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Design and synthesis of metal coordinating polyaromatic compounds having magnetic response

Research Project

Project/Area Number 15K13647
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

Ishikawa Hayato  熊本大学, 大学院先端科学研究部(理), 准教授 (80453827)

Co-Investigator(Kenkyū-buntansha) 松田 真生  熊本大学, 大学院先端科学研究部(理), 准教授 (80376649)
Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords多環芳香族化合物 / オルトキノン構造 / 酸化還元スイッチング / 磁性金属錯体 / 有機電子材料 / オルトキノン / 磁場応答性金属錯体 / レドックススイッチング / ヒドロキノン / ねじれひずみ
Outline of Final Research Achievements

The unique redox-switching system of orthoquinone-containing pentacyclic aromatic compounds using molecular hydrogen and oxygen in the presence of a heterogeneous Pd nano particle catalyst (SAPd) was discovered. These molecules were predicted by in silico screening before synthesis. Efficient synthetic protocols for orthoquinone-containing aromatic compounds via Pd-mediated homocoupling and the benzoin condensation reaction were developed. The obvious switching phenomena in photoluminescence property between orthoquinone and hydroquinone aromatic compounds were observed. In addition, the twist strain of the orthoquinone moiety could induce dramatic changes in color and emission. In addition, these polyaromatic compounds were applied to the ligand of magnetic metal complex.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (37 results)

All 2017 2016 2015 Other

All Journal Article (10 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 10 results,  Acknowledgement Compliant: 2 results,  Open Access: 2 results) Presentation (21 results) (of which Int'l Joint Research: 2 results,  Invited: 3 results) Book (1 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Triterpenes and Coumaroyltyramide from Ochthocosmus Africanus2017

    • Author(s)
      Raissa Viviane Tala Sipowo, Blandine Marlyse Wache Ouahouo, Hermine Laure Djomkam Maza, Hayato Ishikawa, Hiroshi Nishino, Pierre Mkounga*, Augustin Ephrem Nkengfack
    • Journal Title

      Journal of Diseases and Medicinal Plants

      Volume: 3 Issue: 1 Pages: 12-16

    • DOI

      10.11648/j.jdmp.20170301.13

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Triterpenoids from seeds of Tapinanthus bangwensis2017

    • Author(s)
      Hermine Maza, Pierre Mkounga*, Sandra Larissa Fenkam, Sylvain Kamdem Sado, Hayato Ishikawa, Hiroshi Nishino, Ephrem Augustin Nkengfack
    • Journal Title

      Phytochemistry Letters

      Volume: 19 Pages: 23-29

    • DOI

      10.1016/j.phytol.2016.11.002

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Acid-Mediated Aryl Migration Reaction of C3 Aryl Substituted Pyrrolidinoindolines2017

    • Author(s)
      S. Tadano, H. Ishikawa
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 1 Pages: 5-8

    • DOI

      10.1016/j.tetlet.2016.11.069

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] New lupan-type triterpenoids2016

    • Author(s)
      Pierre Mkounga*, Hermine L.D. Maza, Blandine M.W. Ouahouo, Lydie N. Tyon, Hayato Ishikawa, Hiroshi Nishino, Augustin E. Nkengfack
    • Journal Title

      Zeitschrift fur Naturforschung C

      Volume: 71 Issue: 11-12 Pages: 381-386

    • DOI

      10.1515/znc-2015-0235

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Moss Chloroplasts Are Surrounded by a Peptidoglycan Wall Containing D-Amino Acids2016

    • Author(s)
      T. Hirano, K. Tanidokoro, Y. Shimizu, Y. Kawarabayasi, T. Ohshima, M. Sato, S. Tadano, H. Ishikawa, S. Takio, K. Takechi, H. Takano
    • Journal Title

      The Plant Cell

      Volume: 28 Issue: 7 Pages: 1521-1532

    • DOI

      10.1105/tpc.16.00104

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Redox Switching of Orthoquinone-Containing Aromatic Compounds using Hydrogen and Oxygen Gas2016

    • Author(s)
      Kazuki Urakawa, Michinori Sumimoto, Mitsuhiro Arisawa, Masaki Matsuda*, Hayato Ishikawa*
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Collective Synthesis and Biological Evaluation of Tryptophan-based Dimeric Diketopiperazine Alkaloids2016

    • Author(s)
      Shine Tadano, Yukihiro Sugimachi, Michinori Sumimoto, Sachiko Tsukamoto, Hayato Ishikawa*
    • Journal Title

