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Novel porphyrinoids with hybrid characters of porpyrins and heteroles

Research Project

Project/Area Number 18K14198
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionKyoto University

Principal Investigator

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

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsポルフィリン / リン / ホスホール / 硫黄 / チオフェン / 芳香族性 / 光物性 / 典型元素 / ヘテロール
Outline of Final Research Achievements

In this study, we aimed to synthesize porphyrinoids with hybrid characters of porphyrins and heteroles possessing main group elements such as sulfur and phosphorus. We synthesized various heterole-fused porphyrinoids and investigated their properties. We found that we can modulate the properties of porphyrinoids by electronic and structural features of main group elements. In addition, we reported the thiophene-fused porphyrin as promising sensitizer for dye-sensitized solar cells.

Academic Significance and Societal Importance of the Research Achievements

ポルフィリン類縁体やヘテロールはともに機能性材料の開発において中心的な骨格として用いられてきた。これらを組み合わせることで両方の特徴を活用できる分子の開発に成功したことは、ポルフィリン化学・ヘテロール化学双方の観点において、新たな一面を切り拓いたと言える。また、有機太陽電池の一種である色素増感太陽電池の材料として有望な分子の開発にも成功していることから、機能性材料としての分子改良が進むことで、将来的な有機デバイスの発展にも寄与できると考えられる。

Report

(3 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Research Products

    (33 results)

All 2020 2019 2018 Other

All Journal Article (12 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 12 results,  Open Access: 1 results) Presentation (19 results) (of which Int'l Joint Research: 6 results,  Invited: 3 results) Remarks (2 results)

  • [Journal Article] Effect of Ligand Structures of Copper Redox Shuttles on Photovoltaic Performance of Dye-Sensitized Solar Cells2020

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

      Inorg. Chem.

      Volume: 59 Issue: 1 Pages: 452-459

    • DOI

      10.1021/acs.inorgchem.9b02740

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Modulation of Frontier Molecular Orbitals on Dithieno[3,4-b:3’,4’-d]phosphole Derivatives by Donor-pi-Acceptor Interaction2020

    • Author(s)
      T. Higashino, K. Ishida, and H. Imahori
    • Journal Title

      Chem. Lett.

      Volume: 49 Issue: 3 Pages: 272-275

    • DOI

      10.1246/cl.190879

    • NAID

      130007805929

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effects of meso-Diarylamino Group of Porphyrins on Optical and Electrochemical Properties2020

    • Author(s)
      T. Higashino, Y. Fujimori, I. Nishimura, and H. Imahori
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 24 Issue: 01n03 Pages: 67-74

    • DOI

      10.1142/s1088424619500652

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Renaissance of Fused Porphyrins: Substituted Methylene-bridged Thiophene-Fused Strategy for High-Performance Dye-Sensitized Solar Cells2019

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

      J. Am. Chem. Soc.

      Volume: 141 Issue: 25 Pages: 9910-9919

    • DOI

      10.1021/jacs.9b03302

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoconductivity in Metal-Organic Framework (MOF) Thin Films2019

    • Author(s)
      X. Liu, M. Kozlowska, T. Okkali, D. Wagner, T. Higashino, G. Brenner-Weis, S. Marschner, Z. Fu, Q. Zhang, H. Imahori, S. Brase, W. Wenzel, C. Woll, and L. Heinke
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 58 Issue: 28 Pages: 9590-9595

    • DOI

      10.1002/anie.201904475

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Phosphole-Fused Dehydropurpurins via Titanium-Mediated [2+2+1] Cyclization Strategy2019

    • Author(s)
      T. Higashino, I. Nishimura, and H. Imahori
    • Journal Title

      Chem. Eur. J.

      Volume: 25 Issue: 60 Pages: 13816-13823

    • DOI

      10.1002/chem.201903269

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thiazolocatechol: Electron-withdrawing Catechol Anchoring Group for Dye-Sensitized Solar Cells2019

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

      ChemPhysChem

      Volume: 20 Issue: 20 Pages: 2689-2695

    • DOI

      10.1002/cphc.201900342

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Phosphole-bridged Porphyrin Dimers2019

    • Author(s)
      Higashino Tomohiro、Nishimura Issei、Imahori Hiroshi
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 3 Pages: 257-259

    • DOI

      10.1246/cl.180943

    • NAID

      130007607563

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Pluripotent Features of Doubly Thiophene‐Fused Benzodiphospholes as Organic Functional Materials2019

    • Author(s)
      Higashino Tomohiro、Ishida Keiichi、Sakurai Tsuneaki、Seki Shu、Konishi Tatsuki、Kamada Kenji、Kamada Kenji、Imahori Hiroshi
    • Journal Title

      Chemistry - A European Journal

      Volume: 印刷中 Issue: 25 Pages: 6425-6438

    • DOI

      10.1002/chem.201900661

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Calix[5]phyrin for Fluoride Ion Sensing with Visible and Near Infrared Optical Responses2018

