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2012 Fiscal Year Final Research Report

Precise synthesis and properties of open-shell graphenefragments with heteroatomic modification

Research Project

  • PDF
Project/Area Number 22350018
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

MORITA Yasushi  大阪大学, 大学院・理学研究科, 准教授 (70230133)

Project Period (FY) 2010 – 2012
Keywords構造有機化学 / 開殻有機分子 / 開殻グラフェンフラグメント / 二次電池
Research Abstract

In quest of novel electronic-/magnetic materials based on open-shell graphene fragments, design and synthesis of trioxotriangulene (TOT) derivatives, air-stable organic neutral radicals with three oxygen atoms on a triangulene skeleton, and disclosure of their properties in the solution and solid state have been carried out. We have successfully controlled molecular stability, π-stacking mode by SOMO-SOMO interaction, redox ability in terms of modification of the frontier molecular orbitals and the electronic-spin density distribution by substituent effect in a controlled manner

  • Research Products

    (56 results)

All 2013 2012 2011 2010 Other

All Journal Article (28 results) (of which Peer Reviewed: 28 results) Presentation (17 results) Book (7 results) Remarks (1 results) Patent(Industrial Property Rights) (3 results) (of which Overseas: 1 results)

  • [Journal Article] Hexamethoxyphenalenyl as a Possible Quantum Spin Simulator: An Electronically Stabilized Neutral π Radical with Novel Quantum Coherence Owing to Extremely High Nuclear Spin Degeneracy2013

    • Author(s)
      Y. Morita, 他 7 人
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 52 Pages: 4795-4799

    • DOI

      DOI:10.1002/anie.201301435

    • Peer Reviewed
  • [Journal Article] Organic Rechargeable Batteries with Tailored Voltage and Cycle Performance2013

    • Author(s)
      S. Nishida, Y. Yamamoto, T. Takui, Y. Morita , 他3人
    • Journal Title

      ChemSusChem

      Volume: 6 Pages: 794-797

    • DOI

      DOI:10.1002/cssc.201300010

    • Peer Reviewed
  • [Journal Article] Cooperation of Hydrogen-Bond and Charge-transfer Interactions in Molecular Complexes in the Solid State2013

    • Author(s)
      Y. Morita, T. Murata, K. Nakasuji
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 86 Pages: 183-197

    • DOI

      DOI:10.1246/bcsj.20120241

    • Peer Reviewed
  • [Journal Article] An ExtremelyRedox-active Air-stable Neutral π-Radical: Dicyanomethylene-substituted Triangulene with a Three-fold Symmetry2012

    • Author(s)
      Y. Morita , 他7人
    • Journal Title

      Chem. Eur. J.

      Volume: 18 Pages: 16272-16276

    • DOI

      DOI:10.1002/chem.201203755

    • Peer Reviewed
  • [Journal Article] Nucleobase-Functionalized 1,6-Dithiapyrene-type Electron-donors: Supramolecular Assemblies by Complementary Hydrogen-bonds and π-Stacks2012

    • Author(s)
      T. Murata, E. Miyazaki, K. Nakasuji, Y. Morita
    • Journal Title

      Cryst. Growth Des.

      Volume: 12 Pages: 5815-5822

    • DOI

      DOI: 10.1021/cg301414s

    • Peer Reviewed
  • [Journal Article] Crystal Surface Mediated Structure Transformation of Kinetic Framework Composed of Multi-interactive Ligand TPHAP and Co(II)2012

    • Author(s)
      Y. Yakiyama, A. Ueda, Y. Morita, M. Kawano
    • Journal Title

      Chem. Commun

      Volume: 48 Pages: 10651-10653

    • DOI

      DOI:10.1039/C2CC35078E

    • Peer Reviewed
  • [Journal Article] Tetrathiafulvalene-fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor-acceptor Systems2012

    • Author(s)
      Y. Morita , S. Fukuzumi, 他12人
    • Journal Title

      ChemPhysChem

      Volume: 13 Pages: 3370-3382

    • DOI

      DOI:10.1002/cphc.201200350

    • Peer Reviewed
  • [Journal Article] A Synthetic Two-spin Quantum Bit: g-Engineered Exchange-coupled Biradical Designed for Controlled-NOT Gate Operations2012

    • Author(s)
      Y. Morita , T. Takui, 他13人
    • Journal Title

      Angew. Chem Int. Ed.

