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Study on exploitation of near-infrared dyes for organic photovoltaic cells

Research Project

Project/Area Number 23655044
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

UNO Hidemitsu  愛媛大学, 大学院・理工学研究科, 教授 (20168735)

Co-Investigator(Renkei-kenkyūsha) OKUJIMA Tetsuo  愛媛大学, 大学院・理工学研究科, 准教授 (60359924)
MORI Shigeki  愛媛大学, 総合科学研究支援センター, 講師 (30572028)
YAMADA Hiroko  奈良先端科学技術大学院大学, 物質創成科学研究科, 教授 (20372724)
KOBAYASHI Nagao  東北大学, 大学院・理学研究科, 教授 (60124575)
Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2011: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機太陽電池 / ペリ環状分解反応 / ボロンジピロメテン / 近赤外色素 / ビスボロンジピロメテン / BODIPY / ピロロイソインドール / フィルター / 近赤外フィルター
Research Abstract

Highly conjugated organic compounds absorbing near-infrared light are essential materials for improvement of organic photovoltaic cells. In this study, we synthesize dyes with a novel skeleton bearing near-infrared absorption and investigate their electronic properties as well as potentials for organic photovoltaic-cell materials by the solution-processed fabrication of their precursors. When the two-dimensional πsystems such as porphyrins are fused with a benzene unit, there must be two major transitions: a longitudinal transition directed along the fused rings and short transitions due to the individual porphyrin rings. Therefore, strong absorption remains in a visible region, even if the absorption with the longest wavelength reaches to the near-infrared region. On the other hand, the πsystem of boron-dipyrromethene (BODIPY) spreads one-dimensionally and has one strong absorption band at ca. 500 nm. We succeeded in the synthesis of bisBODIPY dyes having absorption only in the near-infrared region due to the longitudinal transition by fusion of the BODIPY chromophores in the longitudinal fashion. In addition, we succeeded inthe preparation of stable near-infrared dyes under air by introduction of electron-withdrawing groups. Now, the application studies for near-infrared specific filters, organic photovoltaic cells, etc. are underway in the cooperative companies.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (27 results)

All 2013 2012 2011 Other

All Journal Article (5 results) (of which Peer Reviewed: 2 results) Presentation (18 results) (of which Invited: 1 results) Remarks (1 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] π-Fused bis-BODIPY as a candidate for NIR dyes2012

    • Author(s)
      M. Nakamura, H. Tahara, K. Takahashi, T. Nagata, H. Uoyama, D. Kuzuhara, S. Mori, T. Okujima, H. Yamada, and H. Uno
    • Journal Title

      Org. Biomol. Chem

      Volume: 10 Pages: 6840-6849

    • Related Report
      2012 Final Research Report
  • [Journal Article] π-Fused bis-BODIPY as a candidate for NIR dyes2012

    • Author(s)
      Mitsunori Nakamura, Hiroyuki Tahara, Kohtaro Takahashi, Toshi Nagata, Hiroki Uoyama, Daiki Kuzuhara, Shigeki Mori, Tetsuo Okujima, Hiroko Yamada and Hidemitsu Uno
    • Journal Title

      Org. Biomol. Chem

      Volume: 10 Issue: 34 Pages: 6840-6849

    • DOI

      10.1039/c2ob25930c

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cyclo[8]isoindoles: Ring-Expanded and Annelated Porphyrinoids2011

    • Author(s)
      T. Okujima, G. Jin, N. Matsumoto, J. Mack, S. Mori, K. Ohara, D. Kuzuhara, C. Ando, N. Ono, H. Yamada, H. Uno, and N. Kobayashi
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 50 Pages: 5699-5703

    • Related Report
      2012 Final Research Report
  • [Journal Article] Synthesis of π-Expanded O-Chelated Boron-Dipyrromethene As an NIR Dye2011

    • Author(s)
      Y. Tomimori, T. Okujima, T. Yano, S. Mori, N. Ono, H. Yamada, and H. Uno
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 3187-3193

    • Related Report
      2012 Final Research Report
  • [Journal Article] Synthesis of π-Expanded O-Chelated Boron-Dipyrromethene As an NIR Dye2011

    • Author(s)
      Y.Tomimori, T.Okujima, T.Yano, S.Mori, N.Ono, H.Yamada, H.Uno
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 18 Pages: 3187-3193

    • DOI

      10.1016/j.tet.2011.03.016

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] B,O-キレート型ジピロメテンホウ素錯体の合成2013

    • Author(s)
      志田陽一、富盛祐也、奥島鉄雄、森重樹、中江隆博、宇野英満
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] 近赤外色素としての共役拡張bisBODIPYの合成研究2012

    • Author(s)
      北束政波、中村光則、中江隆博、森重樹、奥島鉄雄、宇野英満
    • Organizer
      2012 ハロゲン利用ミニシンポジウム
    • Place of Presentation
      岡山
    • Year and Date
      2012-11-30
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] B,O-キレート型ジピロメテンホウ素錯体の合成2012

    • Author(s)
      志田陽一、西岡紀理、富盛祐也、森重樹、中江隆博、宇野英満、奥島鉄雄
    • Organizer
      2012 ハロゲン利用ミニシンポジウム
    • Place of Presentation
      岡山
    • Year and Date
      2012-11-30
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] ペリ環状分解反応によるπ電子系の構築2012

    • Author(s)
      宇野英満
    • Organizer
      第6回有機π電子系シンポジウム
    • Place of Presentation
      松山
    • Related Report
      2012 Final Research Report
  • [Presentation] BisBODIPY近赤外色素の合成とその電子状態の解明2012

