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Design and synthesis of buckybowls having unique solid-state properties

Research Project

Project/Area Number 26288020
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

SAKURAI HIDEHIRO  大阪大学, 工学(系)研究科(研究院), 教授 (00262147)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2016: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2015: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2014: ¥12,090,000 (Direct Cost: ¥9,300,000、Indirect Cost: ¥2,790,000)
Keywordsバッキーボウル / スマネン / 固体物性 / 内部炭素 / フィリーデルクラフツ反応 / カルベン / 合成化学 / ナノ材料 / 有機工業化学 / 可溶媒分解 / フリーデルクラフツ反応 / カラム状積層構造 / 還元反応 / ヘリングボーン構造
Outline of Final Research Achievements

Our aim of this research is to establish a method to precisely control the unique morphology in the solid state of the bowl-shaped conjugate compound "Buckybowl" corresponding to the partial skeleton of fullerenes or the cap structure of carbon nanotubes, and to establish a rational molecular design for expressing various physical properties such as light emitting property and ferroelectric property, and development of a synthesis method thereof.
The most important result of this research is that it succeeded in developing a method for introducing a substituent to Sumanene internal carbon. As a result, we also succeeded in developing a method of aligning curved surfaces of Sumanene skeleton to metal surfaces. Development of chemical sensors utilizing curved / curved surface interaction of curved π plane is expected.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (35 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (3 results) Journal Article (16 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 15 results,  Acknowledgement Compliant: 13 results,  Open Access: 6 results) Presentation (13 results) (of which Int'l Joint Research: 9 results,  Invited: 9 results) Book (2 results) Remarks (1 results)

  • [Int'l Joint Research] Central Drug Research Institute(India)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] National Cheng-Kung University(Taiwan)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] IICT/CDRI(India)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Synthesis of Triaryltriazasumanenes2017

    • Author(s)
      P. Kaewmati, Q. Tan, S. Higashibayashi, Y. Yakiyama, H. Sakurai,
    • Journal Title

      Chem. Lett.

      Volume: 46 Issue: 1 Pages: 146-148

    • DOI

      10.1246/cl.160978

    • NAID

      130005308280

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Sumanene Derivatives Functionalized at the Internal Carbon2017

    • Author(s)
      N. Ngamsomprasert, J.-S. Dang, S. Higashibayashi, Y. Yakiyama, H. Sakurai
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 4 Pages: 697-700

    • DOI

      10.1039/c6cc08970d

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] lectronic and vibrational structures in the S0 and S1 states of coronene2017

    • Author(s)
      S. Kunishige, A. Kanaoka, T. Katori, M. Kawabata, M. Baba, T. Yamanaka, S. Higashibayashi, H. Sakurai,
    • Journal Title

      J. Chem. Phys.

      Volume: 146 Issue: 4 Pages: 044309-044309

    • DOI

      10.1063/1.4974336

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Two-way Correspondence Between Carbon Nanotubes and Caps: Development of a Numerical Algorithm and a Tool for Organic Cap Synthesis2017

    • Author(s)
      T. Sugai, H. Sakurai,
    • Journal Title

      Carbon

      Volume: 116 Pages: 678-685

    • DOI

      10.1016/j.carbon.2017.02.038

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Sumanene-Based Aryne, “Sumanyne”2017

    • Author(s)
      N. Ngamsomprasert, Y. Yakiyama, H. Sakurai
    • Journal Title

      Chem. Lett.

      Volume: 46 Issue: 4 Pages: 446-448

    • DOI

      10.1246/cl.161117

    • NAID

      130005549116

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Bowl Inversion and Electronic Switching of Buckybowls on Gold2016

    • Author(s)
      S. Fujii, M. Zlatdinov, S. Higashibayashi, H. Sakurai, M. Kiguchi,
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 37 Pages: 12142-12149

    • DOI

      10.1021/jacs.6b04741

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Hydroxysumanene and Substituent Effect of Hydroxy Group on Bowl Inversion Dynamics and Electronic Structure2016

    • Author(s)
      N. Ngamsomprasert, G. Panda, S. Higashibayashi, H. Sakurai
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 23 Pages: 11978-11981

    • DOI

      10.1021/acs.joc.6b02046

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Thermal stability, solubility, and fluorescence property of poly(arylene vinylene ketone)s bearing 1,1’-binaphthylene units2016

    • Author(s)
      T. Tsukamoto, K. Maeyama, S. Higashibayashi, H. Sakurai
    • Journal Title

      React. Funct. Polym.

