This work presents a systematic study of five novel closely related pyridine-substituted quinoxaline and pyridopyrazine derivatives 3a-e. Modifying the quinoxaline framework by introducing electron donating and accepting units led to fine-tuning of optical, thermal, and electrochemical properties. The single crystal X-ray diffraction studies revealed a Y-shaped structure with a herringbone packing arrangement. These compounds showed aggregation-induced emission (AIE) with the formation of J-aggregates. These compounds emitted blue fluorescence with one of the compounds showing CIEy as low as 0.08 in CHCl3 and 0.09 in the solid state. The band gaps were evaluated using UV-visible spectroscopy and density functional theory (DFT). The optical band gaps in the solid state were in the 2.81–3.05 eV range. They exhibited reversible switching of emission properties upon treatment with trifluoroacetic acid (TFA) followed by triethylamine (TEA) in both solution and solid states, which was utilized to fabricate filter paper strips to detect volatile acids. The emission of compounds also displayed linear temperature dependence.