    • Author(s)
      中村光則、高橋功太郎、森重樹、中江隆博、奥島鉄雄、宇野英満
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Final Research Report
  • [Presentation] 多環式芳香族縮環シクロ[8]ピロールの合成と物性2012

    • Author(s)
      安藤千恵、松本直樹、奥島鉄雄、森重樹、小原敬士、中江隆博、宇野英満
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] Synthesis of π-Expanded Cyclo[8]pyrroles2012

    • Author(s)
      T. Okujima, T. Nakae, S. Mori, K. Ohara, H. Uno, N. Matsumoto, C. Ando, G. Jin, H. Yamada
    • Organizer
      Seventh International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      Jeju, Korea
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] Synthesis and Properties of β-Substituted Cyclo[8]pyrroles2012

    • Author(s)
      T. Okujima, T. Nakae, S. Mori, K. Ohara, H. Uno, C. Ando, N. Matsumoto
    • Organizer
      Seventh International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      Jeju, Korea
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] 安定なbisBODIPY 近赤外色素の合成と物性2012

    • Author(s)
      中村光則、高橋 功太郎、永田央、宇野英満、奥島鉄雄、森重樹
    • Organizer
      高次π空間の創発と機能開発第7回公開シンポジウム
    • Place of Presentation
      松山
    • Related Report
      2012 Final Research Report
  • [Presentation] BisBODIPY近赤外色素のとその電子状態の解明2012

    • Author(s)
      中村光則、高橋功太郎、森 重樹、中江 隆博、奥島 鉄雄、宇野 英満
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] ペリ環状分解反応によるπ電子系の構築2012

    • Author(s)
      宇野 英満
    • Organizer
      第6回有機π電子系シンポジウム
    • Place of Presentation
      松山
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 安定なbisBODIPY 近赤外色素の合成と物性2012

    • Author(s)
      宇野 英満、奥島 鉄雄、森 重樹、中村 光則、高橋 功太郎、永田 央
    • Organizer
      高次π空間の創発と機能開発第7回公開シンポジウム
    • Place of Presentation
      松山
    • Related Report
      2011 Research-status Report
  • [Presentation] ベンゼン架橋BODIPY 二量体の分光特性と置換基効果2011

    • Author(s)
      田原寛之、中江隆博、森重樹、奥島鉄雄、宇野英満
    • Organizer
      2011ハロゲン利用ミニシンポジウム(第4回臭素化学懇話会年会)
    • Place of Presentation
      宇都宮
    • Year and Date
      2011-11-25
    • Related Report
      2012 Final Research Report
  • [Presentation] Construction of New pi-Conjugated Heterocyclic Systems Based on the Pericyclic Cycloreversion2011

    • Author(s)
      H. Uno, T. Okujima, and S. Mori
    • Organizer
      3rd International Conference on Heterocyclic Chemistry
    • Place of Presentation
      Jaipur, India
    • Related Report
      2012 Final Research Report 2011 Research-status Report
  • [Presentation] ベンゼン連結bisBODIPYの合成と物性2011

    • Author(s)
      田原寛之、中村光則、森重樹、中江隆博、奥島鉄雄、宇野英満、高橋功太郎
    • Organizer
      2011年日本化学会西日本大会
    • Place of Presentation
      徳島
    • Related Report
      2012 Final Research Report
  • [Presentation] Efficient synthesis of highly pi-expanded heterocycles based on the pericyclic cycloreversion2011

    • Author(s)
      H. Uno
    • Organizer
      23rd International Congress of Heterocyclic Chemistry
    • Place of Presentation
      Glasgow, UK
    • Related Report
      2012 Final Research Report 2011 Research-status Report
  • [Presentation] ベンゼン連結 bisBODIPYの合成と物性2011

    • Author(s)
      森 重樹、中江 隆博、奥島 鉄雄、宇野 英満、高橋功太郎、田原寛之、中村光則
    • Organizer
      2011年日本化学会西日本大会
    • Place of Presentation
      徳島
    • Related Report
      2011 Research-status Report
  • [Presentation] ベンゼン架橋 BODIPY 二量体の分光特性と置換基効果2011

    • Author(s)
      中江 隆博、森 重樹、奥島 鉄雄、宇野 英満、田原 寛之
    • Organizer
      2011ハロゲン利用ミニシンポジウム(第4回臭素化学懇話会年会)
    • Place of Presentation
      宇都宮
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://chem.sci.ehime-u.ac.jp/~orgchem1/

    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] ビス-ボロンジメテン系色素及びその前駆体2012

    • Inventor(s)
      宇野英満、中村光則、高橋功太郎
    • Industrial Property Rights Holder
      独立行政法人愛媛大学、日本触媒
    • Industrial Property Number
      2012-027806
    • Filing Date
      2012-02-10
    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] 特許2012

    • Inventor(s)
      宇野英満、中村光則、高橋功太郎
    • Industrial Property Rights Holder
      宇野英満、中村光則、高橋功太郎
    • Industrial Property Number
      2012-027806
    • Filing Date
      2012
    • Related Report
      2011 Research-status Report
  • [Patent(Industrial Property Rights)] 新規化合物2011

    • Inventor(s)
      大橋幸恵、杉山直樹、宇野英満、奥島鉄雄、松本直樹
    • Industrial Property Rights Holder
      独立行政法人愛媛大学、JSR
    • Filing Date
      2011-09-06
    • Related Report
      2012 Final Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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