A series of novel 1,2,3-triazole-linked tetrahydrobenzo[b]thiophene derivatives were synthesized through a Green and sustainable sonochemical protocol by employing copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in a recyclable [BMIM][BF]/ HO (1:1) medium to explore their antimicrobial and antioxidant potential. The method features mild reaction conditions, excellent yields and notably, the ionic liquid (IL) employed was effectively recycled for five runs without significant loss of its efficiency. A comparative study under conventional conditions also demonstrated improved green metrics, such as high atom economy (100%) and reaction mass efficiency (94%), and low E-factor (0.064) and process mass intensity (1.06). The in-vitro biological assessment showed significant antimicrobial potency of these compounds, compound 3a demonstrated the highest potency against Staphylococcus aureus and Escherichia coli, with a low MIC value of 8 μg/mL, as well as activity against Candida albicans and Candida glabrata (MIC = 16 μg/mL). Additionally, antioxidant assays revealed moderate free-radical scavenging activity for compound 3c. Molecular docking simulation validated the binding interaction of the synthesized molecules with selected key proteins. This supports the proposed mechanism of action, as stable binding was observed in the target protein's active site. Moreover, ADMET analysis revealed that the synthesized compounds have good drug-like properties, which include efficient gastrointestinal absorption and adherence to Lipinski's rule. Overall, the present study describes an environmentally friendly approach with significant biological potential of designed scaffolds.