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Development of three-dimensional pi-electronic compounds originated from tripyrrin subunits

Research Project

Project/Area Number 24750034
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionShimane University (2014)
Chiba University (2012-2013)

Principal Investigator

SUZUKI Masaaki  島根大学, 総合理工学研究科(研究院), 講師 (90506891)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsポルフィリノイド / 環拡張ポルフィリン / ペンタフィリン / 芳香族性 / トリフルオロメチル化 / 求核置換反応
Outline of Final Research Achievements

The major target of this project utilizing tripyrrine precursors was switched to development of a wide variety of three-dimensional π-systems. As a result, it was successfully achieved that novel three-dimensionalπ-electronic modes bearing a branchedπ-plane had been constructed based on peculiar nucleophilic substitution reactions onto recombined N-fused pentaphyrin bromide. In the meantime, meso-trifluoromethyl substituted octaalkylporphyrins were obtained by scrambling side reactions of oligo-pyrrolic precursors. The strongly electron-withdrawing nature and the spatial steric hindrance of trifluoromethyl group caused a large distortion of the macrocyclic plane and improvement of the absorption property. Furthermore, the trifluoromethyl groups undertook solvolysis when the centeral metal ion was zinc, affording meso-methoxycarbonyl derivatives.

Report

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

    (21 results)

All 2015 2014 2013 2012 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Acknowledgement Compliant: 3 results,  Open Access: 1 results) Presentation (15 results)

  • [Journal Article] 5,20-Bis(α-Oligothienyl)-Substituted [26]Hexaphyrins(1.1.1.1.1.1): 26π Aromatic Hexaphyrin Circuit versus Acyclic Helical Conjugation2015

    • Author(s)
      Hirotaka Mori, Masaaki Suzuki, Woojae Kim, Jong Min Lim, Dongho Kim, Atsuhiro Osuka
    • Journal Title

      Chemical Science

      Volume: 6 Issue: 3 Pages: 1696-1700

    • DOI

      10.1039/c4sc03394a

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Skeletal recombination reaction of N-fused pentaphyrin(1,1,1,1,1) via bromination2014

    • Author(s)
      Masaaki Suzuki, Tyuji Hoshino, and Saburo Neya.
    • Journal Title

      Org Lett

      Volume: 16 Issue: 2 Pages: 327-329

    • DOI

      10.1021/ol403242z

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Highly Distorted meso-Trifluoromethyl-Substituted β-Octaalkylporphyrins2014

    • Author(s)
      Masaaki Suzuki, Shuto Ishii, Tyuji Hoshino, Saburo Neya
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 10 Pages: 1563-1565

    • DOI

      10.1246/cl.140561

    • NAID

      130004427212

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Computational and statistical study on the molecular interaction between antigen and antibody2014

    • Author(s)
      T. Osajima, M. Suzuki, S. Neya, T. Hoshino
    • Journal Title

      J. Mol. Graphics Model.

      Volume: 53 Pages: 128-139

    • DOI

      10.1016/j.jmgm.2014.07.005

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ralaxation analysis of ligand binding to the myoglobin reconstituted with cobartic heme.2013

    • Author(s)
      Neya S, Suzuki M, Hoshino T, Kawaguchi AT.
    • Journal Title

      Inorganic Chemistry

      Volume: 52 Issue: 13 Pages: 7387-7393

    • DOI

      10.1021/ic400078w

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Deprotonation-Induced Aromaticity Enhancement and New Conjugated Networks in meso-Hexakis(pentafluorophenyl)[26]hexaphyrin2012

    • Author(s)
      W.-Y. Cha, J. M. Lim, M.-C. Yoon, Y. M. Sung, B. S. Lee, S. Katsumata, M. Suzuki, H. Mori, A. Osuka, Y. Ikawa, H. Furuta, and D. Kim
    • Journal Title

      Chem. Eur. J

      Volume: 18 Issue: 49 Pages: 15838-15844

    • DOI

      10.1002/chem.201200991

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 非環状らせん共役系を有するヘキサフィリンの合成と物性2015

