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Syntheses and Properties of Nonplanar Circulene Featuring a Structural Motif in Carbon Cluster

Research Project

Project/Area Number 05453036
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionUniversity of Osaka Prefecture

Principal Investigator

YAMAMOTO Koji  Integurated Arts and Sciences, University of Osaka Prefecture Professor, 総合科学部, 教授 (80029438)

Co-Investigator(Kenkyū-buntansha) MATSUBARA Hiroshi  Interurated Arts and Sciences, University of Osaka Prefecture Research Associate, 総合科学部, 助手 (20239073)
Project Period (FY) 1993 – 1995
Project Status Completed (Fiscal Year 1995)
Budget Amount *help
¥5,900,000 (Direct Cost: ¥5,900,000)
Fiscal Year 1995: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1994: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1993: ¥3,700,000 (Direct Cost: ¥3,700,000)
KeywordsCondensed Aromatic Compound / Strained Molecule / Nonplanar Molecule / Cluster / Circulene / フラーレン
Research Abstract

Recent advances in large carbon cluster chemistry (fullerenes) with curved molecular surfaces on sp^2 carbon lattices have aroused a interest in the field of nonplanar polycyclic aromatic compounds with circular arrangement of benzene rings known as circulene. The nonplanar circulenes featuring a structural motif present in carbon clusters were prepared and their unusual physical and chemical properties resulting from their stained and nonplanar structure were reported.
1. Convenient new synthesis of [7] Circulene [7] Circulene with saddle-shaped geometry was prepared by a convenient new method via 2,15-ethanobridged hexahelicene intermediate and its electrochemical properties was also examined.
2. Synthesis and characterization of hepta [5][5] circulene The polycyclic aromatic compound with a S-shaped circular arrangement of seven benzene rings, hepta [5][5] circulene, was prepared by FVP of bis- (1-chlorovinyl) acenaphthofluorancene. The structure and electrochemical properties were examined.
3. Ring inversion of [7] circulene derivative Our recent development of a convenient new route to [7] circulene and derivatives ther of has enabled us to measure the saddle-to-saddle inversion barrier for twisted saddle-shaped network at trigonal carbon atoms from variable temperature NMR experiments.
4. Synthesis of [7][7] circulene The preparation of [7][7] circulene whose carbon framework represents a subunit of helix-shaped nanotube inner surface was reported.

Report

(4 results)
  • 1995 Annual Research Report   Final Research Report Summary
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] Koji Yamamoto: "Synthesis and Characterization of [7]- and [7.7] Circulene" Pure Appl.Chem.65. 157-163 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of Methano-Bridged Dichlorodidehydro[20]-,and -[24]-annulenones" J.Chem.Soc.,Perkin Trans.I. 1453-1468 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto: "Synthesis of Nonplanar Circulene Featuring a Structural Motif in Carbon Cluster" J.Syn.Org.Chem.Jpn.53. 318-325 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto: "Novel Optically Active 7,7'-Bridged-1,1'-biiso- quinol ines and Their Cheration to Rhodium (I) lon" J.Chem.Soc.,Chem.Commun.1637-1638 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto: "Conveni ent New Synthesis of [7] Circulene" Angew.Chem.Int.Ed.Engl.35. 69-70 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masanori Matsuda: "Synthesis and Characterization of Hepta[5][5]-circulene as a Subunit of C_<70> Fullerene" Chem.Lett.157-158 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto: "Synthesis and Characterization of [7]- and [7.7] Circulene" Pure Appl.Chem. 65. 157-163 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Hiroyuki Higuchi, Kaoru Asano, Juro Ojima, Koji Yamamoto, Toshikatsu Yoshida, Tomohiro Adachi, Gaku Yamamoto: "Synthesis and Properties of Methano-bridged Dichlorodidehydro [16]-, [20]-, [24] annulenediones" J.Chem.Soc., Perkin Trans.1. 67. 778-791 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto, Hiroshi Matsubara: "Synthesis of Nonplanar Circulenes Featuring a Structural Motif in Carbon Cluster" J.Syn.Org.Chem.Jpn. 53. 318-325 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto, Hirohisa Tateishi, Kazuaki Watanabe, Tomohiro Adachi, Hiroshi Matsubara, Tatsuo Ueda, Toshikatsu Yoshida: "Novel Optically Active 7,7' -Bridged-1,1' -biiso-quinolines and their Cheration to Rhodium (l) lon" J.Chem.Soc., Chem.Commun. 1637-1638 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto, Hiroyuki Sonobe, Hiroshi Maysubara, Masaaki Sato, Susumu Okamoto, Kazuo Kitaura: "Convenient New Synthesis of [7] Circulene" Angew.Chem.Int.Ed.Engl. 35. 69-70 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Masanori Matsuda, Hiroshi Matsubara, Susumu Okamoto, Koji Yamamoto: "Synthesis and Characterization of Hepta- [5][5] circulene as Subunit of C_<70> Fullerene" Chem.Lett. 157-158 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1995 Final Research Report Summary
  • [Publications] Koji Yamamoto: "Synthesis of Nonplanar Circulene Featuring a Structural Motif in Carbon Cluster" J.Syn.Org.Chem.Jpn.53. 318-325 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Koji Yamamoto: "Novel Optically Active 7,7'-Bridged-1,1'-biisoquinolines and Their Cheration to Rhodium(I)lon" J.Chem.Sco.,Chem.Commun.1637-1638 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Koji Yamamoto: "Convenient New Synthesis of [7]Circulene" Angew.Chem.Int.Ed.Engl.35. 69-70 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Masanori Matsuda: "Synthesis and Characterization of Hepta[5][5]circulene as a Subunit of C_<70> Fullerene" Chem.Lett.157-158 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Koji Yamamoto: "Extended Systems of Closed Helicene.Synthesis and Characterization of [7]-and[7.7]Circulene" Pure Appl.Chem.65. 157-163 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] Masahiko Iyoda: "Synthesis and Properties of a Bisdehydro[14]annuleno[c]furan and an Ortho-Annelated Tetrakisdehydro[14]annulene" Bull.Chem.Soc.Jpn.67. 778-791 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of Methano-Bridged Dichlorodidehydro-[16]-,[20]-,and-[24]-annulenones" J.Chem.Soc.,Perkin Trans.I. 1453-1468 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Koji Yamamoto: "Synthesis of Nonplanar Circulenes Featuring a Structural Motif in Carbon Cluster" J.Syn.Org.Chem.Jpn.53(in press). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Koji Yamamoto: "A Convenient Synthesis of [7]Circulene" J.Chem.Soc.,Chem.Commun.(in press). (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] Koji Yamamoto: "Extended Systems of Closed Helicene.Synthesis and Characterization of [7]-and[7.7]Circulene" Pure Appl.Chem.65. 157-163 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masahiko Iyoda: "Synthesis and Properties of a Bisdehydro[14]annuleno[c]furan and an Ortho-Annelated Tetrakisdehydro[14]annulene" Bull.Chem.Soc.Jpn.(in press). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hiroyuki Higuchi: "Synthesis and Properties of Methano-Bridged Dichlorodidehydro-[16]-,-[20]-,and-[24]-annulenones" J.Chem.Soc.,Perkin Trans.I. (in press). (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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