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Synthesis of cyclic pi-conjugated molecules through the template synthetic approach and elucidation of their properties

Research Project

Project/Area Number 24750087
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

KAYAHARA Eiichi  京都大学, 化学研究所, 助教 (10610553)

Co-Investigator(Renkei-kenkyūsha) YAMAGO Shigeru  京都大学, 化学研究所, 教授 (30222368)
Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsπ共役系化合物 / 白金 / スズ / 金属交換反応 / 還元的脱離 / 単結晶構造解析 / 光物性 / 酸化還元特性
Research Abstract

Curved pi-conjugated molecules with closed and three dimensional (3D) structures, such as fullerenes and carbon nanotube have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because of the lack of a rational and selective synthetic method by organic synthesis. We succeeded in the synthesis of 3D pi-conjugated molecule based on a new synthetic strategy, which involves the platinum-mediated assembly of pi-units by transmetallation and subsequent reductive elimination of the platinum.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (30 results)

All 2014 2013 2012 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (22 results) (of which Invited: 5 results) Remarks (1 results)

  • [Journal Article] Organoplatinum-Mediatde Syntesis of Cyclic π-Conjugated Molecules : Towards a New Era of Three-Dimensional Aromatic Comounds2014

    • Author(s)
      Yamago, S. ; Kayahara, E. ; Iwamoto, T.
    • Journal Title

      Chem. Rec.

      Volume: 14 Issue: 1 Pages: 84-100

    • DOI

      10.1002/tcr.201300035

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Isolation and Characterization of Cycloparaphenylene Radical Cation and Dication2013

    • Author(s)
      Kayahara E., Kouyama T., Kato T., Takaya H., Yasuda N., Yamago S.
    • Journal Title

      Angew. Chem. Int. Ed.(Highlighted in Editor's Choice, Science 2013, 342, 1147)

      Volume: 52 Issue: 51 Pages: 13722-13726

    • DOI

      10.1002/anie.201306881

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and pysical properties of a ball-lie three-dimensional π^-conjugated molecule2013

    • Author(s)
      Kayahara, E. ; Iwamoto, T. ; Takaya, H. ; Suzuki, T. ;
    • Journal Title

      Nat. Commun.

      Volume: 4 Issue: 1 Pages: 2-694

    • DOI

      10.1038/ncomms3694

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Selective Synthesis of [6], [8], and [10]Cycloparaphenylenes2013

    • Author(s)
      Kayahara E., Iwamoto T., Suzuki T., Yamago S.
    • Journal Title

      Chem. Lett.

      Volume: 42 Issue: 6 Pages: 621-623

    • DOI

      10.1246/cl.130188

    • NAID

      10031176028

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enhancement of quinoidal character of smaller [n] cycloparaphenylenes probed by Raman spectroscopy2013

    • Author(s)
      Fujitsuka, M., Iwamoto, T., Kayahara, E., Yamago, S., Majima, T.
    • Journal Title

      Chem Phys Chem.

      Volume: (巻未定)(掲載確定)(未定)(頁未定) Issue: 8 Pages: 1570-1572

    • DOI

      10.1002/cphc.201300144

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective Synthesis of [6], [8], and [10]Cyacloparaphenylenes2013

    • Author(s)
      Eiichi Kayahara, Takahiro Iwamoto, Toshiyasu Suzuki, Shigeru Yamago
    • Journal Title

      Chemistry Letters

      Volume: 42

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective Synthesis and Crystal Structure of [10]Cycloparaphenylene2012

    • Author(s)
      Kayahara E., Sakamoto Y., Suzuki T., Yamago S.
    • Journal Title

      Org. Lett.

      Volume: 14 Issue: 13 Pages: 3284-3287

    • DOI

      10.1021/ol301242t

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis of Carbon-bridged Cycloparaphenylene Derivatives2013

    • Author(s)
      Iwamoto, T., Kayahara, E., Yamago, S.
    • Organizer
      15^<th> International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      Taipei, Taiwan
    • Year and Date
      2013-07-28
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of a Ball-like Three Dimensionalπ-Conjugated Compound and Its Physical Properties2013

    • Author(s)
      Kayahara, E., Takaya, H., Suzuki, T., Yamago, S.
    • Organizer
      Gordon Research Conference on Physical Organic Chemistry
    • Place of Presentation
      Holdness, NH, USA
    • Year and Date
      2013-06-29
    • Related Report
      2013 Final Research Report
  • [Presentation] かご型白金多核錯体を用いた含歪み三次元π共役系化合物の合成とその基礎的物性2013

    • Author(s)
      茅原栄一, 岩本貴寛, 高谷光, 鈴木敏泰, 山子茂
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津市
    • Year and Date
      2013-03-22
    • Related Report
      2013 Final Research Report
  • [Presentation] 環状白金多核錯体を前駆体とした含硫黄環状π-共役系化合物の合成2013

    • Author(s)
      茅原栄一, Zhai Xue, 山子茂
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津市
    • Year and Date
      2013-03-22
    • Related Report
      2013 Final Research Report
  • [Presentation] 種々の炭素架橋鎖を持つシクロパラフェニレン誘導体の合成2013

