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Novel design strategy of near-infrared absorbing dyes enabling photo-electric conversion in the near-infrared light

Research Project

Project/Area Number 16H06048
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic and hybrid materials
Research InstitutionOsaka Prefecture University

Principal Investigator

Maeda Takeshi  大阪府立大学, 工学(系)研究科(研究院), 准教授 (90507956)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥10,660,000 (Direct Cost: ¥8,200,000、Indirect Cost: ¥2,460,000)
Fiscal Year 2018: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2017: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2016: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Keywords機能性色素 / 近赤外 / 励起子相互作用 / 有機半導体 / Davydov分裂 / 潜在顔料 / 有機太陽電池 / スクアレン / 自己組織化材料
Outline of Final Research Achievements

In this study, near-infrared (NIR) absorbing organic dyes based on the manipulation of exciton interaction were developed for the efficient photo-electric conversion in the invisible NIR light. The fusion of two chromophores in one molecule caused intramolecular exciton interaction between chromophores. As a result, the absorption bands of these dyes were shifted to the long-wavelength region. The photophysical properties of intramolecular exciton-coupled dyes were elucidated by various spectroscopic measurements. Furthermore, organic photovoltaics based on exciton-coupled dyes were fabricated. These dyes exhibited high performance as the light-harvesting materials in the NIR regions due to the properties brought about intramolecular exciton interaction such as energy levels of frontier orbitals, broadening and red-shifting of absorption bands. These results proved the design strategy based on exciton interaction was benefit in the synthesis of NIR absorbing dyes.

Academic Significance and Societal Importance of the Research Achievements

近赤外光は太陽放射エネルギー量の約50%を占め,その有効活用で有機太陽電池(OPV)の高効率化が見込める上,可視光透明な太陽電池への展開も期待される.本課題では,励起子相互作用に基づく新分類の近赤外吸収色素群を創成した.これらは,近赤外光を利用可能とする次世代有機太陽電池の開発に繋がると予想される.得られる安定な近赤外吸収色素はセキュリティー用途,生体イメージングや光線力学的治療等に高い潜在性を有する上,1μmを超える領域に光吸収能を持つ堅牢な色素の創出も期待され,学術・産業的な視点からも波及効果が期待できる.

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (47 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (3 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 3 results) Presentation (39 results) (of which Int'l Joint Research: 11 results,  Invited: 9 results) Book (1 results) Remarks (3 results)

  • [Int'l Joint Research] CSIR-NIIST(インド)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Malachite Green Derivatives for Dye-Sensitized Solar Cells: Optoelectronic Characterizations and Persistence on TiO22018

    • Author(s)
      Harle Jean-Baptiste, Arata Shuhei, Mine Shinya, Kamegawa Takashi, Nguyen Van Tay, Maeda Takeshi, Nakazumi Hiroyuki, Fujiwara Hideki
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 91 Issue: 1 Pages: 52-64

    • DOI

      10.1246/bcsj.20170289

    • NAID

      130006309058

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Exciton-Coupled Squaraine Dyes for Dye-Sensitized Solar Cells2018

    • Author(s)
      T. Maeda, T. V. Nguyen, X. Chen, K. Miyanaga, H. Nakazumi, S. Yagi, S. Soman, A. Ajayaghosh
    • Journal Title

      J. Phys. Chem. C

      Volume: 122 Issue: 38 Pages: 21745-21754

    • DOI

      10.1021/acs.jpcc.8b06131

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and properties of functional dyes with squaraine?naphthalene diimide hybrid structure2018

    • Author(s)
      Maeda Takeshi、Zhou Jin、Oda Yuya、Nakazumi Hiroyuki、Yagi Shigeyuki
    • Journal Title

      Research on Chemical Intermediates

      Volume: - Issue: 8 Pages: 4783-4795

    • DOI

      10.1007/s11164-018-3284-5

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis of Functionalized Perylene Bisimides for Optical Sensing Based on Their Electron-Accepting Feature2019

