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Development of near-infrared light responsive fluorescent diarylethenes

Research Project

Project/Area Number 19H02692
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 32020:Functional solid state chemistry-related
Research InstitutionKumamoto University

Principal Investigator

Fukaminato Tsuyoshi  熊本大学, 大学院先端科学研究部(工), 准教授 (80380583)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,420,000 (Direct Cost: ¥13,400,000、Indirect Cost: ¥4,020,000)
Fiscal Year 2021: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2020: ¥6,630,000 (Direct Cost: ¥5,100,000、Indirect Cost: ¥1,530,000)
Fiscal Year 2019: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000)
Keywordsフォトクロミズム / 近赤外光 / ジアリールエテン / 蛍光 / 可視光フォトクロミズム / 三重項 / 光反応
Outline of Research at the Start

近年、生命現象の光制御や超解像蛍光イメージングへの応用の観点から、紫外光を必要とせず生体の光学的窓となる近赤外光でフォトクロミック反応を示す蛍光スイッチング分子材料の開発が切望されている。
本研究では申請者らが最近見出したスイッチングユニットが吸収を持たない可視域の光で光反応が進行するという特異な現象のメカニズムを解明し、その知見を基に、その波長感受性を近赤外光領域までシフトさせた近赤外光応答型の蛍光スイッチング分子材料を開発することを目的とする。

Outline of Final Research Achievements

In this study. we successfully prepared all-vivible-light activatable fluorescence photoswitching molecule. We found a DAE derivative covalently linked to a fluorescent perylenebisimide (PBI) exhibited unexpected photocyclization reaction upon visible light (500-550 nm) irradiation, where DAE unit has no absorption band. From several detailed experiments, it was suggested that the direct conversion from the excited singlet-state of PBI unit to the excited triplet-state of DAE unit took place upon excitation to the PBI unit.
Furthermore, we also demonstrated reversible and efficient near-infrared fluorescence photoswitching by utilizing the efficient nonlinear fluorescence quenching property in a photochromic nanoparticle state.
It is expected that these results will pave the way for new molecular design to develop visible or near-infrared light switching molecules.

Academic Significance and Societal Importance of the Research Achievements

これまでに提案されてきた可視光応答型のフォトクロミック分子のほとんどが450 nm以下という短い可視領域の光での反応に留まっていた。また、酸素が存在する通常の環境下で使用できない点も大きな障害となっていた。それに対し、本研究で開発した分子は、500 nmを超える長波長側の可視光のみで光反応が起こるだけでなく、酸素存在下においても反応性が全く減少しないことが確認できており、学術的な観点だけでなく応用の観点からも興味深い分子として期待される。
また、近赤外領域の蛍光を効率よくスイッチングできる分子系は今後のバイオイメージング等の分野において重要なツールとして発展していく可能性が十分に期待できる。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • Research Products

    (39 results)

All 2022 2021 2020 2019

All Journal Article (16 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 16 results,  Open Access: 4 results) Presentation (20 results) (of which Int'l Joint Research: 6 results,  Invited: 1 results) Book (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Photo-control of cellular uptake by the selective adsorption of spiropyran derivatives on albumin2022

    • Author(s)
      Mai Shinohara, Wei Xu, Sunnum Kim, Tsuyoshi Fukaminato,Takuro Niidome, Seiji Kurihara
    • Journal Title

      Chemistry Letters

      Volume: 51 Issue: 6 Pages: 594-597

    • DOI

      10.1246/cl.220082

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Photochemical OFF/ON cytotoxicity switching by using a photochromic surfactant with visible light irradiation2022

    • Author(s)
      Mai Shinohara, Yuya Ashikaga, Sunnam Kim, Tuyoshi Fukaminato, Wei Xu, Takuro Niidome, Seiji Kurihara
    • Journal Title

      ACS Omega

      Volume: 7 Issue: 7 Pages: 6093-6098

    • DOI

      10.1021/acsomega.1c06473

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Luminescence Photoswitching of Colloidal CsPbBr3 Nanocrystals by Photochromic Diarylethene Ligands2021

    • Author(s)
      Ashkan Mokhtar, Ryuki Morinaga, Yuji Akaishi, Michio Koinuma, Sunnam Kim, Seiji Kurihara, Tetsuya Kida, Tuyoshi Fukaminato
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 8 Pages: 1534-1538

