This work describes the successful synthesis of salicylaldehyde-derived Schiff baselinked organosilicon compounds following a highly efficient click approach. Hydroxyl-terminated Schiff bases were alkylated to bis-acetylenes (1-3) which upon 3 + 2 cycloaddition with 3-azidopropyltriethoxysilane yielded triazole-decorated bis-silanes (4-6). These silanes further underwent base-catalyzed transesterification to afford Schiff base-linked triazole-bound organosilatranes (7-9). The final silatranes as well as precursor alkynes and silanes were comprehensively characterized using NMR ( 1 H and 13 C) and infrared spectroscopic techniques together with elemental analysis and mass spectrometry of compounds 7-9. Also, the structures of alkynes 1-3 and silatrane 7 were validated using single-crystal X-ray crystallography. Organosilatranes were initially screened for their pharmacokinetic profile using absorption, distribution, metabolism, excretion and toxicity (ADMET) tools and then explored for their antimicrobial activities, with compound 9 emerging as the most potent antimicrobial agent. Compounds 1-3 and 7-9 also underwent thorough computational analysis by applying the density functional theory (DFT) approach with B3LYP/6-31G(d) level of theory and the results were found to be consistent with the experimental data. Several DFT-based descriptors were also evaluated providing a valuable insight into molecular stability and reactivity.