Synthesis and ultraviolet/aggregation-induced emission investigation of novel tetraphenylvinyl hydrazone derivatives: efficient multimodal chemosensors for fluoride ion

Abstract

Herein, three novel tetraphenylethylene hydrazone chemosensors TC12, SC16, and TC16 are prepared for the selective detection of F⁻. Two NH and one C=N units are incorporated into the sensors for better colorimetric responses, whereas the tetraphenyl unit is in charge of the aggregation-induced emission effect. Among them, compounds SC16 and TC16 form stable gels with some organic solvents. All the tetrahydrofuran/H₂O solutions of the three compounds exhibit aggregation-induced emission effect, whereby the fluorescence emission increases by varying degrees with the volume of poor solvent water. Moreover, good aggregation-induced emission effects are observed in the self-assembly of SC16 and TC16. As a sample chemosensor, TC12 in tetrahydrofuran responds to F⁻ selectively with high sensitivity, with the colorimetric and fluorometric detection limits of 8.25 × 10⁻⁷ mol·L^–1 and 2.69 × 10⁻⁷ mol·L^–1, respectively. The reversible gel-sol-gel phase transition and color changes indicate that both SC16-dimethyl sulfoxide and TC16-ethyl acetate gels specifically respond to F^– with good sensitivity. The detection results are well supported by ultraviolet-visible spectroscopy, fluorescent spectroscopy, and ¹H nuclear magnetic resonance. More importantly, the driving forces of gelation are visually clarified through the single crystal X-ray analysis of compound TOMe.

Key words： organogelator; tetraphenylvinyldrazone; single crystal; aggregation-induced emission effect; ion sensing

Competing interests

The authors declare that they have no competing interests.

Acknowledgements

This work was financially supported by the National Key Research and Development Program of China (Grant No. 2018YFA0903700)

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-023-2366-0 and is accessible for authorized users.

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