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1994 Fiscal Year Final Research Report Summary

Synthesis of Conjucated pi-Systems for the Elusidation of Biological Functions

Research Project

Project/Area Number 04403007
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionOsaka University

Principal Investigator

SAKATA Yoshiteru  Osaka University, The Institute of Scientific and Industrial Research, Professor, 産業科学研究所, 教授 (60029874)

Co-Investigator(Kenkyū-buntansha) TAKEHISA Chiaki  Osaka University, The Institute of Scientific and Industrial Research, Research, 産業科学研究所, 教務職員 (00243270)
SUGIURA Ken-ichi  Osaka University, The Institute of Scientific and Industrial Research, Research, 産業科学研究所, 助手 (60252714)
IMAHORI Hiroshi  Osaka University, The Institute of Scientific and Industrial Research, Research, 産業科学研究所, 助手 (90243261)
KANEDA Takahiro  Osaka University, The Institute of Scientific and Industrial Research, Associate, 産業科学研究所, 助教授 (50029899)
Project Period (FY) 1992 – 1994
KeywordsBiological Function / Conjugated pi-systems / Photosynthetic Charge Separation / Molecular Recognition / Electron Tranfer / Porphyrin / Host-Guest Complementarity / Donor-Acceptor
Research Abstract

In order to understand the biological function of photosynthetic electron transfer and molecular recognition, we prepared various organic compounds having conjugated pi-system and obtained the following results for photosynthetic electron transfer. 1) By preparing porphyrin-quinone compounds with rigid spacer, the large influence of the orientation of sigma-orbitals of the spacer upon electron transfer has been revealed. 2) By preparing a porphyrin with two quinones, it was concluded that electron transfer rate becomes doubled when there are two electron transfer pathways. 3) Porphyrins linked by a double bond at meso position have been prepared and the relationship between the structure and physical properties has been revealed. 4) A long alkyl chain in which a porphyrin ring is linked at an end and a thiol groupe is connected at the other end has been prepared and the molecule has been self-assembled on gold surface to show redox waves. 5) Porphyrin-linked fullerene was prepared and efficient electron transfer between the redox pair has been observed. In addition, chiral chromogenic crown ethers have been prepared and found that these compounds recognize chiral amines enantioselectively to give different corolation.

  • Research Products

    (46 results)

All Other

All Publications (46 results)

