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2002 Fiscal Year Final Research Report Summary

Creation of Characteristic Delocalized Electronic Systems

Research Project

Project/Area Number 10146104
Research Category

Grant-in-Aid for Scientific Research on Priority Areas (A)

Allocation TypeSingle-year Grants
Research InstitutionOsaka University

Principal Investigator

NAKASUJI Kazuhiro  Osaka University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (60028230)

Co-Investigator(Kenkyū-buntansha) TOBE Yoshito  Osaka University, Graduate School of Engineering Science, Professor, 大学院・基礎工学研究科, 教授 (60127264)
KOBAYASHI Keiji  The University of Tokyo, Graduate School of Arts and Sciences , Professor, 大学院・総合文化研究科, 教授 (50012456)
ODA Masaji  Osaka University, Graduate School of Science, Professor, 大学院・理学研究科, 教授 (60004438)
Project Period (FY) 1998 – 2000
KeywordsDelocalized electronic system / Extended electronic system / Spin conjugated system / Hydrogen-electron interacted system
Research Abstract

This research project aims to create organic materials which show characteristic functions and physical properties, by designing and synthesizing novel conjugated, molecules and molecular systems having characteristic mode of electronic delocalization. Especially, unprecedented and complex functions are searched by constructing dynamic electronic delocalized systems which can interchange functions by applying heat, light, magnetic field, eletric field, and so on. The main research results are as follows :
(AO1) The. Group of "Extended conjugated systems" have intensively carried the synthesis and development of novel extended conjugated molecules and supramolecules with new topologies and new functions.
(AO2) The group of "Spin conjugated electronic systems" has explored and characterized various stable open-shell species which include satiable carbene, persilylbenzen dianion, divalent species of Si and Pb, and chiral organic magnets with reasonable stability and high spin states.
(AO3) The group of "Proton-electron coupling systems" has explored the proton-electron cooperative systems, proton dynamic dielectric response systems, and electron-hydrogen-charge transfer systems by creating new concept, constructing new molecular systems and controlling molecular electronic functions.

  • Research Products

    (54 results)

All Other

All Publications (54 results)

