The reactions of polyfluorochalcones with o aminothiophenol in methanol in the presence of HCl afford polyfluorine substituted 2,3 dihydrobenzo[b] [1,5]thiazepines. In some cases, the cyclization is accompanied by fluorine substitution in the perfluorophenyl ring. Probably, the formation of thiazepines proceeds through the Michael thia adduct. The Zn salt of o amino thiophenol reacts with chalcones in DMF exclusively via fluorine substitution.
New substituted azomethines of benzanthrone with heterocyclic substituents were synthesized by condensation reaction of 3-aminobenzo[de]anthracen-7-one with appropriate aromatic aldehydes. The resulting imines were reduced with sodium borohydride to the corresponding amines, the luminescence of which is more pronounced in comparison with the initial azomethines. The novel benzanthrone derivatives were characterized by NMR, IR, MS, UV/Vis, and fluorescence spectroscopy. The structure of three dyes was studied by the X-ray single crystal structure analysis. The solvent effect on photophysical behaviors of synthesized imines and amines was investigated. The obtained compounds absorb at 420–525 nm, have relatively large Stokes shifts (up to 150 nm in ethanol), and emit at 500–660 nm. The results testify that emission of the studied compounds is sensitive to the solvent polarity, exhibiting negative fluorosolvatochromism for the synthesized azomethines and positive fluorosolvatochromism for the obtained amines. The results obtained indicate that the synthesized compounds are promising as luminescent dyes.
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