Fluorescence Aggregation-Caused Quenching versus Aggregation-Induced Emission: A Visual Teaching Technology for Undergraduate Chemistry Students

A laboratory experiment visually exploring two opposite basic principles of fluorescence of aggregation-caused quenching (ACQ) and aggregation-induced emission (AIE) is demonstrated. The students would prepared two salicylaldehyde-based Schiff bases through a simple one-pot condensation reaction of one equiv of 1,2-diamine with 2 equiv of salicylaldehyde. The resulting fluorescent dyes have similar chemical structures but possess ACQ and AIE properties, respectively. Their ACQ/AIE properties and pH sensing applications would then examined by visually qualitative analysis (UV lamp, light-emitting diode, and naked eye) and quantitative analysis (fluorometer). Finally, in a deeper level, X-ray single crystal structure analysis was utilized to reveal the inherent relationships between molecular structures/molecular arrangements and ACQ/AIE properties. This lesson is suitable for many areas of chemistry, especially for organic and analytical chemistry.