    • DOI

      10.1246/cl.210254

    • NAID

      130008072840

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Adsorption and release on three-dimensional graphene oxide network structures2021

    • Author(s)
      Sunnam Kim, Sho Moriya, Sakura Maruki, Tuyoshi Fukaminato, Tomonari Ogata, Seiji Kurihara
    • Journal Title

      Royal Society Open Science

      Volume: 8 Issue: 5 Pages: 201585-201585

    • DOI

      10.1098/rsos.201585

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Determining Factor of the Quantum Yield of the Cyclization Reaction via Triplet States for Dye-Attached Diarylethene2021

    • Author(s)
      Shinoda Keiko、Yokojima Satoshi、Fukaminato Tuyoshi、Nakamura Shinichiro
    • Journal Title

      The Journal of Physical Chemistry A

      Volume: 125 Issue: 27 Pages: 5895-5902

    • DOI

      10.1021/acs.jpca.1c02912

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient NIR-I fluorescence photoswitching based on a giant fluorescence quenching in photochromic nanoparticles2021

    • Author(s)
      Shinya Yamasaki, Sanae Ishida, Sunnam Kim, Mihoko Yamada, Takuya Nakashima Tsuyoshi Kawai, Seiji Kurihara, Tuyoshi Fukaminato
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 44 Pages: 5422-5425

    • DOI

      10.1039/d1cc01389k

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 水溶性ミセル型カプセルを利用した疎水性ナノグラフェン分子膜形成2021

    • Author(s)
      織口 咲,村岡 智子,佐々野 仙梨,橋口 春太,深港 豪,吉沢 道人,吉本 惣一郎
    • Journal Title

      表面と真空

      Volume: 64 Issue: 7 Pages: 306-311

    • DOI

      10.1380/vss.64.306

    • NAID

      130008064270

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reversible Luminescence Photoswitching of Colloidal CsPbBr3 Nanocrystals Hybridized with a Diarylethene Photoswitch2020

    • Author(s)
      Mokhtar Ashkan、Morinaga Ryuki、Akaishi Yuji、Shimoyoshi Manami、Kim Sunnam、Kurihara Seiji、Kida Tetsuya、Fukaminato Tuyoshi
    • Journal Title

      ACS Materials Letters

      Volume: 2 Issue: 7 Pages: 727-735

    • DOI

      10.1021/acsmaterialslett.0c00131

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and fluorescence photoswitching of a diarylethene derivative having a dibenzoylmethanato boron difluoride complex2020

    • Author(s)
      Ikariko Issei、Hashimoto Takuma、Kim Sunnam、Kurihara Seiji、Ito Fuyuki、Fukaminato Tuyoshi
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Issue: 29 Pages: 152108-152108

    • DOI

      10.1016/j.tetlet.2020.152108

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly-stable red-emissive photochromic nanoparticles based on a diarylethene-perylenebisimide dyad2020

    • Author(s)
      Ikariko Issei、Deguchi Sei、Fabre Nicolas、Ishida Sanae、Kim Sunnam、Kurihara Seiji、Metivier Remi、Fukaminato Tuyoshi
    • Journal Title

      Dyes and Pigments

      Volume: 180 Pages: 108490-108490

    • DOI

      10.1016/j.dyepig.2020.108490

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Assembling Structures of Diphenylalanine Linked with Dibenzoylmethanatoboron Difluoride Depending on the Solvent as Probed by Fluorescence Changes2020

    • Author(s)
      Katsumi Shiho、Sagawa Takehiro、Fukaminato Tsuyoshi、Ito Fuyuki
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 7 Pages: 802-805

    • DOI

      10.1246/cl.200215

    • NAID

      130007872567

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Multi-color fluorescence photoswitching in fluorescent diarylethene nanoparticles2019

    • Author(s)
      Ishida, Sanae, Kim, Sunnam, Kurihara, Seiji, Fukaminato, Tuyoshi.
    • Journal Title

      Proceedings of SPIE - The International Society for Optical Engineering

      Volume: 11098 Pages: 25-25

    • DOI

      10.1117/12.2531350

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorescence modulation and non-destructive fluorescence readout based on the cooperative orientation of a fluorescent dye in an azobenzene liquid crystalline polymer film2019

