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Antenna dye for visible light: synthesis of antiaromatic pentalenes and their application to optical materials

Research Project

Project/Area Number 18K05134
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionOkayama University of Science

Principal Investigator

Orita Akihiro  岡山理科大学, 工学部, 教授 (30262033)

Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsアセチレン / ペンタレン / 渡環反応 / 光反応 / 光触媒 / ピレン / アントラセン / フェナントレン / スルホン / オレフィン / クリック反応 / アミノトリアゾール / ペリレン / エテニルスルホン / 色素 / ホスホリル / 保護 / アミノ / アンテナ分子 / 可視光色素 / 反芳香族
Outline of Final Research Achievements

Visible light-absorbing acetylenic dyes bearing electron-donating and -withdrawing groups were synthesized. When these dyes were substituted with ferrocene which showed attractive interaction with single-wall carbon nanotube (SWCNT), dye-SWCNT composites were easily fabricated simply by mixing them and sonication.
Ortho-, meta- and para-alkoxy substituted pai-expanded pyrene photocatalysts were prepared. By selecting the most proper catalyst of them, dienyl sulfones were successfully transformed to the desired dienes in irradiation of green light although the diene products were somewhat labile in the reductive conditions.

Academic Significance and Societal Importance of the Research Achievements

再生可能エネルギーとして太陽光が高い注目を集めている。太陽光を高効率で利用するために可視光色素と単層カーボンナノチューブとを簡便に複合化する技術を開発した。ここで得られた色素-カーボンナノチューブ複合体はフレキシブルな光電変換素子として応用展開できる可能性を秘める。
光はクリーンエネルギーとして様々な化学反応に利用できる。ここでは還元能が異なる3種のピレン光触媒を合成し、精密光還元反応へ応用した。この方法論は他の光反応を用いた精密合成へも応用展開が可能である。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (39 results)

All 2022 2021 2020 2019 2018 Other

All Journal Article (10 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 10 results,  Open Access: 1 results) Presentation (27 results) (of which Int'l Joint Research: 6 results,  Invited: 4 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Syntheses of π-Expanded Alkynes and Alkenes by Using Sulfones as Starting Compounds2022

    • Author(s)
      Okuda Yasuhiro、Orita Akihiro、Otera Junzo
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 80 Issue: 2 Pages: 126-138

    • DOI

      10.5059/yukigoseikyokaishi.80.126

    • NAID

      130008158496

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2022-02-01
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Head‐to‐Tail Oligomerization by Silylene‐Tethered Sonogashira Coupling on Ag(111)2021

    • Author(s)
      Sun Kewei、Sagisaka Keisuke、Peng Lifen、Watanabe Hikaru、Xu Feng、Pawlak R?my、Meyer Ernst、Okuda Yasuhiro、Orita Akihiro、Kawai Shigeki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 36 Pages: 19598-19603

    • DOI

      10.1002/anie.202102882

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Dephosphinylative [4 + 2] Benzannulation of Phosphinyl Ynamines: Application to the Modular Synthesis of Polycyclic Aromatic Amines2021

    • Author(s)
      Okuda Yasuhiro、Fujimoto Mayo、Akashi Haruo、Orita Akihiro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 86 Issue: 24 Pages: 17651-17666

    • DOI

      10.1021/acs.joc.1c01897

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes2021

    • Author(s)
      Watanabe, Hikaru; Nakajima, Kazuki; Ekuni, Kento; Edagawa, Ryota; Akagi, Yuta; Okuda, Yasuhiro; Wakamatsu, Kan; Orita, Akihiro
    • Journal Title

      Synthesis

      Volume: in press Issue: 17 Pages: 2984-2994

    • DOI

      10.1055/s-0040-1706025

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Process-Controlled Regiodivergent Copper-Catalyzed Azide-Alkyne Cycloadditions: Tailor-made Syntheses of 4- and 5-Bromotriazoles from Bromo(phosphoryl)ethyne2020