  • [Publications] H.Kurata: "Synthesis of novel cage molecules bicapped with tris(2-thienyl)methanes,"J. Chern. Soc. Chem. Commun. 529-530 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Kurata: "Adamantane-.2,4-bis(p-quinone methide) and -2,6-bis(p-quinone methide) as New Models for Intramolecular Interactions between Spatially Separated Redox Systems"Bull. Chem. Soc. Jpn. 74. 1327-1332 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Kawase: "The newly modified McMurry reaction toward the improved synthesis of cyclic paraphenylacetylenes"Tetrahedron Lett.. 42. 5509-5511 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Hosokawa: "8,16,24,32,40,48-Hexamethoxy[2.6]metacyclophane-1,9,17,25,33,41-hexayne: a novel near-planar ammonium selective ionophore"J. Chem. Soc. Chem. Commun. 1948-1949 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Kuwatani: "Synthesis of benzocyclobutadiene trimers and all-Z-tribenzo[12]annulene. A new family of concave π-systems"Tetrahedron. 57. 3567-3576 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Matsumoto: "Hexakis(2-pyridyl)-and hexakis(3-pyridyl) [3] radialene: novel, water-soluble[3]radialnes with potential utility for supramolecular chemistry"J. Chem. Soc. Chem. Commun. 324-325 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Matsumoto: "Synthesis of tetrakis(2-thienyl)methane"Tetrahedron Letters. (in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tobe: "[2+2] Cycloreversion of [4.3.2]Propella-1,3, 11-trienes: An Approach to Cyclo [n]carbons from Propellane-Annelated Dehydro [n]annulenes"J. Am. Chem. Soc.. 122. 1762-1775 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tobe: "Synthesis and Association Bihavior of Butadiyne-Bridged[44] (2,6)-Pyridinophane and [46](2,6)Pyridinophane Derivatives"Org. Lett.. 2. 3265-3269 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tobe: "Polyyne Cydization to Form Carbon Cages: [16.16.16](1,3,5)-Cyclophanetetracosayne Derivatives C60H6 and C60C16 as Precursors to C60 Fullerene"Tetrahedron. 57. 3629-3636 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tobe: "Vinylidene to Alkyne Rearrangement to Form Polyynes: Synthesis and Photolysis of Dialkynylmethylenebicyclo [4.3.1]deca-1,3,5-triene Derivatives"Tetrahedron Lett.. 42. 5485-5488 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Sonoda: "Synthesis of Differentially-Substituted Hexaethynylbenzenes Based on Tandem"Org. Lett.. 3. 2419-2421 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tobe.: "Syntheis of Butadiyne-Bridged [4n]Metacyclophanes Having Exo-annular t-ButylGroups"Tetrahedron. 57. 8075-8083 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tobe: "[12.12]Paracyclophanedodecaynes C36H8 and C36C18: The Smallest Paracyclophyne and their Transformation into Carbon Cluster Ion C36 -"Angew. Chem. Int. Ed.. 40. 4072-4074 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Tobe: "meta-Diethynylbenzene Macrocycles : Syntheses and Self-Association Behavior in Solution"J. Am. Chem. Soc.. (in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Takahashi: "Furane-fused TCNQ and DCNQ; Synthesis and Properties"J. Org. Chem.. 65. 2577-2579 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] R.Sekiya: "Intramolecular Migration of Bulky Substituents in the Solid State; Vinylogous"J. Am. Chem. Soc.. 122. 10282-10288 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Tanaka: "Solid State Solvolysis of Thiophene-Substituted Trityl-Type Alcohols: Nucleophilic Substitution Induced via Solid State Cogrinding with DDQ Followed by Exposure to Methanol Vapor"J. Org. Chem.. 66. 803-808 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Tanifuji: "Pseudo-Polymorphs Arising from Weak and Strong ミOH---N=C-Hydrogen Bonding in Inclusion Crystals of the Same Host and Guest in Different Compositions"Cryst. En. Comm.. 3. 2001

