Modulating Dual Fluorescence Emissions in Imine-Based Probes to Distinguish D₂O and H₂O

How to distinguish D₂O and H₂O and determine the trace H₂O content in D₂O solvent, by using molecule-based spectral probes, is an intriguing topic in analytical chemistry, yet considerably few examples remain up to now, likely due to the very similar physical/chemical properties between D₂O and H₂O. In this work, we found that both the hydrolysis reactions to release fluorescent amines and aggregation-induced emission (AIE) of imines, functioning as dual fluorescence signals to distinguish D₂O and H₂O, could be modulated by changing the imine structures. The hydrophobicity of imines showed an important contribution to the ability of modulating the hydrolysis reactions and AIE, demonstrating a significant difference on fluorescence signals in D₂O and H₂O solvents. Among all tested imines, probe 3, condensed from 2-naphthylamine and salicylaldehyde, was found to have the potential ability to act as an ideal candidate for probing the H₂O content in D₂O solvent, particularly in a low H₂O content range, using the ratiomeric emission signals.