      Volume: 51 Pages: 9860-9864

    • DOI

      DOI:10.1002/anie.201204489

    • Peer Reviewed
  • [Journal Article] Modulation of Charge-transfer Complexes Assisted by Complementary Hydrogen Bonds of Nucleobases: TCNQ Complexes of a Uracil-substituted EDO-TTF2012

    • Author(s)
      Y. Morita, 他4人
    • Journal Title

      CrystEngComm

      Volume: 14 Pages: 6881-6887

    • DOI

      DOI:10.1039/C2CE25889G

    • Peer Reviewed
  • [Journal Article] Pulsed Electron Spin Nutation Spectroscopy of Weakly Exchange-coupled Biradicals: A General Theoretical Approach and Determination of the Spin Dipolar Interaction2012

    • Author(s)
      Y. Morita , T. Takui, 他9 人
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 14 Pages: 9137-9148

    • DOI

      DOI:10.1039/C2CP40778G

    • Peer Reviewed
  • [Journal Article] Tetrathiafulvalene-type Electron Donors Bearing Biimidazole Moieties: MultifunctionalUnits with Hydrogen Bonding Abilities2012

    • Author(s)
      T. Murata, K. Nakasuji, Y. Morita
    • Journal Title

      Eur. J. Org. Chem

      Volume: 22 Pages: 4123-4129

    • DOI

      DOI:10.1002/ejoc.201200426

    • Peer Reviewed
  • [Journal Article] Development of Organic Conductors with Self-assembled Architectures of Biomolecules: Synthesis and Crystal Structures of Nucleobase-functionalized Tetrathiafulvalene Derivatives2012

    • Author(s)
      Y. Morita, 他6人
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 85 Pages: 995-1006

    • DOI

      DOI:10.1246/bcsj.20120102

    • Peer Reviewed
  • [Journal Article] Chiral Stable Phenalenyl Radical: Synthesis, Electronic-spin Structure, and Optical Properties of [4]Helicene-structured Diazaphenalenyl2012

    • Author(s)
      Y. Morita, 他6人
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Pages: 6691-6695

    • DOI

      DOI:10.1002/anie.201202654

    • Peer Reviewed
  • [Journal Article] Intermolecular Hydrogen-bond Networks and Physical Properties of BF4-and TCNQ・-Salts of Three-fold Symmetric Tris(alkylamino)phenalenyliums2012

    • Author(s)
      T. Murata, E. Miyazaki, T. Yokoyama, K. Nakasuji, Y. Morita
    • Journal Title

      Cryst. Growth Des

      Volume: 12 Pages: 804-810

    • DOI

      DOI:10.1021/cg201120s

    • Peer Reviewed
  • [Journal Article] 空気中でも安定な開殻有機分子:電子スピン非局在型中性ラジカルの合成と動的電子スピン物性2012

    • Author(s)
      森田 靖、西田辰介、工位武治、中筋一弘
    • Journal Title

      有機合成化学協会誌(総合論文)J. Synth. Org. Chem. Jpn

      Volume: 70 Pages: 50-59

    • URL

      http://dx.doi.org/10.5059/yukigoseikyokaishi.70.50

    • Peer Reviewed
  • [Journal Article] Organic Tailored Batteries Materials Using Stable Open-shell Molecules with Degenerate Frontier Orbitals2011

    • Author(s)
      Y. Morita , T. Takui, 他7 人
    • Journal Title

      Nature Mater

      Volume: 10 Pages: 947-951

    • DOI

      DOI:10.1038/nmat3142

    • Peer Reviewed
  • [Journal Article] Redox-active Tubular Frameworks with TTF: Self-assemblies by Complementary Hydrogen-bonds and π-Stacks of TTF-phenyluracil2011

    • Author(s)
      T. Murata, S. Maki, M. Ohmoto, E. Miyazaki, Y. Umemoto, K. Nakasuji, Y. Morita
    • Journal Title

      CrystEngComm

      Volume: 13 Pages: 6880-6884

    • DOI

      DOI:10.1039/C1CE05794D

    • Peer Reviewed
  • [Journal Article] Heteroatom Functionalization of Phenalenyl: Synthesis, Structures, and Properties of Hexa-substituted Phenalenyliums2011

    • Author(s)
      A. Ueda, K. Yoshida, S. Suzuki, K. Fukui, K. Nakasuji, Y. Morita
    • Journal Title

      J. Phys. Org. Chem

      Volume: 24 Pages: 952-959

    • DOI

      DOI:10.1002/poc.1916

    • Peer Reviewed
  • [Journal Article] Solution-stable Triple-helicates of Quaterimidazole: Three-dimensional Crystal Structures and Optical Resolution by Chiral-Column HPLC2011

    • Author(s)
      Y. Morita , 他7人
    • Journal Title

      Eur. J. Inorg. Chem.