  • [Publications] V.V.Borovkov: "Synthesis and Properties of Pheophorhide-Quinone Compounds" Bull. Chem. Soc. Jpn.65. 1533-1537 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Sakata: "Synthesis of Dithia(1,5)[3,3]anthracenophane with Crossed Structure and Its Excimer Emission" Tetrahedron Lett.33. 5077-5080 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Yamamoto: "Synthesis and Enantioselective Coloration of Optically Active Azophenolic Acerands Incorporating Two 1,1'-Binaphthyl Moieties as the Chiral Center." J. Chem. Soc. Chem. Commun.1992. 791-793 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 坂田 祥光: "人工光合成を目指してー分子システムにおける光誘起電子移動" 生産と技術. 44. 12-17 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] G.V.Ponomarev: "Synthesis and Properties of Cis-1,2-Bio(octraethyl-porphyrinyl)ethylene" tetrahedron Lett.34. 2153-2156 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] V.V.BorovKov: "Mechanistic Studies on Oxidation Reaction of Ethare-Bridged Porphyrin Dimers to Trans-Ethlene-Bridged Species" Chem.Lett.1993. 1409-1412 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Imahori: "Porphyrin-Quinone Compounds with a Spacer of Diacetylene Unit" Chem.Lett.1993. 1215-1218 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Kitagawa: "Highly Crowded trans-Olefin, Molecular Structure of trans-1,2{meso-[nichel(II)octaethylporphyrinyl]}ethane" Chem.Lett.1993. 1071-1074 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] V.V.BorovKov: "A New Approach to Study of Solvent Effect on Electron Transfer" Chem.Lett.1993. 737-740 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] V.V.BorovKov: "Evidence for Parallel Photo induced Electron Transfer in Diquinon Substituted Porphyrins" Chem.Lett.1993. 145-148 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Naemura: "Azophenolic Acerands Having Chiral 1-phenyl-ces-1,2-cyclo haxunediol Units:A Correlation between Enantio-recognitive Colonation and Host-Guest Complementarity" J.Am.Chem.Soc.115. 8475-8476 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sawada: "Enantioselective Complexation of Carbohydrate or Crown Ether Hosts with Organic Ammonium Ion Guests Detected by FAB Moss Spectrometry" J.Am.Chem.Soc.115. 7381-7388 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 坂田 祥光: "光合成における光電荷分離中心モデルの分子設計" 太陽エネルギー. 19. 19-25 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Tsue: "Orientation Dependence of Photoinduced Electron Transfer in Covalently Linked Porphyrin-Quinone Molecules" Mem.Inst.Sci.& Ind.Res.,Osaka Univ.50. 55-61 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Akiyama: "Preparation of Molecular Assemblies of Porphyrin-Linked Alkanethiol on Gold Surface and Their Redox Properties" Chem.Lett.1994. 1447-1450 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Sakata: "Effect of Donor-Acceptor Orientation on Ultrafast Photoinduced Electron Transfer and Dark Charge Recombination in Porphyrin-Quinone Molecules" J.Am.Chem.Soc.116. 6904-6909 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Naemura: "The Synthesis of Azophenolic Crown Ethers of C,Symmetry Incorporating Cis-1-Phenyl-cyclohexane,-1,2-diol Residuos and Dia-stireotopic Face solectivity in Complexation of Ethanolamine by Their Diastereotipic" J.Chem.Soc.,Chem.Commun.1994. 711-712 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.V.Anikin: "Observation of Conformational Relaxation Hindrance in the Singlet Excited Sate for Porphyrin Incorporated in a Lipid Membrane." Chem.Phys.Lett.226. 337-343 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Imahori: "Synthesis and Properties of Conjugated Porphyrins with a Diacetylene Spacer." Bull.Chem.Soc.Jpn.67. 2500-2506 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H. Tsue: "Synthesis of Rigid Porphyrin-Quinone Compounds for Studying Mutual Orientation Effects on Electron Transfer and Their Photophysical Properties" Bull.Chem.Soc.Jpn.67. 3067-3075 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] G.V.Ponomarev: "Cis-Trans Isomerization and Atropisomerism of Octaethyl-1,2-Bis(coproporphyrisyl)ethylene Ester" J.Chem.Soc.,Commun.1994. 1927-1928 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Sugiura: "Interaction of Two Porphyrin Rings" Proc.Indian Acad.Sci.106. 735-742 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A.A.GribKov: "Synthesis of Rigidly Linked Triadic Molecules on the Basis of Octalhylporphyrin Capable to Multistep Electron Transfer" Heterocycl.Compd.1994. 1052-1062 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Imahori: "Synthesis and Photophysical Property of Porphyrin-Linked Fullerene" Chem.Lett.1995(in press). (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] V.V.Brovkov, A.A.Gribkov, A.N.Kozyrev, A.S.Brandis, A.Ishida, and Y.Sakata: "Synthesis and Properties of Pheophorbide-Quinone Compounds" Bull.Chem.Soc.Jpn.Vol.65-No.6. 1533-1537 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Sakata, T.Toyoda, S.Misumi, T.Yamazaki, and I.Yamazaki: "Synthesis of Dithia (1,5) [3.3] anthracenophane with Crossed Structure and Its Excimer Emission." Tetrahedron Lett.Vol.33-No.35. 