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Development and functionalization of NIR-light-responsive diazaporphyrin sensitizers

Research Project

Project/Area Number 18H01961
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionNiigata University

Principal Investigator

Matano Yoshihiro  新潟大学, 自然科学系, 教授 (40231592)

Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2021: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2020: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2019: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2018: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Keywordsアザポルフィリン / 近赤外光 / 一重項酸素 / 酸化還元 / 光線力学療法 / 金属錯体 / ジアザポルフィリン / 鋳型環化 / 水溶性 / 金属触媒 / 医療用増感剤 / ラジカル / 増感剤 / ジアサポルフィリン
Outline of Final Research Achievements

In this research project, we have investigated several subjects concerning the chemistry of azaporphyrins where meso carbons are partially replaced with nitrogen atoms. First, we established several convenient methods for the synthesis of several types of azaporphyrin derivatives. Second, we revealed the aromaticity, optical and electrochemical properties, and singlet-oxygen-generating ability of a series of novel azaporphyrins obtained. Finally, we constructed near-infrared-light-responsive azaporphyrin-based sensitizers and shed light on their potential as functional dyes used for medical application such as photodynamic therapy.

Academic Significance and Societal Importance of the Research Achievements

期間内に実施した研究で、主に三つの成果を手にすることができた。すなわち、(1)アザポルフィリン骨格を構築し、外周部を化学修飾するための簡便な方法の確立、(2)近赤外光に高い感度で応答するアザポルフィリン色素設計指針の確立、(3)光照射により一重項酸素を発生するアザポルフィリン増感剤の開発、である。これらの成果は、広くアザポルフィリンの学理を構築する上で重要な知見となるほか、医療応用への道を拓いた点で社会的な意義が深い。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (36 results)

All 2022 2021 2020 2019 2018

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 1 results) Presentation (25 results) (of which Int'l Joint Research: 5 results,  Invited: 3 results) Book (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Copper(II) Complexes of 10,20-Diaryl-5,15-diazaporphyrin: Alternative Synthesis, Excited State Dynamics, and Substituent Effect on the 1O2-Generation Efficiency2022

    • Author(s)
      Ochiai Hikari、Miura Tomoaki、Ikoma Tadaaki、Minoura Mao、Nakano Haruyuki、Matano Yoshihiro
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 95 Issue: 3 Pages: 427-432

    • DOI

      10.1246/bcsj.20220002

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Hydrophilic Copper(II) Complexes of 5,10,15,20-Tetraaryl-5,15-diazaporphyrins Substituted with Carboxy or (2,3-Dihydroxypropyl)carbamoyl Groups2021

    • Author(s)
      Yuki Shimizu and Yoshihiro Matano
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 25 Issue: 10n12 Pages: 1004-1014

    • DOI

      10.1142/s1088424621500917

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Optical Properties, and Electrochemical Behavior of 5,10,15,20‐Tetraaryl‐5,15‐diazaporphyrin‐Amine Hybrids2021

    • Author(s)
      Satoh Yuna、Fujita Yutaro、Muramatsu Naoya、Furukawa Ko、Ikoma Tadaaki、Minoura Mao、Nakano Haruyuki、Matano Yoshihiro
    • Journal Title

      ChemPlusChem

      Volume: 86 Issue: 10 Pages: 1476-1486

    • DOI

      10.1002/cplu.202100429

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Doubly Strapped Redox-Switchable 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids: Promising Platforms for the Evaluation of Paratropic and Diatropic Ring-Current Effects2021

    • Author(s)
      Ochiai Hikari、Furukawa Ko、Nakano Haruyuki、Matano Yoshihiro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 86 Issue: 3 Pages: 2283-2296

    • DOI

      10.1021/acs.joc.0c02433

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and optical, magnetic, and electrochemical properties of 5,10,15,20-tetraaryl-5,15-diazaporphyrin -- tertiary amine conjugates2020

    • Author(s)
      Sudoh Keisuke、Satoh Yuna、Furukawa Ko、Nakano Haruyuki、Matano Yoshihiro
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 24 Issue: 01n03 Pages: 286-297

