A novel difunctional acylhydrazone with isoxazole and furan heterocycles: Syntheses, structure, spectroscopic properties, antibacterial activities and theoretical studies of (E)-N′-(furan-2-ylmethylene)-5-methylisoxazole-4-carbohydrazide

In order to explore new functional materials, a novel acylhydrazone with isoxazole and furan heterocycles was synthesized and thoroughly investigated by X-ray crystallography, UV and fluorescence spectroscopy, cyclic voltammetry, thermoanalysis, density functional theory (DFT) and time-dependent density functional theory (TDDFT). The molecule has been demonstrated to crystallize in the monoclinic space group P21/c, with the unit cell parameters of (a = 11.3522(19) Å, b = 8.0700(14) Å, c = 12.872(2) Å; α = 90°, β = 106.969(12)°, γ = 90°). In addition, this compound shows characteristic UV absorption peaks at 205, 222 and 308 nm, and fluorescence emission peak at 486.1 nm, which according to our theoretic calculation can all be attributed to (p, π) → π∗ and π → π∗ intraligand charge-transfer transition (ILCT) respectively. According to our cyclic voltammetry result, an oxidation peak of the compound can be observed with onset oxidation potential (Eox) of 0.44 V. Furthermore, the results of antibacterial activities indicate the compound has broad-spectrum against Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli and Staphylococcus aureus, which can be supported by the molecular electrostatic potential (MEP). Therefore, this compound exhibits both antibacterial activity and photoluminescent property, namely difunctionality, suggesting that it has potential applications in many fields such as material science and photodynamic therapy.

► A novel acylhydrazone from 5-methylisoxazole-4-carboyl hydrazine and furfuraldehyde.
► In this work, both crystalline and molecular structure is determined.
► Fluorescence emission peak at 486.1 nm is assigned to ILCT by TD DFT/HF CIS.
► UV–Vis absorption peaks at 205, 222 and 308 nm are attributed to ILCT by DFT.
► The title compound has both antibacterial activity and photoluminescent property.