Abstract: Aggregation-induced emission (AIE) materials represent a cutting-edge system in fluorescence sensing and bioimaging. Introducing these materials into undergraduate laboratory courses holds significant pedagogical value for cultivating innovative chemistry talents. This experiment designed and synthesized an AIE fluorescent probe (TPE-Th-1-OH) based on a tetraphenylethylene (TPE) framework. The target molecule was selected through density functional theory (DFT) calculations and synthesized via Knoevenagel condensation. Structural confirmation was achieved through Proton Nuclear Magnetic Resonance spectroscopy and melting point determination, systematically training students in computational chemistry, organic synthesis, and structural characterization. Photophysical studies demonstrated the probe’s excellent fluorescence stability across a wide pH range (3.0–10.0), with intensity variations below 10%. When applied for fingerprint visualization on various substrates (cardboard, basswood, alumina ceramic, acrylic plate, cover glass, and aluminum foil), the probe exhibited high resolution and strong anti-interference capabilities against complex backgrounds. This experiment effectively integrates AIE research with undergraduate teaching, encompassing four key modules: computational chemistry, organic synthesis, spectral characterization, and practical applications. The established “theory-synthesis-characterization-application” integrated teaching system significantly enhances senior undergraduates’ comprehensive analytical skills and research innovation capabilities.

Key words: Aggregation-induced emission, Fluorescent probe, Tetraphenylethylene derivative, Fingerprint development, Comprehensive chemistry experiment