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Development of heteroarene-fused and pi-expanded diazaporphyrins as n-type semiconductors

Research Project

Project/Area Number 15K13762
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Energy-related chemistry
Research InstitutionNiigata University

Principal Investigator

MATANO YOSHIHIRO  新潟大学, 自然科学系, 教授 (40231592)

Co-Investigator(Renkei-kenkyūsha) IMAHORI Hiroshi  京都大学, 大学院工学研究科, 教授 (90243261)
Research Collaborator NAKANO Haruyuki  九州大学, 大学院理学研究科, 教授 (90251363)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
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: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsジアザポルフィリン / 有機太陽電池 / 酸化還元 / ラジカル / 電荷移動特性 / 二量体 / π拡張 / 複素環 / 光物性 / 電気化学特性 / π共役 / 縮環 / 吸収特性 / X線結晶構造解析 / 電子スピン共鳴
Outline of Final Research Achievements

In order to develop the chemistry of diazaporphyrins that have high electron-accepting and light-harvesting properties, we have (i) synthesized new diazaporphyrin derivatives bearing various substituents at the periphery, (ii) disclosed their structure-property relationships, and (iii) applied some derivatives in organic solar cells. As a result, we have found that the amino-substituted donor-acceptor-type diazaporphyrins show the intramolecular charge-transfer character derived from the intrinsically electron-withdrawing nature of the diazaporphyrin. Furthermore, we have succeeded in fabricating dye-sensitized solar cells using some diazaporphyrin-based dyes and revealed their potential as the photofunctional materials.

Report

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

    (24 results)

All 2018 2017 2016 2015

All Journal Article (6 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 6 results,  Acknowledgement Compliant: 3 results) Presentation (16 results) (of which Int'l Joint Research: 4 results,  Invited: 5 results) Book (2 results)

  • [Journal Article] Synthesis of 3,5-Disubstituted BODIPYs Bearing N-Containing Five-membered Heteroaryl Groups via Nucleophilic C-N Bond Formation2018

    • Author(s)
      Takaharu Satoh, Kaori Fujii, Yoshifumi Kimura, Yoshihiro Matano
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 9 Pages: 5274-5281

    • DOI

      10.1021/acs.joc.8b00087

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Redox Switchable 19π and 18π 5,10,20-Triaryl-5,15-diazaporphyrinoid-Nickel(II) Complexes2018

    • Author(s)
      Keisuke Sudoh, Takuroh Hatakeyama, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 22 Issue: 07 Pages: 542-551

    • DOI

      10.1142/s1088424618500529

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines: A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers2018

    • Author(s)
      Omomo, S.; Sugai, T.; Minoura, M.; Nakano, H.; Matano, Y.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 14 Pages: 3797-3800

    • DOI

      10.1002/anie.201800471

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Aza-, Oxa-, and Thiaporphyrins and Related Compounds2017

    • Author(s)
      Yoshihiro Matano
    • Journal Title

      Chem. Rev.

      Volume: 117 Issue: 4 Pages: 3138-3191

    • DOI

      10.1021/acs.chemrev.6b00460

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Unsymmetrically Substituted D-π-A Type 5,15-Diazaporphyrin Sensitizers: Synthesis and Optical and Photovoltaic Properties2017

    • Author(s)
      Satoshi Omomo, Yukihiro Tsuji, Kenichi Sugiura, Tomohiro Higashino, Haruyuki Nakano, Hiroshi Imahori, and Yoshihiro Matano
    • Journal Title

      ChemPlusChem

      Volume: 印刷中 Issue: 5 Pages: 695-704

    • DOI

      10.1002/cplu.201700051

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nitrogen-Bridged Metallodiazaporphyrin Dimers: Synergistic Effects of Nitrogen Bridges and meso-Nitrogen Atoms on Structure and Properties2017

    • Author(s)
      Masahiro Kawamata, Takuma Sugai, Mao Minoura, Yasuhisa Maruyama, Ko Furukawa, Cole Holstrom, Victor N. Nemykin, Haruyuki Nakano, and Yoshihiro Matano
    • Journal Title

      Chem. Asian J.

