Tetraphenylethene-Modified Colorimetric and Fluorescent Chemosensor for Hg2+ With Aggregation-Induced Emission Enhancement, Solvatochromic, and Mechanochromic Fluorescence Features.

Jin-Jin Tian,Shouzhi Pu,Long Wang,Dian-Dian Deng,Zhao Chen

doi:10.3389/fchem.2021.811294

Jin-Jin Tian, Shouzhi Pu + Show 3 more

Open Access

https://doi.org/10.3389/fchem.2021.811294

Copy DOI

Abstract

A tetraphenylethene (TPE)-modified rhodanine derivative was successfully designed and prepared, and this luminophor showed intramolecular charge transfer nature from the TPE unit to the rhodanine-3-acetic acid unit. Interestingly, this luminogen not only exhibited typical aggregation-induced emission enhancement (AIEE) behavior but also showed good cell imaging performance. Remarkably, this AIEE-active TPE-containing rhodanine derivative possessed noticeable solvatochromic fluorescence effect involving multiple fluorescent colors of green, yellow-green, yellow, orange, and red. Meanwhile, this fluorescigenic compound displayed reversible mechanochromic fluorescence behavior based on the mutual transformation of between stable crystalline and metastable amorphous states. On the other hand, this multifunctional fluorophor could selectively and sensitively detect Hg2+ in an acetonitrile solution. Furthermore, this chemosensor could also be used to detect Hg2+ on test paper strips.

Highlights

The exploitation of fluorescent chemosensors for the detection of transition-metal ions has received immense interest because contamination caused by heavy metal ions may have adverse influence on human health and the natural environment (Que et al, 2008; Zhang et al, 2011)
In 2001, it was discovered by Tang and coworkers that 1-methyl-1,2,3,4,5-pentaphenylsilole showed an interesting “aggregation-induced emission (AIE)” effect, and emitted strong aggregative-state fluorescence (Luo et al, 2001)
We reported a TPE-modified rhodanine derivative (Chart 1), and the compound exhibited aggregation-induced emission enhancement (AIEE) and mechanofluorochromic characteristics

Summary

INTRODUCTION

The exploitation of fluorescent chemosensors for the detection of transition-metal ions has received immense interest because contamination caused by heavy metal ions may have adverse influence on human health and the natural environment (Que et al, 2008; Zhang et al, 2011). In 2001, it was discovered by Tang and coworkers that 1-methyl-1,2,3,4,5-pentaphenylsilole showed an interesting “aggregation-induced emission (AIE)” effect, and emitted strong aggregative-state fluorescence (Luo et al, 2001). Molecules have received special attention from researchers due to their excellent aggregative-state emissive performance. The structurally twisted TPE molecules cannot pack in through a tight π-π stacking interactions network, and restrict the formation of ACQ effect. We reported a TPE-modified rhodanine derivative (Chart 1), and the compound exhibited AIEE and mechanofluorochromic characteristics. This fluorescent molecule could selectively and sensitively detect Hg2+ in an acetonitrile solution and on test paper strips. Organic layer was dried by anhydrous MgSO4, the organic solvent was removed under vacuum, the residues were purified by column chromatography on silica gel, affording

RESULTS AND DISCUSSION

CONCLUSION

DATA AVAILABILITY STATEMENT