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Development of Multifunctional π-Conjugated Molecules Modulated by Rigid Spiro Structures

Research Project

Project/Area Number 22350087
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic industrial materials
Research InstitutionKyoto University

Principal Investigator

OHE Kouichi  京都大学, 大学院・工学研究科, 教授 (90213636)

Co-Investigator(Kenkyū-buntansha) OKAMOTO Kazuhiro  京都大学, 大学院・工学研究科, 助教 (30552658)
MIKI Koji  京都大学, 大学院・工学研究科, 講師 (60422979)
Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥19,110,000 (Direct Cost: ¥14,700,000、Indirect Cost: ¥4,410,000)
Fiscal Year 2012: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2011: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2010: ¥9,100,000 (Direct Cost: ¥7,000,000、Indirect Cost: ¥2,100,000)
Keywordsスピロフルオレン / インデノフラン / インデノチオフェン / インデノピロール / インデノイミダゾール / BODIPY 色素 / 白色発光 / ESIPT / スピロ化合物 / フルオレン / カップリング反応 / 9.9'-スピロフルオレン / 複素環 / C-H結合アリール化反応 / BODIPY色素 / ラダー型ジスピロ化合物 / スピロ共役
Research Abstract

We have developed structurally rigid spirofluorene-indenoheterocycles involving furan, thiophene, pyrrol, imidazole, and investigated their optical and electrochemi cal properties. Rigid spirofluorene structures can enhance planarity of π-conjugated substructures and thereby reduce intermolecular interaction involving π-π interaction in solid state. Through this study, we disclosed that spiro-conjugation affects optical properties of these compounds. Newly developed compounds, which bear high thermodynamic stability, were applicable to near infrared dye or white-light emitting materials.

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (48 results)

All 2013 2012 2011 2010 Other

All Journal Article (14 results) (of which Peer Reviewed: 8 results) Presentation (30 results) (of which Invited: 1 results) Remarks (4 results)

  • [Journal Article] Gold-catalysed Cycloisomerisation Reactions of2-(2-Propynyl)pyridine N-Oxides Leading to Indolizinones2012

    • Author(s)
      Masahito Murai, Sachie Kitabata.Kazuhiro Okamoto, Kouichi Ohe
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 61 Pages: 7622-7624

    • DOI

      10.1039/c2cc32628k

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Pd- and Cu-Catalyzed One-Pot Multi Component Synthesis of Hetero Dimers of Heterocycles2012

    • Author(s)
      T.Murata, M.Murai, Y.Ikeda, K.Miki, K.Ohe
    • Journal Title

      Org.Letters

      Volume: 14(appear on Web) Issue: 9 Pages: 2296-2299

    • DOI

      10.1021/ol300718x

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Practical synthesis of aromatic nitriles via gallium-catalysed electrophilic cyanation of aromatic C-H bonds2012

    • Author(s)
      Kazuhiro Okamoto, Masahito Watanabe, Masahito Murai, Ryo Hatano, Kouichi Ohe
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 25 Pages: 3127-3129

    • DOI

      10.1039/c2cc18008a

    • Related Report
      2012 Annual Research Report 2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Near-infrared BODIPY dyes modulated with spirofluorene moieties2011

    • Author(s)
      Kowada, T.; Yamaguchi, S.; Fujinaga, H.; Ohe, K
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 17 Pages: 3105-3110

    • DOI

      10.1016/j.tet.2011.02.073

    • Related Report
      2012 Final Research Report
  • [Journal Article] Rhodium-Catalyzed Carbene-Transfer Reactions via Thienylcarbene Complexes Generated from Thiocarbamoyl-ene-yne Compounds2011

    • Author(s)
      Tsuneishi, A.; Okamoto, K.;Ikeda, Y .; Murai, M.; Miki, K.; Ohe, K
    • Journal Title

      Synlett

      Volume: 2011 Issue: 05 Pages: 655-658

    • DOI

      10.1055/s-0030-1259559

    • NAID

      120004205119

    • Related Report
      2012 Final Research Report
  • [Journal Article] Gallium(III)-catalysed bromocyanation of alkynes : regio- and stereoselective synthesis of β-bromo-α,β-unsaturated nitriles2011

    • Author(s)
      M.Murai, R.Hatano, S.Kitabata, K.Ohe
    • Journal Title

      Chem.Commun.

