Preparation, regulation and biological application of a Schiff base fluorescence probe

• A facile fluorescence switch with Schiff base units was designed and synthesized.
• The fluorescence of the probe can be illumined by Al3 + ion.
• The fluorescence of the probe/Al3 + ensemble may be quenched by Cu2 + ion.
• It is a fluorescence “off–on–off” change probe by metal ions.
• The regulation role of the probe can be applied in cell imaging.

A facile fluorescence switch with Schiff base units was designed and achieved by nucleophilic addition and dehydration reaction. The fluorescence of the probe can be regulated by metal ions (Al3 + and Cu2 +). The whole process shows that the weak fluorescence of the probe enhances with the addition of Al3 +, and then the strong fluorescence of the probe/Al3 + ensemble reduces by introducing Cu2 +. Meanwhile, the solution color changes of the probe with metal ions can be observed under 365 nm UV–vis light from weak light, pale green, green, pale green to weak light. Noticeably, the photo regulation processes of the probe by metal ions can be realized in the biological system and applied in cells imaging. The work provides a new strategy for designing facile regulation probe and develops a new application for Schiff base derivatives.

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