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

      Chemistry - An Asian Journal

      Volume: 13 Issue: 16 Pages: 2019-2022

    • DOI

      10.1002/asia.201800856

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Reversible π-system switching of thiophene-fused thiahexaphyrins by solvent and oxidation/reduction2018

    • Author(s)
      Higashino Tomohiro、Kumagai Atsushi、Sakaki Shigeyoshi、Imahori Hiroshi
    • Journal Title

      Chemical Science

      Volume: 9 Issue: 38 Pages: 7528-7539

    • DOI

      10.1039/c8sc02448k

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] ABC-ABC-Type Directly meso-meso Linked Porphyrin Dimers2018

    • Author(s)
      Higashino Tomohiro、Kurumisawa Yuma、Iiyama Hitomi、Imahori Hiroshi
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 2 Pages: 538-547

    • DOI

      10.1002/chem.201805405

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] 色素増感太陽電池における銅レドックス錯体の配位子構造の効果2020

    • Author(s)
      東野智洋、飯山瞳、今堀博
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 高い電子供与性を有するメゾアミノポルフィリンの合成2020

    • Author(s)
      西村一晟、東野智洋、藤森大和、今堀博
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Thiophene-fused Expanded Porphyrins with π-System Switching2019

    • Author(s)
      Tomohiro Higashino, Hiroshi Imahori
    • Organizer
      The 235th ECS Meeting
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Thiophene-fused Expanded Porphyrins with π-System Switching2019

    • Author(s)
      Tomohiro Higashino, Hiroshi Imahori
    • Organizer
      18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Functionalization of Doubly Thiophene-fused2019

    • Author(s)
      Keiichi Ishida, Tomohiro Higashino, Hiroshi Imahori
    • Organizer
      18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 高効率色素増感太陽電池を指向したメチレン架橋チオフェン縮環ポルフィリン色素2019

    • Author(s)
      東野智洋、楜澤佑真、二村晋平、辻幸大、飯山瞳、今堀博
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] チアゾロカテコール基を吸着基とするポルフィリン色素を用いた色素増感太陽電池2019

    • Author(s)
      飯山瞳、東野智洋、今堀博
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ABC-ABC型メゾ-メゾ結合ポルフィリンダイマーの合成2019

    • Author(s)
      東野智洋、楜澤佑真、飯山瞳、今堀博
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ホスホール縮環ポルフィリンの合成と物性2019

    • Author(s)
      西村一晟、東野智洋、今堀博
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Thiophene-fused Phosphole Derivatives as Phosphole-Thiophene Hybrid Molecules2019

    • Author(s)
      Tomohiro Higashino, Keiichi Ishida, Hiroshi Imahori
    • Organizer
      The 9th East Asia Symposium on Functional Dyes and Advanced Materials (EAS9))
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Properties of Phosphole-fused Porphyrins2019

    • Author(s)
      Issei Nishimura, Tomohiro Higashino, Hiroshi Imahori
    • Organizer
      The 9th East Asia Symposium on Functional Dyes and Advanced Materials (EAS9))
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] [2+2+1]付加環化反応を用いたヘテロール縮環ポルフィリンの合成2019

    • Author(s)
      東野智洋、西村一晟、今堀博
    • Organizer
      第46回 有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] チオフェン縮環カリックス[5]フィリンの合成とそのフッ化物イオン認識能2019

    • Author(s)
      東野智洋、熊谷篤、今堀博
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] π拡張ベンゾジホスホールの合成とその機能化2019

    • Author(s)
      石田圭一、東野智洋、小西龍生、鎌田賢司、今堀博
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ホスホール縮環ポルフィリンの合成と物性2019

    • Author(s)
      西村一晟、東野智洋、今堀博
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] チアゾロカテコール基を有するプッシュ-プル型ポルフィリン色素の合成と色素増感太陽電池性能2019

    • Author(s)
      飯山瞳、東野智洋、今堀博
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Development of Robust Anchoring Groups for Durable Porphyrin-Sensitized Solar Cells2018

    • Author(s)
      Tomohiro Higashino, Hiroshi Imahori
    • Organizer
      10th International Conference on Porphyrins and Phthalocyanines
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ナフトビスチアジアゾール基を導入した新規D-π-A型ポルフィリン色素の合成と物性2018

    • Author(s)
      楜澤佑真、東野智洋、今堀博
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジチエノベンゾジホスホールの合成と物性2018

    • Author(s)
      石田圭一、東野智洋、今堀博
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Remarks] 研究室Webサイト内の研究内容紹介ページ

    • URL

      http://www.moleng.kyoto-u.ac.jp/~moleng_05/higashino_research.html

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
  • [Remarks] 新規色素設計指針を開発 -世界最高の太陽光エネルギー変換効率の実現に向けて-

    • URL

      http://www.kyoto-u.ac.jp/ja/research/research_results/2019/190613_2.html

    • Related Report
      2019 Annual Research Report

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Published: 2018-04-23   Modified: 2021-02-19  

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