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Synthesis of New Heterobuckybowls

Research Project

Project/Area Number 25410124
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionInstitute for Molecular Science

Principal Investigator

HIGASHIBAYASHI Shuhei  分子科学研究所, 協奏分子システム研究センター, 助教 (30338264)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsバッキーボウル / ヘテロバッキーボウル / おわん型 / ヒドラジン / カルバゾール / 構造 / 酸化還元
Outline of Final Research Achievements

We succeeded to synthesize a new heterobuckybowl, bow-shaped heteroatom-containing aromatic compound, possessing two neighboring nitrogen atoms in the bowl skeleton. It was revealed that the molecule possesses bowl and twist structures in the neutral state, a shallower bowl structure in the one-electron oxidized state, and a planar structure in the two-electron oxidized state. Since the molecule is reversibly oxidized and reduced, the structure can be changed an controlled between the curved and planar structures by transfer of electrons.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (46 results)

All 2016 2015 2014 2013

All Journal Article (16 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 16 results,  Acknowledgement Compliant: 8 results,  Open Access: 5 results) Presentation (28 results) (of which Int'l Joint Research: 3 results,  Invited: 1 results) Book (2 results)

  • [Journal Article] Synthesis of three-dimensional butterfly slit-cyclobisazaanthracenes and hydrazinobisanthenes via one-step cyclodimerization and their properties2016

    • Author(s)
      Koji Yamamoto, Shuhei Higashibayashi
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 2 Pages: 663-671

    • DOI

      10.1002/chem.201504144

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [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 acid-responsive electron transfer disproportionation of non- and tetramesityl-substituted 1,1',9,9'-bicarbazole2015

    • Author(s)
      Palash Pandit, Toshikazu Nakamura, Shuhei Higashibayashi
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 10 Pages: 1336-1338

    • DOI

      10.1246/cl.150557

    • NAID

      130005101493

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Acid-regulated electron transfer disproportionation of a non-substituted tetramethyl-biacridine derivative2015

    • Author(s)
      Koji Yamamoto, Toshikazu Nakamura, Shuhei Higashibayashi
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 9 Pages: 1229-1231

    • DOI

      10.1246/cl.150498

    • NAID

      130005096898

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Acid/Base-Regulated Reversible Electron Transfer Disproportionation of N-N linked Bicarbazole and Biacridine Derivatives2015

    • Author(s)
      Palash Pandit,† Koji Yamamoto,† (†: equally contributed) Toshikazu Nakamura, Katsuyuki Nishimura, Yuki Kurashige, Takeshi Yanai, Go Nakamura, Shigeyuki Masaoka, Ko Furukawa, Yumi Yakiyama, Masaki Kawano and Shuhei Higashibayashi
    • Journal Title

      Chemical Science

      Volume: 印刷中 Issue: 7 Pages: 4160-4173

    • DOI

      10.1039/c5sc00946d

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Investigation of the Dynamic Behavior of Bisumanenyl2015

    • Author(s)
      Binod Babu Shrestha, Sangita Karanjit, Shuhei Higashibayashi, Toru Amaya, Toshikazu Hirao, and Hidehiro Sakurai
    • Journal Title

      Asian J. Org. Chem.

      Volume: 4 Issue: 1 Pages: 62-68

    • DOI

      10.1002/ajoc.201402226

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [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 Research-status 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 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] DFT Studies of Mechanism and Origin of Stereoselectivity of Palladium-Catalyzed Cyclotrimerization Reactions Affording syn-Tris(norborneno)benzenes2014

    • Author(s)
      Yamanaka, M.; Morishima, M.; Shibata, Y.; Higashibayashi, S.; Sakurai, H.
    • Journal Title

      Organometallics

      Volume: 33 Issue: 12 Pages: 3060-3068

    • DOI

      10.1021/om500322b

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [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 Research-status 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 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [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 Issue: 28 Pages: 7314-7316

    • DOI

      10.1002/anie.201303134

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Jet spectroscopy of buckybowl: Electronic and vibrational structures in the S0 and S1 states of triphenylene and sumanene2013

    • Author(s)
      S. Kunishige, M. Kawabata, M. Baba, T. Yamanaka, Y. Morita, S. Higashibayashi, H. Sakurai
    • Journal Title

      J. Chem. Phys.

      Volume: 139 Issue: 4 Pages: 44313-44321

    • DOI

      10.1063/1.4816636

    • NAID

      120005322888

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluorinated and Trifluoromethylated Corannulenes2013

    • Author(s)
      Bernd M. Schmidt, Berit Topolinski, Mihoko Yamada, Shuhei Higashibayashi, Mitsuhiko Shionoya, Hidehiro Sakurai, Dieter Lentz
    • Journal Title

      Chemistry A European Journal

      Volume: 19 Issue: 41 Pages: 13872-13880

    • DOI

      10.1002/chem.201301910

    • Related Report
      2013 Research-status Report
    • 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 Issue: 38 Pages: 13809-13812

    • DOI

      10.1039/c3dt51569a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Beam-induced graphitic carbon cage transformation from sumanene aggregates2013

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

      Appl. Phys. Lett.

