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Synthesis of macrocyclic acenequinones as a substructure of zigzag-type carbon nanotubes

Research Project

Project/Area Number 25620022
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionKanazawa University

Principal Investigator

AKINE Shigehisa  金沢大学, 物質化学系, 教授 (30323265)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords大環状化合物 / ポリアセン / キノン / 多環芳香族 / 自己集合 / ナノチューブ
Outline of Final Research Achievements

Macrocyclic acenes are of interest because of the unique structure, which can be regarded as a substructure of zigzag-type carbon nanotubes. However, theoretical studies have already revealed that macrocyclic acenes are too unstable to be isolated. In this study, we focused on macrocyclic acenequinones, which could also be useful as carbon nanotube substructure.
We developed synthetic strategy to several kinds of 2,3,9,10-tetrasubstituted pentacenequinones. We found that a pentacenequinone derivative having crown ether moieties forms a macrocyclic acene structure upon binding with larger alkali metal ions (K, Rb, Cs).

Report

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

    (36 results)

All 2015 2014 2013

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (27 results) (of which Invited: 18 results)

  • [Journal Article] Oxidation Reactivity of a Structurally and Spectroscopically Well-Defined Mononuclear Peroxocarbonato-Iron(III) Complex2015

    • Author(s)
      Tsugawa, T.; Furutachi, H.; Marunaka, M.; Endo, T.; Hashimoto, K.; Fujinami, S.; Akine, S.; Sakata, Y.; Nagatomo, S.; Tosha, T.; Nomura, T.; Kitagawa, T.; Ogura, T.; Suzuki, M.
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 3 Pages: 330-332

    • DOI

      10.1246/cl.141058

    • NAID

      130004868402

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dynamic Helicity Control of a Single-Helical Oligooxime Complex and Acid-Base Triggered Repeated Helicity Inversion Mediated by Amino Acids2014

    • Author(s)
      Sairenji, S.; Akine, S.; Nabeshima, T.
    • Journal Title

      Chem. Lett.

      Volume: 印刷中 Issue: 7 Pages: 1107-1109

    • DOI

      10.1246/cl.140263

    • NAID

      130004868263

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Increased Nuclearity of Salen-Type Transition Metal Complexes by Incorporation of O-Alkyloxime Functionality2014

    • Author(s)
      Akine, S.; Nabeshima, T.
    • Journal Title

      Heteroat. Chem.

      Volume: 25 Issue: 5 Pages: 410-421

    • DOI

      10.1002/hc.21205

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Perfect encapsulation of guanidinium ion in a helical trinickel(II) metallocryptand for efficient regulation of helix inversion rate2014

    • Author(s)
      Akine, S.; Miyashita, M.; Piao, S.; Nabeshima, T.
    • Journal Title

      Inorg. Chem. Front.

      Volume: 1 Issue: 1 Pages: 53-57

    • DOI

      10.1039/c3qi00067b

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Dynamic helicity control of single-helical oligooxime metal complexes by coordination of chiral carboxylate ions2014

    • Author(s)
      Sairenji, S.; Akine, S.; Nabeshima, T.
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Issue: 12 Pages: 1987-1990

    • DOI

      10.1016/j.tetlet.2014.02.009

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Programmed multiple complexation for the creation of helical structures from acyclic phenol-bipyridine oligomer ligands2013

    • Author(s)
      Akine, S.; Nagumo, H.; Nabeshima, T.
    • Journal Title

      Dalton Trans.

      Volume: 42 Issue: 45 Pages: 15974-15986

    • DOI

      10.1039/c3dt51240a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stepwise Helicity Inversions by Multisequential Metal Exchange2013

    • Author(s)
      Akine, S.; Sairenji, S.; Taniguchi, T.; Nabeshima, T.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 35 Pages: 12948-12951

    • DOI

      10.1021/ja405979v

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Planar Metal Complexes and the Stacking Abilities of Naphthalenediol-Based Acyclic and Macrocyclic Salen-Type Ligands2013

    • Author(s)
      Akine, S.; Varadi, Z.; Nabeshima, T.
    • Journal Title

      Eur. J. Inorg. Chem.

      Volume: 2013 Issue: 35 Pages: 5987-5998

    • DOI

      10.1002/ejic.201300917

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cage-like tris(salen)-type metallocryptand for cooperative guest recognition2013

    • Author(s)
      Akine, S.; Piao, S.; Miyashita, M.; Nabeshima, T.
    • Journal Title

      Tetrahedron Lett.

      Volume: 54 Issue: 48 Pages: 6541-6544

    • DOI

      10.1016/j.tetlet.2013.09.098

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 新規なクラウンエーテル型環状二核ニッケル(II)メタロホストの合成と性質2015

    • Author(s)
      小林聖弥・酒田陽子・秋根茂久
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] キラルなカルボン酸イオンの配位を利用したらせん型四核錯体の動的ヘリシティー制御2015

    • Author(s)
      高槻百合・酒田陽子・鍋島達弥・秋根茂久
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] ルテニウム(II)saloph 錯体の軸配位を利用した集合型メタロホストの合成とカチオン認識2015

    • Author(s)
      中村優理・酒田陽子・秋根茂久
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] コバルト(III)を含む新規な環状二核メタロホストの合成とゲスト認識2015

    • Author(s)
      村田千穂・酒田陽子・秋根茂久
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] らせん型錯体のヘリシティーを自在に制御する:有機化学的設計による挑戦2014

    • Author(s)
      秋根茂久
    • Organizer
      高分子学会 第8回超分子若手懇談会
    • Place of Presentation
      加賀
    • Year and Date
      2014-10-09
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] クラウンエーテルによるイオン認識を利用したペンタセンキノン二量体の形成2014

