Preparation and Characterization of New Azo Dyes Based on Aminoacetophenone for Staining Living Tissues and Studying of Spectroscopy Applications

Abstract

Through monoazo-coupling processes, H-imidazol and 2,4-dichloroaniline were linked to 4-amino acetophenone to create two novel azo dyes: (E)-1-(4-((1H-imidazol-2-yl)diazenyl) phenyl) ethan-1-one (IDPE) and (E)-1-(4-((2-amino-3,5-dichlorophenyl)diazenyl)phenyl) ethan-1-one (APDE). The electronic transitions spectra in the visible and UV ranges, FT-IR spectra and ¹H NMR, were used to confirm the structures of prepared azo dyes. The pH-sensitive chemical sensors based on the IDPE and APDE were investigated. Excellent sensitivity in the pH range of 3–9 and a significant wavelength shift (>85 nm) was demonstrated by these chemical sensors. It was demonstrated that these chemical pH sensors were fully reversible, which is essential for chemical pH sensors in practical applications. Additionally, the produced compounds were used in a bioimaging assay with mouse ovarian cells under confocal fluorescence microscopy to explore their potential as an effective cell staining agent.