Bulletin of the Chemical Society of Japan p. 3633 - 3638 (1996)
Update date:2022-08-03
Topics:
Minabe, Masahiro
Takabayashi, Yutaka
Setta, Yuji
Nakamura, Hidenao
Kimura, Takao
Tsubota, Motohiro
The title azine was obtained by a reaction of the corresponding fluorenone hydrazone and p-substituted benzaldehyde. The hydrazone formed from the unsymmetrical fluorenone afforded configurational isomers; the E-isomer was thermodynamically more stable than the Z-isomer. The structure of the title azines, derived from symmetrical fluorenone, was assigned to be (s-translE) 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-[p-(diethylamino)benzylidenehydrazono]-2,4,7-trinitrofluorene, compared to the mother azine. 9-[p-(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) M1 (185)M2 (187) I between the crystalline and liquid phases.
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