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汎用的な新規π拡張反応を鍵とする湾曲π造形

Publicly Offered Research

Project Areapi-System Figuration: Control of Electron and Structural Dynamism for Innovative Functions
Project/Area Number 17H05149
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionNagoya University

Principal Investigator

瀬川 泰知  名古屋大学, 理学研究科, 特任准教授 (60570794)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥6,240,000 (Direct Cost: ¥4,800,000、Indirect Cost: ¥1,440,000)
Fiscal Year 2018: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2017: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywordsπ拡張 / 芳香族炭化水素 / π造形 / 芳香族化合物 / π拡張反応 / 湾曲π共役化合物 / 有機化学 / 合成化学
Outline of Annual Research Achievements

本研究では、π拡張を可能にする新反応開発を基軸として新奇湾曲π共役化合物を合成することを目的に研究を行なった。今年度の実績は以下の4点である。
・3つの7員環をもつプロペラ型芳香族炭化水素の合成と構造的性質の解明を行なった。パラジウム触媒を用いた脱塩化水素型環化反応によって、予期しない7員環形成型のπ拡張反応が進行することを発見した。得られたプロペラ型分子について、各種物性測定および量子化学計算を併せ用いることで、隣接する7員環構造によって[4]ヘリセンのらせん不斉が安定化されていることを明らかにした。
・コラニュレンを中心に有する5重[6]ヘリセンの合成および構造解析に成功した。この化合物は、パラジウム触媒による分子内π拡張反応を鍵反応とする3段階で合成できた。X線結晶構造解析により、5回対称プロペラ型構造および固体状態での一次元配列が明らかになった。
・芳香族炭化水素の新規チオフェン環π拡張反応を用いることで、市販の化合物から2段階でチオフェン含有π共役化合物を合成した。これらを鉛ペロブスカイト太陽電池のホール輸送層として利用したところ、ホール輸送層を用いない場合よりも光電変換効率が上昇したことから、ホール輸送剤として有用であることを明らかにした。
・チオフェンπ拡張型ダブルヘリセンを合成し、溶解度と3次元πスタックを両立する分子を実現した。電界効果トランジスタデバイスに実際に組み込み、実用化に耐えうるホール輸送能をもつことを明らかにした。

Research Progress Status

平成30年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

平成30年度が最終年度であるため、記入しない。

Report

(2 results)
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (43 results)

All 2019 2018 2017 Other

All Int'l Joint Research (1 results) Journal Article (13 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 11 results,  Open Access: 3 results) Presentation (29 results) (of which Int'l Joint Research: 8 results,  Invited: 4 results)

  • [Int'l Joint Research] ボストン・カレッジ(米国)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Polycyclic Arene Synthesis by Annulative pi-Extension2019

    • Author(s)
      Hideto Ito, Yasutomo Segawa, Kei Murakami, and Kenichiro Itami
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 141 Issue: 1 Pages: 3-10

    • DOI

      10.1021/jacs.8b09232

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Structural Features of Thiophene-fused Analogues of Warped Nanographene and Quintuple Helicene2019

    • Author(s)
      Hsing-An Lin, Kenta Kato, Yasutomo Segawa, Lawrence T. Scott, and Kenichiro Itami
    • Journal Title

      Chem. Sci.

      Volume: 10 Issue: 8 Pages: 2326-2330

    • DOI

      10.1039/c8sc04470h

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis and Size-Dependent Properties of [12], [16], and [24]Carbon Nanobelts2018

    • Author(s)
      Guillaume Povie, Yasutomo Segawa, Taishi Nishihara, Yuhei Miyauchi, and Kenichiro Itami
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 31 Pages: 10054-10059

    • DOI

      10.1021/jacs.8b06842

    • NAID

      120006545941

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Symmetric Multiple Carbohelicenes2018

    • Author(s)
      Kenta Kato, Yasutomo Segawa, and Kenichiro Itami
    • Journal Title

      Synlett

      Volume: 30 Issue: 04 Pages: 370-377

    • DOI

      10.1055/s-0037-1610283

    • NAID

      120006545942

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] A Quintuple [6]Helicene with a Corannulene Core as a C5-symmetric Propeller-shaped マ?System2018

