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A fluorescent probe for highly selective detection of mercury ions and its synthesis method and application

A synthesis method and technology of fluorescent molecular probes, which are applied in the application field of fluorescent probes for highly selective detection of mercury ions and detection of mercury ions, achieving high sensitivity, strong recognition ability, and stable optical properties

Active Publication Date: 2022-03-25
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Considering the similarities and differences of nitrile and alkyne bonds, and the different reaction products produced under the catalysis of mercury ions, it can be used as a mercury ion fluorescent probe molecule, which has not been reported so far.

Method used

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  • A fluorescent probe for highly selective detection of mercury ions and its synthesis method and application
  • A fluorescent probe for highly selective detection of mercury ions and its synthesis method and application
  • A fluorescent probe for highly selective detection of mercury ions and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of the dipeptide-mimetic compound 1

[0032] In a 250mL round-bottom flask, add L-valine benzyl ester hydrochloride (1.3g, 6mmol), 40mL tetrahydrofuran, triethylamine (2.6mL), stir at room temperature for 0.5h, and then add 6-amino-2- Naphthoic acid (1.3 g, 6 mmol), 1-hydroxybenzotriazole (HOBt, 0.9 g), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.5 g). The reaction was stirred for 24 hours. After the reaction, the organic phase was obtained by washing, drying, and extraction. The crude product was purified by column chromatography to obtain 1.9 g of compound 1 as a pink solid with a yield of 83%. The reaction formula is as follows:

[0033]

[0034] m.p.=131.1–131.6℃, =+51.13(c 0.20, in CHCl 3 ); 1H NMR(400MHz, CDCl3)δ8.18-8.17(d,J=1.2Hz,1H),7.75-7.74(t,2H),7.62-7.61(d,J=8.6Hz,1H),7.39-7.26( q,4H),7.00-6.98(d,2H),5.27-5.17(dd,J=27.1,12.2Hz,2H),4.91-4.88(dd,J=8.7,4.7Hz,2H),4.01(s, 2H), 2.36-2.28 (qd, J=11.7, 6.8Hz, 2...

Embodiment 2

[0035] Example 2: Synthesis of pseudo-dipeptide carboxamide compound 2

[0036] To a 100 mL round-bottomed flask, formic acid (14.12 mL, 10.2 mmol) was added, and compound 1 (1.8 g, 4.79 mmol) was weighed under stirring at room temperature and reacted for about 48 h. When the TLC tracking reaction showed that the reaction of the raw materials was complete, 20 mL of water was added to quench the reaction, extracted with ethyl acetate, and the layers were separated. 1.6 g, 82% yield. The reaction formula is as follows:

[0037]

[0038] m.p.=147.5–148.1℃, =+49.91(c 0.20, in CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ10.53(s,1H),8.77-8.75(d,J=7.7Hz,1H),8.43-8.37(q,J=14.3,12.7Hz,2H),8.01-7.99(d,J=8.9Hz ,1H),7.66(s,1H)7.41-7.32(m,4H),5.22-5.13(q,J=12.5Hz,2H),4.40-4.36(t,J=7.6Hz,1H).4.04-4.02 (d,1H),1.02-0.95(q,4H). 13 C NMR (100MHz, CDCl 3 )δ172.2,159.1,135.5,131.2,130.1,128.7,128.6,128.5,128.3,127.4,125.0,124.4,120.4,119.4,116.6,114.4,67.3,57.6,31.8,19.1,17.9.

Embodiment 3

[0039] Example 3: Synthesis of fluorescent probe molecule 1

[0040] Weigh compound 2 (0.85 g, 2.1 mmol), triethylamine (0.75 mL, 5.5 mmol, 2.0 eq.), 25 mL of anhydrous dichloromethane, add them to a dry flask, evacuate and fill with nitrogen, and place in an ice bath Stir for half an hour to cool. The solid phosgene (BTC, 443 mg, 1.5 mmol) was dissolved in 10 mL of dry dichloromethane, and added dropwise to the reaction system with a syringe. After warming to room temperature, stirring was continued for 3 h, and saturated sodium bicarbonate solution was added to quench the reaction. , extracted and separated, washed with brine, and the organic layer was dried over anhydrous sodium sulfate. The excess solvent was removed by rotary evaporation, and the obtained crude product was separated by flash column chromatography to obtain fluorescent probe molecule 1, a yellow solid of 0.61 g with a yield of 81%. The reaction formula is as follows:

[0041]

[0042] m.p.=128.1–128....

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Abstract

The invention discloses a fluorescent probe for detecting heavy metal mercury ions with high selectivity, a synthesis method and an application thereof, and belongs to the technical field of chemical analysis and detection. The probe of the present invention has a naphthalene ring aromatic hydrocarbon pseudo-dipeptide isonitrile structure, and the structural formula is as follows: the fluorophore of the probe is a large π system of a naphthalene ring, and the response group to mercury ions is an isonitrile group. The probe molecule has high selectivity and sensitivity to mercury ions, and the detection range is 0–1.8 μmol L ‑1 , with a detection limit of 0.1 μmol L ‑1 . The probe can be used for qualitative or quantitative detection of mercury ions in water, soil and biological systems.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and in particular relates to a fluorescent probe for detecting mercury ions with high selectivity, a combination method thereof, and applications in detecting mercury ions. Background technique [0002] Mercury is very small in nature but widely distributed. It is a relatively common metal ion in river and soil pollution. Mercury pollution is a research hotspot in the world today. Mercury cannot be degraded naturally in the environment. After the inorganic mercury in the environment is converted into organic mercury and absorbed by the organism, it will be enriched in the body of higher-level animals through the food chain, and finally enter the human body, which will cause serious harm to human health. Excessive accumulation of mercury may induce severe central nervous system damage, leading to various cognitive and motor impairments. In view of the importance of mercury...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C291/10C09K11/06G01N21/64
CPCC07C291/10C09K11/06G01N21/6428G01N21/643C09K2211/1011
Inventor 李高伟王晓娟郝远强孙秋灵程怡鹏
Owner SHANGQIU NORMAL UNIVERSITY
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