How to distinguish DO and HO and determine the trace HO content in DO 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 DO and HO. 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 DO and HO, 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 DO and HO 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 HO content in DO solvent, particularly in a low HO content range, using the ratiomeric emission signals.
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