      Volume: 104 Issue: 4 Pages: 43107-43112

    • DOI

      10.1063/1.4863739

    • NAID

      120007130565

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 剛直なスリットバタフライ型シクロビスアザアントラセン類と柔軟なヒドラジノビスアンテン類の合成2016

    • Author(s)
      山本浩司, 東林修平
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都府京田辺市同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヒドラジノバッキーボウルの合成と性質2016

    • Author(s)
      東林修平, Palash Pandit, 春木理恵, 足立伸一, 熊井玲児
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京都府京田辺市同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Acid/base-regulated reversible electron transfer disproportionation of hydrazinohelicenes2015

    • Author(s)
      Shuhei Higashibayashi
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      アメリカ合衆国ハワイ州ホノルル市ハワイアンコンベンションセンター
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] 三次元スリットシクロビスアザアセン類と三次元または二次元ヒドラジノペリアセン類の合成2015

    • Author(s)
      山本浩司, 東林修平
    • Organizer
      第108回有機合成シンポジウム
    • Place of Presentation
      東京都新宿区早稲田大学国際会議場
    • Year and Date
      2015-11-05
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヒドラジノバッキーボウルの合成2015

    • Author(s)
      Palash Pandit, 東林修平
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛県松山市愛媛大学城北キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヒドラジノヘリセン型ビカルバゾール誘導体の酸応答性電子移動不均化反応2015

    • Author(s)
      Palash Pandit,山本浩司,中村敏和,西村勝之, 倉重佑輝,柳井毅,中村豪,正岡重行,古川貢, 焼山佑美, 河野正規, 東林修平
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛県松山市愛媛大学城北キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 三次元スリットシクロビスアザアントラセン類と三次元,二次元ヒドラジノビスアンテン類の合成と性質2015

    • Author(s)
      山本浩司, 東林修平
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛県松山市愛媛大学城北キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヒドラジノヘリセン型ビアクリジン誘導体の酸塩基刺激による可逆的電子移動不均化反応2015

    • Author(s)
      山本浩司,Palash Pandit,中村敏和,西村勝之, 倉重佑輝,柳井毅,中村豪,正岡重行,古川貢, 焼山佑美, 河野正規, 東林修平
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛県松山市愛媛大学城北キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Acid-responsive electron transfer disproportionation of N-N linked bicarbazole derivatives2015

    • Author(s)
      Palash Pandit, Koji Yamamoto, Toshikazu Nakamura, Katsuyuki Nishimura, Yuki Kurashige, Takeshi Yanai, Go Nakamura, Shigeyuki Masaoka, Ko Furukawa, Yumi Yakiyama, Masaki Kawano, Shuhei Higashibayashi
    • Organizer
      16th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      スペイン, マドリッドコンプルテンセ大学
    • Year and Date
      2015-07-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Acid/base-regulated reversible electron transfer disproportionation of N-N linked biacridine derivatives2015

    • Author(s)
      Koji Yamamoto, Palash Pandit, Toshikazu Nakamura, Yuki Kurashige, Takeshi Yanai, Go Nakamura, Shigeyuki Masaoka, Shuhei Higashibayashi
    • Organizer
      16th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      スペイン, マドリッドコンプルテンセ大学
    • Year and Date
      2015-07-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Columnar crystal structure and redox property of sumanenetrione2015

    • Author(s)
      Shuhei Higashibayashi, Binod B. Shreshta, Yuki Morita, Kei Ohkubo, Shunichi Fukuzumi, Tatsuhiro Kojima, Masaki Kawano, Masahiro Ehara, Hidehiro Sakurai
    • Organizer
      16th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      スペイン, マドリッドコンプルテンセ大学
    • Year and Date
      2015-07-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ジアザヘリセン類の酸応答性電子移動不均化反応2015

    • Author(s)
      東林修平, 山本浩司,Palash Pandit,中村敏和,西村勝之, 倉重佑輝,柳井毅,中村豪,正岡重行,古川貢, 焼山佑美, 河野正規
    • Organizer
      第107回有機合成シンポジウム
    • Place of Presentation
      東京都港区慶應義塾大学薬学部マルチメディア講堂
    • Year and Date
      2015-06-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] 酸応答性ビアクリジン誘導体2015

    • Author(s)
      山本浩司,Palash Pandit,中村敏和,倉重佑輝,柳井毅,中村豪,正岡重行,東林修平
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉県船橋市日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 酸応答性ビカルバゾール誘導体2015

    • Author(s)
      Palash Pandit,山本浩司,中村敏和,西村勝之, 倉重佑輝,柳井毅,中村豪,正岡重行,古川貢, 東林修平
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉県船橋市日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] スマネントリオンの結晶構造とアニオン種2014

