Mechanofluorochromic (MFC) materials are emerging as a versatile candidate for optoelectronic and biomedical applications. In the present work, we designed and synthesized four MFC materials, namely BT-PTZ-1, BT-PTZ-2, BT-PTZO-1, and BT-PTZO-2, using Suzuki cross-coupling reaction. These materials possess benzothiazole (BT) as an acceptor moiety and different donors, including phenothiazine (PTZ) and triphenylamine (TPA), with variations in their spacer units. The photophysical properties of these derivatives have been explored, revealing solvatochromism, aggregation-induced emission (AIE), acid sensing, and mechanochromic behaviour. Single crystal X-ray analysis of BT-PTZO-2 provides crucial structural insights, revealing the twisted conformation of the TPA donor and the bent structure of the PTZ oxide spacer. The biological studies of these BT derivatives reveal the therapeutic potential against benzo[