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novel method to link independent conjugated systems in biary compounds

Research Project

Project/Area Number 24655030
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

YASUDA Makoto  大阪大学, 工学(系)研究科(研究院), 教授 (40273601)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords有機合成化学 / 有機合成反応 / 共役系 / 非平面 / スルースペース / 電荷移動 / 発光
Outline of Final Research Achievements

The control of photoluminescence wavelength is significant for the design of emitting materials, and a compound having aryl-aryl bonds is one of the most useful candidates for the synthesis of these materials. However, the biaryl system lacks an efficient linkage of independent conjugated moieties. In this research, a novel method to link independent π-systems in biaryl compounds was studied. The oxy-substituents at the peri-position in 1-arylnaphthalene systems showed interesting and unexpected photophysical properties. In particular, peri-OH-substituted arylnaphthalenes showed a large bathochromic shift. The through-space interaction between the peri-substituted OH and aryl groups generated an unexpected extended conjugation system.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (34 results)

All 2015 2014 2013 2012

All Journal Article (10 results) (of which Peer Reviewed: 10 results,  Acknowledgement Compliant: 3 results) Presentation (24 results) (of which Invited: 4 results)

  • [Journal Article] GaBr3-Catalyzed Coupling between α-Iodo Esters with Alkynylstannanes under UV Irradiation2014

    • Author(s)
      Itaru Suzuki, Naoto Esumi, Makoto Yasuda, Akio Baba
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 1 Pages: 38-40

    • DOI

      10.1246/cl.140888

    • NAID

      130004699192

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Chiral Transfer in the Reaction of Aminoallylic Stannanes with Carbonyls in Two Different Modes using Tin(II) and Indium(III) Halides for the Synthesis of Each Enantiomer2014

    • Author(s)
      Makoto Yasuda, Yoshitaka Nagano, Hiroshi Yunoki, Kensuke Tsuruwa, Akio Baba
    • Journal Title

      Organometallics

      Volume: 33 Issue: 15 Pages: 3924-3927

    • DOI

      10.1021/om500768e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Gallium Trihalide Catalyzed Sequential Addition of Two Different Carbon Nucleophiles to Esters by Using Silyl Cyanide and Ketene Silyl Acetals2014

    • Author(s)
      Yoshihiro Inamoto, Yuta Kaga, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Journal Title

      Chemistry - A European Journal

      Volume: 37 Issue: 37 Pages: 11664-11668

    • DOI

      10.1002/chem.201403734

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium Chloride Catalyzed Alkylative Rearrangement of Propargylic Acetates Using Alkyl Chlorides, Alcohols, and Acetates: Facile Synthesis of α-Alkyl-α,β-Unsaturated Carbonyl Compounds2014

    • Author(s)
      Yoshiharu Onishi, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 4 Pages: 1176-1179

    • DOI

      10.1021/ol500046e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Indium Triiodide Catalyzed Reductive Functionalization of Amides via the Single-Stage Treatment of Hydrosilanes and Organosilicon Nucleophiles2013

    • Author(s)
      Yoshihiro Inamoto, Yuta Kaga, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 13 Pages: 3452-3455

    • DOI

      10.1021/ol4015317

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Alkylbismuths by Regiodivergent Carbobismuthination of Simple Alkenes2013

    • Author(s)
      Yoshihiro Nishimoto, Midori Takeuchi, Makoto Yasuda, Akio Baba
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 43 Pages: 14411-14415

    • DOI

      10.1002/chem.201302194

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Aldol Products and Cyanohydrins from Carboxylic Acids Using Hydrosilanes, Organosilicon Reagents, and Indium Triiodide Catalyst2013

    • Author(s)
      Yoshihiro Inamoto, Yoshihiro Nishimoto, Makoto Yasuda, Akio Baba
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 12 Pages: 1551-1553

    • DOI

      10.1246/cl.130790

    • NAID

      130004867849

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Zn(II) Chloride-Catalyzed Direct Coupling of Various Alkynes with Acetals: Facile and Inexpensive Access to Functionalized Propargyl Ethers2013