    • Author(s)
      東林修平, Binod Babu Shrestha, 森田悠紀, 大久保敬, 福住俊一, 小島達弘, 河野正規, 江原正博, 櫻井英博
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      宮城県仙台市青葉区東北大学川内北キャンパス
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis and Properties of Hydroxysumanene2014

    • Author(s)
      Niti Ngamsomprasert, Binod Babu Shrestha, 東林修平, 櫻井英博
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学, 愛知, 名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis and Properties of π-Extended Derivatives of Sumanene2014

    • Author(s)
      Binod Babu Shrestha, Sangita Karanjit, 東林修平, 櫻井英博
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学, 愛知, 名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] スマネンの環拡大反応によるC70の部分バッキーボウルの合成2014

    • Author(s)
      岡部佑紀, 東林修平, 櫻井英博
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学, 愛知, 名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] スマネントリオンの結晶構造とアニオン種2014

    • Author(s)
      東林修平, Binod Babu Shrestha, 森田悠紀, 大久保敬, 福住俊一, 櫻井英博
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学, 愛知, 名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Substituted Sumanenes by Aromatic Electrophilic Substitution Reaction2013

    • Author(s)
      Binod Babu Shrestha, Sangita Karanjit, Gautam Panda, Shuhei Higashibayashi, Hidehiro Sakurai
    • Organizer
      Nagoya Symposium 2013
    • Place of Presentation
      名古屋大学, 愛知, 名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] Stereoelectronic effect of curved aromatic structure dominating the endo/exo conformational stability in buckybowl, benzylic substituted sumanenes2013

    • Author(s)
      Shuhei Higashibayashi, Satoru Onogi, Hemant Kumar Srivastava, G. Narahari Sastry, Yao-Ting Wu, Hidehiro Sakurai
    • Organizer
      The 11th International Symposium on Functional π-Electron Systems
    • Place of Presentation
      the Palais des Congress, France, Archachon
    • Related Report
      2013 Research-status Report
  • [Presentation] First stereoelectronic effect of curved aromatic structure: conformational stability of buckybowl, substituted sumanene2013

    • Author(s)
      Shuhei Higashibayashi
    • Organizer
      The 1st Asian Conference for “MONODUKURI” Strategy by Synthetic Organic Chemistry
    • Place of Presentation
      Southern Beach Hotel & Resort, 沖縄, 糸満
    • Related Report
      2013 Research-status Report
  • [Presentation] Rearrangement Reaction from Sumanene to Shallower Benzopyrene Bowl2013

    • Author(s)
      Yuki Okabe, Shuhei Higashibayashi, Hidehiro Sakurai
    • Organizer
      15th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Howard Civil Service International House, Taiwan, Taipei
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of Sumanene Derivatives and Their Physical Properties2013

    • Author(s)
      Binod Babu Shrestha, Sangita Karanjit, Shuhei Higashibayashi, Hidehiro Sakurai
    • Organizer
      15th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Howard Civil Service International House, Taiwan, Taipei
    • Related Report
      2013 Research-status Report
  • [Presentation] Stereoelectronic Effect of Curved Aromatic Structure Dominating the endo/exo Conformational Stability in Buckybowl2013

    • Author(s)
      huhei Higashibayashi, Satoru Onogi, Hemant Kumar Srivastava, G. Narahari Sastry, Yao-Ting Wu, Hidehiro Sakurai
    • Organizer
      15th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Howard Civil Service International House, Taiwan, Taipei
    • Related Report
      2013 Research-status Report
  • [Presentation] C3 Symmetric Chrial Triazasumanene2013

    • Author(s)
      Shuhei Higashibayashi, Qitao Tan, Sangita Karanjit, Masaki Kawano, Hidehiro Sakurai
    • Organizer
      15th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Howard Civil Service International House, Taiwan, Taipei
    • Related Report
      2013 Research-status Report
  • [Presentation] スマネンの環拡大反応によるC70の部分バッキーボウルの合成2013

    • Author(s)
      岡部佑紀, 東林修平, 櫻井英博
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学, 東京
    • Related Report
      2013 Research-status Report
  • [Presentation] おわん型π共役分子バッキーボウルの合成2013

    • Author(s)
      東林修平
    • Organizer
      第30回有機合成化学セミナー
    • Place of Presentation
      せとうち児島ホテル, 岡山, 倉敷
    • Related Report
      2013 Research-status Report
    • Invited
  • [Book] Polycyclic Arenes and Heteroarenes: Synthesis, Properties, and Applications2015

    • Author(s)
      Shuhei Higashibayashi, Hidehiro Sakurai(共著)
    • Total Pages
      360
    • Publisher
      Wiely-VCH
    • Related Report
      2015 Annual Research Report
  • [Book] Chemical Science of π-Electron Systems2015

    • Author(s)
      Shuhei Higashibayashi, Hidehiro Sakurai(共著)
    • Total Pages
      777
    • Publisher
      Springer
    • Related Report
      2015 Annual Research Report

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Published: 2014-07-25   Modified: 2019-07-29  

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