Designing novel benzofuran derived AIE-probes: dual-mode fluorescence turn-off and naked-eye color change for hydrazine detection

Abstract

Hydrazine, a compound known for its toxicity to human health and the environment, finds extensive use across various industries and potentially contributes to several diseases. Hence, the accurate measurement of hydrazine levels is paramount. This study introduces three new aggregation induced emissive luminogens (AIEgens) GBY-7, GBY-8, and GBY-9 crafted from benzofuran infused with a dicyanovinylidene group, tailored specifically for hydrazine monitoring. These probes feature a D–π–A core with a rotor, providing an optimal fluorescent base. Additionally, a potent electron-attracting nitrile group aids in the nucleophilic addition of N₂H₄ to form hydrazone, thereby blocking the intramolecular charge transfer (ICT) process and inducing optical signal modulation. Notably, luminogens GBY-8 and GBY-9 exhibit high selectivity in detecting hydrazine amidst competing amine-based compounds, showing detection limits of 0.00020 mM and 0.0043 mM, respectively.