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 42 Pages: 6626-6633

    • DOI

      10.1016/j.tet.2016.08.079

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 異なる17位側鎖を有するバクテリオクロロフィル-a誘導体の合成と太陽電池素材としての性能評価2019

    • Author(s)
      酒井琴和、Shengnan Duan、王暁峰、藤井律子、山野由美子、池内俊貴、佐々木真一
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] クロロフィル誘導体の3層構造を基盤とする太陽電池2019

    • Author(s)
      佐々木真一、酒井琴和、Wenjie Zhao、陳春香、Shengnan Duan、民秋均、王暁峰
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Effects of Solvent for Construction of Chlorophyll-Based Bulk-Heterojunction Organic-Inorganic Solar Cells2018

    • Author(s)
      Shin-ichi Sasaki, Wenjie Zhao, Hitoshi Tamiaki, and Xiao-Feng Wang
    • Organizer
      14th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP18)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Bilayer Chlorophyll-Based Solar Cells Mimicking the Z-Scheme Process of Oxygenic Photosynthesis2018

    • Author(s)
      Yuya Yamamoto, Shengnan Duan, Xiao-Feng Wang, Hitoshi Tamiaki, Toshitaka Ikeuchi, and Shin-ichi Sasaki
    • Organizer
      14th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP18)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Self-Assembling J-Aggregates of Semi-Synthetic Bacteriochlorins as Hole-Transporting Materials for Perovskite Solar Cells2017

    • Author(s)
      Shin-ichi Sasaki, Mengzhen Li, Tsutomu Miyasaka, Hitoshi Tamiaki, Toshitaka Ikeuchi, and Xiao-Feng Wang
    • Organizer
      2017 International Conference on Artificial Photosynthesis (ICARP2017)
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2017-03-02
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Construction of Solid-State Chlorophyll-Based Solar Cells2017

    • Author(s)
      Kotowa Sakai, Yue Li, Wenjie Zhao, Mengzhen Li, Gang Chen, Xiao-Feng Wang, Xueqi Fu, Hitoshi Tamiaki, Toshitaka Ikeuchi, and Shin-ichi Sasaki
    • Organizer
      13th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP17)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Free-Base Chlorophyll and Bacteriochlorophyll Derivatives as Electron Donor for Organic Solar Cells2017

    • Author(s)
      Shin-ichi Sasaki, Shengnan Duan, Guo Chen, Mengzhen Li, Gang Chen, Kotowa Sakai, Toshitaka Ikeuchi, Hitoshi Tamiaki, and Xiao-Feng Wang
    • Organizer
      13th International Workshop on Supramolecular Nanoscience of Chemically Programmed Pigments (SNCPP17)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 光合成色素を素材とする太陽電池用ホール輸送材の開発2017

    • Author(s)
      佐々木真一、李梦真、民秋均、王暁峰
    • Organizer
      第36回 固体・表面光化学討論会
    • Related Report
      2017 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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