      Chemistry A European Journal

      Volume: 22 Issue: 4 Pages: 1277-1291

    • DOI

      10.1002/chem.201503417

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Unified Total Synthesis of Tryptophan-based Dimeric Diketopiperazine Alkaloids2016

    • Author(s)
      Hayato Ishikawa
    • Journal Title

      有機合成化学協会誌

      Volume: 74 Pages: 104-116

    • NAID

      130005138524

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Alkaloid Synthesis using Chiral Secondary Amine Organocatalysts2016

    • Author(s)
      Hayato Ishikawa*, Shinya Shiomi
    • Journal Title

      Organic & Bimolecular Chemistry

      Volume: 14 Issue: 2 Pages: 409-424

    • DOI

      10.1039/c5ob02021b

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Efficient Organocatalytic Construction of C4-Alkyl Substituted Piperidines and Their Application to the Synthesis of (+)-α-Skytanthine2015

    • Author(s)
      Shinya Shiomi, Erika Sugahara, Hayato Ishikawa*
    • Journal Title

      Chemistry A European Journal

      Volume: 21 Issue: 42 Pages: 14758-14763

    • DOI

      10.1002/chem.201503117

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] ヒドロキサム酸ーホウ素錯体を基質とした超原子価ヨウ素試薬による芳香族炭素ー窒素結合形成反応2017

    • Author(s)
      松本真、石川勇人
    • Organizer
      日本化学会第97回春期年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2017-03-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] 配糖体型モノテルペノイドインドールアルカロイド全合成を志向したセコロガニンの全合成研究2017

    • Author(s)
      楽満健太、石川勇人
    • Organizer
      日本化学会第97回春期年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 放線菌由来新規Nーオキシピロール誘導体の単離・合成及び植物成長抑制活性2017

    • Author(s)
      吉村華夏、石川勇人
    • Organizer
      日本化学会第97回春期年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] オルトキノン含有フェナセン型化合物の合成とレドックススイッチングへの応用2016

    • Author(s)
      浦川一樹、川畑佑太、隅本倫徳、有澤光弘、松田真生、石川勇人
    • Organizer
      第6回 CSJ化学フェスタ
    • Place of Presentation
      タワーホール船掘
    • Year and Date
      2016-11-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] オルトキノン構造を組み込んだ多環芳香族化合物の創製と機能開発2016

    • Author(s)
      浦川一樹、隅本倫徳、有澤光弘、松田真生、石川勇人
    • Organizer
      第27回 基礎有機化学討論会
    • Place of Presentation
      広島国際会議場
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] 水素ガス・酸素ガスで色と蛍光を制御する分子技術の開発2016

    • Author(s)
      石川勇人
    • Organizer
      JST主催 くまもと発新技術説明会
    • Place of Presentation
      JST東京本部別館
    • Year and Date
      2016-08-23
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 有機合成におけるバイオインスパイアード反応と有機触媒反応2016

    • Author(s)
      石川勇人
    • Organizer
      第26回 万有福岡シンポジウム
    • Place of Presentation
      九州大学
    • Year and Date
      2016-04-23
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Syntheses of Orthoquinone-Containing Aromatic Compounds and Their Redox Chromism2016

    • Author(s)
      浦川一樹、隅本倫徳、有澤光弘、松田真生、石川勇人
    • Organizer
      日本化学会第96回春期年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 水を溶媒とするバイオインスパイアードインドールプレニル化反応の開発2016

    • Author(s)
      田中聡美、塩見慎也、石川勇人
    • Organizer
      日本化学会第96回春期年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ジヒドロリコルシンの不斉全合成研究2016

    • Author(s)
      合志圭、森永侑加、石川勇人
    • Organizer
      日本化学会第96回春期年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ガイソチザールの不斉全合成研究2016

    • Author(s)
      福長亜紀、中島梨絵、牛島大佑、石川勇人
    • Organizer
      日本化学会第96回春期年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ジヒドロリコルシンの不斉全合成研究2016

    • Author(s)
      合志圭、森永侑加、石川勇人
    • Organizer
      「有機分子触媒による未来型分子変換」第6回公開シンポジウム
    • Place of Presentation
      大阪科学技術センター
    • Year and Date
      2016-01-22
    • Related Report
      2015 Research-status Report
  • [Presentation] チアゾリニウム塩触媒を用いたオルトキノン含有多環芳香族化合物の合成と光学特性評価2016

    • Author(s)
      浦川一樹、隅本倫徳、有澤光弘、松田真生、石川勇人
    • Organizer
      「有機分子触媒による未来型分子変換」第6回公開シンポジウム
    • Place of Presentation
      大阪科学技術センター
    • Year and Date
      2016-01-22
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthetic Study of Biologically Active Piperidine Alkaloids using Asymmetric Organocatalytic Reactions2015