    • Author(s)
      高槻百合・秋根茂久・鍋島達弥
    • Organizer
      高分子学会 第8回超分子若手懇談会
    • Place of Presentation
      加賀
    • Year and Date
      2014-10-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Control of helix inversion of helical multinuclear complexes by molecular recognition2014

    • Author(s)
      秋根茂久
    • Organizer
      錯体化学会第64回討論会
    • Place of Presentation
      東京
    • Year and Date
      2014-09-18
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 分子認識を利用した三重らせん型かご型錯体のヘリシティー保持2014

    • Author(s)
      秋根茂久・宮下真人・鍋島達弥
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07
    • Related Report
      2014 Annual Research Report
  • [Presentation] A Helical Trinickel(II) Metallo-cryptand for Efficient Regulation of the Helix Inversion Rate2014

    • Author(s)
      S. Akine, M. Miyashita, T. Nabeshima
    • Organizer
      41st International Conference on Coordination Chemistry
    • Place of Presentation
      Singapore
    • Year and Date
      2014-07-24
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルカリ金属イオンとの錯形成によるペンタセンキノンダイマーの形成2014

    • Author(s)
      高槻百合・秋根茂久・鍋島達弥
    • Organizer
      第12回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-06-01
    • Related Report
      2014 Annual Research Report
  • [Presentation] らせん型メタロクリプタンドの合成と分子認識によるらせん反転速度の制御2014

    • Author(s)
      秋根茂久・宮下真人・鍋島達弥
    • Organizer
      第12回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2014-05-31
    • Related Report
      2014 Annual Research Report
  • [Presentation] 開口部に架橋ジアミン配位子をもつ新規かご型コバルト三核錯体の合成とゲスト認識2014

    • Author(s)
      宮下真人・秋根茂久・鍋島達弥
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] アルカリ金属イオンとの錯形成を利用したペンタセンキノン二量体の形成2014

    • Author(s)
      高槻百合・秋根茂久・鍋島達弥
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] シリル基の除去反応を活用したらせん型亜鉛多核錯体の動的ヘリシティー反転2014

    • Author(s)
      西連地志穂・秋根茂久・鍋島達弥
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Formation of Pentacenequinone Dimer by Sandwich Complexation with Alkali Metal Ion2014

    • Author(s)
      Yuri Takatsuki, Shigehisa Akine, Tatsuya Nabeshima
    • Organizer
      CENIDE-CNMM-TIMS Joint Symposium on Interdisciplinary Nano-Science and Technology
    • Place of Presentation
      Hsinchu, Taiwan
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Multi-step Helicity Inversion of Helical Multinuclear Complex by Stepwise Metal Exchange2014

    • Author(s)
      Shigehisa Akine, Shiho Sairenji, Tatsuya Nabeshima
    • Organizer
      International Symposium on Coordination Programming (ISCP2014)
    • Place of Presentation
      Tokyo, Japan
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] キラルカウンターイオンの化学変換によるらせん型錯体の動的ヘリシティー制御2013

    • Author(s)
      西連地志穂・秋根茂久・鍋島達弥
    • Organizer
      第10回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      和歌山
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 三つの遷移金属錯体部位をもつメタロクリプタンドの合成と分子認識2013

    • Author(s)
      宮下真人・秋根茂久・鍋島達弥
    • Organizer
      第10回ホスト・ゲスト化学シンポジウム
    • Place of Presentation
      和歌山
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] キラルなカルボン酸イオンの化学変換を活用したらせん型メタロフォルダマーの動的ヘリシティー制御2013

    • Author(s)
      西連地志穂・秋根茂久・鍋島達弥
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 直鎖オリゴオキシムの錯形成によるらせん構造の創製と段階的な金属添加による多段階ヘリシティー反転2013

    • Author(s)
      西連地志穂・秋根茂久・鍋島達弥
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 三つのsaloph部位を有するニッケル三核メタロクリプタンドの合成とゲスト認識2013

    • Author(s)
      宮下真人・秋根茂久・鍋島達弥
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] 複数のフェニル基を導入したビピリジンおよびテルピリジン配位子の合成と錯形成2013

    • Author(s)
      小林 愛・秋根茂久・鍋島達弥
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] クラウンエーテル部位を導入したペンタセンキノンの合成と錯形成2013

    • Author(s)
      高槻百合・秋根茂久・鍋島達弥
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] らせん構造をもつニッケル三核メタロクリプタンドの合成と分子認識2013

    • Author(s)
      宮下真人・秋根茂久・鍋島達弥
    • Organizer
      錯体化学会第63回討論会
    • Place of Presentation
      西原
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Stepwise Helicity Inversion of Helical Complex by Exchange of Constituent Metal Ions2013

    • Author(s)
      Shiho Sairenji, Shigehisa Akine, Tatsuya Nabeshima
    • Organizer
      The 3rd German-Japan Nanoworkshop ~ Energy Conversion and Storage ~
    • Place of Presentation
      Tsukuba, Japan
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Multi-step helicity inversion of helical oligooxime complex by exchange of constituent metal ions2013

    • Author(s)
      Shiho Sairenji, Shigehisa Akine, Tatsuya Nabeshima
    • Organizer
      4th Tetrahedron Symposium-Asian Edition
    • Place of Presentation
      Seoul, Korea
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Development of a rational strategy for helicity inversion of helical metal complexes2013

    • Author(s)
      Shigehisa Akine, Tatsuya Nabeshima
    • Organizer
      4th Asian Conference on Coordination Chemistry
    • Place of Presentation
      Jeju, Korea
    • Related Report
      2013 Research-status Report
    • Invited

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

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