      Volume: 12 Issue: 7 Pages: 816-821

    • DOI

      10.1002/asia.201700204

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] New Methods for Peripheral Functionalization of 5,15-Diazaporphyrins2018

    • Author(s)
      Yoshihiro Matano
    • Organizer
      Itoshima International Mini-Symposium on Porphyrin and Related Compounds
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 5,10,20-トリアリール-5,15-ジアザポルフィリン金属錯体の合成と物性2018

    • Author(s)
      須藤啓佑・畠山琢郎・佐藤隆治・俣野善博
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 直接求核置換反応を利用したジアザポルフィリン環の官能基化2018

    • Author(s)
      須貝拓馬・大桃理志・俣野善博
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] リン、硫黄、酸素官能基を有する5,15-ジアザポルフィリンの合成と物性2017

    • Author(s)
      須貝拓馬・大桃理志・中野晴之・俣野善博
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Donor-π-Acceptor-Type Amine-Oligothiophene-Phosphole Derivatives: Synthesis and Application to Dye-Sensitized Solar Cells2017

    • Author(s)
      Yoshihiro Matano, Sora Kasuga
    • Organizer
      12th International Conference on Heteroatom Chemistry
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 含窒素複素環の求核置換反応を利用したBODIPY誘導体の合成2017

    • Author(s)
      佐藤隆治・俣野善博
    • Organizer
      新潟大学ユビキタスグリーンケミカルエネルギー連携教育研究センター第8回研究シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] メソ位が窒素で置換された擬ポルフィリン誘導体の合成および物性2017

    • Author(s)
      須藤啓佑・畠山琢朗・佐藤隆治・古川貢・俣野善博
    • Organizer
      新潟大学ユビキタスグリーンケミカルエネルギー連携教育研究センター第8回研究シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 5,10,15-トリアリール-5,15-ジアザポルフィリン金属錯体の合成2017

    • Author(s)
      畠山琢朗・須藤啓佑・佐藤隆治・俣野善博
    • Organizer
      第74回有機合成化学協会関東支部シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] アミンによる直接アミノ化を利用した3,7,13,17-テトラアミノ-5,15-ジアザポルフィリンの合成2017

    • Author(s)
      大桃理志・須貝拓馬・中野晴之・俣野善博
    • Organizer
      第27回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 新規メソ位ヘテロ原子置換擬ポルフィリン誘導体の合成および物性2017

    • Author(s)
      須藤啓佑・畠山琢朗・佐藤隆治・古川 貢・俣野善博
    • Organizer
      第27回基礎有機化学討論会
    • Related Report
      2017 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金属錯体の合成と酸化還元特性2017

    • Author(s)
      須藤啓佑・佐藤隆治・雨夜 徹・古川 貢・俣野善博
    • Organizer
      第41回有機電子移動化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 15族元素の個性を活かした新奇なπ電子系の構築2016

    • Author(s)
      俣野善博
    • Organizer
      埼玉大学特別講演会
    • Place of Presentation
      埼玉大学(さいたま市)
    • Year and Date
      2016-12-02
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Covalently Linked Dimers of 10,20-Diaryl-5,15-Diazaporphyrin-Metal Complexes2016

    • Author(s)
      Yoshihiro Matano
    • Organizer
      9th International Conference on Porphyrins and Phthalocyaninces
    • Place of Presentation
      Nanjing (China)
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 新規ジアザポルフィリン誘導体の酸化還元挙動2016

    • Author(s)
      俣野善博
    • Organizer
      第40回有機電子移動化学討論会
    • Place of Presentation
      新潟大学(新潟市)
    • Year and Date
      2016-06-23
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Structures and Properties of Chemically Modified 5,15-Diazaporphyrins2015

    • Author(s)
      Yoshihiro Matano
    • Organizer
      Frontiers of Macrocyclic Chemistry
    • Place of Presentation
      信州大学繊維学部(長野県上田市)
    • Year and Date
      2015-11-03
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] β-アミノジアザポルフィリンの合成、反応、および光物性2015

    • Author(s)
      川俣昌弘、大桃理志、中野晴之、俣野善博
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学・松山大学(愛媛県松山市)
    • Year and Date
      2015-09-23
    • Related Report
      2015 Research-status Report
  • [Book] Main Group Strategies towards Functional Organic Materials2018

    • Author(s)
      Editors: Frieder Jakle and Thomas Baumgartner; Yoshihiro Matano, Kensuke Naka, Joji Oshita, Masaki Shimizu, Takanobu Sanji, Pierre‐Antoine Bouit, Muriel Hissler, Francois P. Gabbai, Derek P. Gates, Richard S. Glass, Atsushi Wakamiya, Yi Ren, and others
    • Total Pages
      560
    • Publisher
      Wiley-VCH
    • ISBN
      9781119235972
    • Related Report
      2017 Annual Research Report
  • [Book] Chemical Science of π-Electron Systems2015

    • Author(s)
      Yoshihiro Matano
    • Publisher
      Springer
    • Related Report
      2015 Research-status Report

URL: 

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

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