Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu2+ and Glyphosate

doi:10.6023/cjoc202109049

Abstract

A novel fluorescent probe L based on coumarin-derived acylhydrazone was designed and synthesized by using 7-(4-methoxyphenyl)ethynyl coumarin as report group. The probe L showed high selectivity and good anti-interference ability towards Cu²⁺ ion through the color of solution changed from light brown to yellow for naked-eye detection and significant fluorescence intensity quenched in the dimethyl sulfoxide (DMSO)/H₂O [V:V=7:3, 2-[4-(2-hydroxyethyl)piperazin-1- yl]ethanesulfonic acid (HEPES) 10 mmol/L, pH=7.4] solution, and the detection limit of probe L to Cu²⁺ could reach 5.6×10^–8 mol/L. Meanwhile, the L-Cu²⁺ system has high selectivity, good sensitivity, wide pH range (5~9) and low detection limit (11.3 ng/mL) for the detection of glyphosate by ligand replacement method. In addition, glyphosate detection was assessed within the actual water samples for testing the L-Cu²⁺actual application and the method was expected to the detection in environmental samples.

Key words: coumarin-derived acylhydrazone, fluorescent probe, sequential recognition, glyphosate

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Mianyuan Wu, Yanchao Yu, Yang Liu, Jun You, Wenju Wu, Bo Liu. Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu²⁺ and Glyphosate[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 803-811.

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Fig. & Tab. 13

Scheme 1. Synthetic route of probe L

Figure 1. Fluorescence intensity (a) and UV-Vis absorption spectra (b) of probe L (10 μmol/L) in the presence of different metal ions (50 μmol/L) (λex=435 nm) Inset: visual color changes observed in solution of probe L (left) and L+Cu2+ (right) after addition of Cu2+ ion

Figure 2. (a) Fluorescence spectra of probe L (10 μmol/L) upon addition of different concentrations of Cu2+ (0~20 μmol/L) and (b) linear relationship between the fluorescence intensity at 550 nm and the concentration of Cu2+ (0~15 μmol/L) Inset: fluorescence intensity at 550 nm of probe L (10 μmol/L) upon addition of different concentrations of Cu2+ (0~20 μmol/L)

Figure 3. Anti-interference ability of probe L (10 μmol/L) recognition for Cu2+ (50 μmol/L) in the presence of various metal ions (a) or anions (b) (50 μmol/L)

Figure 4. Job’s plot of probe L with Cu2+

Figure 5. Fluorescence intensity (a) and UV-Vis absorption spectra (b) of L-Cu2+ in the presence of different organophosphorus pesticides (50 μmol/L) Inset: visual color changes observed in solution of L-Cu2+ (left) and L-Cu2++Glyphosate (right) after addition of Glyphosate

Figure 6. (a) Fluorescence spectra of L-Cu2+ upon addition of different concentrations of Glyphosate (0~20 μmol/L) and (b) linear relationship between the fluorescence intensity at 550 nm and the concentration of Glyphosate (0~16 μmol/L) Inset: fluorescence intensity at 550 nm of L-Cu2+ upon addition of different concentrations of Glyphosate (0~20 μmol/L)

Figure 7. Anti-interference ability of L-Cu2+ recognition for Glyphosate (50 μmol/L) in the presence of various OPs (a) or anions (b) (50 μmol/L)

Figure 8. Job’s plot of L-Cu2+ with Glyphosate

Scheme 2. Proposed sequential recognition mechanism of probe L with Cu2+ and Glyphosate

Figure 9. Fluorescence intensity change of probe L, probe L+Cu2+ and L-Cu2++Glyphosate in different pH

Figure 10. Fluorescence spectra of probe L without or with the addition of Cu2+ and/or Glyphosate (A) and the truth table and scheme for the INHIBIT logic gate (B)

Sample	Added/(μg•mL^–1)	Found/(μg•mL^–1)	Recovery rate/%	RSD/% (n=3)
Tap water	—	—	—	0.49
	0.25	0.253	101.2	2.26
	0.5	0.492	98.4	2.51
	1.0	0.978	97.8	1.84
	2.0	2.072	103.6	2.30
Songhua River water	—	—	—	1.62
	0.25	0.242	96.8	2.11
	0.5	0.494	98.8	2.98
	1.0	1.025	102.5	1.34
	2.0	1.982	99.1	1.87

Table 1. Detection results of Glyphosate in actual water samples

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一种连续识别Cu²⁺和草甘膦荧光探针的合成及应用研究

Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu²⁺ and Glyphosate

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一种连续识别Cu2+和草甘膦荧光探针的合成及应用研究