Development of functional polymer materials is essential for enabling a myriad of advanced applications ranging from autonomous stress-sensing to self-powered sensors. In this talk, I will discuss the design and synthesis of several material systems tailored to stress sensing and bacteria detection by leveraging the concepts in covalent polymer mechanochemistry and triboelectric nanogenerators (TENG). Incorporation of force-responsive Diels-alder adducts into polymer materials prove useful for visualizing mechanical stress experienced by polymer chains. Force-induced chemical reactions allow for detection of molecular level bond cleavage through fluorescence emission. On the other hand, the inherent antimicrobial properties of guanidinium side groups enables TENG to be sensitive to both gram-positive and gram-negative bacteria at a concentration of 10⁵ CFU/mL, resulting in decreasing voltage output as bacteria concentration increases. These results demonstrate that efforts in creating new functional polymer materials are critical for next-generation smart material systems.