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 tetra-phenylethene (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 mu M). The piperazine group allows TPE-Pz to possesses high specificity for lysosome with low cytotoxicity and high contrast in comparison with LysoTracker Red.

Automated summary

We report the synthesis and investigation of a piperazine-modified tetraphenylethene (TPE-Pz) with multi-functional properties. After acidification, the cationic TPE-Pz(+) molecules can form stable suspensions in tetrahydrofuran/water mixture solutions and exhibit aggregation-induced emission. The suspension can be used as a fluorescent probe for the detection of hazardous chemicals, such as aldehydes and picric acid. The piperazine group in TPE-Pz allows for high specificity for lysosome with low cytotoxicity and high contrast compared to LysoTracker Red.