      Volume: 47 Issue: 8 Pages: 2375-2375

    • DOI

      10.1039/c0cc04385k

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] High-Contrast Fluorescence Imaging of Tumors In Vivo Using Nanoparticles of Amphiphilic Brush-Like Copolymers Produced by ROMP2011

    • Author(s)
      K.Miki, A.Kimura, H.K.Oride, Y.Kuramochi, Matsuoka, H.Harada, M.Hiraoka, K.Ohe
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: 50 Issue: 29 Pages: 6567-6570

    • DOI

      10.1002/anie.201101005

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Near-infrared BODIPY Dyes Modulated with Spirofluorene Moieties2011

    • Author(s)
      T.Kowada, S.Yamaguchi, H.Fujinaga, K.Ohe
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 3105-3110

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Atom -efficient Synthesis of α-Alkylidene-N-furylimines via Catalytic Vinylcarbene-transfer Reactions to Carbonylene-nitrile Compounds2010

    • Author(s)
      Murai, M.; Yoshida, S.; Miki, K.; Ohe, K
    • Journal Title

      Chem. Commun

      Volume: 46 Issue: 19 Pages: 3366-3368

    • DOI

      10.1039/b924752a

    • Related Report
      2012 Final Research Report
  • [Journal Article] Synthesis, Structures, and Optical Properties of Heteroarene-Fused Dispiro Compounds2010

    • Author(s)
      Kowada, T .; Kuwabara, T .; Ohe, K
    • Journal Title

      J. Org. Chem

      Volume: 75 Issue: 3 Pages: 906-913

    • DOI

      10.1021/jo902482n

    • Related Report
      2012 Final Research Report
  • [Journal Article] Synthesis of Strained Pyridine-Containing Cyclyne via Reductive Aromatization2010

    • Author(s)
      Miki, K.; Fujita, M.; Inoue, Y . ; Senda, Y .; Kowada, T .; Ohe, K
    • Journal Title

      J. Org. Chem

      Volume: 75 Issue: 10 Pages: 3537-3540

    • DOI

      10.1021/jo1006202

    • Related Report
      2012 Final Research Report
  • [Journal Article] Synthesis and Characterization of Highly Fluorescent and Thermally Stable π-Conjugates involving Spiro[fluorene-9,4'-[4H]indeno[1,2-b]furan]2010

    • Author(s)
      Kowada, T .; Ohe, K
    • Journal Title

      Bull. Korean Chem. Soc.

      Volume: 31 Issue: 3 Pages: 577-581

    • DOI

      10.5012/bkcs.2010.31.03.577

    • Related Report
      2012 Final Research Report
  • [Journal Article] Synthesis, Structures, and Optical Properties of Heteroarene-Fused Dispiro Compounds2010

    • Author(s)
      T.Kowada, T.Kuwabara, K.Ohe
    • Journal Title

      J.Org.Chem.

      Volume: 75 Pages: 906-913

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Fluorescent BODIPY Dyes Modulated with Spirofluorene Moieties2010

    • Author(s)
      T.Kowada, S.Yamaguchi, K.Ohe
    • Journal Title

      Org.Lett.

      Volume: 12 Pages: 296-299

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] カンジウム触媒によるアリルシランと・-シリルエノンとの[3+2]環化付加反応2013

    • Author(s)
      岡本和紘,田村英祐,大江浩一
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Year and Date
      2013-03-24
    • Related Report
      2012 Final Research Report
  • [Presentation] ルテニウム触媒による 3,4-ジアシルオキシ-1,5-ジイン類の環化異性化による芳香環形成反応2013

    • Author(s)
      岡本和紘,坂田尚紀,三木康嗣,大江浩一
    • Organizer
      日本化学会第93 春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Year and Date
      2013-03-23
    • Related Report
      2012 Final Research Report
  • [Presentation] ヨウ化シアンを用いた銅触媒によるアルキン類のシアノ化反応2013

    • Author(s)
      岡本和紘、渡部昌人、村井征史、大江浩一
    • 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、滋賀
    • Related Report
      2012 Annual Research Report
  • [Presentation] Palladium-catalyzed Cycloisomerization of 2-(Cyanomethyl)phenyl esters leading to 3-acyl-2-aminobenzofurans2012

    • Author(s)
      Murai, M.; Ohe, K
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2012-12-18
    • Related Report
      2012 Final Research Report
  • [Presentation] 有機金属活性種の新規発生法に基づく有機合成2012