      Volume: 23 Pages: 3438-3445

    • DOI

      DOI:10.1002/ejic.201100488

    • Peer Reviewed
  • [Journal Article] Proton-transfer Salts between an EDT-TTF Derivative Having Imidazole-ring and Anilic Acids: Multi-dimensional Networks by Acid-baseHydrogen-bonds, π-Stacks and Chalcogen Atom Interactions2011

    • Author(s)
      Y. Morita , 他3人
    • Journal Title

      CrystEngComm

      Volume: 13 Pages: 3689-3691

    • DOI

      DOI:10.1039/C1CE05326D

    • Peer Reviewed
  • [Journal Article] Electronic Stabilization Effect of a Spin-delocalized Neutral Radical: Synthesis of an 8-Cyano-6-oxophenalenoxyl Derivative and Quantitative Evaluation of the Electronic Spin Structure in terms of Resonance Structures2011

    • Author(s)
      Y. Morita, 他7人
    • Journal Title

      Chem. Asian J

      Volume: 6 Pages: 1188-1196

    • DOI

      DOI:10.1002/asia.201000793

    • Peer Reviewed
  • [Journal Article] Synthetic Organic Spin Chemistry for Structurally Well-defined Open-shell Graphene Fragments2011

    • Author(s)
      Y. Morita, S. Suzuki, K. Sato, T. Takui
    • Journal Title

      Nature Chem

      Volume: 3 Pages: 197-204

    • DOI

      DOI:10.1038/nchem.985

    • Peer Reviewed
  • [Journal Article] ESR and 1H-, 19F-ENDOR/TRIPLE Study of Fluorinated Diphenylnitroxides as Synthetic Bus Spin-qubit Radicals with Client Qubits in Solution2011

    • Author(s)
      Y. Morita , T. Takui, 他8人
    • Journal Title

      J. Phys. Chem. Lett.

      Volume: 2 Pages: 449-453

    • DOI

      DOI:10.1021/jz101650z

    • Peer Reviewed
  • [Journal Article] Air-stable Curved π-Radical Based on Corannulene: Dynamic Electronic-spin Structure Induced by Temperature-dependent Conformational Changes2010

    • Author(s)
      Y. Morita, 他7 人
    • Journal Title

      Aust. J. Chem

      Volume: 63 Pages: 1627-1633

    • DOI

      DOI.org/10.1071/CH10280

    • Peer Reviewed
  • [Journal Article] Supramolecular Architectures and Hydrogen-bond Directionalities of 4,4´-Biimidazole Metal Complexes Depending on Coordination Geometries2010

    • Author(s)
      T. Murata, Y. Yakiyama, K. Nakasuji, Y. Morita
    • Journal Title

      Cryst. Growth Des

      Volume: 10 Pages: 4898-4905

    • DOI

      DOI:10.1021/cg100958r

    • Peer Reviewed
  • [Journal Article] Hexaazaphenalene Derivatives: One-pot Synthesis, Hydrogen-bonded Chiral Helix, and Fluorescence Properties2010

    • Author(s)
      Y. Morita , 他 6 人
    • Journal Title

      Org. Lett

      Volume: 12 Pages: 5036-5039

    • DOI

      DOI:10.1021/ol102200v

    • Peer Reviewed
  • [Journal Article] Alternating Covalent Bonding Interactions in a One-dimensional Chain of a Phenalenyl-based Singlet Biradical Molecule Having KekuleStructures2010

    • Author(s)
      Y. Morita , 他12人
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 132 Pages: 14421-14428

    • DOI

      DOI:10.1021/ja1037287

    • Peer Reviewed
  • [Journal Article] A Bowl-shaped ortho-Semiquinone Radical Anion: Quantitative Evaluation of the Dynamic Behavior of Structural and Electronic Features2010

    • Author(s)
      Y. Morita , 他9 人
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 Pages: 6333-6337

    • DOI

      DOI:10.1002/anie.201002626

    • Peer Reviewed
  • [Presentation] 電子スピン非局在型中性ラジカルの新展開「金属錯体の固体物性最前線-金属錯体と固体物性物理と生物物性の連携新領域を目指して-2013