    • Author(s)
      Kenta Kato, Yasutomo Segawa, Lawrence T. Scott, and Kenichiro Itami
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 5 Pages: 1337-1341

    • DOI

      10.1002/anie.201711985

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A Water-soluble Warped Nanographene: Synthesis and Applications for Photo-induced Cell Death2018

    • Author(s)
      Hsing-An Lin, Yoshikatsu Sato, Yasutomo Segawa, Taishi Nishihara, Nagisa Sugimoto, Lawrence T. Scott, Tetsuya Higashiyama, and Kenichiro Itami
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 11 Pages: 2874-2878

    • DOI

      10.1002/anie.201713387

    • NAID

      120006473539

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis and Structure of a Propeller-shaped Polycyclic Aromatic Hydrocarbon Containing Seven-Membered Rings2018

    • Author(s)
      Kazuya Kawai, Kenta Kato, Lingqing Peng, Yasutomo Segawa, Lawrence T. Scott, Kenichiro Itami
    • Journal Title

      Org Lett.

      Volume: 20 Issue: 7 Pages: 1932-1935

    • DOI

      10.1021/acs.orglett.8b00477

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of a Carbon Nanobelt2017

    • Author(s)
      Guillaume Povie, Yasutomo Segawa, Taishi Nishihara, Yuhei Miyauchi, Kenichiro Itami
    • Journal Title

      Science

      Volume: 356 Issue: 6334 Pages: 172-175

    • DOI

      10.1126/science.aam8158

    • NAID

      120006318708

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Properties, and Crystal Structures of pi-Extended Double [6]Helicenes: Contorted Multi-Dimensional Stacking Lattice2017

    • Author(s)
      Takao Fujikawa, Nobuhiko Mitoma, Atsushi Wakamiya, Akinori Saeki, Yasutomo Segawa, and Kenichiro Itami
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 21 Pages: 4697-4703

    • DOI

      10.1039/c7ob00987a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Laterally pi-Extended Dithia[6]helicenes with Heptagons: Saddle-Helix Hybrid Molecules2017

    • Author(s)
      Takao Fujikawa, Yasutomo Segawa, and Kenichiro Itami
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 15 Pages: 7745-7749

    • DOI

      10.1021/acs.joc.7b01540

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hole-transporting materials based on thiophene-fused arenes from sulfur-mediated thienannulations2017

    • Author(s)
      Lin Hsing-An, Nobuhiko Mitoma, Meng Lingkui, Yasutomo Segawa, Atsushi Wakamiya, and Kenichiro Itami
    • Journal Title

      Mater. Chem. Front.

      Volume: 2 Issue: 2 Pages: 275-280

    • DOI

      10.1039/c7qm00473g

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] カーボンナノベルトの合成2017

    • Author(s)
      瀬川泰知・伊丹健一郎
    • Journal Title

      現代化学

      Volume: 7 Pages: 36-39

    • NAID

      40021219716

    • Related Report
      2017 Annual Research Report
  • [Journal Article] カーボンナノベルト合成までの軌跡 12年の歴史とドラマ2017

    • Author(s)
      伊丹健一郎・瀬川泰知・大町遼・八木亜樹子
    • Journal Title

      化学

      Volume: 72 Pages: 29-37

    • Related Report
      2017 Annual Research Report
  • [Presentation] One-dimensional Self-assembly of a Negatively Curved Aromatic Hydrocarbon2019

    • Author(s)
      KATO, Kenta; HIJIKATA, Yuh; PIRILLO, Jenny; NISHIHARA, Taishi; NAKANISHI, Yusuke; SEGAWA, Yasutomo; SCOTT, Lawrence T.; ITAMI, Kenichiro
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Ir触媒C-Hホウ素化を用いたデカアリールワープドナノグラフェンの合成2019

    • Author(s)
      加藤 健太・林 興安・瀬川 泰知・スコット ローレンス・伊丹 健一郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] オールベンゼンカテナンおよびトレフォイルノットの合成2019

    • Author(s)
      瀬川 泰知・桑山 元伸・土方 優・伏見 雅子・西原 大志・ピリッロ ジェニー・白崎 淳哉・久保田 夏実・伊丹 健一郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthetic Chemistry of Strained Molecular Nanocarbons2019

