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Novel reactions in the multi-nuclear complexes compcsed of dipyrrylmethene platform

Research Project

Project/Area Number 18550058
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Inorganic chemistry
Research InstitutionKobe University

Principal Investigator

SETSUNE Jun-ichro  Kobe University, Graduate Schcol of Science, Department of Chemsilay, Professor (10117997)

Co-Investigator(Kenkyū-buntansha) LINTULUTOT Juha Mikael  Kobe University, Graduate Scheel of Science, and Technology, Department of Chemsitry, Assistant Professor (20379481)
Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥3,950,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2007: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2006: ¥2,000,000 (Direct Cost: ¥2,000,000)
Keywordsporphyrinoids / octaphyrin / rhodium / palladium / pyrrole / bipyrrole / multinuclear complexes
Research Abstract

Novel multinuclear complexes of porphyrinoids are of interest because their dipyrrylmethene components can serve as monoanionic bidentate ligation to various metal. Two new dipyrrole building blacks for the porphyrinoids have been developed in this study. α-Free bipynoles having various aromatic spacers between the pyrroles were synthesized via Suzuki-coupling reactions of α-borylpyrrole with aryl dihalides. bis(azafulvene)s having various substituents were prepared via dehydration reaction from the dipyrrole dicarbinols. These new building blocks served as donors and acceptors in the macrocyclization reactions to give good yields of porphyrinoids having various aromatic spacers such as 1,4-phenylene, 1,3-phenylene, 2,5-thienylene, and 2,6-pyridylene groups. Dinurlear Rh complexes of tetraphyrins with two 1,3-phenylene spacers and the corresponding RhPd heterodinuclear complexes, the trinalear Rh complex of hexaphyrin with three 2,5-thienylene spacers, and the tetranudear Rh complex of octaphyrin with four 2,5-thienylene spacers were synthesized and their structures were determined by X-ray crystallography. Metallation of the porphyrinoids reduces flexibility of the macroring skeleton and thus the spatial arrangement of metal atoms tends to be fixed. This leads to new multi metallo sites for binding substrates and their transformations. A bowl shaped trinulear Rh complexes and a saddle shaped tetranuclear Rh complexes are of great interest as host molecules for molecular recognition. In fact, chloroform molecules were incorporated into the cavity of the tetranudear complexes in the crystal structure. The carbonyl ligands on Rh and the π-allyl ligand on Pd in the heterodinuelear RhPd complexes are considered to be very cloes. Novel cage compounds having three dipynylpyridine chains have been created in this study and their interesting binding ability was proven

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (31 results)

All 2008 2007 2006

All Journal Article (18 results) (of which Peer Reviewed: 7 results) Presentation (13 results)

  • [Journal Article] Synthesis and Dynamic Structure of Multinuclear Rh Complexes of Porphyrinoids2008

    • Author(s)
      J. Setsune
    • Journal Title

      Chemical Communications

      Pages: 1425-1427

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Cryptand-like Porphyrinoid Assembled with Three Dipyrryl-pyridine Chains:Synthesis, Structure, and Homotropic Positive Allosteric Binding of Carboxylic Acids2008

    • Author(s)
      J. Setsune
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 2404-2405

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis and Dynamic Structure of Multinuclear Rh Complexes of Porphyrinoids2008

    • Author(s)
      J. Setsune, M. Toda, T. Yoshida
    • Journal Title

      Chant Commun., 2008

      Pages: 1425-1427

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Cryptand-like Porphyrinoid Assembled with Three Dipyrrylpyridine Chains: Synthesis, Structure, and Homotropic Positive Allosteric Binding of Carboxylic Acids2008

    • Author(s)
      J. Setsune, K. Watanabe
    • Journal Title

      J. Am. Chem. Soc 130

      Pages: 2404-2405

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis and Dynamic Structure of Multinuclear Rh Complexes of Porphyrinoids2008

    • Author(s)
      J. Setsune
    • Journal Title

      Chem. Commun.

      Pages: 1425-1427

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cryptand-like Porphyrinoid Assembled with Three Dipyrryl-pyridine Chains: Synthesis, Structure, and Homotropic Positive Allosteric Binding of Carboxylic Acids2008

    • Author(s)
      J. Setsune
    • Journal Title

      J. Am. Chem. Soc. 130

      Pages: 2404-2405

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Regioselective Metallation of Octaphyrin-(1.0.1.0.1.0.1.0)with Mixed Bipyrrole Units.2007

    • Author(s)
      M. Mori
    • Journal Title

      Chemistry Letters 36

      Pages: 244-245

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis and structures of Co(II) complexes of meso-tetrapheny loctaphyrin-(1.0.1.0.1.0.1.0)s2007

    • Author(s)
      J. Setsune
    • Journal Title

      Journal of Organometallic Chemistry 692

      Pages: 166-174

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis and structures of Co(II) complexes of meso-tetraphenyl-octaphyrin-(1.0.1.0.1.0.1.0)s2007

    • Author(s)
      J. Setsune, M. Mori, T. Okawa, S. Maeda, J. M. Lintuluoto
    • Journal Title

      J. Organometal. Chem 692

      Pages: 166-174

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Regioselective metallation of Octaphyrin(1.0.1.0.1.0.1.0) with Mixed Bipyrrole Units2007

    • Author(s)
      M. Mori, J. Setsune
    • Journal Title

      Chem. Lett 36

      Pages: 244-245

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis and structures of Co(II) complexes of meso-tetraphenyloctaphyrin-(1.0.1.0.1.0.1.0)s2007

    • Author(s)
      J.Setsune, M.Mori, T.Okawa, S.Maeda, J.M.Lintuluoto
    • Journal Title