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Imakubo: "A newsynthetic route to TTF-vinylogues"Synthetic Metals. 120. 899-900 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Kubo: "4,7,11,14,18,21-Hexa-tert-butyltribenzodecacyclenyl radical: A Six-Stage Ampho-teric Redox System"Bull. Chem. Soc. Jpn. 74(in press). 1999-2009 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] J.Inoue: "The First Detection of a Clar's Hydrocarbon, 2,6,10-Tri-tert-Butyltriangulene: A Ground-State Triplet of Non-Kekule Polynuclear Benzenoid Hydrocarbon"J. Am. Chem. Soc. 40. 5476-5478 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasushi Morita: "6-Oxophenalenoxyl Derivatives Covalently Linked to the TTF Moieties: Synthesis, ESR/ENDOR Measurements, and DFT Calculations"Tetrahedron Lett. 42. 7991-7995 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Kubo: "Tetra-tert-butyl-as-indaceno[1,2,3-cd:6,7,8-c'd]diphenalene : A four-stage ampho-teric redox system"Tetrahedron Lett.. 42. 7997-8001 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasushi Morita: "New Stable Neutral Radical with Intramolecular Hydrogen Bonding: Synthesis and Characterization of 2,5,8-Tri-tert-butyl-7-hydroxy-6-oxophenalenoxyl"Org. Lett.. 3. 3099-3102 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Zaman, Md.B: "Preparation of a Mott Insulator based on a BEDT-TTF Charge Transfer Complex of Hydrogen Cyananilate:_'-(BEDT-TTF)2HCNAL"J. Mater. Chem.. 11. 2211-2215 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Maki: "A Novel Charge-Transfer Complex of TTF having Uracil Moiety with TCNQ"Synth. Met.. 120. 741-742 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Fukui: "The First Non-Kekule Polynuclear Aromatic High-spin Hydrocarbon: Generation of a Triangulene Derivative and Band Structure Calculation of Triangulene-based High-spin Hydrocarbons"Synth. Met.. 121. 1824-1825 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Fukui: "Electronic Spin Structure of Novel Persistent Neutral Radical with 1,3-Diaza-phenalene Skeleton as Studied by Electron-nuclear Magnetic Resonance"Synth. Met.. 121. 1770-1771 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Morita, T. Ohba, N. Haneda, S. Maki, J. Kawai, K. Hatanaka, D. Shiomi, K. Sato, T. Takui, and K, Nakasuji: "New Persistent Radicals : Synthesis and Electronic Spin Structure of 2, 5-Di-t-Butyl-6-Oxo-phenalenoxyl Derivatives."J. Am. Chem. Soc.. 122. 4825-4826 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Tadokoro, K. Nakasuji: "Hydrogen Bonded 2. 2-Biimidazolate Transition Metal Complexes as a Tool of Crystal Engineering."Cord. Chem. Rev.. 198. 205-218 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Kubo, K. Yamamoto, K, Nakasuji, T. Takui, I. Murata: "4, 7, 11, 14, 18, 21-Hexa-tert-butyltribenzodeca-cyclenyl radical : A Six-Stage Ampho-teric Redox System"Bull. Chem. Soc. Jpn.. 74, in press. (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J. Inoue, K. Fukui, T. Kubo, S. Nakazawa, K. Sato, D. Shiomi, Y. Morita, K. Yamamoto, T. Takui, and K. Nakasuji: "The First Detection of a Clar's Hydrocarbon, 2, 6, 10-Tri-tert-Butyltriangulene : A Ground-State Triplet of Non-Kekule Polynuclear Benzenoid Hydrocarbon"J. Am. Chem. Soc.. 123. 12702-12703 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Tadokoro, T. Shiomi, K. Isobe, K. Tashiro and K. Nakasuji: "Cesium(I)-Mediated 3-D Superstructures by One-Pot Self-Organization of Hydrogen-Bonded Nickel Complexes"Inorg. Chem.. 40. 5476-5478 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Morita, J. Kawai, Haneda, S. Nishida, K, Fukui, S, Nakazawa, D. Shiomi, K. Sato, T. Takui, Ta. Kawakami, K. Yamaguchi, K. Nakasuji: "6-Oxophenalenoxyl Derivatives Covalently Linked to the TTF Moieties Synthesis, ESR/ENDOR Measurements, and DFT Calculations"Tetrahedron Lett.. 42. 7991-7995 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Kubo, K. Yamamoto, K. Nakasuji, T. Takui: "Tetra-tert-butyl-as-indaceno[1, 2, 3-cd ; 6, 7, 8-c'd']diphenalene : A four-stage ampho-teric redox system"Tetrahedron Lett.. 42. 7997-8001 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Morita, S. Maki, K. Fukui, T. Ohba, J. Kawai, K, Sato, D. Shiomi, T. Takui, K. Nakasuji: "New Stable Neutral Radical with Intramolecular Hydrogen Bonding : Synthesis and Characterization of 2, 5, 8-Tri-tert-butyl-7-hydroxy-6-oxophenalenoxyl"Org. Lett.. 3. 