    • Author(s)
      瀬川泰知
    • Organizer
      JST ERATO Itami Molecular Nanocarbon Project Final Symposium
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Properties of a Quintuple [6]Helicene with a Corannulene Core2018

    • Author(s)
      加藤健太・瀬川泰知・Scott T. Lawrence・伊丹健一郎
    • Organizer
      Enabling Excellence Japanege-European Workshop -Carbon Nanoscience and Nanotechnology-
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] One-dimentional Self-assembly of Warped Nanographene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第50回構造有機若手の会
    • Related Report
      2018 Annual Research Report
  • [Presentation] One-dimentional Self-assembly of Warped Nanographene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 湾曲ナノグラフェンの一次元自己集積化2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] One-dimentional Self-assembly of Warped Nanographene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      第5回π造形科学若手研究会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis and Structure of a Propeller-Shaped Polycyclic Aromatic Hydrocarbon Containing Seven-Membered Rings2018

    • Author(s)
      川井 一矢・加藤 健太・Lingqing Peng・瀬川 泰知・Lawrence T. Scott・伊丹 健一郎
    • Organizer
      第5回π造形科学若手研究会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 湾曲ナノグラフェンの一次元自己集積化2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      ITbM/IGER Chemistry Workshop
    • Related Report
      2018 Annual Research Report
  • [Presentation] シクロパラフェニレンカテナンの合成2018

    • Author(s)
      瀬川泰知・桑山元伸・伏見雅子・西原大志・伊丹健一郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis and Properties of a Quintuple [6]Helicene with a Corannulene Core2018

    • Author(s)
      加藤健太・瀬川泰知・Scott T. Lawrence・伊丹健一郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis and stractures of a corannulene-cored quintuple [6]helicene2018

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      IGER Annual Meeting 2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] 湾曲した芳香族炭化水素の合成化学2017

    • Author(s)
      瀬川泰知
    • Organizer
      第八回南方研若手研究者セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] カーボンナノベルトの合成2017

    • Author(s)
      瀬川泰知・Guillaume Povie・西原大志・宮内雄平・伊丹健一郎
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] カーボンナノベルトの合成と構造2017

    • Author(s)
      瀬川泰知
    • Organizer
      π造形科学 第4回公開シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] カーボンナノベルトができるまで2017

    • Author(s)
      瀬川泰知
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 高度に湾曲したプロペラ型π共役炭化水素の合成と構造2017

    • Author(s)
      川井一矢・瀬川泰知・伊丹健一郎
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] コラニュレンを中心にもつ5重ヘリセンの合成と構造2017

    • Author(s)
      加藤健太・瀬川泰知・伊丹健一郎
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] コラニュレンを基盤とする新奇湾曲芳香族炭化水素の合成と構造2017

    • Author(s)
      加藤健太・瀬川泰知・Lawrence T. Scott・伊丹健一郎
    • Organizer
      π造形科学 第4回公開シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 高度に湾曲したプロペラ型π共役炭化水素の合成と構造2017

    • Author(s)
      川井一矢・瀬川泰知・伊丹健一郎
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Annual Research Report
  • [Presentation] コラニュレンを基盤とする新奇湾曲多環芳香族炭化水素の合成と構造2017

    • Author(s)
      加藤健太・瀬川泰知・伊丹健一郎
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis of a Carbon Nanobelt2017

    • Author(s)
      瀬川泰知
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC) 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of a Carbon Nanobelt2017

    • Author(s)
      瀬川泰知
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemical Synthesis of Molecular Nanocarbons2017

    • Author(s)
      瀬川泰知
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and structures of a corannulene-cored quintuple [6]helicene2017

    • Author(s)
      Kenta Kato, Yasutomo Segawa, Lawrence T. Scott, Kenichiro Itami
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Structure of Corannulene-Based Quintuple [6]helicene2017

    • Author(s)
      Kenta Kato, Yasutomo Segawa, Lawrence T. Scott, Kenichiro Itami
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Structure of a Highly Warped Propeller-Shaped π-Conjugated Hydrocarbon2017

    • Author(s)
      Kazuya Kawai, Yasutomo Segawa, Kenichiro Itami
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research

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Published: 2017-04-28   Modified: 2022-02-28  

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