    • Author(s)
      大江浩一
    • Organizer
      第64回有機合成化学協会関東支部シンポジウム-新潟(長岡)シンポジウム
    • Place of Presentation
      長岡技術科学大学(招待講演)
    • Year and Date
      2012-12-02
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis of Twin carbon Nanorings and Their Inclusion of Fullerenes2012

    • Author(s)
      Matsushita, T.; Miki, K.; Ohe, K.
    • Organizer
      The 12thInternational Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto.
    • Year and Date
      2012-11-15
    • Related Report
      2012 Final Research Report
  • [Presentation] 不飽和炭化水素の触媒的求電子シアノ化反応2012

    • Author(s)
      岡本和紘,渡部昌仁,村井征史,波多野諒,大江浩一
    • Organizer
      第2回CSJ化学フェスタ2012
    • Place of Presentation
      東京工業大学蔵前会館
    • Year and Date
      2012-10-16
    • Related Report
      2012 Final Research Report
  • [Presentation] 還元的芳香環化を経るフェニレンジエチニレン含有双環状化合物の合成とフラーレンの包接2012

    • Author(s)
      松下 剛,三木康嗣,大江浩一
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ
    • Year and Date
      2012-09-20
    • Related Report
      2012 Final Research Report
  • [Presentation] Generation and Synthetic Application of Vinylnitrene Complexes2012

    • Author(s)
      Ohe, K
    • Organizer
      French-Japanese "Kinki-Divio Symposium"
    • Place of Presentation
      Dijion, France
    • Year and Date
      2012-07-24
    • Related Report
      2012 Final Research Report
  • [Presentation] 白色発光を指向したスピロ型 π 共役分子の合成と物性2012

    • Author(s)
      藤永浩輝,若宮淳志,大江浩一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学日吉・矢上キャンパス
    • Year and Date
      2012-03-28
    • Related Report
      2012 Final Research Report
  • [Presentation] ガリウム触媒による芳香族化合物の求電子的シアノ化反応2012

    • Author(s)
      岡本和紘, 渡部昌仁,村井征史,波多野諒,大江浩一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学日吉・矢上キャンパス
    • Year and Date
      2012-03-28
    • Related Report
      2012 Final Research Report
  • [Presentation] 段階的クロスカップリングを用いる環状化合物の合成とフラーレン含有眼鏡状分子への変換2012

    • Author(s)
      下 剛,三木康嗣,大江浩
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学日吉・矢上キャンパス
    • Year and Date
      2012-03-28
    • Related Report
      2012 Final Research Report
  • [Presentation] Transition Metal-catalyzed Vinylnitrene Transfer Reactions Using N-Heterocycles: A Revisit2012

    • Author(s)
      Ohe, K
    • Organizer
      The 6th Kansai-CMDSMeeting on OMCOS 2012
    • Place of Presentation
      Kensington Star Hotel, Seorak Mt., Korea
    • Related Report
      2012 Final Research Report
  • [Presentation] Palladium-catalyzed Decarboxylative Transformation of 4H-Isooxazol-5-ones Leading to 1-Azabicyclo[3.1.0]hex-2-enes2012

    • Author(s)
      Ohe, K.; Okamoto, K.; Oda, T.; Kohigashi, S.
    • Organizer
      The 6th Spanish-Portuguese-Japanese Organic Chemistry Symposium
    • Place of Presentation
      University of Lisbon, Lisbon, Portugal
    • Related Report
      2012 Final Research Report
  • [Presentation] Me3SiOTf-catalyzed Direct Conjugate Addition of Styrenes to beta-Silicon-substituted alpha,beta-Unsaturated Ketones2012

    • Author(s)
      K. Okamoto, E. Tamura, K. Ohe
    • Organizer
      The 59th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Osaka University, Osaka
    • Related Report
      2012 Annual Research Report
  • [Presentation] Palladium-catalyzed Decarboxylative Carbonylation of 4H-Isoxazol-5-ones2012

    • Author(s)
      K. Okamoto, T. Oda, T. Shimbayashi, K. Ohe
    • Organizer
      The 59th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Osaka University, Osaka
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of Twin Carbon Nanorings and Their Inclusion of Fullerrenes2012

    • Author(s)
      T. Matsushita, K. Miki, K. Ohe
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都、京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] 有機金属活性種の新規発生法に基づく有機合成2012

    • Author(s)
      大江浩一
    • Organizer
      第64回有機合成化学協会関東支部シンポジウムー新潟(長岡)シンポジウム
    • Place of Presentation
      長岡技術科学大学、新潟
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Palldium-catalyzed Decarboxylative Transformation of Cyclic Oxime Esters2011