    • Author(s)
      Okuda, Yasuhiro; Imafuku, Kazuto; Tsuchida, Yoshiyuki; Seo, Tomoyo; Akashi, Haruo; Orita, Akihiro
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 13 Pages: 5099-5103

    • DOI

      10.1021/acs.orglett.0c01681

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Diarylethenes by Perylene-catalyzed Photodesulfonylation from Ethenyl Sulfones2020

    • Author(s)
      Watanabe Hikaru、Takemoto Mai、Adachi Kazumasa、Okuda Yasuhiro、Dakegata Aki、Fukuyama Takahide、Ryu Ilhyong、Wakamatsu Kan、Orita Akihiro
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 4 Pages: 409-412

    • DOI

      10.1246/cl.200046

    • NAID

      130007828854

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of Ph2P(O)-stabilized Ynamines via C(sp)?N Bond Formation and Their Dephosphorylative Copper-catalyzed Click Reaction2019

    • Author(s)
      Okuda Yasuhiro、Seo Tomoyo、Shigezane Yuki、Watanabe Hikaru、Akashi Haruo、Iwanaga Tetsuo、Orita Akihiro
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 12 Pages: 1484-1487

    • DOI

      10.1246/cl.190647

    • NAID

      130007757505

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Regioisomeric Graphene Nanoribbon Junctions via Heteroprecursors2019

    • Author(s)
      Sun Kewei、Krej?i Ond?ej、Foster Adam S.、Okuda Yasuhiro、Orita Akihiro、Kawai Shigeki
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 123 Issue: 28 Pages: 17632-17638

    • DOI

      10.1021/acs.jpcc.9b05881

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Disproportionation-induced solid-state fluorescence in 6,13-dihydropentacenes2019

    • Author(s)
      Tajima Tomoyuki、Sanda Rai、Nishihara Katsuya、Shirai Hitoshi、Okuda Yasuhiro、Orita Akihiro、Takaguchi Yutaka
    • Journal Title

      RSC Advances

      Volume: 9 Issue: 30 Pages: 17035-17039

    • DOI

      10.1039/c9ra03297e

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Diacetylene Linked Anthracene Oligomers Synthesized by One-Shot Homocoupling of Trimethylsilyl on Cu(111)2018

    • Author(s)
      Kawai Shigeki, Krejci Ondrej, Foster Adam S., Pawlak Remy, Xu Feng, Peng Lifen, Orita Akihiro, Meyer Ernst
    • Journal Title

      ACS Nano

      Volume: 12 Issue: 8 Pages: 8791-8797

    • DOI

      10.1021/acsnano.8b05116

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] イナミンの芳香環形成反応による多環芳香族アミンの合成: 光学特性のチューニングを指向したパイ拡張戦略2022

    • Author(s)
      奥田靖浩,藤本真世,清原和也,桑山愛菜,折田明浩
    • Organizer
      日本化学会 第 102 春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] イナミンを用いた多環芳香族アミン合成:合成プロセス制御によるアミノ基の位置転換戦略2021

    • Author(s)
      奥田靖浩, 藤本真世, 清原和也, 桑山愛菜, 折田明浩
    • Organizer
      第10回JACI/GSCシンポジウム
    • Related Report
      2021 Annual Research Report
  • [Presentation] ホスフィニルイナミンと2-ヨードビフェニルの[4 + 2]環化による含窒素・リン多環式化合物の合成と光学的特性の調査2021

    • Author(s)
      奥田靖浩,藤本真世,桑山愛菜,清原和也,折田明浩
    • Organizer
      第31回 基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ホスフィニル基を置換した多環芳香族アミンの位置選択的合成とリン官能基が光学特性に及ぼす影響2021

    • Author(s)
      奥田靖浩,藤本真世,清原和也,桑山愛菜,折田明浩
    • Organizer
      第48回 有機典型元素化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 塩基および合成プロセスの制御によるホスホリルイナミンの位置選択的[4+2]芳香環形成2021