      Volume: 100 Pages: 123-129

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of organosoluble and fluorescent aromatic polyketones bearing 1,1’-binaphthyl units through Suzuki-Miyaura coupling polymerization2015

    • Author(s)
      K. Maeyama, T. Tsukamoto, H. Kumagai, S. Higashibayashi, H. Sakurai
    • Journal Title

      Polym. Bull.

      Volume: 72 Issue: 11 Pages: 2903-2916

    • DOI

      10.1007/s00289-015-1443-z

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intra- and Intermolecular Reactivity of Triplet Sumanenetrione2015

    • Author(s)
      Kanahara, K.; Badal, Md. Mizanur Rahman; Hatano, S.; *Abe, M.; Higashibayashi, S.; Takashina, N.; Sakurai, H.
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 88 Issue: 11 Pages: 1612-1617

    • DOI

      10.1246/bcsj.20150230

    • NAID

      130005108574

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Synthesis and Characterization of Poly(arylene vinylene ketone)s Bearing 1,1′-Binaphthylene Units through Mizoroki–Heck Coupling Polymerization2015

    • Author(s)
      Tadashi Tsukamoto, Katsuya Maeyama, Shuhei Higashibayashi, Hidehiro Sakurai
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 12 Pages: 1780-1782

    • DOI

      10.1246/cl.150833

    • NAID

      130005112558

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 有機合成からのナノサイエンスへの貢献~ナノ(バッキー)ボウルとナノクラスターに関する研究2015

    • Author(s)
      櫻井英博
    • Journal Title

      生産と技術

      Volume: 67 Pages: 59-61

    • Related Report
      2015 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Columnar/herringbone dual crystal packing of pyrenylsumanene and its photophysical properties2014

    • Author(s)
      Binod Babu Shrestha, Shuhei Higashibayashi, Hidehiro Sakurai
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 10 Pages: 841-847

    • DOI

      10.3762/bjoc.10.80

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Correlation between bowl-inversion energy and bowl depth in substituted sumanenes2014

    • Author(s)
      Binod Babu Shrestha, Sangita Karanjit, Shuhei Higashibayashi, Hidehiro Sakurai
    • Journal Title

      Pure Appl. Chem.

      Volume: 86 Issue: 5 Pages: 747-753

    • DOI

      10.1515/pac-2013-1212

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Eclipsed Columnar Packing in Crystal Structure of Sumanenetrione2014

    • Author(s)
      B. B. Shrestha, Y. Morita, T. Kojima, M. Kawano, S. Higashibayashi, H. Sakurai
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 8 Pages: 1294-1296

    • DOI

      10.1246/cl.140350

    • NAID

      130004427145

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Sumanenetrione Anions Generated by Electrochemical and Chemical Reduction2014

    • Author(s)
      S. Higashibayashi, B. B. Shrestha, Y. Morita, M. Ehara, K. Ohkubo, S. Fukuzumi, H. Sakurai
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 8 Pages: 1297-1299

    • DOI

      10.1246/cl.140351

    • NAID

      130004427150

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Synthesis of Nitrogen-doped Curved Aromatic Molecules2017

    • Author(s)
      Hidehiro Sakurai
    • Organizer
      PACCON 2017
    • Place of Presentation
      Bangkok, Thailand
    • Year and Date
      2017-02-03
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Substituted Sumanenes at the Internal Carbon: An Example of pi-Figuration2016

    • Author(s)
      Hidehiro Sakurai
    • Organizer
      12th IUPAC International Symposium on Novel Materials and their Synthesi
    • Place of Presentation
      Changsha, China
    • Year and Date
      2016-10-15
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Substitution at the Intenal Carbon of Sumanene: An Example of pi-Figuration2016