    • Author(s)
      Y. Yoshikawa, T. Maeda, S. Yagi
    • Organizer
      日本化学会 第99春季年会 (2019)
    • Related Report
      2018 Annual Research Report
  • [Presentation] 励起子相互作用の精密制御による遠赤色/近赤外スーパークロモフォアの構築と機能開拓2019

    • Author(s)
      前田壮志
    • Organizer
      群馬先端材料シンポジウム2019
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Intramolecular Exciton-Coupled Squaraine Dyes for Dye-Sensitized Solar Cells2018

    • Author(s)
      T. Maeda, K. Miyanaga, Y. Kuwano, X. Chen, S. Yagi
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C2v-Symmetric Squaraine Dyes with Intramolecular Hydrogen-Bonding and Their Application to Organic Field-Effect Transistors2018

    • Author(s)
      T. Maeda, I. Nakamura, S. Yagi, A. Liess, M. Stolte, F. Wuerthner
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 分子内励起子相互作用を示す2発色団型スクアレン色素の合成と光物理特性2018

    • Author(s)
      前田壮志,小田侑哉,八木繁幸
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 分子内水素結合を持つスクアレン色素の合成と有機薄膜トランジスタへの応用2018

    • Author(s)
      前田壮志,中村伊万理,八木繁幸,A. Liess,M. Stolte,F. Wuerthner
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 対称型スクアレン色素で構成されたに二発色団型色素の合成と光学特性2018

    • Author(s)
      木下早紀,前田壮志,八木繁幸
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 室内光利用を指向した色素増感太陽電池へ適用可能なスクアレン色素の合成と特性2018

    • Author(s)
      二宮裕一郎,前田壮志,Pradhan C Sourava,Soman Suraj,Ayyappanpillai Ajayaghosh,八木繁幸
    • Organizer
      2018年度色材研究発表会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 励起子相互作用の精密制御による遠赤色/近赤外スーパークロモフォアの構築2018

    • Author(s)
      前田壮志
    • Organizer
      第38回キャピラリー電気泳動シンポジウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 励起子相互作用の精密制御~分子から超分子まで~2018

    • Author(s)
      前田壮志
    • Organizer
      第1回先端機能分子材料シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 屋内照明下で用いる色素増感太陽電池に適用可能な非対称型スクアレン色素の開発2018

    • Author(s)
      二宮裕一郎,前田壮志,Sourava C. Pradhan,Suraj Soman,Ayyappanpillai Ajayaghosh,八木 繁幸
    • Organizer
      日本化学会 第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] カルバメート基を持つスクアレン色素の合成と熱分解性評価2018

    • Author(s)
      桑野裕貴,前田壮志,八木繁幸
    • Organizer
      日本化学会 第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] カルバゾール骨格からなる非対称型スクアレン色素の合成と色素増感太陽電池への応用2017

    • Author(s)
      二宮裕一郎,前田壮志,Tay Van Nquyen,八木繁幸,Suraj Soman,Ayyappanpillai Ajayaghosh
    • Organizer
      日本化学会 第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学日吉キャンパス(横浜市,神奈川県)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 近赤外吸収スクアレン色素を用いた近赤外光電変換2017

    • Author(s)
      田中翔太,前田壮志,藤原秀紀,八木繁幸
    • Organizer
      日本化学会 第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学日吉キャンパス(横浜市,神奈川県)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Construction of p-n Heterojunction by Self-Assembly of Triads Composed of Naphthalene Dimide and Squaraine Chromophores2017

    • Author(s)
      T. Maeda, N. Okamura, S. Das, I. Nakamura, S. Yagi, A. Ajayaghosh
    • Organizer
      13th International Symposium on Functional π-Electron Systems
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Squaraine-Based Donor-Accepter-Donor Triads for Bottom-Up Construction of Well-Defined D/A Interfaces2017

    • Author(s)
      T. Maeda
    • Organizer
      8th East Asia Symposium on Functional Dyes and Advanced Materials
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Optical Properties of Cross Conjugated Bichromophoric Squaraine Dyes2017