    • Author(s)
      ○奥田靖浩・益田和法・赤木伸行・折田明浩
    • Organizer
      日本化学会第101春季年会(2021)
    • Related Report
      2020 Research-status Report
  • [Presentation] ピレン光触媒による還元的脱スルホニル化を経由した環境調和型Juliaオレフィン反応の開発2021

    • Author(s)
      ○渡部光・中嶋和輝・枝川領太・奥田靖浩・折田明浩
    • Organizer
      日本化学会第101春季年会(2021)
    • Related Report
      2020 Research-status Report
  • [Presentation] ブロモホスホリルエチンの位置選択的環化付加による4-および5-ブロモトリアゾールの合成2020

    • Author(s)
      ○奥田靖浩・益田和法・赤木伸行・折田明浩
    • Organizer
      2020年日本化学会中国四国支部大会島根大会
    • Related Report
      2020 Research-status Report
  • [Presentation] 緑色LED 照射下ピレン光触媒を用いた重金属フリーの還元的脱スルホニル化反応2020

    • Author(s)
      ○渡部光・中嶋和輝・奥田靖浩・折田明浩
    • Organizer
      2020年日本化学会中国四国支部大会島根大会
    • Related Report
      2020 Research-status Report
  • [Presentation] Syntheses of pai-System Expanded Compounds by Using Ph2P(O)-Protected Terminal Ethynes2019

    • Author(s)
      A. Orita
    • Organizer
      The 8th Japanese-Sino Symposium on Organic Chemistry for Young Scientists
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ホスホリルエチン: Ph2P(O) 基で置換した末端アセチレンの合成とπ拡張化合物への変換反応2019

    • Author(s)
      折田明浩
    • Organizer
      2019 年度先端錯体工学研究会(SPACC) 年会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Amino(phosphoryl)ethynes: Synthesis, Physical Properties and Transformation to Aminotriazoles2019

    • Author(s)
      A. Orita
    • Organizer
      The 2nd International Symposium on Middle Molecular Strategy for Young Scientists (ISMMYSys-2)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Monoiododiarenopentalene: Addition of in situ Prepared Hydrogen Iodide to Sondheimer-Wong Diyne2018

    • Author(s)
      ○Akihiro Orita, Yasuhiro Okuda, Sakimaru Mori, Masaki Taniguchi
    • Organizer
      The Third International Symposium on the Synthesis and Application of Curved Organic pi-Molecules & Materials (CURO-pai III)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] アセチレン誘導体の簡略化合成法の開発と有機材料創製への応用2018

    • Author(s)
      折田明浩
    • Organizer
      第34回若手化学者のための化学道場(in 高知)
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] One-shot Oligomerization of 9,10-Diethynylanthracene on Cu(111): Consecutive Desilylation and Homo-coupling of 9,10-Bis(trimethylsilylethynyl)anthracene2018

    • Author(s)
      Akihiro Orita, Shigeki Kawai, Adam S. Foster, Yasuhiro Okuda, and Ernst Meyer
    • Organizer
      The 4th International Symposium on Middle Molecular Strategy
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 9,10-ビス(トリメチルシリル)アントラセンを用いた銅(111)面上でのワンショット脱シリル-Glaserカップリング2018

    • Author(s)
      ○折田明浩、川井 茂樹、Foster Adam S.、奥田靖浩、Meyer Ernst
    • Organizer
      日本化学会第99春季年会(2019)
    • Related Report
      2018 Research-status Report
  • [Presentation] One-shot desilylation and Glaser coupling of 9,10-bis(trimethylsilylethynyl)anthracene on Cu(111).2018

    • Author(s)
      ○ORITA, Akihiro; KAWAI, Shigeki; FOSTER, Adam S.; OKUDA, Yasuhiro; MEYER, Ernst
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Development of Aminoacetylene Derivatives for Effective Synthesis of Organonitrogen Bioactive Compounds2018