    • Author(s)
      K.Okamoto, T.Oda, S.Kohigashi, K.Ohe
    • Organizer
      The Seventh International Symposium on Integrated Synthesis
    • Place of Presentation
      Kobe, Japan
    • Year and Date
      2011-10-10
    • Related Report
      2011 Annual Research Report
  • [Presentation] ESIPTを利用したスピロ型白色発光性単一分子の合成と物性2011

    • Author(s)
      藤永浩輝,小和田俊行, 大江浩一
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば国際会議場
    • Year and Date
      2011-09-22
    • Related Report
      2012 Final Research Report
  • [Presentation] 階的クロスカップリングを用いるフェニレンジエチニレン含有環状化合物の合成と歪を持つπ共役分子への変換2011

    • Author(s)
      松下剛,三木康嗣,大江浩一
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば国際会議場
    • Year and Date
      2011-09-21
    • Related Report
      2012 Final Research Report
  • [Presentation] ニッケル触媒による2H-アジリン類の2-アザジエン類への変換反応2011

    • Author(s)
      岡本和紘,増田綾乃,大江浩一
    • Organizer
      本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-29
    • Related Report
      2012 Final Research Report
  • [Presentation] Gold-catalyzed Reactions of Pyridine N-Oxides having Alkyne Moieties leading to N-Heterocycles2010

    • Author(s)
      Kitabata, S.; Murai, M.; Okamoto, K.; Ohe, K
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-18
    • Related Report
      2012 Final Research Report
  • [Presentation] New Approach to Bis-heterocycles via Coupling and Double Cyclization Cascade2010

    • Author(s)
      Ohe, K.; Murata, T.; Okamoto, K.; Miki, K
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2010-12-17
    • Related Report
      2012 Final Research Report
  • [Presentation] アルキン部位を有するピリジンN-オキシドの金触媒による環化異性化反応2010

    • Author(s)
      北畑幸恵,村井征史,岡本和紘,大江浩一
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学多摩キャンパス
    • Year and Date
      2010-09-18
    • Related Report
      2012 Final Research Report
  • [Presentation] 還元的芳香環形成反応によるパイ共役系大環状分子の合成とその包接機能2010

    • Author(s)
      三木康嗣,井上友喜,藤田充康,小和田俊行,大江浩一
    • Organizer
      第21回基礎有機化学討論会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Year and Date
      2010-09-11
    • Related Report
      2012 Final Research Report
  • [Presentation] スピロフルオレン骨格を有するpH応答性BODIPY誘導体の発光特性2010

    • Author(s)
      山口修平,小和田俊行,大江浩一
    • Organizer
      第21回基礎有機化学討論会
    • Place of Presentation
      名古屋大学東山キャンパス.
    • Year and Date
      2010-09-09
    • Related Report
      2012 Final Research Report
  • [Presentation] High-Contrast Fluorescence Tumor Imaging In Vivo Utilizing Self-Assemblies of ROMP-Based Copolymers2010

    • Author(s)
      Kouichi Ohe
    • Organizer
      The 5th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Hsinchu, Taiwan(招待講演)
    • Related Report
      2012 Final Research Report
  • [Presentation] A New Route to Bis-Heterocycles via Coupling and Double Cyclization Cascade2010

    • Author(s)
      Ohe, K
    • Organizer
      China-japan Symposium on Catalytic Organic Synthesis
    • Place of Presentation
      Tianjin, China(招待講演)
    • Related Report
      2012 Final Research Report
  • [Presentation] A New Route to Bis-heterocycles via Coupling and Cyclization Cascade2010

    • Author(s)
      Ohe, K.
    • Organizer
      China-Japan Symposium on Catalytic Organic Synthesis
    • Place of Presentation
      Tianjin, China
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.eh.t.kyoto-u.ac.jp/ja/research/introduction/eh31

    • Related Report
      2012 Final Research Report
  • [Remarks] 大江研究室

    • URL

      http://www.ehcc.kyoto-u.ac.jp/eh31/home/index-j.html

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.eh.t.kyoto-u.ac.jp/ja/research/introduction/eh31

    • Related Report
      2011 Annual Research Report
  • [Remarks]

    • URL

      http://www.eh.t.kyoto-u.ac.jp/ja/research/introduction/eh31

    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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