This study focuses on the electronic properties and intrinsic chemical reactivity of four organic molecules derived from benzoxazole. The research extends to the impact of both the polar solvent methanol and the non-polar solvent toluene; in addition, the impact of substitutions that give rise to individual resonance effects, as well as the simultaneous push-pull effect of substituents, one electron donor and one electron acceptor. The chosen substituents include a fragment of the ammonia NH2 amino radical and a fragment of the nitrogen dioxide NO2 radical. Using Gaussian as a computational tool within the framework of density functional theory (DFT), we use the three-parameter functional of Becke, Lee, Yang and Parr (B3LYP) and the Gaussian Pople 6-31+g(d) base set. To simulate solute-solvent interactions, the polarizable continuum model (PCM) was used. In this context, it was possible to estimate the electronic properties and intrinsic chemical reactivity of the benzoxazole-derived molecules, highlighting a notable result, especially with molecule IV in both the polar solvent methanol and toluene. Its constitution, which simultaneously involves electron donor and acceptor fragments, induced the push-pull effect. This resulted in a decrease in energy, the energy gap and molecular hardness for both solvent cases, along with an increase in electronegativity, transition wavelength and dipole moment. In conclusion, the identified electronic properties, when compared with similar studies, suggest the possible utility of these organic molecules as active layers in solar cells, particularly those designed to absorb in the far violet and blue regions. In addition, their application in OLED devices or as new active media for tunable lasers in the violet and UV regions could be a promising avenue to explore