Synthesis, Structure, Spectral-Luminescent Properties, and Biological Activity of Chlorine-Substituted N-[2-(Phenyliminomethyl)phenyl]-4-methylbenzenesulfamide and Their Zinc(II) Complexes

Abstract

New azomethine compounds of 2-(N-tosylamino) benzaldehyde or 5-chloro-2-(N-tosylamino)benzaldehyde and the corresponding chlorine-substituted anilines, zinc(II) complexes based onthem have been synthesized. The structures of azomethines and their complexes were determinedby elemental analysis, IR, 1H NMR, X-ray spectroscopy, and X-ray diffraction. It is found that allZnL2 complexes have a tetrahedral structure according to XAFS and X-ray diffraction data. Thephotoluminescent properties of azomethines and zinc complexes in methylene chloride solution andin solid form have been studied. It is shown that the photoluminescence quantum yields of solidsamples of the complexes are an order of magnitude higher compared to the solutions and range from11.34% to 48.3%. The thermal properties of Zn(II) complexes were determined by thermal gravimetricanalysis (TGA) and differential scanning calorimetry. The TGA curves of all the compounds suggesttheir high thermal stability up to temperatures higher than 290 C. The electrochemical propertiesof all complexes were investigated by the cyclic voltammetry method. The multilayered devicesITO/PEDOT:PSS/NPD/Zn complex/ TPBI/LiF/Al with wide electroluminescence (EL) color rangespanning the range from bluish-green (494 nm) to green (533 nm) and the high values of brightness,current and power efficiency were fabricated. The biological activity of azomethines and zinccomplexes has been studied. In the case of complexes, the protistocidal activity of the zinc complexwith azomethine of 5-chloro-2-(N-tosylamino)benzaldehyde with 4-chloroaniline was two timeshigher than the activity of the reference drug toltrazuril.