    • Author(s)
      Zn(II) Chloride-Catalyzed Direct Coupling of Various Alkynes with Acetals: Itaru Suzuki, Makoto Yasuda, Akio Baba
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 99 Pages: 11620-11622

    • DOI

      10.1039/c3cc46570e

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Gallium Tribromide Catalyzed Coupling Reaction of Alkenyl Ethers with Ketene Silyl Acetals2012

    • Author(s)
      Nishimoto, Y.; Ueda, H.; Yasuda, M.; Baba, A
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Issue: 32 Pages: 8073-8076

    • DOI

      10.1002/anie.201203778

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] InCl_3/Me_3SiCl-Catalyzed Direct Michael Addition of Enol Acetates to α,β-Unsaturated Ketones2012

    • Author(s)
      大西祥晴・米田勇樹・西本能弘・安田 誠・馬場章夫
    • Journal Title

      Organic Letter

      Volume: 14 Issue: 22 Pages: 5788-5791

    • DOI

      10.1021/ol302888k

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] インジウム触媒によるα-アルコキシケトンとアルコールの直接カップリング反応2015

    • Author(s)
      鈴木 至・川口 奈々・安田 誠
    • Organizer
      日本化学会代95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] エノール誘導体とシリルケテンアセタールの臭化ガリウム触媒カップリングの反応機構解明2015

    • Author(s)
      西本 能弘・喜多 悠二・安田 誠・馬場 章夫
    • Organizer
      日本化学会代95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 複素環を骨格に導入したかご型ホウ素錯体の光によるルイス酸性制御2015

    • Author(s)
      安永 亮佑・西本 能弘・安田 誠
    • Organizer
      日本化学会代95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 有機色素触媒を用いたトリフルオロボラート塩によるα-ハロカルボニル化合物のアリル化反応2015

    • Author(s)
      江住 直人・鈴木 至・安田 誠
    • Organizer
      日本化学会代95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Cage-Shaped Borates as a Catalysis for Selective Recognition of Aromatic Compounds2014

    • Author(s)
      Makoto Yasuda
    • Organizer
      The Ninth International Symposium on Integrated Synthesis
    • Place of Presentation
      夢舞台国際会議場(兵庫県淡路市)
    • Year and Date
      2014-11-14 – 2014-11-15
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Development of GaBr3-Catalyzed Cross Coupling Using Enol Derivatives as Alkenyl Electrophiles2014

    • Author(s)
      Yoshihiro Nishimoto, Yuji Kita, Makoto Yasuda, Akio Baba
    • Organizer
      The 2nd International Conference on Organometallics and Catalysis
    • Place of Presentation
      東大寺総合文化センター(奈良県奈良市)
    • Year and Date
      2014-10-26 – 2014-10-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Zinc-Catalyzed Coupling of Acetals with Terminal Alkynes: Facile Access to Functionalized Prooargyl Ethers2014

    • Author(s)
      Itaru Suzuki, Makoto Yasuda, Akio Baba
    • Organizer
      The 2nd International Conference on Organometallics and Catalysis
    • Place of Presentation
      東大寺総合文化センター(奈良県奈良市)
    • Year and Date
      2014-10-26 – 2014-10-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] アセタール類と末端アルキンの塩化亜鉛触媒直接カ ップリング反応2014

    • Author(s)
      鈴木 至・安田 誠・馬場章夫
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] 可視光酸化還元触媒を用いたアリルホウ素試薬とα-ハロカルボニル化合物のカップリング反応2014

    • Author(s)
      江住 直人・鈴木至・安田 誠
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] Control of Selectivity for Aromatic Compounds by Cage-Shaped Metal Complexes with Modification of Their Ligands2014

    • Author(s)
      Hikaru Maruyama, Koichi Nakaoka, Makoto Yasuda, Akio Baba
    • Organizer
      ETH Zurich-Osaka Univ. Joint Symposium
    • Place of Presentation
      大阪大学(大阪府豊中市)
    • Year and Date
      2014-10-09 – 2014-10-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] Lewis Acid Catalyst for Recognition of Aromatic Compounds2014

