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Creation and Function of Novel Open-Shell π-Conjugated Systemswith a Weak π-Bond

Research Project

Project/Area Number 23750040
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

SHIMIZU Akihiro  京都大学, 大学院・工学研究科, 助教 (30584263)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2011: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsπ 共役系ラジカル / 一重項ビラジカル / キノジメタン / インデノフルオレン / 近赤外吸収 / π共役系 / ラジカル / 一重項テトララジカル / シクロブタジエン / ビラジカル / π電子系
Research Abstract

An indeno[2,1-b]fluorene derivative, a 20π electron hydrocarbon, was synthesized to clarify novel properties associated with singlet diradical characters. The moderate amplitude diradical character of the indeno[2,1-b]fluorene derivative was theoretically and experimentally proved. The indeno[2,1-b]fluorene derivative exhibits an extremely low-energy light absorption band whose absorption end extends to 2000 nm despite its small conjugation space consisting of only 20 π electrons. The present knowledge is useful for the design of new classes of materials based on small molecules with low-energy light absorption.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (36 results)

All 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (21 results) Book (2 results) Remarks (1 results)

  • [Journal Article] Oxidative Cyclodimerization that Follows Tandem Cyclization of Dehydro[14]annulenes Induced by Alkyllithium2013

    • Author(s)
      Shunpei Nobusue, Akihiro Shimizu, Kenji Hori, Ichiro Hisaki, Mikiji Miyata, Yoshito Tobe
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 52 Issue: 15 Pages: 4184-4188

    • DOI

      10.1002/anie.201210233

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Electrochemical C-H Amination : Synthesis of Aromatic Primary Amines via N-Arylpyridinium Ions2013

    • Author(s)
      諸藤達也・清水章弘・吉田潤一
    • Journal Title

      Journal of American Chemical Society

      Volume: 135 Issue: 13 Pages: 5000-5003

    • DOI

      10.1021/ja402083e

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Indeno[2,1-b]fluorene: A 20 pi electron hydrocarbon with extremely low energy light absorption2013

    • Author(s)
      A. Shimizu, R. Kishi, M. Nakano, D. Shiomi, K. Sato, T. Takui, I. Hisaki, M. Miyata, and Y. Tobe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Issue: 23 Pages: 6076-6079

    • DOI

      10.1002/anie.201302091

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Theoretical Consideration of Singlet Open-Shell Character of Polyperiacenes Using Clar’s Aromatic Sextet Valence Bond Model and Quantum Chemical Calculations2012

    • Author(s)
      Akihiro Shimizu
    • Journal Title

      AIP Conf. Proc.

      Volume: 1504 Pages: 399-405

    • DOI

      10.1063/1.4771733

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Theoretical Aspects on the Evaluation and Interpretation of the Third-Order Nonlinear Optical Properties of Diradical Compounds2012

    • Author(s)
      Benoit Champagne
    • Journal Title

      AIP Conf. Proc.

      Volume: 1504 Pages: 844-847

    • DOI

      10.1063/1.4771826

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Singlet Open-Shell Character of Conjugated Kekulé Molecules2012

    • Author(s)
      Takashi Kubo
    • Journal Title

      AIP Conf. Proc.

      Volume: 1504 Pages: 883-886

    • DOI

      10.1063/1.4771836

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Aromaticity and π-bond covalency: prominent intermolecular covalent bonding interaction of a Kekule hydrocarbon with very significant singlet biradical character2012

    • Author(s)
      Shimizu, A.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kubo, T.; Uruichi M.; Yakushi, K
    • Journal Title

      Chem. Commun

      Volume: 48 Issue: 45 Pages: 5629-5631

    • DOI

      10.1039/c2cc31955a

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Morofuji, T.; Shimizu, A.; Yoshida, J2012

    • Author(s)
      Metal- and Chemica-Oxidant-Free C-H/C-H Cross- Coupling of Aromatic Compounds Using "Radical Cation Pools"
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Issue: 29 Pages: 7259-7262

    • DOI

      10.1002/anie.201202788

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Polymer-Bound Pyrene-4,5,9,10-tetraone for Fast-Charge and-Discharge Lithium-Ion Batteries with High Capacity.2012

    • Author(s)
      Nokami, T.; Matsuo, T.; Inatomi, Y.; Hojo, N.; Tsukagoshi, T.; Yoshizawa, H.; Shimizu, A.; Kuramoto, H.; Komae, K.; Tsuyama, H.; Yoshida, J.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 48 Pages: 19694-19700

    • DOI

      10.1021/ja306663g

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Experimental consideration of covalent bonding interactions in stacks of singlet biradicals having Kekule structures2011

    • Author(s)
      清水章弘
    • Journal Title

      J.Phys.Org.Chem.

