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Development of Novel Porphyrinoids with Heterole-fused Structure

Research Project

Project/Area Number 15K17822
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

Higashino Tomohiro  京都大学, 工学研究科, 助教 (90711804)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsポルフィリン / ピロール / 典型元素 / リン / チオフェン / ホスホール / ポルフィリノイド / 有機化学 / 典型元素化学
Outline of Final Research Achievements

We synthesized phosphole-fused porphyrin dimer for the first time as a representative of a new class of porphyrins with a phosphorus atom. This porphyrin dimer possesses excellent electron-accepting character. Then, we synthesized octaphyrins with a dithieno[3,4-b:3',4'-d]thiophene unit as thiophene-fused dithiaoctaphyrin. The octaphyrins revealed cross-conjugated and macrocyclic 36π-electron networks.
In addition, we synthesized dithieno[3,4-b:3',4'-d]phosphole derivatives as a new type of thiophene-fused phopholes. They exhibit the unique hybrid character of electron-withdrawing phosphole and electron-donating thiophene.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (18 results)

All 2018 2017 2016 2015

All Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (10 results) (of which Invited: 1 results)

  • [Journal Article] Phosphole-Thiophene Hybrid: A Dual Role of Dithieno[3,4-b:3′,4′-d]phosphole as Electron Acceptor and Electron Donor2018

    • Author(s)
      Tomohiro Higashino, Keiichi Ishida, Takaharu Satoh, Yoshihiro Matano, Hiroshi Imahori
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 6 Pages: 3397-3402

    • DOI

      10.1021/acs.joc.8b00030

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hexaphyrin as a potential theranostic dye for photothermal therapy and 19F magnetic resonance imaging2017

    • Author(s)
      Tomohiro HIGASHINO, Hirotaka NAKATSUJI, Ryosuke FUKUDA, Haruki OKAMOTO, Hirohiko IMAI, Tetsuya Matsuda*, Hidehito TOCHIO, Masahiro SHIRAKAWA*, Nikolai V. TKACHENKO, Mitsuru HASHIDA, Tatsuya MURAKAMI*, and Hiroshi IMAHORI*
    • Journal Title

      Chembiochem

      Volume: - Issue: 10 Pages: 951-959

    • DOI

      10.1002/cbic.201700071

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis of Partially meso-Free 2,3-Di(arylethynyl)porphyrins2017

    • Author(s)
      T. Higashino, Y. Ohashi, and H. Imahori
    • Journal Title

      Chem. Lett.

      Volume: 46 Issue: 7 Pages: 976-978

    • DOI

      10.1246/cl.170350

    • NAID

      130005709495

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Hydroxamic Acid Anchoring Group for Durable Dye-Sensitized Solar Cells Incorporating a Cobalt Redox Shuttle2017

    • Author(s)
      T. Higashino, Y. Kurumisawa, N. Cai, Y. Fujimori, Y. Tsuji, S. Nimura, D. Packwood, J. Park, and H. Imahori
    • Journal Title

      ChemSusChem

      Volume: 10 Issue: 17 Pages: 3347-3351

    • DOI

      10.1002/cssc.201701157

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photovoltaic Properties and Long-Term Durability of Porphyrin-Sensitized Solar Cells with Silicon-Based Anchoring Groups2017

    • Author(s)
      T. Higashino, S. Nimura, K. Sugiura, Y. Kurumisawa, Y. Tsuji, and H. Imahori
    • Journal Title

      ACS Omega

      Volume: 2 Issue: 10 Pages: 6958-6967

    • DOI

      10.1021/acsomega.7b01290

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Thiophene-fused dithiaoctaphyrins: π-system switching between cross-conjugated and macrocyclic π-networks2017

    • Author(s)
      Tomohiro Higashino, Atsushi Kumagai, Hiroshi Imahori
    • Journal Title

      Chemical Communications

      Volume: 印刷中 Issue: 37 Pages: 5091-5094

    • DOI

      10.1039/c7cc01273j

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Fusing Porphyrins and Phospholes: Synthesis and Analysis of a Phosphorus-Containing Porphyrin2016

    • Author(s)
      T. Higashino, T. Yamada, T. Sakurai, S. Seki and H. Imahori
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 40 Pages: 12311-12315

    • DOI

      10.1002/anie.201607417

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hybrid [5]Radialenes with Bispyrroloheteroles: New Electron-Donating Units2015

    • Author(s)
      Tomohiro Higashino, Hiroshi Imahori
    • Journal Title

      Chemisty - A European Journal

      Volume: 21 Issue: 38 Pages: 13375-13381

    • DOI

      10.1002/chem.201501822

    • NAID

      120005672558

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] アクセプターおよびドナーの両性質を有するジチエノホスホールの合成2018

    • Author(s)
      石田圭一、東野智洋、今堀博
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ホスホール架橋ポルフィリンダイマーの合成と物性2018

    • Author(s)
      西村一晟、東野智洋、今堀博
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis of Thiophene-fused Thiahexaphyrin and Its Moebius Aromaticity2018

    • Author(s)
      Tomohiro Higashino, Atsushi Kumagai, Hiroshi Imahori
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of Porphyrinoids with Radialene-type Heteroles2018

    • Author(s)
      東野智洋
    • Organizer
      Reaxys Prize Clubシンポジウム in Japan 2018
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] チオフェン縮環ジチアオクタフィリンの合成と物性2017

    • Author(s)
      熊谷篤、東野智洋、今堀博
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜 慶應義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] チオフェン縮環ジチアオクタフィリンの酸化による共役系のスイッチングと光学特性の変化2017

    • Author(s)
      熊谷篤、東野智洋、今堀博
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 高耐久性トリエトキシシリル吸着基を導入した新規プッシュ-プル型ポルフィリンの合成と太陽電池特性2017

    • Author(s)
      二村晋平、東野智洋、今堀博
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 高耐久性ヒドロキサム酸吸着基を有する新規ポルフィリン色素の合成と色素増感太陽電池性能2017

    • Author(s)
      楜澤佑真、東野智洋、今堀博
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ホスホール縮環ポルフィリンダイマーの合成と物性2016

    • Author(s)
      東野智洋、山田智紀、今堀博
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島 広島国際会議場
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Presentation] ハイブリッド[5]ラジアレン骨格を有するビスピロロヘテロールの合成2016

    • Author(s)
      東野智洋、今堀博
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都 同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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