    • Author(s)
      Y. Oda, T. Maeda, S. Yagi
    • Organizer
      8th East Asia Symposium on Functional Dyes and Advanced Materials
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Unsymmetrical Squaraine Dyes Bearing a Carbazolyl Carbazol Moiety for Dye-Sensitized Solar Cells2017

    • Author(s)
      Y. Ninomiya, S. Soman, T. Maeda, S. Yagi, A. Ajayaghosh
    • Organizer
      8th East Asia Symposium on Functional Dyes and Advanced Materials
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Optical Property of Squaraine Dyes Bound to PVA through Boronic Acid Residue2017

    • Author(s)
      M. Ishida, T. Maeda, S. Yagi
    • Organizer
      90th JSCM Anniversary Conference
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Extraordinary Optical Properties of Cross Conjugated Bichromophoric Squaraine Dyes2017

    • Author(s)
      Y. Oda, T. Maeda, S. Yagi
    • Organizer
      Joint Symposium of Asia Five Universities
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Squaraine Sensitizer with a Carbazolylcarbazol Donor Component for Dye-Sensitized Solar Cells2017

    • Author(s)
      Y. Ninomiya, S. Soman, T. Maeda, S. Yagi, A. Ajayaghosh
    • Organizer
      Joint Symposium of Asia Five Universities
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of n- and z-Shaped Dicyanovinylene-substituted Squaraine Dyes and Their Application to Organic Photovoltaics2017

    • Author(s)
      Y. Liang, T. Maeda, S. Yagi
    • Organizer
      Joint Symposium of Asia Five Universities
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] D/Aナノドメインのボトムアップ構築を指向したスクアレンとナフタレンジイミドから成るトリアド分子2017

    • Author(s)
      中村伊万理,前田壮志,岡村奈生己,Satyajit Das,佐伯昭紀,八木繁幸,Ayyappanpillai Ajayaghosh
    • Organizer
      第27回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 分子内励起子相互作用を引き起こすスクアレン色素の特異な蛍光挙動2017

    • Author(s)
      小田侑哉,前田壮志,八木繁幸
    • Organizer
      第27回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis of a Dicyanovinylene-Substituted Squaraine Dye and Its Application to Organic Photovoltaics2017

    • Author(s)
      Y. Liang, T. Maeda, S. Yagi
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] スクアレン色素の合目的的設計・合成と特性2017

    • Author(s)
      前田壮志
    • Organizer
      近畿化学協会機能性色素部会第94回例会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 電子受容性色素を用いた蛍光化学センサーの開発2017

    • Author(s)
      前田壮志
    • Organizer
      大阪府立大学・和歌山大学 工学研究シーズ合同発表会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 近赤外吸収色素を利用した色素増感型太陽電池の開発2016

    • Author(s)
      前田壮志
    • Organizer
      日本分光学会近赤外分光部会 第12回シンポジウム
    • Place of Presentation
      近畿大学東大阪キャンパス(東大阪市,大阪府)
    • Year and Date
      2016-12-22
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 有機薄膜太陽電池用材料への応用可能な近赤外吸収対照型スクアレン色素2016

    • Author(s)
      田中翔太,前田壮志,藤原秀紀,八木繁幸,中澄博行
    • Organizer
      大阪府立大学21世紀科学研究機構分子エレクトロニックデバイス研究所第18回研究会
    • Place of Presentation
      大阪府立大学中百舌鳥キャンパス(堺市,大阪府)
    • Year and Date
      2016-11-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] 2つの発色団の配向を制御可能なスクアレン色素の合成と光学特性2016

    • Author(s)
      小田侑哉,前田壮志,八木繁幸
    • Organizer
      大阪府立大学21世紀科学研究機構分子エレクトロニックデバイス研究所第18回研究会
    • Place of Presentation
      大阪府立大学中百舌鳥キャンパス(堺市,大阪府)
    • Year and Date
      2016-11-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] 熱脱離性置換基を有する近赤外スクアレン色素2016