    • DOI

      10.1142/s1088424619500822

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Redox-switchable 5,15-Dialkyl-10,20-diaryl-5,15-diazaporphyrins and Diversification of their N-Alkyl Groups2019

    • Author(s)
      Mutoh Mai、Sudoh Keisuke、Furukawa Ko、Minoura Mao、Nakano Haruyuki、Matano Yoshihiro
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 8 Issue: 3 Pages: 352-355

    • DOI

      10.1002/ajoc.201900085

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effects of the Peripheral Substituents, Central Metal, and Solvent on the Photochemical and Photophysical Properties of 5,15-Diazaporphyrins2019

    • Author(s)
      Satoshi Omomo, Ryosuke Fukuda, Tomoaki Miura, Tatsuya Murakami, Tadaaki Ikoma, and Yoshihiro Matano
    • Journal Title

      ChemPlusChem

      Volume: 84 Issue: 6 Pages: 1-7

    • DOI

      10.1002/cplu.201900087

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] β-Functionalization of 5,15-Diazaporphyrins with Phosphorus, Oxygen, and Sulfur-Containing Substituents2018

    • Author(s)
      Sugai Takuma、Minoura Mao、Nakano Haruyuki、Matano Yoshihiro
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 91 Issue: 8 Pages: 1264-1266

    • DOI

      10.1246/bcsj.20180123

    • NAID

      130007434221

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and properties of redox-switchable zinc complexes of 10,15,20-triaryl-15-aza-5-oxaporphyrin2018

    • Author(s)
      Sudoh Keisuke、Furukawa Ko、Nakano Haruyuki、Shimizu Soji、Matano Yoshihiro
    • Journal Title

      Heteroatom Chemistry

      Volume: 29 Issue: 5-6

    • DOI

      10.1002/hc.21456

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] フェニレン架橋5,10,15,20-テトラアリール-5,15-ジアザポルフィリン三量体の合成と物性2022

    • Author(s)
      秋葉健人・藤田裕太郎・俣野善博
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 新規アントラセン連結ポルフィリン誘導体の合成2022

    • Author(s)
      梅宮亜香音・俣野善博
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Air-stable 19π Radicals of 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids and Related Derivatives2021

    • Author(s)
      Yoshihiro Matano
    • Organizer
      11th International Conference on Porphyrins and Phthalocyaninces
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 10,20-ジアリール-5,15-ジアザポルフィリン銅錯体の光物性に対する置換基効果2021

    • Author(s)
      落合ひかり・三浦智明・生駒忠昭・俣野善博
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] トリフェニルアミンと連結した5,10,15-20-テトラアリール-5,15-ジアザポルフィリンの合成と電気化学特性2021

    • Author(s)
      佐藤悠那・藤田裕太郎・村松直哉・中野晴之・生駒忠昭・俣野善博
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ジアザポルフィリン類縁体の光励起高スピン状態の時間分解ESR研究2021

    • Author(s)
      大隣 仁・丸山裕久・落合ひかり・古川 貢・俣野善博
    • Organizer
      第24回ESRフォーラム研究会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 親水性置換基を持つ5,10,15,20-テトラアリール-5,15-ジアザポルフィリン銅(II)錯体の合成と物性2021

    • Author(s)
      清水祐希・俣野善博
    • Organizer
      2021ハロゲン利用ミニシンボジウム
    • Related Report
      2021 Annual Research Report
  • [Presentation] メソ窒素上にアルキル基を持つ5,15-ジアザポルフィリン銅錯体の合成と反応2021

    • Author(s)
      石塚ゆか・俣野善博
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 親水性官能基を持つ5,15-ジアザポルフィリン誘導体の合成と物性2021

    • Author(s)
      清水祐希・俣野善博
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 5,10,15,20-テトラアリール-5,15-ジアザポルフィリンの光物性に対するメソ位置換基の効果2021

