Coumarin-based palladium ion fluorescent probe compound and preparation method thereof

A technology for fluorescent probes and compounds, applied in the field of coumarin-based palladium ion fluorescent probe compounds and their synthesis, can solve many problems, and achieve the effects of simple post-processing, high sensitivity, and efficient synthesis methods

Active Publication Date: 2021-06-08
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, a number of palladium ion fluorescent probes based on rhodamine B, fluorescein, cyanine dyes, perylene diimide (PDI) and other different fluorophores have been reported in the literature. not many needles

Method used

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  • Coumarin-based palladium ion fluorescent probe compound and preparation method thereof
  • Coumarin-based palladium ion fluorescent probe compound and preparation method thereof
  • Coumarin-based palladium ion fluorescent probe compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of compound 3

[0036] To a solution of 4-(diethylamino)salicylaldehyde (0.193 g, 1 mmol) in ethanol (5 mL) was added diethyl malonate (0.52 mL, 3.4 mmol). Add 50 μL and two drops of glacial acetic acid in 4 mL ethanol to the reaction. The reaction was stirred at 80° C. for 24 h, water (30 mL) was added to the system, and extracted with ethyl acetate (3×20 mL). The combined organic phases were washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. After the solvent was spin-dried, the obtained crude product was subjected to silica gel chromatography with petroleum ether / ethyl acetate as the eluent to obtain compound 3 as a yellow solid (0.323 g, 78%).

[0037] 1H NMR (400MHz, DMSO-d6) δ8.55(s, 1H), 7.63(d, J=9.0Hz, 1H), 6.77(dd, J=9.0, 2.4Hz, 1H), 6.53(d, J= 2.4Hz, 1H), 4.23(q, J=7.1Hz, 2H), 3.48(q, J=7.0Hz, 4H), 1.28(t, J=7.1Hz, 3H), 1.14(t, J=7.0Hz ,6H).13C NMR(101MHz,DMSO)δ163.85,158.51,157.50,15...

Embodiment 2

[0038] Embodiment 2: the preparation of compound 5

[0039] Compound 3 (0.29 g, 1 mmol) obtained in Example 1 was dissolved in 15 mL of methanol, hydrazine hydrate (240 μL, 4 mmol, 80%) was added to the system and stirred at room temperature for 12 min, the system was frozen in a refrigerator, and suction filtered to obtain yellow solid. The crude product was dried under vacuum for 12h to obtain compound 5 (0.22g, 80%).

[0040]1H NMR (400MHz, Chloroform-d) δ9.72(t, J=4.3Hz, 1H), 8.68(s, 1H), 7.43(d, J=8.9Hz, 1H), 7.27(s, 0H), 6.65 (dd, J=8.9,2.5Hz,1H),6.49(d,J=2.4Hz,1H),4.13(d,J=4.3Hz,2H),3.46(q,J=7.1Hz,4H),1.24 (t,J=7.1Hz,7H).13C NMR(101MHz,CDCl3)δ163.90,162.13,157.65,152.69,148.05,131.16,110.01,109.12,108.25,96.62,77.35,77.03,76.72,45.122,12.

Embodiment 3

[0041] Embodiment 3: the preparation of palladium ion fluorescent probe compound CCB

[0042] Under nitrogen protection, compound 5 (55 mg, 0.2 mmol) obtained in Example 2 was dissolved in 20 mL of methanol, 4-chloro-2-pyridinecarbaldehyde (28 mg, 0.2 mmol) was added, and heated to reflux for 12 h. The system was frozen in the refrigerator, and a yellow solid was obtained by suction filtration. The crude product was dried under vacuum for 12 hours to obtain the palladium ion fluorescent probe compound CCB (64mg, 80%). product of 1 H NMR spectrum and 13 The C NMR spectra are as follows figure 1 and as shown in Fig.

[0043] 1H NMR (400MHz, Chloroform-d) δ12.10(s,1H),8.84(s,1H),8.50(d,J=5.4Hz,1H),8.26(d,J=2.9Hz,2H),7.48 (d,J=8.9Hz,1H),7.28(dd,J=5.3,1.9Hz,1H),6.69(dd,J=9.0,2.5Hz,1H),6.52(d,J=2.5Hz,1H) ,3.48(q,J=7.1Hz,4H),1.26(t,J=7.1Hz,6H).13C NMR(101MHz,Chloroform-d)δ162.74,160.24,157.95,154.78,153.17,150.19,149.48,147.16, 144.65, 131.55, 124.38, 121.26, 110.39, 108.58, 1...

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Abstract

The invention discloses a coumarin-based palladium ion fluorescent probe compound and a preparation method thereof, and belongs to the technical field of organic small molecule fluorescent probes. The palladium ion fluorescent probe compound has a structural formula shown in the specification. The preparation method comprises the following steps of: adding diethyl malonate, glacial acetic acid and piperidine into an ethanol solution of a compound 1, namely 4-(diethylamino)-salicylaldehyde, purifying, adding hydrazine hydrate, heating and the like. The prepared palladium ion probe is in a fluorescence enhancement mode and is high in sensitivity, and the detection limit is as low as 4.45*10<-8>. The probe shows high selectivity to palladium ions and strong anti-interference performance.

Description

Technical field: [0001] The invention belongs to the technical field of organic small molecule fluorescent probes, in particular to a coumarin-based palladium ion fluorescent probe compound and a synthesis method thereof. Background technique: [0002] In modern industrial synthesis methods, heavy metals are widely used in the preparation of compounds and polymer materials in different fields, among which palladium (Pd) is the most widely used metal-supported catalyst, and its application is particularly common. In addition, palladium is also an indispensable key material in industries such as electronics, jewelry, aerospace, medical devices, and fuel cells. Palladium discharged from industrial production pollutes soil and water resources, posing a serious threat to ecosystems and human health. Therefore, it is necessary to develop effective methods to detect palladium in industrial, pharmaceutical and environmental samples. [0003] In addition to the instrumental detecti...

Claims

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Application Information

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IPC IPC(8): C07D405/12C09K11/06G01N21/64
CPCC07D405/12C09K11/06G01N21/6428C09K2211/1029C09K2211/1088G01N2021/6432Y02E60/50
Inventor 宋志光任爱民于玮玮冯国栋
Owner JILIN UNIV
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