    • Author(s)
      芦田拓弘,前田壮志,八木繁幸,中澄博行
    • Organizer
      大阪府立大学21世紀科学研究機構分子エレクトロニックデバイス研究所第18回研究会
    • Place of Presentation
      大阪府立大学中百舌鳥キャンパス(堺市,大阪府)
    • Year and Date
      2016-11-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] 色素増感太陽電池への応用を指向したBODIPY骨格をもつスクアリリウム色素2016

    • Author(s)
      前田壮志,垣尾大輔,八木繁幸,中澄博行
    • Organizer
      2016年度色材研究発表会
    • Place of Presentation
      大阪大学豊中キャンパス(豊中市,大阪府)
    • Year and Date
      2016-10-13
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] リチウムーハロゲン交換反応を利用した新規スクアレン色素の合成2016

    • Author(s)
      西出聖司,本山智博,前田壮志,八木繁幸,中澄博行
    • Organizer
      2016年度色材研究発表会
    • Place of Presentation
      大阪大学豊中キャンパス(豊中市,大阪府)
    • Year and Date
      2016-10-13
    • Related Report
      2016 Annual Research Report
  • [Presentation] 近赤外吸収対称型スクアレン色素からなる有機薄膜太陽電池2016

    • Author(s)
      田中翔太,前田壮志,藤原秀紀,八木繁幸,中澄博行
    • Organizer
      2016年度色材研究発表会
    • Place of Presentation
      大阪大学豊中キャンパス(豊中市,大阪府)
    • Year and Date
      2016-10-13
    • Related Report
      2016 Annual Research Report
  • [Presentation] Halochromic Squaric Acid Functionalized Perylene Bisimide Based pH and Humidity Sensor2016

    • Author(s)
      Takeshi Maeda
    • Organizer
      The 5th KIST-OPU-ECUST-TKU Joint Symposium on Advanced Materials and Application
    • Place of Presentation
      KIST (Seoul, Korea)
    • Year and Date
      2016-09-25
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 機能性色素からなるダイアド分子の自己組織化によるp-nヘテロ接合の構築2016

    • Author(s)
      前田壮志,岡村奈生己,中村伊万里,八木繁幸,Ayyappanpillai Ajayaghosh
    • Organizer
      第65回高分子討論会
    • Place of Presentation
      神奈川大学横浜キャンパス(横浜市,神奈川県)
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機薄膜太陽電池のドナー材料へ応用可能な近赤外吸収スクアレン色素2016

    • Author(s)
      田中翔太,前田壮志,八木繁幸
    • Organizer
      第27回基礎有機化学討論
    • Place of Presentation
      広島国際会議場(広島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] 四角酸残基を有するペリレンビスイミドの合成と光学特性2016

    • Author(s)
      吉川雄介,前田壮志,八木繁幸
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場(広島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] 発色団の配向が制御された二発色団型スクアレン色素の合成と光学特性2016

    • Author(s)
      小田侑哉,前田壮志,八木繁幸
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場(広島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Book] 機能性色素の新規合成・実用化動向 新規合成技術編 第1章 新規スクアレン色素の開発2016

    • Author(s)
      前田壮志
    • Total Pages
      17
    • Publisher
      シーエムシー出版
    • Related Report
      2016 Annual Research Report
  • [Remarks]

    • URL

      http://www2.chem.osakafu-u.ac.jp/ohka/ohka6/index.html

    • Related Report
      2018 Annual Research Report
  • [Remarks] 有機機能化学研究グループ

    • URL

      http://www2.chem.osakafu-u.ac.jp/ohka/ohka6/index.html

    • Related Report
      2017 Annual Research Report
  • [Remarks] 大阪府立大学大学院工学研究科物質・化学系専攻応用化学分野有機機能化学研究グループ

    • URL

      http://www2.chem.osakafu-u.ac.jp/ohka/ohka6/index.html

    • Related Report
      2016 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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