Study on the modulating effect of halogen atom substitution on the detection range of water content detection probes in organic solvents

Fluorescence probes based on the variations of aggregation state (Aggregation-Induced Emission (AIE) and Aggregation-Caused Quenching (ACQ)) have received widespread attention due to their simplicity, efficiency and intuitiveness. However, typical probes are highly sensitive to changes in polarity and slight variations in the external environment can cause a complete change in the aggregation state. With the aim of expanding the detection range of the molecular probe, this work adopts a different design strategy from adjusting the molecular backbone but regulates the fluorescence behavior of the Schiff base molecular backbone by introducing different halogen atoms. Systematic studies show that when chlorine serves as substitutional atoms (3,5-Cl Salen), the probe can achieve full-range detection of water content (0-100 vol%) in ethanol and DMF. To our knowledge, the 3,5-Cl Salen represents the best water content probe in organic molecules. Experimental and theoretical studies have shown that the adjustment of halogen atoms can linearly change the charge distribution on the benzene ring and precisely control the strength of intermolecular interactions. At the same time, we developed a fluorescent filter paper based on 3,5-Cl Salen and used smartphones for rapid, sensitive and precise on-site measurement of water content in organic solvents.