      Volume: 24 Issue: 10 Pages: 876-882

    • DOI

      10.1002/poc.1873

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Indeno[2,1-a]fluorene: An Air-Stable ortho-Quinodimethane Derivatives2011

    • Author(s)
      Shimizu, A.; Tobe, Y.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 50 Issue: 30 Pages: 6906-6910

    • DOI

      10.1002/anie.201101950

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Crystal Structure and Physical Properties of Sterically Unprotected Hydrocarbon Radicals2011

    • Author(s)
      T.Kubo
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 133 Issue: 36 Pages: 14240-14243

    • DOI

      10.1021/ja2065768

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] C-H/C-H Cross-Coupling of Aromatic Compounds Using Electrochemically Generated "Radical Cation Pools"2013

    • Author(s)
      Shimizu, A
    • Organizer
      The First Bristol-Kyoto Symposium
    • Place of Presentation
      ブリストル大学 イギリス
    • Year and Date
      2013-01-11
    • Related Report
      2012 Final Research Report
  • [Presentation] C-H/C-H Cross-Coupling of Aromatic Compounds Using Electrochemically Generated "Radical Cation Pools"2013

    • Author(s)
      Shimizu, A.
    • Organizer
      The First Bristol-Kyoto Symposium
    • Place of Presentation
      ブリストル大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 電解酸化による芳香族第一級アミンの合成2013

    • Author(s)
      諸藤達也・清水章弘・吉田潤一
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学草津キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 電解酸化による芳香族化合物のC-Hアミノ化2013

    • Author(s)
      諸藤達也・清水章弘・吉田潤一
    • Organizer
      電気化学会創立第80周年記念大会
    • Place of Presentation
      東北大学川内キャンパス
    • Related Report
      2012 Annual Research Report
  • [Presentation] 金属・酸化剤を用いない芳香族化合物のC-H/C-H クロスカップリング2012

    • Author(s)
      諸藤達也・清水章弘・吉田潤一
    • Organizer
      第1回 JACI/GSCシンポジウム(第12回 GSCシンポジウム)
    • Place of Presentation
      ベルサール神田
    • Related Report
      2012 Annual Research Report
  • [Presentation] ラジカルカチオンプール法による芳香族化合物の脱水素型クロスカップリング2012

    • Author(s)
      諸藤達也・清水章弘・吉田潤一
    • Organizer
      第36回有機電子移動討論会
    • Place of Presentation
      ルミエール府中
    • Related Report
      2012 Annual Research Report
  • [Presentation] C-H/C-H Cross-Coupling of Aromatic Compounds Based on the “Radical-Cation Pool” Method2012

    • Author(s)
      Morofuji, T.; Shimizu, A.; Yoshida, J.
    • Organizer
      IKCOC-12
    • Place of Presentation
      リーガロイヤル京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] ジゼトレニルアセチレンの合成2012

    • Author(s)
      北林賢一・日比大治郎・清水章弘・戸部義人
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川、慶應義塾大学
    • Related Report
      2011 Research-status Report
  • [Presentation] 電子移動による芳香族化合物の酸化的クロスカップリング2012

    • Author(s)
      諸藤達也・清水章弘・吉田潤一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川、慶應義塾大学
    • Related Report
      2011 Research-status Report
  • [Presentation] 環状ビシナルジケトン類の電気化学特性2012

    • Author(s)
      松尾隆宏・清水章弘・野上敏材・吉田潤一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川、慶應義塾大学
    • Related Report
      2011 Research-status Report
  • [Presentation] インデノフルオレンの特徴的な電子構造の解明2012

    • Author(s)
      清水章弘・岸亮平・中野雅由・塩見大輔・佐藤和信・工位武治・戸部義人
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川、慶應義塾大学
    • Related Report
      2011 Research-status Report
  • [Presentation] インデノフルオレンの特徴的な電子構造の解明2011

