A novel receptor based on azo-derivatives of 1-naphthylamine (2-((E)-((4-chloro-3-(trifluoromethyl)phenyl) imino)methyl)-4-((E)-naphthalene-1-yldiazenyl)phenol(2) abbreviated CTNP was successfully designed and synthesized. Its sensing propertieswere studied deeply. Systematic studies of CTNPwith HCO3 − and AcO− anions in DMSO disclosed that there is hydrogen-bonding between CTNP and incoming anions. Significant changes in the visible region of the spectrum, as well as a drastic color change of CTNP from pale yellow to red, observed due to interaction as mentioned earlier. The stoichiometry of [CTNP: HCO3 − or AcO−] complexes and association constants determined through Job'smethod and Benesi-Hildebrand (B-H) plot, respectively. Taking into account the analysis results, CTNP performs the selective recognition of sub-millimolar concentrations of HCO3 − and AcO− efficiently. The antifungal activity of the receptor was tested against Aspergillus brasiliensis and Aspergillus niger. CTNP exhibited excellent antifungal activity against both strains. CTNP also represented antibacterial activity against Gram-positive bacteria: Staphylococcus epidermidis. It was cleared that designed receptor can be applied under physiological conditions for a long duration.