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Synthesis of Extended Bifluorenylidenes as Acceptors for Thin-Layer Organic Photovoltaics

Research Project

Project/Area Number 25620032
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

TOBE Yoshito  大阪大学, 基礎工学研究科, 教授 (60127264)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機薄膜太陽電池 / アクセプター / ビフルオレニリデン / インデノフルオレン
Outline of Final Research Achievements

To develop new acceptors for thin-film organic solar cells of bulk-hetero-junction type, we synthesized new polycyclcic aromatic hydrocarbons bearing a biindenylidene substructure, which was expected to function as a key component of good acceptors, by dimerization of indenofluorene intermediates generated in situ, and investigated their performance as acceptor components of bulk-hetero-junction potovoltaics. As a result, the target compound was revealed to exhibit better photoenergy conversion efficiency than the commonly used fullerene derivative. However, the synthesis of its derivatives turned out to be limited because of narrow scope of the key reaction with respect to the substituents. The reason for the limited scope was elucidated by theoretical calculations. Moreover, a polycyclic aromatic hydrocarbon having a structure similar to that of the target compound was synthesized.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (21 results)

All 2015 2014 2013 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 5 results) Presentation (13 results) (of which Invited: 3 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Tetracyclopenta[def,jkl,pqr,vwx]tetraphenylene: A Potential Tetraradicaloid Hydrocarbon2015

    • Author(s)
      S. Nobusue, H. Miyoshi, A. Shimizu, I. Hisaki, K. Fukuda, M. Nakano, Y. Tobe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 54 Issue: 7 Pages: 2090-2094

    • DOI

      10.1002/anie.201410791

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Non-Alternant Non-Benzenoid Kekulenes: Birth of a New Kekulene Family2015

    • Author(s)
      Shunpei Nobusue, Hirokazu Miyoshi, Akihiro Shimizu, Ichiro Hisaki, Kotaro Fukuda, Masayoshi Nakano, Yoshito Tobe
    • Journal Title

      Chemical Society Reviews

      Volume: 44

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Non-alternant Non-benzenoid Aromatic Compounds: Past, Present, and Future2015

    • Author(s)
      Yoshito Tobe
    • Journal Title

      The Chemical Record

      Volume: 15 Issue: 1 Pages: 86-96

    • DOI

      10.1002/tcr.201402077

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Transformation of Ocatadehydrodibenzo[12]annulene to Benzonaphthopentalene by Successive Nucleophilic and Electrophilic Transannular Cyclizations2014

    • Author(s)
      Shunpei Nobusue, Ayumi Yoshizaki, Masahito Miki, Hirokazu Miyoshi, Akihiro Shimizu, Yoshito Tobe
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 45 Pages: 8474-8479

    • DOI

      10.1016/j.tet.2014.09.079

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Electrophilic Tandem Transannular Cyclization of Octadehydrotribenz[14]annulenes to Benzodiindenocyclooctatetraenes2014

    • Author(s)
      Shunpei Nobusue, Yoshito Tobe
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 8 Pages: 1210-1212

    • DOI

      10.1246/cl.140361

    • NAID

      130004427126

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indenofluorene Congeners: Biradicaloids and Beyond2014

    • Author(s)
      Akihiro Shimizu, Shunpei Nobusue, Hirokazu Miyoshi, Yoshito Tobe
    • Journal Title

      Pure and Applied Chemistry

      Volume: 36

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] [2n](2,7)ナフタレのファン(n=2-4)の合成と構造2015

    • Author(s)
      大塚健太, 日比大治郎, 戸部義人
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(千葉・船橋)
    • Year and Date
      2015-03-26 – 2015-04-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 9,10-ジヒドロ-as-インダセノ[3,2-b:6,7-b’]ジチオフェン類の合成と物性2015

    • Author(s)
      名部玲乃, 三好宏和, 信末俊平, 戸部義人
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(千葉・船橋)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Creation of Exitoc π-Conjugated Organic Molecules and their Assemblies2015

    • Author(s)
      Yoshito Tobe
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(千葉・船橋)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 求核的および求電子的な連続した渡環環化によるオクタデヒドロベンゾ[12]アヌレンからベンゾナフトペンタレンへの変換2014

