Reaction-based fluorescent probe for the selective and sensitive detection of thiophenols with a large Stokes shift and its application in water samples

Abstract

Although widely used in organic synthesis, pharmaceuticals and agrochemicals, thiophenol has brought about a series of ecological problems due to its high toxicity. Therefore, the development of efficient methods to discriminate thiophenols from aliphatic thiols is of great importance. In this work, a new reaction-based turn-on red fluorescence probe for the detection of thiophenols has been developed for the first time by employing dicyanomethylene-4H-pyran (DCM) as a fluorescence reporter and 2,4-dinitrobenzene-sulfonate (DNBS) as a recognition unit. The probe displayed a highly selective and sensitive (63 fold-fluorescence enhancement) response to thiophenols over aliphatic thiols. Additionally, the probe also exhibited a large Stokes shift (159 nm) and the detection limit reached as low as 8.3 nM. Moreover, this probe was also proved suitable for the quantification of thiophenol in real environmental water samples.

A fluorescent probe for the dual detection of mercury ions and thiols based on a simple coumarin derivative

“…However, the fluorescence emission spectra of the E1 probe changed in accordance with the nature of each amino acid which was added: Cys, Phe, Asn, Val, His, Glu and Gly all led to a decrease in intensity of the fluorescence emission band at 466 nm. The Changes in the fluorescence emission spectra of probe E1 (20 µmol/L) upon the addition of different amounts of Cys (0, 2,4,6,8,10,12,14,16,18,20 and 40 µmol/L) were measured ( Figure 8). The strongly fluorescent E1 probe gradually turned weakly fluorescent as increasing amounts of Cys were added to E1.…”

“…8,9 Therefore, a vast number of fluorescent probes for the detection of thiophenols have been developed. [10][11][12][13][14][15][16] On the other hand, pollution by mercury ions (Hg(ii)) triggers severe environmental and human health problems. Therefore, rapid and sensitive detection of Hg(ii) is of major significance.…”

“…However, thiophenols are a highly toxic and pollutant species . Therefore, a vast number of fluorescent probes for the detection of thiophenols have been developed . On the other hand, pollution by mercury ions (Hg( ii )) triggers severe environmental and human health problems.…”

Recent Progress in the Development of Fluorescent Probes for Thiophenol

“…Probe 22 was also shown to be very sensitive for PhSH, as the LOD was determined to be 10.3 nM. Based on the similar designing strategy, several other fluorescent probes ( 23 [85], 24 [86], 25 [79], and 26 [87]) bearing a piperazine linker were also built for the detection of PhSH (Figure 10). Notably, probe 26 , which was developed by He and Chen et al, consisted of two types of fluorophores (naphthalimide and dansyl) linked by the piperazine group.…”

Thiophenol detection using an AIE fluorescent probe through self-assembly with TPE-based glycoclusters

“…19 A dicyanomethylene-4H-pyran (DCM) based probe with a large Stokes shift (159 nm) and low detection limit (8.3 nM) was also constructed. 24 However, most fluorescent probes exhibited low reactivity and fluorescence intensity due to their poor watersolubility and the notorious ACQ (aggregation-induced quenching) effect.…”