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2013 Fiscal Year Final Research Report

Synthesis and Properties of Functionalized Buckybowls

Research Project

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Project/Area Number 23350024
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionInstitute for Molecular Science

Principal Investigator

SAKURAI Hidehiro  分子科学研究所, 協奏分子システム研究センター, 准教授 (00262147)

Project Period (FY) 2011-04-01 – 2014-03-31
Keywordsバッキーボウル / 湾曲π / 電子輸送性 / 立体電子効果
Research Abstract

Synthetic methods for various type of functionalized buckybowls has been developed including C3 symmetric and unsymmetrical sumanenes, C2 symmetric corannulene derivatives, and fluorinated buckybowls.
The thus-prepared functionalized buckybowls exhibit unique properties. In particular, crystals having columnar stacking structure shows high electron mobility even in the case of corannulene derivatives, which does not usually shows the electron mobility.
The first example of the through-bond stereoelectronic effect of curved aromatic compounds was found in buckybowls, benzylic substituted sumanenes. Methyl- and hydroxyl-sumanene favour the endo-R conformer due to the different strength of hyperconjugation of the benzylic C-H bond and the bowl between the endo-R and exo-R conformers.

  • Research Products

    (25 results)

All 2014 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (10 results) (of which Invited: 7 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Beam-induced graphitic carbon cage transformation from sumanene aggregates2014

    • Author(s)
      J-i. Fujita, M. Tachi, K. Murakami, H. Sakurai, Y. Morita, S. Higashibayashi, M. Takeguchi
    • Journal Title

      Appl. Phys. Lett

      Volume: 104 Pages: 043107. (5)

    • DOI

      10.1063/1.4863739

    • Peer Reviewed
  • [Journal Article] Fluorinated and Trifluoromethylated Corannulenes2013

    • Author(s)
      B. M. Schmidt, B. Topolinski, M. Yamada, S. Higashibayashi, M. Shionoya, H. Sakurai, D. Lentz
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Pages: 13872-13880

    • DOI

      10.1002/chem.201301910

    • Peer Reviewed
  • [Journal Article] Sumanenylferrocenes and their solid state self-assembly2013

    • Author(s)
      B. Topolinski, B. M. Schmidt, S. Higashibayashi, H. Sakurai, D. Lentz
    • Journal Title

      Dalton Trans

      Volume: 42 Pages: 13809-13812

    • DOI

      10.1039/C3DT51569A

    • Peer Reviewed
  • [Journal Article] Stereoelectronic Effect of Curved Aromatic Structure Favouring the Unexpected Endo Conformation of Benzylic Substituted Sumanene2013

    • Author(s)
      S. Higashibayashi, S. Onogi, H. K. Srivastava, G. N. Sastry, Y.-T. Wu, H. Sakurai
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 52 Pages: 7314-7316

    • DOI

      10.1002/anie.201303134

    • Peer Reviewed
  • [Journal Article] Synthesis of Substituted Sumanenes by Aromatic Electrophilic Substitution Reactions2013

    • Author(s)
      B. B. Shrestha, S. Karanjit, G. Panda, S. Higashibayashi, H. Sakurai
    • Journal Title

      Chem. Lett

      Volume: 42 Pages: 386-388

    • DOI

      10.1246/cl.2013.386

    • Peer Reviewed
  • [Journal Article] The Synthesis of Hexaflorosumanene and its Congeners2013

    • Author(s)
      B. M. Schmidt, B. Topolinski, S. Higashibayashi, T. Kojima, M. Kawano, D. Lentz, H. Sakurai
    • Journal Title

      Chem. Eur. J

      Volume: 19 Pages: 3282-3286

    • DOI

      10.1002/chem.201204622

    • Peer Reviewed
  • [Journal Article] Electonic Properties of Trifluoromethylated Corannulenes2012

    • Author(s)
      B. M. Schmidt, S. Seki, B. Topolinski, K. Ohkubo, S. Fukuzumi, H. Sakurai, D. Lentz
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Pages: 11385-11388

    • DOI

      10.1002/anie.201205757

    • Peer Reviewed
  • [Journal Article] Emission Amplification by Sumanene Nanocrystals in an Onigiri-Type Organic-Organic Assembly2012

    • Author(s)
      Y. Morita, S. Nakao, S. Haesuwannakij, S. Higashibayashi, H. Sakurai
    • Journal Title

      Chem. Commun

      Volume: 48 Pages: 9050-9052

    • DOI

      10.1039/C2CC33643J

    • Peer Reviewed
  • [Journal Article] Enantioselective synthesis of a chiral nitrogen-doped buckybowl2012

    • Author(s)
      Q.-T. Tan, S. Higashibayashi, S. Karanjit, H. Sakurai
    • Journal Title

      Nat. Commun

      Volume: 3 Pages: 891

    • DOI

      10.1038/ncomms1896

    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed Arylation of Methylene -Bridged Polyarenes : Synthesis and Structures of 9-Arylfluorene Derivatives2012

    • Author(s)
      J.-J. Chen, S. Onogi, Y.-C. Hsieh, C.-C. Hsiao, S. Higashibayashi, H. Sakurai, Y.-T. Wu
    • Journal Title

