Schiff bases, specially the “salen type” are some of the most widely used organic ligands, due to their easy preparation and ability to bind a variety of metal ions. Their properties (chemical, optical, magnetic, electrical) can be tuned by the proper choice of the precursors amine and carbonylic compounds. These compounds are used as pigments and dyes, catalysts, intermediates in organic synthesis, and play an important role in biological systems, acting as anticancer, antibacterial, antifungal or antiviral agents [1-3]. In this work we report the synthesis, structural characterization, photoluminescence and antimicrobial properties evaluation of new Schiff bases derived from a new silicon-containing diamine (Figure 1) and three different carbonylic compounds: salicylaldehide, 3hydroxysalicylaldehyde and 3-metoxysalicylaldehyde (Figure 2). All the obtained compounds were structurally characterized by spectral analyses and single crystal X-ray diffraction. The obtained Schiff bases proved to be good UV light absorber and fluorescent materials. The antimicrobial activity test results revealed, in the cases of azomethines derived from substituted salycilic aldehyde, an increased efficiency as compared with that of reference compounds Caspofungin and Kanamycin.