This study presents the synthesis and comprehensive characterization of novel thiazole Schiff’s base compound linked to various substituted formylphenyl cholesteryl carbonates. The structures were confirmed by elemental analysis and 1H NMR, 13C NMR, and FT-IR spectroscopy. Optical texture investigations revealed that only compound 7a exhibited liquid crystalline behaviour, specifically showing a chiral nematic (N*) mesophase. Thermal properties were analyzed using differential scanning calorimetry (DSC) showing phase transitions, and thermogravimetric analysis (TGA) indicating their stability ranging from 223 to 361 °C. The compound 7a exhibited significant antibacterial activity with zone of inhibition of 18 mm for Staphylococcus aureus (gram-positive) and 25.5 mm for Escherichia coli (gram-negative), and compound 7a and 8 displayed highest antifungal activity with zone of inhibition of 17.5 mm and 24.5 mm against Aspergillus niger and Candida albicans, respectively. Antioxidant activity was assessed using the DPPH assay, where compound 8 showed superior scavenging activity with IC50 value of 101.32 µg/mL. Additionally, the compounds were UV-active and exhibited photoluminescence, showing emission peaks ranging from 412 to 434 nm and a quantum yield of 0.11 to 0.23. In silico predictions indicated promising drug-likeness and bioactivity scores. Density Functional Theory (DFT) calculations provided insights into the electronic properties and molecular interactions. This research highlights the potential of these thiazole Schiff base derivatives for applications in pharmaceuticals and materials science, contributing valuable data on their multifunctional properties.