Tetrel, halogen and hydrogen bonds in bis(4-((E)-(2,2-dichloro-1-(4-substitutedphenyl)vinyl)diazenyl)phenyl)methane dyes

Reaction of bis(4-hydrazinylphenyl)methane with 4-substitutedbenzaldehyde in the presence of CH3COONa in EtOH at 80 degrees C yields bis(4-((E)-2-(4-substitutedbenzylidene)hydrazinyl)phenyl) methane [-N(CH3)(2) 1, -F 2, -Cl 3, -NO2 4], which subsequently in the presence of CCl4, Cucl and tetramethylethylenediamine in DMSO undergoes Cu-catalyzed olefination products, bis(4-((E)-(2,2-dichloro-1-(4-substitutedphenyl)vinyl)diazenyl) phenyl)methane [-N(CH3)(2) 5, -F 6, -Cl 7, -NO2 8], respectively. All compounds were characterized by IR (for 1-4), H-1 and C-13 NMR spectroscopies, elemental and X-ray diffraction analysis (for 7 and 8). No only intermolecular hydrogen and intramolecular N center dot center dot center dot Cl tetrel bonds, but also the Cl center dot center dot center dot Cl and Cl center dot center dot center dot O types of halogen binding were found in the structures of 7 and 8, respectively. The collected data confirm that bis-azodyes 5-8 exist in DMSO solution and in solid state exclusively in the E-isomeric form, being stabilized by noncovalent interactions. Solvent effects on the UV-vis absorption spectra of 5-8 were studied in CH2Cl2, DMF and EtOH, which lambda(max), is dependent on the type of substituents attached para-position of aromatic moiety.