一种基于喹啉酰腙的接力识别Cu2+和草甘膦的荧光探针及其应用

doi:10.6023/cjoc202203009

摘要/Abstract

以喹啉-2-甲酸和7-(二乙氨基)香豆素-3-甲醛为原料, 设计合成了一种喹啉酰腙类荧光探针L, 并利用紫外/荧光分光光度法考察其光谱性能. 研究结果表明, 在四氢呋喃(THF)/H₂O [V:V=3:7, 4-羟乙基哌嗪乙磺酸(HEPES) 10 mmol/L, pH=7.4]溶液中, 探针L对Cu²⁺表现出显著的荧光猝灭效应, 响应速度快, 特异性强, 灵敏度高, 并且它们之间的结合比为1:1. 同时, 配合物L-Cu²⁺对草甘膦表现出显著的荧光增强效应, 且不受其它有机磷农药、金属离子和阴离子的干扰, 其检测限可达5.6×10^–8 mol/L(即9.5×10^–3 mg/L). 此外, 配合物L-Cu²⁺能够“裸眼”检测草甘膦, 并在实际水样中实现了草甘膦的定量检测.

关键词: 喹啉酰腙, 荧光探针, Cu2+, 草甘膦, 接力识别

A novel quinoline hydrazone-based fluorescent probe L was designed and synthesized using quinoline-2-carboxylic acid and 7-(diethylamino)coumarin-3-carbaldehyde as raw materials. The spectral properties of probe L were studied by UV-Vis/fluorescence spectrophotometry. The results showed that probe L had obvious ON-OFF fluorescence response to Cu²⁺ in the tetrahydrofuran (THF)/H₂O [V:V=3:7, 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid (HEPES) 10 mmol/ L, pH=7.4] solution, and it displayed efficiency, high specificity and sensitivity. Job’s plot and high resolution mass spectrometry showed that the stoichiometry of L-Cu²⁺ complex was estimated to be 1:1. Meanwhile, complex L-Cu²⁺ showed high selectivity and good anti-interference ability towards glyphosate through the significant fluorescence enhancement, and the detection limit of complex L-Cu²⁺ to glyphosate could reach 5.6×10^–8 mol/L (9.5×10^–3 mg/L). In addition, complex L- Cu²⁺ was able to sense glyphosate by “naked-eye” according to the color change, and applied to glyphosate detection in the actual water samples.

Key words: quinoline hydrazone, fluorescent probe, Cu2+, glyphosate, sequential recognition

引用此文

吴绵园, 由君, 喻艳超, 武文菊. 一种基于喹啉酰腙的接力识别Cu²⁺和草甘膦的荧光探针及其应用[J]. 有机化学, 2022, 42(8): 2559-2567.

Mianyuan Wu, Jun You, Yanchao Yu, Wenju Wu. A Novle Quinoline Hydrazone-Based Fluorescent Probe for Sequential Determination of Cu²⁺/Glyphosate and Its Applications[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2559-2567.

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图/表 12

图式1. 探针L的合成路线

Scheme 1. Synthetic route of probe L

图1. 探针L (10 μmol/L)与不同离子(10 μmol/L)作用后的荧光光谱(a)和紫外-可见吸收光谱(b) (λex=450 nm)

Figure 1. Fluorescence emission spectra (a) and UV-Vis absorption spectra (b) of probe L (10 μmol/L) interacted with different ions (10 μmol/L) (λex=450 nm) The fluorescence changes of probe L (100 μmol/L) without and with Cu2+(100 μmol/L) under a portable UV lamp 365 nm

图2. 在各种离子(10 μmol/L)存在下, Cu2+ (10 μmol/L)加入前后, 探针L (10 μmol/L)在530 nm处的荧光强度(λex=450 nm)

Figure 2. Fluorescence intensity of probe L (10 μmol/L) without and with Cu2+ (10 μmol/L) in the presence of various ions (10 μmol/L) at 530 nm 1: Cu2+, 2: Co2+, 3: Zn2+, 4: Ca2+, 5: Cr3+, 6: K+, 7: Ni2+, 8: Al3+, 9: Fe3+, 10: Mg2+, 11: Pb2+, 12: Na+, 13: Sr3+, 14: Ce3+, 15: Ag+, 16: Li+, 17: Cd2+, 18: Hg2+, 19: $\text{SO}_{4}^{2}$, 20: F–, 21: SCN–, 22: Br–, 23: ${{\text{S}}_{2}}\text{O}_{3}^{2}$, 24: ${{\text{H}}_{2}}\text{PO}_{4}^{}$, 25: $\text{HPO}_{4}^{2}$, 26: $\text{NO}_{2}^{}$, 27: I–, 28: $\text{HCO}_{3}^{}$, 29: $\text{CO}_{3}^{2}$, 30: Cl–, 31: CH3COO–

图3. 探针L (10 μmol/L) (a)对不同浓度Cu2+ (0~12 μmol/L)响应的荧光光谱和(b)在530 nm处荧光强度与Cu2+ (0~7 μmol/ L)浓度的线性关系(λex=450 nm)

Figure 3. (a) Fluorescence spectra of probe L (10 μmol/L) toward varying concentrations of Cu2+ (0~12 μmol/L) and (b) linear relationship between the concentration of Cu2+ (0~8 μmol/ L) and the fluorescence intensity at 530 nm of probe L (10 μmol/L) The photo shows the color change of probe L (10 μmol/L) with the addition of Cu2+ (0~12 μmol/L) under natural light; Dot diagram of the fluorescence responses of probe L (10 μmol/L) toward varying concentrations of Cu2+ (0~12 μmol/L) at 530 nm