    • Author(s)
      三木雅仁, 信末俊平, 吉崎亜由美, 三好宏和, 清水章弘, 戸部義人
    • Organizer
      第8回有機π電子系シンポジウム
    • Place of Presentation
      ホテル龍登園(佐賀・佐賀)
    • Year and Date
      2014-11-21 – 2014-11-22
    • Related Report
      2014 Annual Research Report
  • [Presentation] テトラシクロペンタ[def,jkl,pqr,vwx]テトラフェニレン誘導体の分子構造2014

    • Author(s)
      三好宏和, 信末俊平, 清水章弘, 久木一郎, 福田幸太郎, 中野雅由, 戸部義人
    • Organizer
      第8回有機π電子系シンポジウム
    • Place of Presentation
      ホテル龍登園(佐賀・佐賀)
    • Year and Date
      2014-11-21 – 2014-11-22
    • Related Report
      2014 Annual Research Report
  • [Presentation] Transformation of Octadehydrodibenzo[12]annulene to Benzonaphthopentalenes by Successive Nucluophilic and Electrophilic Transannular Cyclizations2014

    • Author(s)
      Masahito Miki, Shunpei Nobusue, Ayumi Yoshizaki, Hirokazu Miyoshi, Akihiro Shimizu, Yoshito Tobe
    • Organizer
      The 9th International Symposium on Integrated Synthesis
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫・淡路)
    • Year and Date
      2014-11-14 – 2014-11-15
    • Related Report
      2014 Annual Research Report
  • [Presentation] Exotic Non-Alternant Non-Benzenoid Hydrocarbons2014

    • Author(s)
      Yoshito Tobe
    • Organizer
      ETH Zurich-Osaka Univ Joint Symposium
    • Place of Presentation
      大阪大学(大阪・豊中)
    • Year and Date
      2014-10-09 – 2014-10-10
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ヨードニウムイオンにより誘起されるテトラエチニルナフタレンのジインデノピレンへの環化2014

    • Author(s)
      藤田和弥, 日比大治郎, 戸部義人
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      大阪大学(大阪・豊中)
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] 新奇な構造をもつ共役パイ電子系炭化水素の創出に関する研究2013

    • Author(s)
      戸部義人
    • Organizer
      第7回有機π電子系シンポジウム
    • Place of Presentation
      高崎市
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Synthesis of Twisted Cyclooctatetraenes by Formal [4+4] Cyclodimerization of in-situ Generated Indenofluorenes2013

    • Author(s)
      Shunpei Nobusue, Kazuya Fujita, Yoshito Tobe
    • Organizer
      8th International Symposium on Integrated Synthesis
    • Place of Presentation
      奈良市
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Twisted Cyclooctatetraenes by Formal [4+4] Cyclodimerization of Highly Reactive Indenofluorenes2013

    • Author(s)
      Yoshito Tobe
    • Organizer
      8th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      大阪市
    • Related Report
      2013 Research-status Report
  • [Presentation] インデノ[2,1-a]フルオレンの[4+4]二量化により生成するねじれたシクロオクタテトラエン類縁体2013

    • Author(s)
      藤田和弥, 信末俊平, 清水章弘, 戸部義人
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      東京都
    • Related Report
      2013 Research-status Report
  • [Presentation] インデノ[2,1-a]フルオレンの[4+4]二量化により生成するねじれたシクロオクタテトラエン類縁体2013

    • Author(s)
      藤田和弥, 信末俊平, 清水章弘, 戸部義人
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      東京都
    • Related Report
      2013 Research-status Report
  • [Book] Polycyclic Arenes and Heteroarenes: Synthesis, Properties, and Applications2015

    • Author(s)
      Shunpei Nobusue, Yoshito Tobe
    • Publisher
      Wiley VCH
    • Related Report
      2014 Annual Research Report
  • [Remarks] 大阪大学大学院基礎工学研究科物質創成専攻未来物質領域新物質創成講座機能分子創製グループ

    • URL

      http://www.supra.chem.es.osaka-u.ac.jp/

    • Related Report
      2013 Research-status Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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