    • Author(s)
      Hayato Ishikawa
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hilton Hawaiian Village
    • Year and Date
      2015-12-18
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] トリプトファン由来二量体型アルカロイド類の網羅的合成と生物活性評価2015

    • Author(s)
      只野慎治、杉町幸寛、塚本佐知子、石川勇人
    • Organizer
      第33回メディシナルケミストリーシンポジウム
    • Place of Presentation
      幕張国際研修センター
    • Year and Date
      2015-11-25
    • Related Report
      2015 Research-status Report
  • [Presentation] ガイソチザールの不斉全合成研究2015

    • Author(s)
      福長亜紀、中島梨絵、牛島大佑、石川勇人
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 不斉形式的アザ[3+3]付加環化反応を鍵工程とするピペリジンアルカロイド類の合成研究2015

    • Author(s)
      塩見慎也、菅原絵里香、石川勇人
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール
    • Year and Date
      2015-09-10
    • Related Report
      2015 Research-status Report
  • [Presentation] Efficient Organocatalytic Construction of C4-Alkyl Substituted Piperidines and It’s Application to Synthesis of (+)-α-Skytanthine2015

    • Author(s)
      Shinya Shiomi, Erika Sugahara, Hayato Ishikawa
    • Organizer
      39th Naito Conference
    • Place of Presentation
      シャトレーゼガトーキングダム
    • Year and Date
      2015-07-08
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 光学活性多置換ピペリジン環の実践的合成法の開発と天然物合成への展開2015

    • Author(s)
      塩見慎也、菅原絵里香、石川勇人
    • Organizer
      第13回 次世代を担う有機化学シンポジウム
    • Place of Presentation
      立命館大学
    • Year and Date
      2015-05-23
    • Related Report
      2015 Research-status Report
  • [Presentation] 光学活性デカヒドロキノリン骨格構築法の開発2015

    • Author(s)
      合志圭, 森永侑加,石川勇人
    • Organizer
      第8回有機触媒シンポジウム兼「有機分子触媒による未来型分子変換」第5回公開シンポジウム
    • Place of Presentation
      沖縄県市町村自治会館・自治会館ホール
    • Year and Date
      2015-05-10
    • Related Report
      2015 Research-status Report
  • [Presentation] ガイソチジンの不斉全合成研究2015

    • Author(s)
      福長亜紀、中島梨絵、牛島大佑、石川勇人
    • Organizer
      第8回有機触媒シンポジウム兼「有機分子触媒による未来型分子変換」第5回公開シンポジウム
    • Place of Presentation
      沖縄県市町村自治会館・自治会館ホール
    • Year and Date
      2015-05-10
    • Related Report
      2015 Research-status Report
  • [Book] 有機触媒の化学 (CSJカレントレビュー22)2016

    • Author(s)
      林雄二郎、石川勇人
    • Total Pages
      7
    • Publisher
      化学同人
    • Related Report
      2016 Annual Research Report
  • [Remarks] 石川研究室ホームページ

    • URL

      http://www.sci.kumamoto-u.ac.jp/~ishikawa/ishikawa-lab/Top.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] 熊本大学研究コア キラル分子生命科学

    • URL

      http://www.sci.kumamoto-u.ac.jp/chiralmolecule/

    • Related Report
      2016 Annual Research Report
  • [Remarks] 熊本大学 石川研究室ホームページ

    • URL

      http://www.sci.kumamoto-u.ac.jp/~ishikawa/ishikawa-lab/Top.html

    • Related Report
      2015 Research-status Report
  • [Patent(Industrial Property Rights)] 植物成長抑制剤、およびそれを用いた植物成長抑制方法2017

    • Inventor(s)
      石川勇人、石田喬志、澤進一郎、谷時雄
    • Industrial Property Rights Holder
      石川勇人、石田喬志、澤進一郎、谷時雄
    • Industrial Property Rights Type
      特許
    • Filing Date
      2017-02-07
    • Related Report
      2016 Annual Research Report
  • [Patent(Industrial Property Rights)] レドックススイッチング材料、並びに、当該レドックススイッチング材料を利用したデバイスおよび当該デバイスの運転方法2016

    • Inventor(s)
      石川勇人、松田真生、隅本倫徳
    • Industrial Property Rights Holder
      石川勇人、松田真生、隅本倫徳
    • Industrial Property Rights Type
      特許
    • Filing Date
      2016-07-14
    • Related Report
      2016 Annual Research Report

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Published: 2015-04-16   Modified: 2018-03-22  

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