Phthalimide Conjugation turns the Aie-active Tetraphenylethylene Unit Non-emissive: Its use in Turn-on Sensing of Hydrazine in Solution and the Solid- and Vapour-phase

Abstract

Hydrazine is a vital precursor used in several pharmaceuticals and pesticide industries and upon exposure can cause severe health hazards. Herein, a new AIEgen, tetraphenylethylene phthalimide (TPE-PMI), is synthesized in a one-step solvent-free mechanochemical approach exploiting the simple condensation between TPE-NH2 and phthalic anhydride and used for the selective and sensitive detection of hydrazine. TPE-PMI with an AIE-active TPE-moiety is non-emissive in the solid phase by design. Hydrazine performs the cleavage of TPE-PMI in a typical “Gabriel synthesis” pathway to release AIE-active TPE-NH2 in an aqueous solution to emit blue fluorescence. A gradual rise in fluorescence intensity at 462 nm was due to the increasing hydrazine concentration and TPE-PMI showed a linear relationship with hydrazine in the concentration range from 0.2 to 3 μM. The selectivity study confirmed that the probe is inert to amines, amino acids, metal anions, anions and even common oxidants and reductants. The detection limit is 6.4 ppb which is lower than the US Environmental Protection Agency standard (10 ppb). The practical utilities of TPE-PMI were successfully demonstrated through quantitative detection of hydrazine vapour on solid platforms like paper strips and TLC plates. Furthermore, on-site detection of hydrazine in the solid phase was demonstrated by spiking the soil samples with measured quantities of hydrazine and quantitation through image analysis. This cost-effective sensing tool was successfully utilized in in vitro detection of hydrazine in live HeLa cells.