Abstract: The incorporation of cutting-edge research achievements into undergraduate laboratory courses represents an effective approach to enhance students’ practical skills and innovative capacities. Herein, we report the rational design and synthesis of a tetraphenylethylene-based aggregation-induced emission (AIE)-active organic cage molecule (TPE-Cage) through dynamic covalent chemistry. Comprehensive characterization was performed using nuclear magnetic resonance (NMR) and matrix-assisted laser desorption/ionization time of flight mass (MALDI-TOF-MS) spectroscopy for structural verification, along with UV-Vis absorption and fluorescence spectroscopy to investigate its photophysical properties. This integrated experiment features innovative molecular architecture design, highly reproducible synthetic routes, and visually distinctive luminescent phenomena. As a well-designed teaching module, it effectively stimulates students’ scientific curiosity, bridges theoretical knowledge with practical implementation, and cultivates research-oriented thinking and innovation capabilities.

Key words: Aggregation-induced emission, Cage-like compound, Dynamic covalent chemistry, Comprehensive chemistry experiment