    • Author(s)
      ○OKUDA, Yasuhiro; SEO, Tomoyo; SHIGEZANE, Yuki; ORITA, Akihiro
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis and Physicochemical Properties of Air-Stable Ynamines, and the Subsequent Dephosphorylative Click Reaction2018

    • Author(s)
      ○OKUDA, Yasuhiro; SEO, Tomoyo; SHIGEZANE, Yuki; ORITA, Akihiro
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 9-ボラフルオレン誘導体を用いた歪みアルキンの芳香環化による湾曲πシステムの構築2018

    • Author(s)
      ○荒井由土・庄子良晃・奥田靖浩・折田明浩・福島孝典
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] カーボンナノチューブ内包配向基を有する可視光色素の合成2018

    • Author(s)
      奥田靖浩・〇渡部光・森咲丸・山田祐嗣・折田明浩
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Research-status Report
  • [Presentation] ブロモホスホリルエチンを用いる機能性アセチレンの合成・変換プロセス2018

    • Author(s)
      ○奥田靖浩・重實悠希・瀬尾朋世・折田明浩
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Research-status Report
  • [Presentation] One-shot Glaser coupling of 9,10-bis(trimethylsilylethynyl)anthracene on Cu(111)2018

    • Author(s)
      〇折田明浩・川井茂樹・Adam S. Foster・奥田靖浩・Ernst Meyer
    • Organizer
      2018年日本化学会中国四国支部大会 愛媛大会
    • Related Report
      2018 Research-status Report
  • [Presentation] One-pot Synthesis of Sondheimer-Wong Diynes and Their Transformations to Pentalene Derivatives through Transannulation2018

    • Author(s)
      ○Akihiro Orita, Yasuhiro Okuda, Sakimaru Mori and Masaki Taniguchi
    • Organizer
      The 8th Spanish-Portuguese-Japanese Organic Chemistry Symposium (8th SPJ-OCS)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 不安定化学種の銅(111)面上でのワンショットオリゴマー化反応:9,10-ビス(トリメチルシリルエチニル)アントラセンの脱シリル化とホモカップリング2018

    • Author(s)
      ○折田明浩,川井茂樹,Adam S. Foster,奥田 靖浩 ,Ernst Meyer
    • Organizer
      フルオラス科学研究会第11回シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] 安定なイナミン等価体を用いる銅触媒クリック反応2018

    • Author(s)
      ○奥田靖浩、瀬尾朋世、重實悠希、竹本真愛、折田明浩
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of Butadiynes via Palladium-Catalyzed Cross-Coupling of Bromo(phosphoryl)ethyne.2018

    • Author(s)
      ○Yasuhiro Okuda, Yuki Shigezane, Akihiro Orita
    • Organizer
      The 4th International Symposium on C-H Activation (ISCHA4)
    • Related Report
      2018 Research-status Report
  • [Presentation] Akihiro Orita, Shigeki Kawai, Adam S. Foster Yasuhiro Okuda, Ernst Meyer2018

    • Author(s)
      One-shot Oligomerization of Unstable Terminal Ethyne on Cu(111): Consecutive Desilylation and Homo-coupling of 9,10-Bis(trimethylsilylethynyl)anthracene
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Book] 有機フッ素化合物の最新動向2018

    • Author(s)
      折田明浩 他 (監修 今野 勉)
    • Total Pages
      317
    • Publisher
      シーエムシー出版
    • ISBN
      9784781313375
    • Related Report
      2018 Research-status Report
  • [Remarks] 岡山理科大学 工学部 バイオ・応用化学科 折田研究室

    • URL

      http://www.dac.ous.ac.jp/orita/index.html

    • Related Report
      2020 Research-status Report 2019 Research-status Report

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Published: 2018-04-23   Modified: 2023-01-30  

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