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.

Graphical abstract

Keywords

organogelator / tetraphenylvinyldrazone / single crystal / aggregation-induced emission effect / ion sensing

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