A novel barbituric-based fluorescent probe with aggregation induced emission for the highly sensitive ratiometric detect
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A novel barbituric-based fluorescent probe with aggregation induced emission for the highly sensitive ratiometric detection of cyanide anions Denghui Li1, Jie Ma1,* 1
, Huiling Wang1, Lian Liu1, and Honggao Yang1
School of Science, University of Shanghai for Science and Technology, Shanghai 200093, People’s Republic of China
Received: 6 August 2020
ABSTRACT
Accepted: 19 September 2020
A new tetraphenylethylene-based barbituric acid derivative (TPEB) with an aggregation induced emission effect is synthesized as a fluorescent probe for CN-. The fluorescence spectra of TPEB in a DMSO–H2O mixture changed with different water fractions (fw). Nano-aggregates of TPEB are formed with the strongest fluorescence emission when fw beyond 60%. TPEB displays high selectivity and anti-interference toward CN- in DMSO–H2O (fw 70%) system at pH around 6, even in the presence of other competitive anions (AcO-, F-, Cl-, Br-, I-, NO3-, SO42-, ClO4-, PO43-, SCN-, HS-, S2- and H2O2). The linear curve is excellently matched between the fluorescence intensity and CN- concentration at 500 nm. By the equation 3r/S, the limit of detection of TPEB for CN- reaches 0.767 9 10–6 mol L-1. The probe TPEB operates via intramolecular charge transfer mechanism, attributed to the unique nucleophilic addition reactions between TPEB and CN-, which is further confirmed by LC–MS spectra, Job’s plot and DFT calculations. By colorimetry and fluorescence approach, CN- ions can be easily detected by the TPEB testing strip. The probe can be used to distinguish the acidity and basicity of the solution qualitatively.
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Springer Science+Business
Media, LLC, part of Springer Nature 2020
Handling Editor: Annela M. Seddon.
Address correspondence to E-mail: [email protected]; [email protected]
https://doi.org/10.1007/s10853-020-05377-w
J Mater Sci
GRAPHIC ABSTRACT
Introduction Anions are widely existed in nature and living organisms, playing important roles in many areas such as biological, medicinal, environmental chemistry and catalysis. The identification and detection of anions have attracted a lot of attention [1–3]. Cyanide and cyanide-containing substances are chronically applied into a wet smelting of gold and silver, electroplating technology, synthetic fiber, herbicides and so on [4–8]. On the other hand, the cyanide anions attract a great deal of attention, because it is incredibly harmful and venomous to the human body, including the nervous system [9], endocrine, cardiovascular, visual and metabolic systems [10]. Besides, even very small amounts of cyanide anions can cause death [9, 11]. According to the World Health Organization (WHO), the maximum allowable safe concentration level of drinking water is 1.9 9 10–6 mol L-1 [12]. Therefore, developing simple, reliable and efficient methods for highly selective, ultrasensitive and ultrafast detection of cyanide anion is quite of great significance in environmental. Over the past decades, many methods have been exploited for the detection of CN-, such as electrochemical probes [13, 14],
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