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Development of Organic Dyes with Phosphorus-Containing pi-Conjugated System toward Application for Dye Sensitized Solar Cell

Research Project

Project/Area Number 26810022
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Miyake Hideaki  山口大学, 理工学研究科, 助教 (30722425)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords増感色素 / 典型元素 / π電子共役系 / 交差共役 / ラジアレン / フェロセン / 低配位リン化合物 / チオカルボニル化合物
Outline of Final Research Achievements

Triphospha[3]radialene, a cross conjugated compound containing phosphorus, have promising properties for functional dye. However, preparation of the precursor, primary phosphine, was a troublesome problem. Here we developed an easier method for preparation of primary phosphines bearing ferrocenyl moiety. We successfully synthesized tungsten and chromium complex with triphospha[3]radialene moiety as a ligand. The complexation brought about changes of light absorption property, redox potential, and reactivity.
We carried out design and syntheses of novel dye molecules bearing ferrocene moiety and sulfur-carbon double bond. The resulting dye molecules presented excellent light absorption property and stable redox behavior, therefore, they are expected to be applied as functional dyes.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (15 results)

All 2016 2015 2014

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Acknowledgement Compliant: 3 results) Presentation (10 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Photochemical (E)-(Z) Isomerization of the P=C Double Bond in Triphospha[3]radialene-[M(CO)5] (M = W, Cr) Complexes2015

    • Author(s)
      Sasamori, T.; Hirano, K.; Miyake, H.; Tokitoh, N.
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 9 Pages: 1240-1242

    • DOI

      10.1246/cl.150422

    • NAID

      130005096872

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Sulfurization of 4,5,6-Triphospha[3]Radialene2015

    • Author(s)
      Miyake, H.; Sasamori, T.; Tokitoh, N.
    • Journal Title

      Phosphorus, Sulfur, and Silicon and the Related Elements

      Volume: 190 Issue: 8 Pages: 1247-1250

    • DOI

      10.1080/10426507.2014.991828

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Structure of Stable Teluradiphosphirane Bearing Bulky Ferrocenyl Ligands2014

    • Author(s)
      笹森貴裕、鈴木裕子、坂上訓康、三宅秀明、時任宣博
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 9 Pages: 1464-1466

    • DOI

      10.1246/cl.140483

    • NAID

      130004427170

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of a Rhodium Carbonyl Phosphaalkenyl–Phosphido Complex : A Phosphorus Congener of Schiff Base Type N,N′-Chelating Monoanionic Ligands2014

    • Author(s)
      Matsumoto, T.; Sasamori, T.; Miyake, H.; Tokitoh, N
    • Journal Title

      Organometallics

      Volume: 33 Issue: 6 Pages: 1341-1344

    • DOI

      10.1021/om500065n

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] チオカルボニル基を有するπ共役系化合物の合成とカーボンナノチューブへの内包2016

    • Author(s)
      三宅 秀明, 田嶋 智之, 高口 豊
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学 (京都府京田辺市)
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] Encapsulation of dye molecules into carbon nanotubes and synthesis of organic end-cap molecules2016

    • Author(s)
      Hideaki Miyake
    • Organizer
      International Workshop for Interplay between Nanocarbon, Supramolecule, and Biochemistry
    • Place of Presentation
      岡山大学 (岡山県岡山市)
    • Year and Date
      2016-03-16
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Syntheses of Compounds Bearing Ferrocenylthiocarbonyl Groups toward Functional Dyes2015

    • Author(s)
      Hideaki Miyake, Tomoyuki Tajima, Yutaka Takaguchi
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Hilton Hawaiian Village (Honolulu, USA)
    • Year and Date
      2015-12-17
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] カーボンナノチューブ内空間を活用する新規な増感色素の設計と開発2015

    • Author(s)
      三宅 秀明
    • Organizer
      2015年日本化学会中国四国支部大会
    • Place of Presentation
      岡山大学 (岡山県岡山市)
    • Year and Date
      2015-11-14
    • Related Report
      2015 Annual Research Report
  • [Presentation] Syntheses of Compounds Bearing Ferrocenylthiocarbonyl Groups toward Application as Functional Dyes2015

    • Author(s)
      Hideaki Miyake, Tomoyuki Tajima, Yutaka Takaguchi
    • Organizer
      The 10th Organoelement Chemistry Seminar
    • Place of Presentation
      京都大学 (京都府宇治市)
    • Year and Date
      2015-06-08
    • Related Report
      2015 Annual Research Report
  • [Presentation] フェロセニルチオカルボニル基を有する化合物の合成とその光吸収特性2015

    • Author(s)
      三宅 秀明, 田嶋 智之, 高口 豊
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 (千葉県船橋市)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] トリホスファ[3]ラジアレンを配位子とした遷移金属錯体の合成2015

    • Author(s)
      平野 晃基, 三宅 秀明, 笹森 貴裕, 時任 宣博
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 (千葉県船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] トリホスファ[3]ラジアレン-6族金属カルボニル錯体の合成・性質・構造2014

    • Author(s)
      平野 晃基, 三宅 秀明, 笹森 貴裕, 時任 宣博
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学 (宮城県仙台市)
    • Year and Date
      2014-09-08
    • Related Report
      2014 Research-status Report
  • [Presentation] Sulfurization of 4,5,6-Triphospha[3]radialene2014

    • Author(s)
      Hideaki Miyake, Takahiro Sasamori, Norihiro Tokitoh
    • Organizer
      26th International Symposium on Organic Chemistry of Sulfur
    • Place of Presentation
      Istanbul Technical University (Istanbul, Turkey)
    • Year and Date
      2014-08-26
    • Related Report
      2014 Research-status Report
  • [Presentation] Structures of a Triphospha[3]radialene and Its Anionic Species2014

    • Author(s)
      Hideaki Miyake, Takahiro Sasamori, Norihiro Tokitoh, Tatsuki, Miyoshi, Daisuke Hashizume, Ko Furukawa, Shigeru Nagase
    • Organizer
      20th International Conference on Phosphorus Chemistry Conference
    • Place of Presentation
      University College Dublin (Dublin, Ireland)
    • Year and Date
      2014-07-01
    • Related Report
      2014 Research-status Report
  • [Patent(Industrial Property Rights)] フェロセニルチオカルボニル基を有するチオフェン化合物2015

    • Inventor(s)
      三宅 秀明, 高口 豊
    • Industrial Property Rights Holder
      山口大学, 岡山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-047219
    • Filing Date
      2015-03-10
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2017-05-10  

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