    • Author(s)
      Makoto Yasuda, Hikaru Maruyama, Koichi Nakaoka, Akio Baba
    • Organizer
      ETH Zurich-Osaka Univ. Joint Symposium
    • Place of Presentation
      大阪大学(大阪府豊中市)
    • Year and Date
      2014-10-09
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 紫外線照射による有機スズ種とアルキルハライド類とのインジウムまたはガリウムハライド触媒ラジカル反応2014

    • Author(s)
      鈴木 至・江住直人・安田 誠・馬場章夫
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] 臭化ガリウム触媒を用いるエノール誘導体とケテンシリルアセタールのカップリング反応の展開と機構解明2014

    • Author(s)
      西本能弘・喜多悠二・安田 誠・馬場章夫
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] アンモニウム塩添加を鍵とする可視光酸化還元触媒によるアリルホウ素試薬を用いたαーハロカルボニル化合物のアリル化反応2014

    • Author(s)
      江住直人・鈴木 至・安田 誠・馬場章夫
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] 配位子修飾によるかご型錯体の芳香族選択性制御2014

    • Author(s)
      丸山 輝・安永亮佑・西本能弘・安田 誠・馬場章夫
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学(宮城県仙台市)
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 複素環導入によるかご型ホウ素錯体のルイス酸性の精密制御2014

    • Author(s)
      安永 亮佑・西本 能弘・安田 誠・馬場章夫
    • Organizer
      第34回有機合成若手セミナー 明日の有機合成を担う人のために
    • Place of Presentation
      大阪大学(大阪府豊中市)
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] 可視光酸化還元触媒によるアリルホウ素試薬を用いたα-ハロカルボニル化合物のアリル化反応2014

    • Author(s)
      鈴木 至・江住 直人・安田 誠
    • Organizer
      第34回有機合成若手セミナー 明日の有機合成を担う人のために
    • Place of Presentation
      大阪大学(大阪府豊中市)
    • Year and Date
      2014-08-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] Effective Synthesis of Functionalized Propargyl Ethers with Acetals and Terminal Alkynes Catalyzed by Zn(II) Chloride2014

    • Author(s)
      鈴木 至・安田 誠・馬場章夫
    • Organizer
      The XXXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Carbobismuthination of Carbon-Carbon Multiple Bonds by Using Bismuth Trihalides and Ketene Silyl Acetals2014

    • Author(s)
      西本能弘・竹内 翠・安田 誠・馬場章夫
    • Organizer
      The XXXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Gallium Tribromide Accelerated Alkynylation of α-halo Carbonyl Compounds with Alkynylstannanes by UV Irradiation2014

    • Author(s)
      鈴木 至・江住直人・安田 誠・馬場章夫
    • Organizer
      The XXXVI International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] 有機化学で金属性状を緻密に制御する -新しい選択性発現をめざして-2014

    • Author(s)
      安田 誠
    • Organizer
      セミナー“化学千一夜” 「あすの化学への夢を語ろう」
    • Place of Presentation
      I&I LAND(大阪府四条畷市)
    • Year and Date
      2014-06-13 – 2014-06-14
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Cage-Shaped Borate Lewis Acid with π-Pocket for Selective Recognition of Aromatic Compounds2013

    • Author(s)
      Makoto Yasuda
    • Organizer
      17th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS17)
    • Place of Presentation
      Colorado State University, Fort Collins, Colorado, USA
    • Related Report
      2013 Research-status Report
  • [Presentation] Structurally Designed Cage-Shaped Borate Esters for Selective Reactions as a Catalyst2013

    • Author(s)
      安田 誠
    • Organizer
      1st International Conference on “Recent Trends in Organometallic Compounds and their Industrial Applications” (OMCA-2013)
    • Place of Presentation
      Kalinga Institute of Industrial Technology (KIIT University), Bhubaneswar, Odisha, India
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] カゴ型ホウ素錯体の多様な修飾によるルイス酸性制御2012

    • Author(s)
      安田 誠
    • 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

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

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