Here, three Schiff bases 3a-c, differing by the substitutions (-H, -Cl, and -N(CH3)2) on the phenyl ring, have been designed and synthesized via the reaction of ortho-aminophenol with benzaldehyde, 2,4-dichlorobenzaldehyde and para-dimethylamine benzaldehyde in 1:1 molar ratio with favourable yields of 89-92%, respectively. Their structural characterizations were studied by FT-IR, NMR, MALDI-MS and elemental analysis. The fluorescence behaviours of compounds 3a and 3b exhibited a severe aggregation caused quenching (ACQ) effect in EtOH/water system. On the contrary, compound 3c had an obvious J-aggregation induced emission (AIE) feature in EtOH/water mixture (v/v = 1:1), and exhibited excellent sensitivity and anti-interference towards Cu2+ with the limit of detection (LOD) of 1.35 × 10-8 M. Job's plot analysis and MS spectroscopic study revealed the 2:1 complexation of probe 3c and Cu2+. In addition, probe 3c was successfully applied to the determination of Cu2+ in real aqueous samples.
Keywords: Fluorescence; Ortho-aminophenol; Schiff base; Sensing Cu2+; aggregation-induced emission.
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