Azulen-1-yl diazenes substituted at C-3 with phenyl-chalcogene moieties: dye synthesis, product characterization and properties

Abstract  

Two synthesis strategies were used for the generation of azulene-1-yl diazenes substituted at C-3 with a phenyl-chalcogenyl moiety, the synthesis of azulenes substituted at C-3 followed by azo-coupling and azulene substitution at C-3 in azulene-azo dyes. The last synthetic route seems to give more satisfactory results for the synthesis of the desired chalcogenic derivatives. Another target of this study was to investigate the changes induced by the phenyl-chalcogenic substitution on the NMR and UV-vis spectra, and also to compare this effect with the one exerted by halogen atoms and by strongly electron donating groups such as AcNH or PhCOO. Whereas the latter groups exhibit a strong influence on the NMR and UV-vis spectra, PhS, PhSe, or PhTe groups as well as halogen atoms produce only a small effect because of the moderate change in electron distribution over the entire molecule.