    • Author(s)
      Fukaminato, Tuyoshi, Kato, Tomoe, Kim, Sunnam, Kurihara, Seiji
    • Journal Title

      Proceedings of SPIE - The International Society for Optical Engineering

      Volume: 11098, Pages: 1109806-1109806

    • DOI

      10.1117/12.2531352

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Reversible ON/OFF switching of photoluminescence from CsPbX3 quantum dots coated with silica using photochromic diarylethene2019

    • Author(s)
      Akaishi Y, Pramata A. D, Tominaga S, Kawashima S, Fukaminato T, Kida T
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 56 Pages: 8060-8063

    • DOI

      10.1039/c9cc03797g

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Efficient “turn-off” fluorescence photoswitching in a highly fluorescent diarylethene single crystal2019

    • Author(s)
      Sanae Ishida, Daichi Kitagawa, Seiya Kobatake, Sunnam Kim, Seiji Kurihara, Tuyoshi Fukaminato
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 40 Pages: 5681-5684

    • DOI

      10.1039/c9cc02441g

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Optical trapping of nanoparticles using dimer and trimer plasmonic nanogap antennas2019

    • Author(s)
      Pin Christophe, Takahashi Gen, Fujikawa Seiya, Sudo Kota, Fukaminato Tuyoshi, Sasaki Keiji
    • Journal Title

      Proceedings of SPIE - The International Society for Optical Engineering

      Volume: 11141

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] フッ化アルキル基を有するシランカップリング剤を用いたジアリールエテン複合ペロブスカイト型量子ドットの発光スイッチング2022

    • Author(s)
      モクタール アシカン、明石 優志、金 善南、栗原 清二、木田 徹也、深港 豪
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 蛍光色素連結ジアリールエテンの可視光フォトクロミズム2022

    • Author(s)
      碇子 壱成、金 善南、栗原 清二、深港 豪
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ペリレンビスイミド連結ジアリールエテンの可視光フォトクロミズムにおける重原子効果2022

    • Author(s)
      垂野航也、金善南、栗原清二、深港豪
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Photoluminescence photoswitching of perovskite quantum dots having photochromic diarylethene ligands2021

    • Author(s)
      MOKHTAR, Ashkan; MORINAGA, Ryuki; AKAISHI, Yuji; KIM, Sunnam; KURIHARA, Seiji; KIDA, Tetsuya; FUKAMINATO, Tsuyoshi
    • Organizer
      2021年光化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 単一成分で黒く着色するジアリールエテン誘導体の合成2021

    • Author(s)
      坂西 麻未、佐藤 文紀、太田 最実、鍋谷 俊太、上久保 真紀、前橋 亮太、小原 朋也、金 善南、栗原 清二、深港 豪
    • Organizer
      2021年光化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ペリレンビスイミド連結ジアリールエテンの可視光閉環反応の長波長化2021

    • Author(s)
      碇子 壱成、金 善南、栗原 清二、深港 豪
    • Organizer
      2021年光化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Visible-light induced photocylization reaction in diarylethene-perylenebisimide dyads2021

    • Author(s)
      Tsuyoshi Fukaminato, Issei Ikariko, Sunnam Kim, Seiji Kurihara, Kenji Higashiguchi, Takashi Hirose, Kenji Matsuda, Hikaru Sotome, Hiroshi Miyasaka
    • Organizer
      Pacifichem 2020
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 有機溶媒中で粒子化する水溶性ジアリールエテンの蛍光スイッチング2020

    • Author(s)
      石田 沙奈恵・金 善南・栗原 清二・深港 豪
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ペリレンビスイミド連結ジアリールエテンの可視光フォトクロミズムに及ぼすスペーサーユニットの影響2020

    • Author(s)
      碇子壱成、東口顕示、広瀬崇、五月女光、金善南、松田建児、宮坂博、栗原清二、深港豪
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ジアリールエテンを配位子 として有するペロブスカイト型量子ドット複合体の発光スイッチング2020

    • Author(s)
      森永竜樹、モクタール アシカン、明石 優志、金 善南、栗原清二、木田 徹也、深港 豪
    • Organizer
      2020年日本化学会九州支部秋期研究発表会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 高ねじり力を有する新規キラル分子の開発2020