    • Author(s)
      森田 靖
    • Organizer
      東北大学卓越大学院研究会
    • Place of Presentation
      東北大学
    • Year and Date
      20130204-06
  • [Presentation] レアメタルフリーの高性能分子スピン電池の開発2013

    • Author(s)
      森田 靖
    • Organizer
      大阪スマートエネルギー・ビジネスシーズコンペ受賞者発表会
    • Place of Presentation
      東京ビッグサイト
    • Year and Date
      2013-02-01
  • [Presentation] 開殻グラフェンフラグメント:空気中でも安定な有機中性ラジカルの設計・合成と蓄電デバイスへの展開2013

    • Author(s)
      森田 靖
    • Organizer
      炭素材料学会セミナー
    • Place of Presentation
      東京 総評会館
    • Year and Date
      2013-01-18
  • [Presentation] Molecular Spin Battery: Tailor-made Rechargeable Battery Based on Air-stable Neutral Radicals2012

    • Author(s)
      Y. Morita
    • Organizer
      International Conference on Molecule-based Magnets (ICMM2012)
    • Place of Presentation
      Orlando, Florida(米国)
    • Year and Date
      20121007-11
  • [Presentation] 空気中でも安定な有機中性ラジカルの新展開:基礎物性と二次電池への応用2012

    • Author(s)
      森田 靖
    • Organizer
      京都大学大学院工学研究科 分子工学コロキウム
    • Place of Presentation
      京都大学
    • Year and Date
      2012-12-18
  • [Presentation] 電子スピン非局在型の安定な有機中性ラジカルの新展開:基礎物性とコバルトフリー高性能Liイオン二次電池への挑戦2012

    • Author(s)
      森田 靖
    • Organizer
      九州大学大学院薬学研究院機能分子合成化学セミナー
    • Place of Presentation
      九州大学
    • Year and Date
      2012-11-30
  • [Presentation] 電子スピン非局在型の安定な有機中性ラジカルを活物質に用いたコバルトフリー高性能Liイオン二次電池2012

    • Author(s)
      森田 靖
    • Organizer
      北海道大学元素戦略教育研究センター講演会
    • Place of Presentation
      北海道大学
    • Year and Date
      2012-05-25
  • [Presentation] π電子系有機分子の合成を基盤にした電子スピンのマニピュレーション2011

    • Author(s)
      森田 靖
    • Organizer
      第99回有機合成シンポジウム 社団法人 有機合成化学協会 2010年度DIC機能性材料賞受賞講演
    • Place of Presentation
      慶應義塾大学薬学部
    • Year and Date
      20110615-16
  • [Presentation] 空気中でも安定な有機中性ラジカルの最前線:基礎物性と分子スピンバッテリーへの展開2011

    • Author(s)
      森田 靖
    • Organizer
      フロンティア機能物質創製センターシンポジウム:機能性物質の最前線 -物質科学の新展開を目指して-
    • Place of Presentation
      財団法人西播地域地場産業振興センター
    • Year and Date
      2011-12-18
  • [Presentation] 電子スピンのマニピュレーション:π電子系有機分子を基盤にした分子技術2011

    • Author(s)
      森田 靖
    • Organizer
      RNシンポジウム
    • Place of Presentation
      名古屋大学
    • Year and Date
      2011-12-10
  • [Presentation] Chiral Neutral Radicals with An Extremely Spin-delocalized Nature2010

    • Author(s)
      Y. Morita
    • Organizer
      Reactive Intermediates and Unusual Molecules" at 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu 米国
    • Year and Date
      20101215-20
  • [Presentation] Solution-stability and Optical Resolution of Triply-helical Metal Complexes of Quaterimidazole2010

    • Author(s)
      Y. Morita
    • Organizer
      Designed Pi SystemsSynthesis, Properties, Theory and Function" at 2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu 米国
    • Year and Date
      20101215-20
  • [Presentation] Air-stable pi-Extended Neutral Radical Chemistry: Molecular Design and Dynamic Electronic-spin Nature2010

    • Author(s)
      森田 靖
    • Organizer
      三菱化学 科学技術研究センターセミナー
    • Place of Presentation
      横浜市
    • Year and Date
      2010-11-08
  • [Presentation] synthetic organic-spin chemistry」: 空気中でも安定な炭素中心型中性ジル新展開2010

    • Author(s)
      森田 靖
    • Organizer
      京大グローバルCOE 「第七回有機元素化学セミナー
    • Place of Presentation
      京都大学 宇治キャンパス
    • Year and Date
      2010-11-01
  • [Presentation] Synthetic Organic-spin Chemistry:空気中でも安定な炭素中心型中性ラジカルの新展開2010