    • Author(s)
      清水章弘, 岸亮平, 中野雅由, 塩見大輔, 佐藤和信, 工位武治, 戸部義人
    • Organizer
      日本化学会第92 春季年会
    • Place of Presentation
      神奈川
    • Year and Date
      2011-03-28
    • Related Report
      2012 Final Research Report
  • [Presentation] Indenofluorene Isomers: 6-5-6-5-6 Membered Ring Hydrocarbons with Singlet Biradical Character2011

    • Author(s)
      Yoshito Tobe, Akihiro Shimizu
    • Organizer
      14th International Symposium on Novel Aromatic Compounds (ISNA 14)
    • Place of Presentation
      Oregon, USA
    • Related Report
      2011 Research-status Report
  • [Presentation] Formation of Unprecedented Polycyclic Aromatic Hydrocarbons by BuLi-induced Tandem Cyclization of Dehydrobenzo[14]annulene2011

    • Author(s)
      Shunpei Nobusue, Akihiro Shimizu, Kazukuni Tahara, Yoshito Tobe
    • Organizer
      14th International Symposium on Novel Aromatic Compounds (ISNA 14)
    • Place of Presentation
      Oregon, USA
    • Related Report
      2011 Research-status Report
  • [Presentation] Highly Delocalized Polycyclic Aromatic Hydrocarbon (PAH) Radical2011

    • Author(s)
      Takashi Kubo, Yoshiki Katada, Akihiro Shimizu, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Robert C. Haddon
    • Organizer
      14th International Symposium on Novel Aromatic Compounds (ISNA 14)
    • Place of Presentation
      Oregon, USA
    • Related Report
      2011 Research-status Report
  • [Presentation] The Singlet Open-shell Character of Anthenes: Synthesis and Characterization of Quarteranthene2011

    • Author(s)
      Akihito Konishi, Akihiro Shimizu, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo, Masayoshi Nakano, Benoît Champagne
    • Organizer
      14th International Symposium on Novel Aromatic Compounds (ISNA 14)
    • Place of Presentation
      Oregon, USA
    • Related Report
      2011 Research-status Report
  • [Presentation] ブチルリチウムの付加により誘起されるデヒドロベンゾ[14]アヌレン類の渡環環化による環状インデノフルオレン二量体の生成2011

    • Author(s)
      信末俊平・清水章弘・田原一邦・戸部義人
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      茨城、つくば国際会議場
    • Related Report
      2011 Research-status Report
  • [Presentation] ヘプタゼトレン誘導体の合成2011

    • Author(s)
      日比大治郎・清水章弘・戸部義人
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      茨城、つくば国際会議場
    • Related Report
      2011 Research-status Report
  • [Presentation] Indeno[2,1-a]fluorene Dimers Formed by Transannular Cyclization of Dehydrobenzo[14]annulene2011

    • Author(s)
      Shunpei Nobusue, Akihiro Shimizu, Kazukuni Tahara, Yoshito Tobe
    • Organizer
      The Seventh International Symposium on Integrated Synthesis (ISIS-7)
    • Place of Presentation
      Kobe、Seaside Hotel Maiko Villa
    • Related Report
      2011 Research-status Report
  • [Presentation] オクタデヒドロベンゾ[12]アヌレンへの求核剤の付加により誘起される渡環環化2011

    • Author(s)
      吉崎亜由美・信末俊平・清水章弘・戸部義人
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      大阪、ホテルアウィーナ大阪
    • Related Report
      2011 Research-status Report
  • [Presentation] ジゼトレニルアセチレンの合成2011

    • Author(s)
      北林賢一・日比大治郎・清水章弘・戸部義人
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      大阪、ホテルアウィーナ大阪
    • Related Report
      2011 Research-status Report
  • [Book] World Scientific2011

    • Author(s)
      Shimizu, A.; Konishi, A.; Hirao, Y.; Kubo, T
    • Publisher
      Singlet Open-Shell Character of polyperiacenes.
    • Related Report
      2012 Final Research Report
  • [Book] Chapter 3: Singlet Open-Shell Character of polyperiacenes, in GRAPHENE AND ITS FASCINATING ATTRIBUTES, Swapan K Pati, Toshiaki Enoki, C N R Rao2011

    • Author(s)
      Akihiro Shimizu, Akihito Konishi, Yasugazu Hirao, Takashi Kubo
    • Total Pages
      270
    • Publisher
      World Scientific
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://www.sbchem.kyoto-u.ac.jp/yoshida-lab/index

    • Related Report
      2012 Final Research Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

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