Undergraduate Laboratory Experiment: Molecular Organic Photocatalyst Synthesis and Its Application in Energy Transfer Photocatalytic E → Z Isomerization of Enone

Abstract This experimental design is tailored for third-year undergraduate students majoring in chemistry and materials science. It integrates the synthesis of the molecular organic photocatalyst 4CzIPN with its application in energy-transfer photocatalysis into a continuous experimental sequence. Students synthesize the molecular organic photocatalyst 4CzIPN through a nucleophilic aromatic substitution reaction under anhydrous and oxygen-free conditions and apply it to the contra-thermodynamic E→Z isomerization of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one ((E)-4′-methoxychalcone) driven by visible light. The experiment strengthens interdisciplinary knowledge integration (inorganic, organic, physical, and analytical chemistry) while focusing on key skills such as Schlenk-line operation, column chromatography purification, TLC monitoring, and NMR quantitative analysis. By analyzing the correlation between reaction mechanisms and the photophysical properties of the catalyst, students gain an understanding of the crucial role of Dexter energy transfer in achieving contra-thermodynamic transformations. This design utilizes visible light as a sustainable energy source and enhances students’ in-depth understanding of green photocatalysis and energy conversion through modular training (synthesis, purification, isomerization, and mechanistic analysis).