    • Author(s)
      Hidehiro Sakurai
    • Organizer
      CURO-pi II
    • Place of Presentation
      Eugene, Oregon, USA
    • Year and Date
      2016-09-13
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Substituted Sumanenes at the Internal Carbon2016

    • Author(s)
      Hidehiro Sakurai
    • Organizer
      PERCH-CIC Comgress IX
    • Place of Presentation
      Pattaya, Thailand
    • Year and Date
      2016-06-27
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Reactivity of Hydroxysumanene: New Reaction Site on Sumanene Skeleton2016

    • Author(s)
      Niti Ngamsomprasert, Jing-Shuang Dang, Yumi Yakiyama, Shuhei Higashibayashi, Hidehiro Sakurai
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] スマネン内部炭素の直接ヒドロキシ化反応及び炭素-炭素結合生成2016

    • Author(s)
      吉田 悠希, Ngamsomprasert Niti, 東林 修平, 燒山 佑美, 櫻井 英博
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Reactivity of Hydroxysumanene: The First Example of the Functionalization at the Internal Carbon2016

    • Author(s)
      Niti Ngamsomprasert, Jing-Shuang Dang, Yumi Yakiyama, Shuhei Higashibayashi, Hidehiro Sakurai
    • Organizer
      PACCON2016
    • Place of Presentation
      バンコク(タイ)
    • Year and Date
      2016-02-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of C3-Symmetric Triazasumanene Derivatives2016

    • Author(s)
      Patcharin Kaewmati, Yumi Yakiyama, Shuhei Higashibayashi, Hidehiro Sakurai
    • Organizer
      PACCON2016
    • Place of Presentation
      バンコク(タイ)
    • Year and Date
      2016-02-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and properties of substituted sumanenes2015

    • Author(s)
      Hidehiro Sakurai
    • Organizer
      PACIFICHEM2015
    • Place of Presentation
      ホノルル(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] バッキーボウルの化学~スマネン合成を中心に~2015

    • Author(s)
      櫻井英博
    • Organizer
      第1回分子技術若手シンポジウム
    • Place of Presentation
      金沢大学(金沢市)
    • Year and Date
      2015-11-04
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Asymmetric Synthesis of C3 Symmetric Buckybowls2015

    • Author(s)
      Hidehiro Sakurai
    • Organizer
      Chiral india 2015
    • Place of Presentation
      ムンバイ(インド)
    • Year and Date
      2015-10-29
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Properties of Sumanene and its Derivatives2015

    • Author(s)
      Shuhei Higashibayashi, Hidehiro Sakurai,
    • Organizer
      ICMAT2015
    • Place of Presentation
      シンガポール(シンガポール)
    • Year and Date
      2015-06-25
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Substituted Sumanenes: From Fundamental to Applied Research2014

    • Author(s)
      Hidehiro Sakurai
    • Organizer
      The International Conference on Advanced Materials and Nanotechnology
    • Place of Presentation
      Kathmandu, Napal
    • Year and Date
      2014-11-04 – 2014-11-06
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Book] “Growing Buckybowl Chemistry”, in Polycyclic Arenes and Heteroarenes: Synthesis, Properties, and Applications2016

    • Author(s)
      S. Higashibayashi, H. Sakurai,
    • Total Pages
      23
    • Publisher
      Wiley-VCH Verlag GmbH &Co. KGaA
    • Related Report
      2015 Annual Research Report
  • [Book] Chapter 6 Chiral Sumanene, Triazasumanene, and Related Buckybowls” in Chemical Science of π-Electron Systems2015

    • Author(s)
      S. Higashibayashi, H. Sakurai
    • Total Pages
      16
    • Publisher
      Springer Japan
    • Related Report
      2015 Annual Research Report
  • [Remarks] 櫻井研究室HP

    • URL

      http://www.chem.eng.osaka-u.ac.jp/~sakurai-lab/

    • Related Report
      2015 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2022-02-16  

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