    • Author(s)
      岩本貴寛, 児島満, 茅原栄一, 山子茂
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津市
    • Year and Date
      2013-03-22
    • Related Report
      2013 Final Research Report
  • [Presentation] 環状炭素π共役系化合物の合成とその物性2013

    • Author(s)
      茅原栄一
    • Organizer
      第20回化学研究所若手の会
    • Place of Presentation
      京都大学化学研究所
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] シクロパラフェニレンラジカルカチオン、ジカチオンの単離と同定2013

    • Author(s)
      茅原栄一、香山貴彦、加藤立久、高谷光、安田伸広, 山子茂
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] かご型三次元π共役系化合物の合成とその基礎的物性2013

    • Author(s)
      茅原栄一、岩本貴寛、高谷光、 鈴木敏泰、山子茂
    • Organizer
      第2回新化学技術推進協会シンポジウム
    • Place of Presentation
      メルパルク大阪
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Sulfur-Containing Cycloparaphenylene Analogue from Cyclic Organoplatinum Complex and Its Physical Properties2013

    • Author(s)
      Zhai Xue、茅原栄一、山子茂
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Sulfur-Containing Cyclic π-Conjugated Compounds from Cyclic Organoplatinum Complexes and Their Physical Properties2013

    • Author(s)
      Zhai Xue、茅原栄一、山子茂
    • Organizer
      第九回有機元素化学セミナー
    • Place of Presentation
      京都大学化学研究所
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] シクロパラフェニレンおよびその類縁体の合成と物性2012

    • Author(s)
      山子茂, 茅原栄一, 岩本貴寛, 児島満
    • Organizer
      財団法人有機合成化学研究所講演会(第27回)
    • Place of Presentation
      京都
    • Year and Date
      2012-11-26
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of Highly Strained Cycloparaphenylenes2012

    • Author(s)
      Kayahara, E., Kojima, M., Iwamoto, T., Yamago, S.
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-12)
    • Place of Presentation
      Kyoto
    • Year and Date
      2012-11-15
    • Related Report
      2013 Final Research Report
  • [Presentation] 環状白金多核錯体を用いたシクロパラフェニレン類の新しい合成法の開発2012

    • Author(s)
      茅原栄一, 児島満, 岩本貴寛, 山子茂
    • Organizer
      第102回有機合成シンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2012-11-08
    • Related Report
      2013 Final Research Report
  • [Presentation] シクロパファレニレン誘導体の合成とその物性2012

    • Author(s)
      山子茂, 茅原栄一, 岩本貴寛, 児島満
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋
    • Year and Date
      2012-09-20
    • Related Report
      2013 Final Research Report
  • [Presentation] シクロパラフェニレンとフラーレンとの超分子錯体の形成2012

    • Author(s)
      山子茂, 岩本貴寛, 茅原栄一, 高谷光, 灰野岳晴
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋
    • Year and Date
      2012-09-19
    • Related Report
      2013 Final Research Report
  • [Presentation] 白金四核錯体を前駆体としたシクロフェナントレンとその誘導体の合成2012

    • Author(s)
      岩本貴寛, 茅原栄一, 児島満, 山子茂
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Year and Date
      2012-09-19
    • Related Report
      2013 Final Research Report
  • [Presentation] A New Synthetic Route for Cycloparaphenylenes and Their Derivatives through Cyclic Bisaryl Platinum Complexes2012

    • Author(s)
      茅原栄一, 児島満, 岩本貴寛, 山子茂
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      吹田市
    • Year and Date
      2012-09-15
    • Related Report
      2013 Final Research Report
  • [Presentation] A New Synthetic Route for Cycloparaphenylenes and Their Derivatives through Cyclic Bisaryl Platinum Complexes2012

    • Author(s)
      茅原栄一, 児島満, 岩本貴寛, 山子茂
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of [N]Cyclic Fluorene Derivatives from a Cyclic Multinuclear Platinum Complexes and Their Physical Properties2012

    • Author(s)
      Kayahara Eiichi, Kojima Mitsuru, Iwamoto Takahiro, Yamago Shigeru
    • Organizer
      The 10th International Conference on Heteroatom Chemistry(ICHAC-10)
    • Place of Presentation
      Kyoto, JAPAN
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of Cycloparaphenylene Derivatives Having Various Carbon Bridges2012

    • Author(s)
      Iwamoto Takahiro, Kojima Mitsuru, Kayahara Eiichi, Yamago Shigeru
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-12)
    • Place of Presentation
      Kyoto, JAPAN
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of Highly Strained Cycloparaphenylenes2012

    • Author(s)
      Kayahara Eiichi, Kojima Mitsuru, Iwamoto Takahiro, Yamago Shigeru
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-12)
    • Place of Presentation
      Kyoto, JAPAN
    • Related Report
      2012 Research-status Report
  • [Presentation] 環状白金多核錯体を用いたシクロパラフェニレン類の新しい合成法の開発2012

    • Author(s)
      茅原栄一, 児島満, 岩本貴寛, 山子茂
    • Organizer
      第102回有機合成シンポジウム
    • Place of Presentation
      早稲田大学
    • Related Report
      2012 Research-status Report
  • [Remarks]

    • URL

      http://www.scl.kyoto-u.ac.jp/~kayahara/

    • Related Report
      2013 Final Research Report

URL: 

Published: 2013-05-31   Modified: 2019-07-29  

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