© 2021 Elsevier LtdIn this study, six new acylthiourea, bearing naphthoquinone moiety, sensors were synthesized in high yield (88–96%) and characterized using 1H/13C NMR, FT-IR and HRMS techniques. All synthesized sensors (4a-f) showed shifts in absorbance and colorimetric changes by CN−, F−, AcO−, and H2PO4−. However, 4e showed a chromogenic different sensitivity response to CN− and F− against competing anions such as AcO− and H2PO4− in DMSO. Furthermore, CN− added 4e showed an increase at the emission intensity and intensive fluorimetric color change was observed in UV-light (λex. 365 nm). All sensors showed chromogenic selectivity towards CN− in aqueous solutions (in DMSO/H2O: 1:1, v/v). Interaction mechanisms between 4e and CN− and F− anions were investigated by experimental studies using various spectroscopic methods such as UV/Vis, fluorescence, 1H/19F NMR, and DFT calculation. The results showed that CN− interacts with 4e by the main mechanism as nucleophilic addition of cyanide to 3,5-dinitrophenyl moiety while F− caused an occurrence of imidazole ring-closing due to deprotonation of NH2. LOD values are reported as 2.7 μM for sensor 4e. Moreover, interaction studies were carried out on food sample such as bitter almond, sprouting potato and apricot seed. Furthermore, UV/vis responses were obtained between sensors (4a-f) and the cations, and found selectivity towards Hg2+ in DMSO.