    • Author(s)
      森裕貴,鈴木優章,大須賀篤弘
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(船橋)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 非平面meso-トリフルオロメチル置換β-オクタアルキルポルフィリンの合成と物性2014

    • Author(s)
      鈴木優章,石井修人,星野忠次,根矢三郎
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内北キャンパス(仙台)
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Porphyrin with a Terpyridine Coordination Unit as the Imaging Probe for SPECT2014

    • Author(s)
      Saburo Neya, Masaaki Suzuki
    • Organizer
      8th International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      トルコ(イスタンブール)
    • Year and Date
      2014-06-22 – 2014-06-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] Skeletally recombined N-fused pentaphyrin(1.1.1.1.1) bromide and its derivatives2014

    • Author(s)
      Masaaki Suzuki, Tyuji Hoshino, Saburo Neya
    • Organizer
      8th International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      トルコ(イスタンブール)
    • Year and Date
      2014-06-22 – 2014-06-27
    • Related Report
      2014 Annual Research Report
  • [Presentation] 人工酸素運搬体素材としてのミオグロビンの分子設計2014

    • Author(s)
      根矢三郎・鈴木優章・星野忠次
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学
    • Related Report
      2013 Research-status Report
  • [Presentation] N-フューズドペンタフィリンの骨格変換と分子内π拡張反応2013

    • Author(s)
      鈴木優章・星野忠次・根矢三郎
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学目白キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 臭素化を経由するN-フューズドペンタフィリンの骨格変換2013

    • Author(s)
      鈴木優章,星野忠次,根矢三郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Research-status Report
  • [Presentation] 緩和法による酸化型コバルトを含むミオグロビンへの配位子結合解析2013

    • Author(s)
      根矢三郎,星野忠次,鈴木優章,川口章
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] インフルエンザエンドヌクレアーゼ活性阻害化合物の探索とその結合構造解析2013

    • Author(s)
      8. 不動聡志,石井和彦,小川博史,松浦崇晃,柳田浩,額賀路嘉,鈴木優章,根矢三郎,星野忠次
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis, Structure, and Aromaticity of the Ni(II) Complex of Pyricorrole, a New Porphyrin Isomer2012

    • Author(s)
      Neya, S., Suzuki, M., Matsugae, T., Hoshino, T.
    • Organizer
      22回金属の関与する生体関連反応シンポジウム
    • Place of Presentation
      金沢
    • Related Report
      2012 Research-status Report
  • [Presentation] Geometric and Electronic Structures of Nickel(II) Pyricorrole: Hybridization of Porphyrin and Corrole2012

    • Author(s)
      Neya, S., Suzuki, M., Matsugae, T., Hoshino, T.
    • Organizer
      7th International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      韓国Jeju
    • Related Report
      2012 Research-status Report
  • [Presentation] Amining at application of expanded porphyrin expecially for medicinal use2012

    • Author(s)
      Suzuki, M., Hoshino, T., Neya, S.
    • Organizer
      7th International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      韓国Jeju
    • Related Report
      2012 Research-status Report
  • [Presentation] 臭素化を経由するN-フューズドペンタフィリンの骨格変換2012

    • Author(s)
      鈴木優章,星野忠次,根矢三郎
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] 新規ポルフィリン異性体ピリコロールの合成と電子状態解析2012

    • Author(s)
      根矢三郎,鈴木優章,星野忠次
    • Organizer
      錯体化学会第62回討論会
    • Place of Presentation
      富山
    • Related Report
      2012 Research-status Report
  • [Presentation] ヨウ素NMR スペクトルによる有機化合物の同定

    • Author(s)
      加川夏子・鈴木優章・小暮紀行
    • Organizer
      第1 6回 ヨウ素学会シンポジム
    • Place of Presentation
      千葉大学けやき会館
    • Related Report
      2013 Research-status Report

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

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