33099-33102 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Suzuki, K. Matsumoto, H. Kurata, and M. Oda: "Synthesis and Characterisation of 2, 6-Di-tert-butyl-1-thio-1, 4-benioquinone, the First Isolable Monothio-1, 4-benzo-quinone"J. Chem. Soc. Chem. Commun.. 1357-1358 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Matsumoto, Y. Harada, T. Kawase and M. Oda: "Hexakis(2-pyridyl)- and hexakis(3-pyridyl)[3] radialene : novel water-soluble [3]radialnes with potential utility for supramolecular chemistry"J. Chem. Soc. Chem. Commun.. 324-325 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Kurata, H. Nakaminami, K. Matsumoto, T. Kawase, and M. Oda: "Synthesis of Novel Cage Molecules Bicapped with Tri(2-thienyl) methanes"J. Chem. Soc. Chem. Commun.. 529-530 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Kurata, T. Shimoyama, K. Matsumoto, T. Kawase, and M. Oda: "Adamantane-2, 4-bis(p-quinone methide)and -2, 6-bis(p-quinone methide) as New Models for Intramolecular Interactions between Spatially Separated Redox Systems"Bull. Chem. Soc. Jpn.. 74. 1327-1332 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Kawase, N. Ueda, K. Tanaka, Y. Seirai, and M.Oda: "The newly modified McMurry reaction toward the Improved synthesis of cyclic paraphenylacetylenes"Tetrahedron Lett.. 42. 5509-5511 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Hosokawa, T. Kawase, and M. Oda: "8, 16, 24, 32, 40, 48-Hexamethoxy[2.6]metacyclophane-1, 9, 17, 25, 33, 41-hexayne : a novel near-planar ammonium selective ionophore"J. Chem. Soc. Chem. Commun. 1948-1949 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Kuwatani, T. Yoshida, A. Kusaka, M. Oda, K. Hara, M. Yoshida, H. Matsuyama, and M. lyoda: "Synthesis of Enzo-cyclobutadiene trimers and all-Z-tribenzo[12]annulene. A new family of concave-systems"Tetrahedron. 57. 3567-3576 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Takahashi and K. Kobayashi: "Furane-fused TCNQ and DCNQ ; Synthesis and Properties"J. Org. Chem.. 65. 2577-2579 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] R. Sekiya, K. Kiyooka, T. Imakubo, and K. Konbayashi: "Intramolecular Migration of Bulky Substituents in the Solid State ; Vinylogous Pinacol Rearrangements Induced Thermally and by Acid Catalysis"J. Am. Chem. Soc.. 122. 10282-10288 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Tanaka, N. Tanifuji, S. Hatada, and K. Kobayashi: "Solid State Solvolysis of Thiophene-Substituted Trityl-Type Alcohols : Nucleophilic Substitution Induced via Solid State Cogrinding with DDFQ Followed by Exposure to Methanol Vapor"J. Org. Chem.. 66. 803-808 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N. Tanifuji and K. Kobayashi: "Pseudo-Polymorphs Arising from Weak and Strong ミOH…N=C- Hydrogen Bonding in Inclusion Crystals of the Same Host and Guest in Different Compositions"Cryst. En Comm.. 3. (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Imakubo, T. Iijima, K. Kobayashi, and R. Kato: "A new synthetic route to TTF-vinylogues"Synthetic Metals. 120. 899-900 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Tobe, N. Utsumi, A. Nagano, and K. Naemura: "Synthesis and Association Behavior of [4. 4. 4. 4. 4. 4]-Metacyclophanedodecayne Derivatives with Interior Binding Groups"Chem., Int. Ed.. 37. 1285-1287 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Tobe, N. Nakagawa, K. Naemura, T. Wakabayashi, T. Shida, and Y. Achiba: "[16. 16. 16](l, 3, 5)Cyclophane-tetracosayne (C_60H_6) : A Precursor to C_60 Fullerene"J. Am. Chem. Soc.. 120. 4544-4545 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Tobe, H. Nakanishi, M. Sonoda, T. Wakabayashi, and Y. Achiba: "Pyridine Analogue of Macrocyclic Polyyne C_58H_4N_2 as a Precursor to Diazafullerene C_58N_2"J. Chem. Soc. Chem. Commun.. 1625-1626 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Tobe, T. Fujii, H. Matsumoto, K. Tsumuraya, D. Noguchi, N. Nakagawa, M. Sonoda, K. Naemura, Y. Achiba, and T. Wakabayashi: "[2+2] Cycloreversion of [4. 3. 2]Propella-1, 3, 11-trienes : An Approach to Cyclo[n]-carbons from Propellane-Annelated Dehydro[n]-annulenes"J. Am. Chem. Soc.. 122. 1762-1775 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Tobe, A. Nagano, K. Kawabata, M. Sonoda, and K. Naemura: "Synthesis and Association Behavior of Butadiyne-Bridged [4_4](2, 6)Pyridinophane and [4_6](2, 6)-Pyridinophane Derivatives"Org. Lett.. 2. 3265-3268 (2000)

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

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Published: 2004-04-14  

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