Myricetin-based fluorescence probes with AIE and ESIPT properties for detection of hydrazine in the environment and fingerprinting

Abstract

Background: Hydrazine (N₂H₄) is a highly toxic and versatile chemical raw material, which poses a serious threat to the environment and human health when used in large quantities. However, the traditional methods for the detection of N₂H₄ have the disadvantages of time-consuming, complicated operation and expensive instruments. In contrast, fluorescence probes have many advantages, such as simple operation, high sensitivity, good selectivity, and fast response time. Therefore, there is an urgent need for a fluorescence probe that can rapidly and accurately detect the presence of N₂H₄ and monitor the changes in its concentration.

Results: For this purpose, we designed and synthesized a series of myricetin fluorescence probes 3-(substituent group)-5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxy. phenyl)-4H-chromen-4-one (Myr-R) for N₂H₄ detection. In the presence of N₂H₄, the probe 5,7-dimethoxy-3-(2,3,4,5,6-pentafluorobenzoate)-2-(3,4,5-trimethoxyphen-yl). -4H-chr-omen-4-one (Myr-3) shows significant fluorescence changes, double emission properties and a large Stokes shift (183 nm), and exhibits high selectivity and sensitivity to N₂H₄ (The detection limit is 93 nM). Importantly, the qualitative and quantitative analysis of N₂H₄ in water, soil, and air can be accomplished using fluorescence, smartphone, and UV lamps coupled with Myr-3. In addition, Myr-3 can be used for monitoring and imaging intracellular N₂H₄. Meanwhile, the fluorophore 3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-benzopyran-4-one (Myr-Me) was applied to fingerprinting of different substrate materials due to the fact that it exhibits strong yellow fluorescence emission in the solid state and shows excellent contrast and high resolution.

Significance: The probe Myr-3 is not only able to rapidly detect N₂H₄ in complex environments, but also can be used for imaging intracellular N₂H₄. In addition, the fluorophore Myr-Me can be used as an effective imaging agent for visual fingerprinting. These properties enable the probe Myr-3 and the fluorophore Myr-Me for a wide range of potential applications in related fields.

Keywords: Fingerprint imaging; Fluorescence probes; Hydrazine; Myricetin.