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Near-infrared palladium ion fluorescent probe compound and synthesis method thereof

A near-infrared palladium ion fluorescent probe compound and its synthesis method technology, applied in the field of palladium ion detection and fluorescent probes, to achieve high sensitivity, high selectivity, and strong anti-interference effects

Pending Publication Date: 2021-11-23
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the biocompatibility of the probe needs to be further improved

Method used

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  • Near-infrared palladium ion fluorescent probe compound and synthesis method thereof
  • Near-infrared palladium ion fluorescent probe compound and synthesis method thereof
  • Near-infrared palladium ion fluorescent probe compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Preparation of Compound 3

[0040] Under nitrogen protection, acetic acid was added to the compound 1 nitro BODIPY (800 mg, 2.16 mmol) and Compound 2 pairs of triethylene glycol monomethyl ether (2.32 g, 8.64 mmol) toluene (80 mL) (2.4 ml) ), Piperidine (8 mL) and catalytic amount of magnesium oxcetic acid, heating reflux for 5 h, Dean-Stark device is divided into water. After the reaction is completed, the solvent was removed under reduced pressure, and the crude product was purified by Ethyl acetate, and the silica gel column chromatography was purified. 1 H NMR (CDCL 3 : Δ8.36 (D, J = 8.3Hz, 2H, ARH), 7.51-7.62 (M, 8H, ARH AND CH), 7.21 (D, J = 16.3Hz, 2H, CH), 6.94 (D, J = 8.5Hz, 4H, ARH, 6.61 (S, 2H, Pyrrole-H), 4.17 (T, J = 4.8 Hz, 4H, CH 2 ), 3.87 (t, j = 4.8 Hz, 4h, CH 2 ), 3.72-3.77 (m, 4h, ch 2 ), 3.64-3.71 (m, 8h, ch 2 ), 3.54-3.56 (m, 4h, ch 2 ), 3.38 (s, 6h, ch 3 ), 1.39 (S, 6H, CH 3 . 13 C { 1 H} NMR (CDCL 3 : δ159.8, 153.4, 148.3, 142.4, 140.9, 136...

Embodiment 2

[0041] Example 2: Preparation of Compound 4

[0042] Under nitrogen protection, the zinc powder (960 mg, 15 mmol) was slowly added to the compound 3 (200 mg, 0.23 mmol), and the mixture was stirred at room temperature for 20 min. After the reaction is completed, the water is added (10 mL), ethyl acetate extraction (50 ml × 3), combined with organic phase, saturated NaHCO 3 Solution wash, no water NASO 4 Dry, filtration, evaporation solvent, and crude products were purified by ethyl acetate, silica gel column chromatography, and n-hexane / ethyl acetate re-crystalline dense blue solid compound 4 (150 mg, 78%). HNMR (CDCL 3 : Δ7.55-7.62 (M, 6H, ARH AND CH), 7.19 (D, J = 16.3 Hz, 2H, CH), 7.05 (D, J = 8.94 (D, J), 6.94 (D, J = 8.7Hz, 4H, ARH), 6.79 (D, J = 8.4 Hz, 2H, ARH), 6.66 (S, 2H, Pyrrole-H), 4.18 (T, J = 4.9 Hz, 4H, CH 2 ), 3.89 (t, j = 4.9 Hz, 4h, CH 2 ), 3.85 (S, 2H, NH 2 ), 3.74-3.78 (m, 4h, ch 2 ), 3.65-3.78 (m, 8h, ch 2 ), 3.54-3.59 (m, 4h, ch 2 ), 3.39 (s, 6h, ch 3 ), 1....

Embodiment 3

[0043] Example 3: Preparation of Compound 6

[0044] Under nitrogen protection, an appropriate amount of activated molecular sieve was added to 1,2-dichloroethane solution (10 mL) of Compound 4 (150 mg, 0.536 mmol) and Compound 5 (85.2 mg, 0.536 mmol). Add a vivo acetic acid, stirred at room temperature for 1 h, add NABH 3 CN (67.7 mg, 1.074 mmol) was continued at room temperature. After the reaction was completed, a saturated sodium hydrogencarbonate solution (10 ml), dichloromethane (3 × 25 mL) was added to the system. The combined organic phase was washed with water, saturated salt water, dried over anhydrous sodium sulfate, filtered, and the crude product obtained after evaporation solvent was dichloromethane / methanol (V : V = 45: 1) was purified by purifying liquid silica gel column chromatography, recrystallization to give a blue-black solid compound 6 (72.1 mg, 41%). 1 H NMR (CDCL 3 : Δ7.54-7.63 (M, 6H, ARH AND CH), 7.18 (D, J = 16.2 Hz, 2H, CH), 7.05 (D, J = 8.5 Hz, 2H,...

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Abstract

The invention discloses a near-infrared palladium ion fluorescent probe compound, as shown in a formula I, and a synthesis method and application thereof. The probe compound has visible-near-infrared light region absorption, fluorescence and high biocompatibility, shows high-sensitivity and high-selectivity 600-800 nm near-infrared fluorescence response to palladium ions in a solution, has the detection limit of 0.85 ppb, is high in anti-interference performance, and has the potential to be applied to a complex biological system, in particular to detection and tracing of palladium ions in a living body.

Description

Technical field: [0001] The present invention relates to the field of palladium ion detection and fluorescence probe, and more particularly to a near-infrared palladium ion fluorescence probe compound and a synthesis method thereof. Background technique: [0002] Palladium (PD) is one of the important transition metal elements of Group VIII platinum, which can be used as a highly efficient catalyst of a variety of chemical reactions, is also indispensable in automotive fields, electronic products, aerospace, medical devices, fuel cells. Key material. The wide application of palladium constantly accumulates in the ecological environment, studies have shown that PD 2+ It can be coordinated with DNA, thiol-containing amino acid, protein, and vitamin B6, interfering with cell processes, also cause allergic reactions, such as stimulating eyes and skin, etc., constitute a serious threat to ecosystems and human health. At present, there are very little toxicity to palladium, and its mec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/6428C09K2211/1055C09K2211/1007
Inventor 赵昕陈晓非姚理巫培山周巧丽
Owner INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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