Characterization of 9-(p-Substituted Benzylidenehydrazono) fluorenes

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Abstract

The title azine was obtained by a reaction of the corresponding fluorenone hydrazone and <i>p</i>-substituted benzaldehyde. The hydrazone formed from the unsymmetrical fluorenone afforded configurational isomers; the <i>E</i>-isomer was thermodynamically more stable than the <i>Z</i>-isomer. The structure of the title azines, derived from symmetrical fluorenone, was assigned to be (<i>s</i>-<i>trans</i>/<i>E</i>) form. The azines from unsymmetrical fluorenone gave isomeric mixtures due to the 9-iminofluorene moiety. The electronic spectra of these azines show an intramolecular charge transfer; the red shift beyond 250 nm is observed in the case of 9-[<i>p</i>-(diethylamino)benzylidenehydrazono]-2,4,7-trinitrofluorene, compared to the mother azine. 9-[<i>p</i>-(Pentyloxy)benzylidenehydrazono]-2,7-dinitrofluorene and some of the homologs possess a liquid-crystalline property; the phase-transition temperature of the dinitro compound is K (172 °C) M<sub>1</sub> (185) M<sub>2</sub> (187) I between the crystalline and liquid phases.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(12), 3633-3638, 1996-12-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008912523
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4098911
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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