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2004 Fiscal Year Final Research Report Summary

Preparation of spin-switching molecules being enable to change their spin-states by step-wise reduction

Research Project

Project/Area Number 15550040
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionYokohama City University, Graduate School of Integrated Science

Principal Investigator

TUKADA Hideyuki  Yokohama City University, Graduate School of Integrated Science, Associate Professor, 大学院・総合理学研究科, 助教授 (40171970)

Project Period (FY) 2003 – 2004
Keywordsnitronylnitroxide / molecular magnet / shin / triplet / sinalet / p-quinone / radical / oxidation-reduction
Research Abstract

In order to prepare a single-molecular magnetic device that can change their spin-states corresponding to stepwise reduction (or oxidation), we tried to synthesize such the organic magnetic molecules having two parts in a molecule; one part can be reduced easily to give a radical anion (or oxidized easily to give a radical cation), and another part has open-shell structure. Thus, we proposed quinines bearing two nitronylnitroxide (NN) moieties.
Density functional theory (DFT) calculations for these molecules at various reduction/oxidation states indicate that hydroquinone bearing two NN moieties at 2,5-positions (and its dimethoxy ether) is a ground-state singlet biradical molecule. The semiquinoneradical, however, has a quartet as its ground-state.
The biradicals, 2,5-bis(4,4,5,5-tetramethylimidazoline-2-yl)-1,4-dimethoxybenzene and 2',5'-dimethoxy-4,4"-bis(4,4,5,5-tetramethylimidazoline-2-yl)-p-terphenyl were obtained from corresponding aldehydes and 2,3-diamino-1,4-dimethylbutane, followed by the oxidation with m-CPBA - NaIO_4. Crystal structure of the former diradical (reddish-purple) was solved. Bis(t-buthyldimethylsilyl)ether of the diradical was also synthesized to obtain the hydroquinone. Synthesis of bisquinone NN-diradicals and the Mn(II)-complexes is in progress.

  • Research Products

    (14 results)

All 2005 2004 2003

All Journal Article (14 results)

  • [Journal Article] Hetero-atom stabilization of zwitterionic non-Kekule molecules : A DFT study on energy gaps between zwitterionic singlet and biradical triplet state2005

    • Author(s)
      H.Tukada
    • Journal Title

      THEOCHEM 724

      Pages: 215-219

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Hetero-atom stabilization of zwitterionic non-Kekule molecules: A DFT study on energy gaps between zwitterionic singlet and biradical triplet state2005

    • Author(s)
      Tukada, H., Bangal, P.R., Tamai, N., Yokoyama, Y.
    • Journal Title

      THEOCHEM 724

      Pages: 215-219

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Electron spectroscopy of extrathin network structures constructed by self-assembly of planar molecules on a solid surface.2004

    • Author(s)
      H.Ozaki
    • Journal Title

      J.Electr.Spec.Relat.Phenom. 137-140

      Pages: 151-154

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Thermally reversible photochromism of pyrazole derivatives2004

    • Author(s)
      Y.Yokoyama
    • Journal Title

      Chem.Lett. 33・2

      Pages: 106-107

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] "Edge-on" orientation of alkyl chains on an iodine-covered Au(111) surface studied by infrared reflection absorption spectroscopy.2004

    • Author(s)
      O.Endo
    • Journal Title

      Surface Science 569

      Pages: 99-104

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Transient spectroscopic study of a non-Kekule molecule generated by photochemical χ-hydrogen abstraction of ethyl 4-formyl-1,3-DMP-carboxylate2004

    • Author(s)
      P.R.Bangal
    • Journal Title

      J.Phys.Chem.-A 108・4

      Pages: 578-585

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Electron spectroscopy of extrathin network structures constructed by self-assembly of planar molecules on a solid surface2004

    • Author(s)
      Ozaki, H., Suhara, M., Ohashi, T., Toda, N., Endo, O., Tukada, H.
    • Journal Title

      J Electr. Spec. Relat. Phenom. 151

      Pages: 137-140

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Transient spectroscopic study of a non-Kekule molecule generated by photochemical γ-hydrogen abstraction of ethyl4-formyl-1, 3-dimethylpyrazole-5-carboxylate2004

    • Author(s)
      Bangal, P.R., Tamai, N., Yokoyama, Y., Tukada, H.
    • Journal Title

      Phys. Chem.-A 108

      Pages: 578-578

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Thermally reversible photochromism of pyrazole derivatives2004

    • Author(s)
      Yokoyama, Y. et al.
    • Journal Title

      Chem. Lett. 33

      Pages: 106-106

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] "Edge-on" orientation of alkyl chains on an iodine-covered Au(111) surface studied by infrared reflection absorption spectroscopy2004

    • Author(s)
      Endo, O., Fukushima, Y., Ozaki, H., Sonoyama, M., Tukada, H.
    • Journal Title

      Surface Science 569

      Pages: 99-99

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Photosublimation of novel π-system photoproduct of ethyl-4-formyl-1,3-dimethylpyrazole-5-carboxylate2003

    • Author(s)
      P.R.Bangal
    • Journal Title

      J.Phys.Chem.-B 107・49

      Pages: 13554-13556

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Crystal structure of 1,3-diphenyladamantane and trans-1,4-diphenyl-cyclohexane : torsion angles about C-Ph bonds in α,ω-diphenyl(alicyclo H.C.)2003

    • Author(s)
      H.Tukada
    • Journal Title

      J.Mol.Structure 655

      Pages: 473-478

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Photosublimation of novel π-system photoproduct of ethyl 4-formyl-1,3-dimethylpyrazole-5-carboxylate2003

    • Author(s)
      Bangal, P.R., Tamai, Naoto, Yokoyama, Yasushi, Tukada, Hideyuki
    • Journal Title

      J. Phys. Chem. (B) 107

      Pages: 13554-13556

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Crystal structure of 1,3-diphenyladamantane and trans-1,4-diphenylcyclohexane: tortion angles about C-Ph bond in α,ω-diphenyl(alicyclic hydrocarbon)2003

    • Author(s)
      Tukada, Hideyuki, Mochizuki, Katsura
    • Journal Title

      J. Mol. Structure 655

      Pages: 473-478

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

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Published: 2006-07-11  

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