A multifunctional piperazine-modified tetraphenylethene derivative: Hazardous chemical detection and lysosome-targeted cell imaging

We report the synthesis and the investigation on the multi-functional property of a piperazine-modified tetraphenylethene (TPE-Pz). After acidification, the cationic TPE-Pz+ molecules can form stable suspensions in tetrahydrofuran/water mixture solutions and the molecular aggregates are highly emissive due to the aggregation-induced emission property of the tetraphenylethene unit. The experimental results showed that the suspension can be directly used as fluorescent probe for the detection of hazardous chemicals such as aldehydes and picric acid. For aldehydes, the probe exhibited high quenching efficiency (up to 80.90%), high sensitivity and low detection limit (0.05–0.97 μM). The piperazine group allows TPE-Pz to possesses high specificity for lysosome with low cytotoxicity and high contrast in comparison with LysoTracker Red. [Display omitted] ∙Pronounced aggregation-induced emission property due to the TPE unit.∙Stable aggregates in aqueous solution due to the amphiphilic structure.∙Directly used as fluorescent probe for the detection of hazardous chemicals in aqueous media.∙Lysosome-specific cell-imaging due to the piperazine functional group