An Ensemble-Based Fluorescent Probe for Real-Time and High Sensitive Detection of Hypochlorite

doi:10.6023/cjoc202310014

Abstract

A novel fluorescent probe TS1 for real-time monitoring of hypochlorite was reported. The introduction of Cu²⁺could lead to the formation of stable complex TS1-Cu and simultaneous remarkable fluorescence quenching. Next, “off-on” fluorescence changes of TS1-Cu were proceeded by the subsequent addition of hypochlorite, which induced the hydrolytic cleavage of the Schiff base in TS1 and the transformation to strongly fluorescent aldehyde. TS1-Cu could recognize hypochlorite through an instantaneous marked fluorescence enhancement with the detection limit as low as 120 nmol/L. Furthermore, the sensitive and rapid detection of hypochlorite with TS1-Cu for the practical application was also performed in commercial disinfectant samples.

Key words: fluorescent probe, real-time response, ensemble-based, hypochlorite, practical application

Cite this article

Xiaohong Cheng, Falong Liu, Jinbo Sun, Rui Zhang. An Ensemble-Based Fluorescent Probe for Real-Time and High Sensitive Detection of Hypochlorite[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1284-1292.

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Fig. & Tab. 7

Scheme 1. Schematic representations of the detection for hypochlorite based on the TS1-Cu

Figure 1. Fluorescent emission spectra of TS1 in the presence of different concentrations of Cu2+ The inset plot showed the intensity changes at 490 nm of compound TS1 with different concentrations of Cu2+ (excitation wavelength: 390 nm)

Figure 2. Fluorescent emission spectra of TS1-Cu2+ in the presence of different concentrations of ClO– The inset plot showed the fluorescence intensities at 595 nm of compound TS1 with different concentrations of ClO– (Excitation wavelength: 390 nm)

Limit of detection	Switching type	Response time	Reference
59 nmol/L	Ratiometric response	<30 s	[15]
0.17 μmol/L	Off-on	2 min	[16]
0.2 μmol/L	Ratiometric response	10 min	[17]
96 nmol/L	Ratiometric response	With 60 s	[18]
0.356 μmol/L	Off-on	5 min	[19]
8.2 nmol/L	Off-on	20 min	[20]
9.6 nmol/L	Off-on	1 min	[21]
787 nmol/L	Ratiometric response	Within 100 s	[22]
28.8 nmol/L	Off-on	Within 30 s	[23]
120 nmol/L	Off-on	Within seconds	This work

Table 1. Brief detail about the reported fluorescence sensors based on the oxidation reaction of hypochlorite

Figure 3. Emission intensity changes of TS1-Cu to ClO– (25 μmol/L) in the presence of other competitive species (100 μmol/L) The error bars represent the standard deviation of three measurements

Figure 4. Calculated HOMOs and LUMOs of compounds TS1 (left) and TS1+Cu2+ (right)

Figure 5. Proposed plausible mechanisms for detection of ClO– by TS1-Cu and the 1H NMR spectra of the reaction product between TS1 and ClO–

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