New simple molecular fluorescent probes for rapid and highly selective sensing of hydrazine by aggregate-induced emission

• Published in: Analyst (London) 2020-07, Vol.145 (13), p.4615-4626
• Main Authors: Pavankumar, B. B, Ranjan, Prabodh, Jha, Prakash C, Sivaramakrishna, Akella
• Format: Article
• Language: English
• Subjects: Acetates - chemistry; Acetates - radiation effects; Acetates - toxicity; Acetyl chloride; Aldehydes; Aliphatic compounds; Amines; Amino acids; Buffer solutions; Density Functional Theory; Drinking Water - analysis; Environmental protection; Ethanol; Fluorescent Dyes - chemistry; Fluorescent Dyes - radiation effects; Fluorescent Dyes - toxicity; Fluorescent indicators; Humans; Hydrazines; Hydrazines - analysis; Hydrazines - chemistry; Hydrogen-Ion Concentration; Limit of Detection; MCF-7 Cells; Microscopy, Fluorescence; Models, Chemical; Rivers - chemistry; Sodium acetate; Spectrometry, Fluorescence; Substitutes; Ultraviolet Rays; Water Pollutants, Chemical - analysis; Water Pollutants, Chemical - chemistry; Water sampling
• ISSN: 0003-2654; 1364-5528
• DOI: 10.1039/d0an00601g

With an aim towards the design of efficient and straightforward fluorescent probes for hydrazine, the synthesis of (2-acetoxyaryl) methylene diacetate derivatives ( 1-4 ) was carried out by reacting substituted aromatic α-hydroxy aldehydes with acetyl chloride and sodium acetate in excellent yields. As a preliminary investigation, the ability of probe 1 was examined for the detection of substituted aliphatic and aromatic amines, amino acids, and other ions in Britton-Robinson buffer solution (50 mM, water/ethanol v/v of 99/1 at pH 7.4). Probe 1 selectively exhibited an intense blue fluorescence with hydrazine in less than 2 minutes, whereas light green or no fluorescence was noticed with substituted amines and amino acids. Among all the probes employed ( 1-4 ) in the present study, probes 1 and 2 were found efficient towards the rapid detection of hydrazine. Furthermore, the fluorescence sensing ability of probes 1 and 2 was tested not only under varying pH conditions but also by varying water-fraction from 0-99%. Moreover, the detection limits of hydrazine using 1 and 2 were found as 8.4 and 8.7 ppb, respectively, which is less than the acceptable limit as per the standards of the US Environment Protection Agency. In this contribution, the probes 1 and 2 demonstrate rapid, selective, sensitive, and ratiometric detection of highly toxic hydrazine by OFF-ON fluorescence switch in water samples as well as living cells. A rapid, selective, and sensitive method is developed and employed in the detection of hydrazine in water and living cells.