Reaction of bis(4-hydrazinylphenyl)methane with 4-substitutedbenzaldehyde in the presence of CH₃COONa in EtOH at 80 °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), ¹H and ¹³C NMR spectroscopies, elemental and X-ray diffraction analysis (for 7 and 8). No only intermolecular hydrogen and intramolecular N⋯Cl tetrel bonds, but also the Cl⋯Cl and Cl⋯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 λ_max is dependent on the type of substituents attached para-position of aromatic moiety.

的反应双（4- hydrazinylphenyl）甲烷与4- substitutedbenzaldehyde在CH的存在₃在80℃下产率COONa在EtOH双（4 - （（ë）-2-（4- substitutedbenzylidene）肼基）苯基）甲烷[ - N（CH ₃）₂ 1，-F 2，-Cl 3，-NO ₂ 4 ]，随后在DMSO中存在CCl ₄，CuCl和四甲基乙二胺的情况下，经过Cu催化的烯烃化产物bis（4-（（E）-（2,2-二氯-1-（4-取代苯基）乙烯基）二氮烯基）苯基）甲烷[-N（CH ₃）₂ 5，-F 6，-Cl 7，-NO ₂ 8 ]。通过IR所有化合物，其特征在于（对于1 - 4），¹ H和^13个C NMR光谱，元素和X射线衍射分析（7和8）。否仅分子间氢键和分子内Ñ ⋯氯tetrel键，而且氯⋯ Cl和氯⋯ O型卤素的结合是在的结构中发现的7和8分别。收集的数据确认双偶氮染料5 – 8存在于DMSO溶液中，并且以固态形式仅以E异构体形式存在，并通过非共价相互作用而稳定下来。上的UV-vis吸收光谱溶剂效应5 - 8中CH研究₂氯₂，DMF和EtOH，其中λ_最大依赖于连接的取代基的类型对位芳族部分的位置。