    • Author(s)
      藤田裕太郎・俣野善博
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] π平面の上下が化学修飾された5,10,15,20-テトラアリール5,15-ジアザポルフィリン金属錯体の合成と物性2021

    • Author(s)
      落合ひかり・俣野善博
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] メソ窒素上に置換基を持つ5,15-ジアザポルフィリンコバルト錯体の合成と物性2021

    • Author(s)
      佐藤悠那・俣野善博
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 5,15-ジアザポルフィリン銅錯体の光増感反応における置換基効果2020

    • Author(s)
      落合ひかり・渡邊拓未・三浦智明・生駒忠昭・俣野善博
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] トリフェニルアミンと連結した5,10,15,20-テトラアリール-5,15-ジアザポルフィリンの光物性2020

    • Author(s)
      佐藤悠那・中野晴之・俣野善博
    • Organizer
      2020年光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 架橋鎖を持つ5,10,15,20-テトラアリール-5,15-ジアザポルフィリンの合成2020

    • Author(s)
      落合ひかり・中野晴之・俣野善博
    • Organizer
      第80回有機合成化学協会関東支部シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] トリフェニルアミンと連結した5,10,15-20-テトラアリール-5,15-ジアザポルフィリンの合成2020

    • Author(s)
      佐藤悠那・須藤啓祐・俣野善博
    • Organizer
      第80回有機合成化学協会関東支部シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] Synthesis and Properties of Redox-switchable meso-N-Substituted 5,15-Diazaporphyrin Derivatives2019

    • Author(s)
      Yoshihiro Matano
    • Organizer
      18th International Symposium on Novel Aromatic Compounds
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 5,15-ジアザポルフィリン金属錯体の光増感反応に与える置換基と中心金属の効果2019

    • Author(s)
      俣野善博・渡邊拓未・三浦智明・生駒忠昭
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 俣野善博・須藤啓祐・武藤舞・佐藤悠那・古川貢・中野晴之2019

    • Author(s)
      メソ窒素上に置換基をもつ新規5,15-ジアザポルフィリン誘導体の合成、構造、および物性
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 俣野善博・渡邊拓未2019

    • Author(s)
      硫黄およびリンによるジアザポルフィリンの化学修飾
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Functionalization of 5,15-Diazaporphyrins at the Periphery2018

    • Author(s)
      Yoshihiro Matano
    • Organizer
      Supramolecular Chemistry of Nitrogen Heterocyclic Ligands
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Redox-Switchable 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids and Their Derivatives2018

    • Author(s)
      Yoshihiro Matano
    • Organizer
      10th International Conference on Porphyrins and Phthalocyaninces
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Redox Properties of Metal Complexes of 5,10,15,20-Tetraaryl-5,15-diazaporphyrins2018

    • Author(s)
      Yoshihiro Matano, Keisuke Sudoh, Takaharu Satoh
    • Organizer
      43rd International Conference on Coordination Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新規メソ位ヘテロ原子置換ポルフィリン金属錯体の合成と酸化還元挙動2018

    • Author(s)
      須藤啓佑・畠山拓朗・古川 貢・中野晴之・俣野善博
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] メソ位にアルキル基をもつ新規5,15-ジアザポルフィリン誘導体の合成と酸化還元特性2018

    • Author(s)
      武藤 舞・須藤啓佑・古川 貢・中野晴之・俣野善博
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Book] Handbook of Porphyrin Science Vol. 462021

    • Author(s)
      Yoshihiro Matano
    • Total Pages
      71
    • Publisher
      World Scientific
    • ISBN
      9814335495
    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] ジアザポルフィリン錯体2021

    • Inventor(s)
      俣野善博・佐藤悠那・荒牧光紀・大泉淳一・水上潤二
    • Industrial Property Rights Holder
      俣野善博・佐藤悠那・荒牧光紀・大泉淳一・水上潤二
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2021-032190
    • Filing Date
      2021
    • Related Report
      2020 Annual Research Report

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Published: 2018-04-23   Modified: 2023-12-25  

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