      Journal of Organometallic Chemistry 692

      Pages: 166-174

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Regioselective metallation of Octaphyrin-(1.0.1.0.1.0.1.0) with Mixed Bipyrrole Units.2007

    • Author(s)
      M.Mori, J.Setsune
    • Journal Title

      Chemistry Letters 36

      Pages: 244-245

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis and Chiroptical Property of C_2-Symmetric Cyclohexapyrrole2007

    • Author(s)
      J.Setsune, A.Tsukajima, J.Watanabe
    • Journal Title

      Tetrahedron Letters 48

      Pages: 1531-1534

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of Bis(pyrrol-2-yl)arenes by Pd-catalyzed Cross Coupling2006

    • Author(s)
      J. Setsune,
    • Journal Title

      Tetrahedron Letters 47

      Pages: 7541-7544

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Synthesis of bis(pyrrol-2-yl)arenes by Pd-catalyzed cross coupling2006

    • Author(s)
      J. Setsune, M. Toda, K. Watanabe, P. K. Panda, T. Yoshida
    • Journal Title

      Tetrahedron Lett 47

      Pages: 7541-7544

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Synthesis of bis(pyrrol-2-yl)arenes by Pd-catalyzed cross coupling2006

    • Author(s)
      J.Setsune, M.Toda, K.Watanabe, P.K.Panda, T.Yoshida
    • Journal Title

      Tetrahedron Letters 47 (43)

      Pages: 7541-7544

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Direct determination of absolute configuration of carboxylic acids by cyclooctapyrrole2006

    • Author(s)
      Juha M.Lintuluoto, Kana Nakayama, Jun-ichiro Setsune
    • Journal Title

      Chemical Communications. 2006

      Pages: 3492-3494

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of bis(azafulvene)s by dehydration of hydroxymethylpyrrole derivatives2006

    • Author(s)
      J.Setsune, A.Tanabe, J.Watanabe, S.Maeda
    • Journal Title

      Organic Biomolecular Chemistry 4

      Pages: 2247-2252

    • Related Report
      2006 Annual Research Report
  • [Presentation] シクロオクタピロールへの金属挿入反応に於ける不斉誘起と速度論的光学分割2007

    • Author(s)
      岡崎菜穂
    • Organizer
      第5・7回錯体化学討論会
    • Place of Presentation
      名古屋工業大学
    • Year and Date
      2007-09-26
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis and Structures of Metal Complexes Coordinated by Arene-containing Cyclotetrapyrroles2007

    • Author(s)
      K. Watanabe
    • Organizer
      第54回有機金属化学討論会
    • Place of Presentation
      広島大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Annual Research Report 2007 Final Research Report Summary
  • [Presentation] Synthesis and Properties of Multinuclear Complexes Ligated by Cyclooligomers of Heterocycles2007

    • Author(s)
      K. Watanabe, J. Setsune
    • Organizer
      54th Symposium of Organometallic
    • Place of Presentation
      Chemistry, Japan, at Hiroshima, Japan
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and Properties of Multinuclear Complexes Ligated by Cyclooligomers of Heterocycles2006

    • Author(s)
      K. Watanabe
    • Organizer
      第53回有機金属化学討論会
    • Place of Presentation
      大阪市立大学
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Dynamic Structures of Cyclopolypyrroles and Their Metal Complexes2006

    • Author(s)
      J. Setsune
    • Organizer
      8th International Symposium of Organic Reactions
    • Place of Presentation
      淡路国際会議場
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Dipyridyl-dipyrromethene Based Macrocycle:A New Class of Expanded Porphyrinoid.2006

    • Author(s)
      P.K. Panda
    • Organizer
      7th International Symposium on Functional pi-Electron Systems
    • Place of Presentation
      大阪国際会議場
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Flexible Octaphyrins Capable of Sensing Chirality of Carboxylic Acids2006

    • Author(s)
      J.M. Lintulunto
    • Organizer
      7th International Symposium on Functional pi-Electron Systems
    • Place of Presentation
      大阪国際会議場
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and Study of Expanded Rosarin Using Fluorene2006

    • Author(s)
      P.K. Panda
    • Organizer
      4th International Conference of Porph yrins and Phthalocyanines
    • Place of Presentation
      Rome, Italy
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and Structures of Metal Complexes Coordinated by2006

    • Author(s)
      K. Watanabe, J. Setsune
    • Organizer
      53rd Symposium of Organometallic
    • Place of Presentation
      Chemistry, Japan, at Osaka, Japan
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Dynamic Structures of Cyclopolypyrroles and Their Metal Complexes2006

    • Author(s)
      J. Setsune, M. Toda
    • Organizer
      8th International Symposium of Organic
    • Place of Presentation
      Reactions, at Hyogo, Japan
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Dipyridyl-dipyrromethene Based Macrocycle: A New Class of Expanded Porphyrinoid2006

    • Author(s)
      P. K. Panda, J. Setsune
    • Organizer
      7th International Symposium on Functional
    • Place of Presentation
      pi-Electron Systems, at Osaka, Japan
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Flexible Octaphyrins Capable of Sensing Chirality of Carboxylic Acids2006

    • Author(s)
      J. M. Lintuluoto, J. Setsune
    • Organizer
      7th International Symposium on Functional
    • Place of Presentation
      pi-Electron Systems, at Osaka, Japan
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and Study of Expanded Rosarin Using Fluorene2006

    • Author(s)
      P. K. Panda, J. Setsune
    • Organizer
      4th International Conference of Porphyrins and Phthalocyanines
    • Place of Presentation
      at Rome, Italy
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2006-04-01   Modified: 2021-04-07  

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