    • Author(s)
      坂井李帆、金善南、深港豪、前橋亮太、甲斐康郎、佐藤文紀、太田最実、栗原清二
    • Organizer
      2020年日本化学会九州支部秋期研究発表会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 光応答性界面活性剤を用いた細胞毒性の光制御2020

    • Author(s)
      足利友弥、篠原真衣、金善南、深港豪、新留琢朗、栗原清二
    • Organizer
      2020年日本化学会CSJフェスタ
    • Related Report
      2020 Annual Research Report
  • [Presentation] 逆フォトクロミズム性スピロピランを用いた細胞膜透過性制御システムについて2020

    • Author(s)
      篠原真衣、足利友弥、金善南、深港豪、新留琢朗、栗原清二
    • Organizer
      2020年日本化学会CSJフェスタ
    • Related Report
      2020 Annual Research Report
  • [Presentation] Reversible Photoluminescence Switching of CsPbBr3 Quantum Dots Hybridized with a Diarylethene Photoswitch2020

    • Author(s)
      Ashkan Mokhtar, Ryuki Morinaga, Yuji Akaishi, Manami Shimoyoshi, Sunnam Kim, Seiji Kurihara, Tetsuya Kida, Tuyoshi Fukaminato
    • Organizer
      The 15th International Student Conference on Advanced Science and Technology (ICAST) 2020 Online Kumamoto
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reversible Luminescence Photoswitching of Perovskite Quantum Dots Hybridized with a Diarylethene Photoswitch2020

    • Author(s)
      Ashkan Mokhtar, Ryuki Morinaga, Yuji Akaishi, Manami Shimoyoshi, Sunnam Kim, Seiji Kurihara, Tetsuya Kida, Tuyoshi Fukaminato
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 超高感度な蛍光スイッチング特性を有する蛍光性フォトクロミック分子材料の開発2019

    • Author(s)
      深港 豪
    • Organizer
      2019年度高分子・ハイブリッド材料研究センター(PHyM)若手フォーラム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Efficient fluorescence photoswitching in photochromic nanoparticles and single crystals2019

    • Author(s)
      Tsuyoshi Fukaminato, Sanae Ishida, Daichi Kitagawa, Seiya Kobatake, Remi Metivier
    • Organizer
      9th International Symposium on Photochromism (ISOP 2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Visible-light photochromism of a perylenebisimide-diarylethene dyad2019

    • Author(s)
      Issei Ikariko, Kenji Higashiguchi, Takashi Hirose, Hikaru Sotome, Sunnam Kim, Kenji Matsuda, Hiroshi Miyasaka, Seiji Kurihara, Tsuyoshi Fukaminato
    • Organizer
      9th International Symposium on Photochromism (ISOP 2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reversible fluorescence photoswitching based on the cooperative orientation in a dye-doped liquid crystalline azobenzene polymer2019

    • Author(s)
      Tomoe Kato, Sunnam Kim, Seiji Kurihara, Tsuyoshi Fukaminato
    • Organizer
      9th International Symposium on Photochromism (ISOP 2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Fluorescence modulation with photochromic-fluorescent nanosystems2019

    • Author(s)
      Nicolas Fabre, Tsuyoshi Fukaminato, Katsuya Mutoh, Jiro Abe, Remi Metivier
    • Organizer
      9th International Symposium on Photochromism (ISOP 2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Book] Photosynergetic Responses in Molecules and Molecular Aggregates, Chapter 202020

    • Author(s)
      Tuyoshi Fukaminato, Sanae Ishida, Su Jia, Keitaro Nakatani, Remi Metivier
    • Total Pages
      14
    • Publisher
      Springer, Singapore
    • ISBN
      9789811554506
    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] フォトクロミック化合物2021

    • Inventor(s)
      深港豪、他6名
    • Industrial Property Rights Holder
      深港豪、他6名
    • Industrial Property Rights Type
      特許
    • Filing Date
      2021
    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 表示装置2019

    • Inventor(s)
      栗原清二、深港 豪、佐藤文紀、甲斐康朗、太田最実、前橋亮太
    • Industrial Property Rights Holder
      栗原清二、深港 豪、佐藤文紀、甲斐康朗、太田最実、前橋亮太
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2019 Annual Research Report

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Published: 2019-04-18   Modified: 2023-01-30  

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