    • Author(s)
      森田 靖
    • Organizer
      日本分析工業 JAIセミナー
    • Place of Presentation
      梅田スカイビル
    • Year and Date
      2010-10-22
  • [Presentation] Synthetic Organic-spin Chemistry: Molecular Design and Dynamic Electronic-spin Nature of Air-stable pi-Extended Neutral Radicals2010

    • Author(s)
      Y. Morita
    • Organizer
      POSTECH WCU AMS Seminar
    • Place of Presentation
      POSTECH
    • Year and Date
      2010-10-13
  • [Presentation] Synthetic Organic-spin Chemistry:空気中でも安定な炭素中心型中性ラジカルの新展開2010

    • Author(s)
      森田 靖
    • Organizer
      日本化学会中国四国支部岡山地区化学講演会
    • Place of Presentation
      岡山大学 津島キャンパス
    • Year and Date
      2010-01-31
  • [Book] 有機中性ラジカルの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Part II研究最前線 11 章、日本化学会 編2013

    • Author(s)
      森田 靖
    • Total Pages
      120-126
    • Publisher
      化学同人
  • [Book] 学術研究活性化委員会、「安定開殻有機分子を活用した次世代型二次電池」第二次先端ウオッチング調査:融合領域の創成 分子エレクトロニクスから分子スピントロニクスへの展望2013

    • Author(s)
      森田 靖
    • Total Pages
      21-24
    • Publisher
      日本化学会
  • [Book] Novel Applications of ESR/EPR: Quantum Computing/Quantum Information Processing" In EPR of Free Radicals in Solids II, Progress in Theoretical Chemistry and Physics Volume 25, edited by A. Lund, M. Shiotani2013

    • Author(s)
      Y. Morita, T. Takui, 他8人
    • Total Pages
      163-204
    • Publisher
      Springer-Verlag, Dordrecht
  • [Book] Author Profile for Angewandte Chemie (published by Wiley-VCH)2013

    • Author(s)
      Y. Morita
    • Total Pages
      4298
    • Publisher
      Angew. Chem. Int. Ed
  • [Book] 有機分子スピンバッテリーの開発 縮重フロンティア分子軌道を利用した二次電池」化学2012

    • Author(s)
      西田辰介・森田 靖・佐藤和信・工位武治
    • Total Pages
      37-43
    • Publisher
      化学同人
  • [Book] New Jersey, "Curved π-Conjugated Stable Open-shell Systems Possessing Three-dimensional Molecular/Electronic-spin Structures" Chapter 4 In Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry, edi2012

    • Author(s)
      Y. Morita
    • Total Pages
      95-134
    • Publisher
      A. Ueda, John Wiley&Sons Ltd
  • [Book] Phenalenyls, Cyclopentadienyls, and Other Carbon-Centered Radicals" Chapter 3 In Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds, edited by Robin Hicks2010

    • Author(s)
      Y. Morita
    • Total Pages
      81-145
    • Publisher
      S. Nishida, John Wiley&Sons Ltd., Chichester
  • [Remarks]

    • URL

      http://www.chem.sci.osaka-u.ac.jp/lab/nakasuji/morita/index.html

  • [Patent(Industrial Property Rights)] 有機半導体を用いた赤外線センサ2012

    • Inventor(s)
      森田 靖、村田剛志、横山正明、辻 良太郎、大塚岳夫、宮里涼子
    • Industrial Property Rights Holder
      森田 靖、村田剛志、横山正明、辻 良太郎、大塚岳夫、宮里涼子
    • Industrial Property Number
      特願2012-035378
    • Filing Date
      2012-02-21
  • [Patent(Industrial Property Rights)] 有機分子スピンバッテリー2011

    • Inventor(s)
      工位武治、佐藤和信、森田 靖
    • Industrial Property Rights Holder
      工位武治、佐藤和信、森田 靖
    • Industrial Property Number
      特願2011-204821
    • Filing Date
      2011-09-20
  • [Patent(Industrial Property Rights)] 有機分子スピンバッテリー2011

    • Inventor(s)
      工位武治、佐藤和信、森田 靖
    • Industrial Property Rights Holder
      工位武治、佐藤和信、森田 靖
    • Industrial Property Number
      PCT/JP2012/74000
    • Filing Date
      2011-09-20
    • Overseas

URL: 

Published: 2014-08-29  

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