图4. 探针L与Cu2+的Job’s plot图([L]+[Cu2+]=10 μmol/L)

Figure 4. Job's plot of probe L and Cu2+ ([L]+[Cu2+]=10 μmol/L)

图5. 配合物L-Cu2+ (10 μmol/L)与不同有机磷农药、金属离子和阴离子(10 μmol/L)作用后的荧光光谱(a)和紫外-可见吸收光谱(b) (λex=450 nm)

Figure 5. Fluorescence emission spectra (a) and UV-Vis absorption spectra (b) of complex L-Cu2+ (10 μmol/L) interacted with organophosphorus pesticides, metal ions or anions (10 μmol/L) (λex=450 nm) The fluorescence changes of probe L (100 μmol/L), complex L-Cu2+ (100 μmol/L) and complex L-Cu2+ (100 μmol/L) with GLY (100 μmol/L) under a portable UV lamp 365 nm

图6. 在其它有机磷农药、金属离子和阴离子(10 μmol/L)存在下, 草甘膦(10 μmol/L)加入前后, 配合物L-Cu2+ (10 μmol/L)在530 nm处的荧光强度(λex=450 nm)

Figure 6. Fluorescence intensity of complex L-Cu2+(10 μmol/L) without and with GLY (10 μmol/L) in the presence of various Ops, metal ions or anions (10 μmol/L) at 530 nm 1: GLY, 2: Trichlorfon, 3: Phosmet, 4: Dichlorvos, 5: Malathion, 6: Omethoate, 7: Dimethoate, 8: Ethoprophos, 9: Fenitrothion, 10: Parathion methyl, 11: Parathion, 12: Glufosinate, 13: $\text{SO}_{4}^{2}$, 14: F–, 15: SCN–, 16: Br–, 17: ${{\text{S}}_{2}}\text{O}_{3}^{2}$, 18: $\text{HPO}_{4}^{2}$, 19: ${{\text{H}}_{2}}\text{PO}_{4}^{}$, 20: $\text{NO}_{2}^{}$, 21: I–, 22: $\text{HCO}_{3}^{}$, 23: $\text{CO}_{3}^{2}$, 24: Cl–, 25: CH3COO–, 26: Co2+, 27: Zn2+, 28: Ca2+, 29: Cr3+, 30: K+, 31: Ni2+, 32: Al3+, 33: Fe3+, 34: Mg2+, 35: Pb2+, 36: Na+, 37: Sr3+, 38: Ce3+, 39: Ag+, 40: Li+, 41: Cd2+, 42: Hg2+

图7. 配合物L-Cu2+ (10 μmol/L) (a)对不同浓度GLY (0~18 μmol/L)响应的荧光光谱和(b)配合物L-Cu2+ (10 μmol/L)在530 nm处荧光强度与GLY (2~12 μmol/L)浓度的线性关系 (λex=450 nm)

Figure 7. (a) Fluorescence spectra of complex L-Cu2+ (10 μmol/L) toward varying concentrations of GLY (0~18 μmol/L) and (b) linear relationship between the concentration of GLY (2~12 μmol/L) and the fluorescence intensity at 530 nm (λex=450 nm) of complex L-Cu2+ (10 μmol/L) The photo shows the color change of complex L-Cu2+ (10 μmol/L) with the addition of GLY (0~15 μmol/L) under natural light; Dot diagram of the fluorescence responses of complex L-Cu2+ (10 μmol/L) toward varying concentrations of GLY (0~18 μmol/L) at 530 nm

图8. 配合物L-Cu2+与草甘膦的Job’s plot图([L-Cu2+]+[GLY]=10 μmol/L)

Figure 8. Job's plot of complex L-Cu2+and GLY ([L-Cu2+]+[GLY]=10 μmol/L)

图式2. 探针L接力识别Cu2+和草甘膦可能的作用机理

Scheme 2. Possible sequential recognition mechanism of probe L with Cu2+ and glyphosate

图9. 不同pH环境下探针L (10 μmol/L)对Cu2+ (10 μmol/L)和草甘膦(10 μmol/L)的荧光响应(λex=450 nm)

Figure 9. Fluorescence response of probe L (10 μmol/L) to Cu2+ (10 μmol/L) and GLY (10 μmol/L) at various pH

Sample	Add/(μmol•L^–1)	Found/(μmol•L^–1)	Recovery/%	RSD/% (n=3)
City water	3.00	2.72	90.67	0.92
	5.00	5.79	115.80	2.14
	7.00	7.27	103.86	2.31
	9.00	9.46	105.11	6.37
	11.00	11.14	101.27	2.42
Songhua River water	3.00	3.70	123.23	0.16
	5.00	5.16	103.20	1.06
	7.00	7.09	101.29	2.82
	9.00	9.43	104.78	0.78
	11.00	11.15	101.36	1.70

表1. 实际水样中草甘膦的测定

Table 1. Determination of GLY in actual water samples

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一种基于喹啉酰腙的接力识别Cu²⁺和草甘膦的荧光探针及其应用

A Novle Quinoline Hydrazone-Based Fluorescent Probe for Sequential Determination of Cu²⁺/Glyphosate and Its Applications

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