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Synthesis of graphene type molecules by carbon-carbon formation reactions and their development

Research Project

Project/Area Number 16K05709
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionFukuoka University

Principal Investigator

Nagahora Noriyoshi  福岡大学, 理学部, 助教 (30402928)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords典型元素 / 芳香族化合物 / 硫黄 / セレン / リン / 有機典型元素化学 / グラフェン / 環変換 / 電子遷移 / 固体構造 / 酸素複素環 / 核磁気共鳴分光法 / 紫外可視吸収分光法 / 単結晶X線構造解析 / 有機合成化学 / ナノ材料
Outline of Final Research Achievements

Dicationic heteroacenes that bear thio- or selenopyrylium moieties were synthesized by addition reactions of the corresponding diones with a Grignard reagent, followed by a dehydration reaction of the resulting diols with Brensted acid. Alternatively, these dicationic heteroacenes were obtained from two-electron oxidations of the corresponding sulfur- or selenium-containing quinoids. The electronic structures of these heteroacenes were examined by NMR and UV-vis-NIR spectroscopy in conjunction with density functional theory calculations. The results of this combined experimental and theoretical approach strongly imply effective conjugation of 22pi-electrons in a system that is distributed over the entire pentacene framework.

Academic Significance and Societal Importance of the Research Achievements

新規グラフェン型分子および典型元素を含む芳香族化合物の新規合成法の開発に成功した。環骨格内に硫黄、セレンもしくはリン原子を含むパイ共役化合物に芳香族性が発現することを見出し、報告族性の定義を拡張するための有用な指針を与えることができた。

Report

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

    (15 results)

All 2019 2018 2017 2016

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 1 results) Presentation (10 results)

  • [Journal Article] Dicationic Heteroacenes Containing Thio- or Selenopyrylium Moieties2019

    • Author(s)
      Nagahora Noriyoshi、Kushida Tomoko、Shioji Kosei、Okuma Kentaro
    • Journal Title

      Organometallics

      Volume: 38 Issue: 8 Pages: 1800-1808

    • DOI

      10.1021/acs.organomet.9b00100

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Buchwald-Hartwig Amination of Phosphinines and the Effect of Amine Substituents on Optoelectronic Properties of the Resulting Coupling Products2018

    • Author(s)
      Nagahora Noriyoshi、Goto Shoko、Inatomi Takahiro、Tokumaru Hiroshi、Matsubara Kouki、Shioji Kosei、Okuma Kentaro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 12 Pages: 6373-6381

    • DOI

      10.1021/acs.joc.8b00592

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 2,5-Diaryltellurophenes: Effect of Electron-Donating and Electron-Withdrawing Groups on their Optoelectronic Properties2018

    • Author(s)
      Nagahora Noriyoshi、Yahata Shuhei、Goto Shoko、Shioji Kosei、Okuma Kentaro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 4 Pages: 1969-1975

    • DOI

      10.1021/acs.joc.7b02906

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthetic studies on a series of functionalized pyrylium salts, 4-chloro- and 4-bromophosphinines2018

    • Author(s)
      Nagahora Noriyoshi、Tokumaru Hiroshi、Ikaga Shinpei、Hanada Takuya、Shioji Kosei、Okuma Kentaro
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 15 Pages: 1880-1887

    • DOI

      10.1016/j.tet.2018.02.053

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stable 1H-Benzo[c]thio- and 1H-Benzo[c]selenophen-2-ium Tetrafluoroborates: Insight into Electronic Structures, Electrochemical Behavior, and Reactivity2017

    • Author(s)
      N. Nagahora, I. Takemoto, M. Fujii, K. Shioji, K. Okuma
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 8 Pages: 2110-2113

    • DOI

      10.1021/acs.orglett.7b00716

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] チオエーテルの分子内フリーデルクラフツ反応によるチオピリリウム塩の合成2019

    • Author(s)
      田中里奈・長洞記嘉・塩路幸生・大熊健太郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] チオフェンを含むチオピリリウム塩の合成と性質解明2019

    • Author(s)
      北原香奈・長洞記嘉・塩路幸生・大熊健太郎
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] カルコゲン元素を含むカチオン性芳香族化合物の合成と性質の解明2018

    • Author(s)
      長洞記嘉・櫛田朋子・北原香奈・田中里奈・塩路幸生・大熊健太郎
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] カルコゲノピリリウムユニットを組み込んだペンタセン誘導体の合成および性質解明2018

    • Author(s)
      櫛田朋子・長洞記嘉・塩路幸生・大熊健太郎
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 硫黄もしくはセレンを含むアセン系ジカチオン種の合成と性質解明2018

    • Author(s)
      櫛田朋子・長洞記嘉・塩路幸生・大熊健太郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 含リン芳香族化合物の酸化還元特性2017

    • Author(s)
      長洞記嘉・花田拓也・小川環樹・塩路幸生・大熊健太郎
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] フェニレン架橋したビホスフィニン一電子酸化体の合成と性質解明2017

    • Author(s)
      花田拓也・長洞記嘉・塩路幸生・大熊健太郎
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Buchwald-Hartwigアミノ化反応を用いた新規ホスフィニン類の合成、構造および性質2017

    • Author(s)
      後藤笙子・長洞記嘉・稲富貴裕・松原公紀・塩路幸生・大熊健太郎
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ホスフィニン類のBuchwald-Hartwigアミノ化反応2016

    • Author(s)
      長洞記嘉・後藤笙子・花田拓也・塩路幸生・大熊健太郎
    • Organizer
      第43回有機典型元素化学討論会
    • Place of Presentation
      仙台市
    • Year and Date
      2016-12-08
    • Related Report
      2016 Research-status Report
  • [Presentation] 硫黄もしくはセレンを含む複素環類の合成と性質解明2016

    • Author(s)
      長洞記嘉・竹本郁恵・花田拓也・後藤笙子・塩路幸生・大熊健太郎
    • Organizer
      第46回複素環化学討論会
    • Place of Presentation
      金沢市
    • Year and Date
      2016-09-26
    • Related Report
      2016 Research-status Report

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

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