5077-5080 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Yamamoto, K.Isoue, Y.Sakata, and T.Kaneda: "Synthesis and Enantioselective Coloration of Optically Active Azophenolic Acerands Invoorporating Two 1,1'-Binaphthyl Moieties as the Chiral Center" J.Chem.Soc., Chem.Commun.Vol.1992. 791-793 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] G.V.Ponomarev, V.V.Borovkov, K.Sugiura, Y.Sakata, and A.M.Shul'ga: "Synthesis and Properties of Cis-1,2-Bis (octaethylporphyrinyl) ethylene" Tetrahedron Lett.Vol.34-No.13. 2153-2156 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] V.V.Borovkov, G.V.Ponomarev, A.Ishida, T.Kaneda, and Y.Sakata: "Mechanistic Studies on Oxidation Reaction of Ethane-Bridged Porphyrin Dimers totrans-Ethylene-Bridged Species" Chem.Lett.Vol.1993. 1409-1412 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Imahori, Y.Tanaka, To.Okada, and Y.Sakata: "Porphyrin-Quinone Compounds with a Spacer of Diacetylene Unit" Chem.Lett.Vol.1993. 1215-1218 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R.Kitagawa, Y.Kai, G.V.Ponomarev, K.Sugiura, V.V.Borovkov, T.Kaneda, and Y.Sakata: "Highly Crowded trans-Olefin. Molecular Structure of trans-1,2 {meso- [nickel (II) octaethylporphyrinyl]} ethene." Chem.Lett.Vol.1993. 1071-1074 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] V.V.Borovkov, A.Ishida, S.Takamuku, and Y.Sakata: "A New Approach to Study of Solvent Effect on Intramolecular Electron Transfer." Chem.Lett.Vol.1993. 737-740 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] V.V.Brovkov, A.Ishida, S.Takamuku, and Y.Sakata: "Evidence for Parallel Photoinduced Electron Transfer in Diquinone Substituted Porphyrines." Chem.Lett.Vol.1993. 145-148 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Naemura, K.Ueno, S.Takeuchi, Y.Tobe, T.Kaneda, and Y.Sakata: "Azophenolic Acerands Having Chiral 1-Phenyl-cis-1,2-cyclohexanediol Units : A Correlation between Enantiorecognitive Coloration and Host-Guest Complementarity" J.Am.Chem.Soc.Vol.115. 8475-8476 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sawada, Y.Okumura, M.Shizuma, Y.Takai, Y.Hdaka, T.Tanaka, T.Kaneda, K.Hirose, S.Misumi, and S.Takahashi: "Enantioselective Complexation of Carabohydrate or Crown Ether Hosts with Organic Ammonium Ion Guests Detected by FAB Mass" J.Am.Chem.Soc.Vol.115. 7381-7388 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Tsue, S.Higashida, and Y.Sakata: "Orientation Dependence of Photoinduced Electron Transfer in Covalently Linked Porphyrin-Quinone Molecules." Mem.Inst.Sci.Ind.Res.Vol.50. 55-61 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Akiyama, H.Imahori, and Y.Sakata: "Preparation of Molecular Assemblies of Porphyrin-Liked Alkanethiol on Gold Surface and Their Redox Properties" Chem.Lett.Vol.1994-No.8. 1447-1450 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Sakata, H.Tsue, M.P.O'Neil, G.P.Wiederrecht, and M.R.: "Wasielewski, Effect of Donor-Acceptor Orientation on Ultrafast Photoinduced Electron Transfer and Dark Charge Recombination in Porphyrin-Quinone Molecules" J.Am.Chem.Soc.Vol.116-No.15. 6904-6909 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Naemura, S.Takeuchi, M.Asada, K.Hirose, Y.Tobe, T.Kaneda, and Y.Sakata: "The Synthesis of Azophenolic Crown Ethers of Cs Symmetry Incorporating Cis-1-Phenyl-cyclohexane-1,2-diol Residues and Diastereotopic Face Selectivity in Complexation of Ethanolamine by Their Diastereotopic Faces" J.Chem.Soc., Chem.Commun.Vol.1994-No.6. 711-712 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.V.Anikin, V.V.Borovkov, A.Ishida, K.Wasa, and Y.Sakata: "Observation of Conformational Relaxation Hindrance in the Singlet Excited State for Porphyrin Incorporated in a Lipid Membrane" Chem.Phys.Lett.Vol.226. 337-343 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Imahori, H.Higuchi, Y.Matsuda, A.Itagaki, Y.Sakai, J.Ojima, and Y.Sakata: "Synthesis and Properties of Conjugated Porphyrins with a Diacetylene Spacer" Bull.Chem.Soc.Jpn.Vol.67-No.9. 2500-2506 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Tsue, S.Nakashima, Y.Goto, H.Tatemitsu, S.Mitsumi, R.J.Abraham, T.Asahi, Y.Tanaka, T.Okada, N.Mataga, and Y.Sakata: "Synthesis of Rigid Porphyrin-Quinone Compounds for Studying Mutual Orientation Effects on Electron Transfer and Their Photophysical Properties" Bull.Chem.Soc.Jpn.Vol.67-No.11. 3067-3075 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] G.V.Ponomarev, V.V.Borovkov, A.M.Shul'ga, and Y.Sakata: "Cis-Trans Isomerization and Atropisomerism of Octaethyl 1,2-Bis (coproporphyrinyl) cthylene Ester." J.Chem.Soc., Chem.Commun.Vol.1994-No.17. 1927-1928 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Sugiura and Y.Sakata: "Interaction of Two Porphyrin Rings" Proc.Indian Acad.Sci.Vol.106-No.3. 735-742 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A.A.Gribkov, V.V.Borovkov, R.P.Evstigneeva, and Y.Sakata: "Synthesis of Rigidly Linked Triadic Molecules on the Basis of Octaalkylporphyrin Capable to Multistep Electron Transfer" Heterocycl.Compd.Vol.1994-No.8. 1052-1062 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Imahori, K.Hagiwara, T.Akiyama, S.Taniguchi, T.Okada, and Y.Sakata: "Synthesis and Photophysical Property of Porphyrin-Linked Fullerene" Chem.Lett.Vol.1995(in press).

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1996-04-15  

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