The design and synthesis of two new fluorescent probes based on dinitrophenyl (1) and 7-nitrobenz-2-oxa-1,3-diazole (2) platforms is reported. Both probes, containing bis(pyridin-2-ylmethyl)amine as a receptor unit can efficiently detect zin ions (Zn2+) in aqueous solution, with limit of detections of 124 nM and 1.06 µM, respectively. Probe 1 and 2 led to 3-fold and 2.4-fold fluorescent enhancements respectively with the addition of Zn2+, that suggested that working mechanism of these probes is based on the inhibition of the photoinduced electron transfer from the electron donating receptor towards the excited fluorophore. Studying binding stoichiometry by job’s plot suggested 1:1 complexation between the probe and Zn2+. The formation of probes-Zn2+ complexes was validated by both FT-IR and 1H NMR wherein marked changes in the absorption frequencies as well as distinct downfield shifts in the resonance peaks of pyridine function along with the CH2 linked directly to the tertiary nitrogen of the DPA unit were observed. Density functional theory (DFT) calculations suggested that the electronic density of the HOMO in 1 is concentrated on the linker between DPA and dinitrophenyl, while, the density of the LUMO is concentrated on dinitrophenyl moiety. Upon Zn2+ binding, the electronic density in HOMO and LUMO are more delocalized. However, in case of probe 2 the delocalization of electronic density does not appreciably occur. Based on DFT simulations, both sensors form thermodynamic stable complexes with Zn2+ ions. However, sensor 2 exhibited slightly better binding preference toward Zn2+ compared to 1. The PET based probes exhibited good selectivity to detect Zn2+ in the presence of a variety of metal cations. These sensors have higher sensitivity and would be able to detect chronic level of Zn2+ in the freshwater (>1.84 μM) as permitted by the US EPA.