      Adv. Synth. Catal

      Volume: 354 Pages: 1551-1558

    • DOI

      10.1002/adsc.201100931

    • Peer Reviewed
  • [Journal Article] Trimethylsumanene : Enantioselective Synthesis, Substituent Effect on Bowl Structure, Inversion Energy, and Electron Conductivity2012

    • Author(s)
      S. Higashibayashi, R. Tsuruoka, Y. Soujanya, U. Purushotham, G. N. Sastry, S. Seki, T. Ishikawa, S. Toyota, H. Sakurai
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 85 Pages: 450-467

    • DOI

      10.1246/bcsj.20110286

    • Peer Reviewed
  • [Journal Article] Selective Synthesis of C3 Symmetric Functionalized Sumanenes2012

    • Author(s)
      S. Higashibayashi, Nasir Baig R. B., Y. Morita, H. Sakurai
    • Journal Title

      Chem. Lett

      Volume: 41 Pages: 84-86

    • DOI

      10.1246/cl.2012.84

    • Peer Reviewed
  • [Presentation] バッキーボウルの特徴を生かした機能開発へ向けて2014

    • Author(s)
      櫻井英博
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学, 名古屋市, 愛知
    • Year and Date
      2014-03-30
    • Invited
  • [Presentation] 精密合成法を基盤とした非平面π共役化合物「バッキーボウル」に関する研究2014

    • Author(s)
      櫻井英博
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学, 名古屋市, 愛知
    • Year and Date
      2014-03-27
    • Invited
  • [Presentation] バッキーボウル化学におけるキラリティ2014

    • Author(s)
      櫻井英博
    • Organizer
      第5回キラルサイエンス&テクノロジーシンポジウム
    • Place of Presentation
      早稲田大学 ,新宿区, 東京
    • Year and Date
      2014-02-28
    • Invited
  • [Presentation] Substituted Sumanenes : From Fundamental to Applied Research2013

    • Author(s)
      H. Sakurai
    • Organizer
      9th IUPAC International Symposium on Novel Materials and their Synthesis and 21th International Symposium on Fine Chemistry and Functional Polymers
    • Place of Presentation
      Fudan University, Shanghai, China
    • Year and Date
      2013-10-21
    • Invited
  • [Presentation] Synthesis of Sumanene and Related Buckybowls2013

    • Author(s)
      H. Sakurai
    • Organizer
      15th Asian Chemical Congress
    • Place of Presentation
      Resort World Sentosa, Singapore
    • Year and Date
      2013-08-20
    • Invited
  • [Presentation] Asymmetric Synthesis of C3 Symmetric Buckybowls, PERCH-CIC Congress VIII2013

    • Author(s)
      H. Sakurai
    • Organizer
      Jomtien Palm Beach Hotel & Resort
    • Place of Presentation
      Pattaya, Thailand
    • Year and Date
      2013-05-06
  • [Presentation] お椀型共役化合物「バッキーボウル」の化学2012

    • Author(s)
      櫻井英博
    • Organizer
      奈良先端未来開拓コロキウム2012
    • Place of Presentation
      奈良先端科学技術大学院大学, 生駒市, 奈良
    • Year and Date
      20121208-09
    • Invited
  • [Presentation] Chemical Synthesis of Nitrogen-doped Buckybowls2012

    • Author(s)
      H. Sakurai, Q.-T. Tan, S. Higashibayashi
    • Organizer
      8th IUPAC International Symposium on Novel Materials and their Synthesis and 21th International Symposium on Fine Chemistry and Functional Polymers
    • Place of Presentation
      Xian Jiaotong University, Xian, China
    • Year and Date
      20121014-19
    • Invited
  • [Presentation] Enantioselective Synthesis of C3 Symmetric Chiral Triazasumanenes2011

    • Author(s)
      Q.-T. Tan, S. Higashibayashi, S. Karanjit, H. Sakurai
    • Organizer
      Catalysis and Fine Chemicals 2011
    • Place of Presentation
      新公会堂, 奈良
    • Year and Date
      20111204-08
  • [Presentation] Synthesis of C3 Symmetric Sumanenes2011

    • Author(s)
      S. Higashibayashi, R. Tsuruoka, R. B. Nasir Baig, H. Sakurai
    • Organizer
      14th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Oregon University, Eugene, Oregon, USA
    • Year and Date
      20110724-29
  • [Book] 精密有機合成によるカーボンπ空間の構築,高次π空間の創発と機能開発,赤阪健編2013

    • Author(s)
      櫻井英博
    • Total Pages
      40-43
    • Publisher
      シーエムシー出版
  • [Book] 精密合成が拓くπ電子科学, CSJ カレントレビュー12未来材料を創出するπ電子系の科学-新しい合成・構造・機能化研究,赤阪健,岩澤伸治,山口茂弘,磯部寛之編2013

    • Author(s)
      櫻井英博, 東林修平
    • Total Pages
      46-53
    • Publisher
      化学同人
  • [Remarks]

    • URL

      http://groups.ims.ac.jp/organization/sakurai_g/home.html

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Published: 2015-06-25  

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