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Rhodamine B derivative fluorescent probe molecule based on monodisperse four-arm polyethylene glycol and preparation method of rhodamine B derivative fluorescent probe molecule

A four-arm polyethylene glycol, fluorescent probe technology, applied in the field of detection, can solve the problems of low total yield, affect practicability, slow development of mercury ion fluorescent probes, etc., and achieve the effect of low concentration detection limit

Pending Publication Date: 2021-08-03
湖南华腾制药有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with other common transition metal cations, the development of fluorescent probes for mercury ions is generally slow. Many small molecule mercury chemical sensors with fluorescent (FL) organic dyes have been developed, but most of them need to be mixed with a certain proportion of organic solvents. detection and / or ion selectivity is unsatisfactory
In addition, some mercury-ion-based fluorescent probes have complicated synthetic routes and low overall yields, all of which disadvantages affect their practicability in real sample monitoring

Method used

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  • Rhodamine B derivative fluorescent probe molecule based on monodisperse four-arm polyethylene glycol and preparation method of rhodamine B derivative fluorescent probe molecule
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  • Rhodamine B derivative fluorescent probe molecule based on monodisperse four-arm polyethylene glycol and preparation method of rhodamine B derivative fluorescent probe molecule

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preparation example Construction

[0061] The preparation of embodiment 1 formula III compound

[0062] Under the protection of argon, dodecaethylene glycol (HO-PEG 12 -OH)I (140.5g, 0.25mol) and tetrahydrofuran (200ml) were added into a 500ml round bottom flask, and cooled to about 0°C under ice bath conditions. Sodium hydride (60% dispersed in mineral oil, 2.4 g) was slowly added to the reaction system in three batches. The reaction mixture was warmed to room temperature, followed by the addition of N by syringe 3 -PEG 4 - A solution of Tos (14.92 g) in tetrahydrofuran (10 ml). The reaction was further stirred for 48 h under an argon atmosphere. After the reaction was monitored by TLC, 200 ml of brine was slowly added to the reaction to quench excess sodium hydride. The organic solvent was removed by distillation under reduced pressure. The crude product was washed three times with dichloromethane (400ml×3), and the organic phase was collected. The organic phase was washed successively with 50 wt % aqu...

Embodiment 2

[0064] The preparation of embodiment 2 formula V compound

[0065] Under the protection of argon, the HO-PEG 16 -N 3 (III) (10g, 13.4mmol) and tetrahydrofuran (200ml) were added into a 500ml round bottom flask, and the reaction solution was cooled to about 0°C under ice bath conditions. Sodium hydride (60% mass fraction dispersed in mineral oil, 1.2 g, 30 mmol) was slowly added to the reaction system in three batches for 30 minutes. The reaction mixture was heated to 40 °C, and the HO-PEG 4 - A solution of Tos(IV) (13.92 g, 40 mmol) in dry tetrahydrofuran (20 ml) was slowly added to the reaction system, and the dropwise addition process continued for 2 hours. The reaction mixture was further stirred for 24 h under argon atmosphere. After the reaction, 200 ml of brine was added to quench the excess sodium hydride, and the organic solvent was evaporated under reduced pressure. The slurry crude product was extracted three times with dichloromethane (200ml×3), the organic ext...

Embodiment 3

[0067] The preparation of embodiment 3 formula VI compound

[0068] Under the protection of argon, the HO-PEG 20 -N 3 (V) (8g, 8.67mmol) and tetrahydrofuran (100ml) were added into a 250ml round bottom flask, and cooled to about 0°C under ice bath conditions. Sodium hydride (60% mass fraction dispersed in mineral oil, 0.8 g, 20 mmol) was slowly added to the reaction system in three batches for 30 minutes. The reaction mixture was heated to 40 °C, and the HO-PEG 4 - A solution of Tos(IV) (8.35 g, 24 mmol) in dry tetrahydrofuran (20 ml) was slowly added to the reaction system, and the dropwise addition process continued for 2 hours. The reaction mixture was further stirred for 24 h under argon atmosphere. After the reaction, 200 ml of brine was added to quench the excess sodium hydride, and the organic solvent was evaporated under reduced pressure. The slurry crude product was extracted three times with dichloromethane (200ml×3), the organic extracts were collected and comb...

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Abstract

The invention aims to provide a rhodamine B derivative fluorescent probe molecule based on monodisperse four-arm polyethylene glycol and a preparation method of the rhodamine B derivative fluorescent probe molecule. The fluorescent probe molecule provided by the invention has very high selectivity on detection of Hg<2+> in an aqueous solution, shows specific fluorescent reaction on Hg<2+> in the aqueous solution, and has relatively low concentration detection limit.

Description

technical field [0001] The invention belongs to the detection field, and specifically designs a fluorescent probe and a preparation method thereof, in particular to a rhodamine B derivative fluorescent probe molecule based on monodisperse four-armed polyethylene glycol and a preparation method thereof Background technique [0002] Heavy metals and their derivatives are widespread pollutants in the world and have caused a series of health and environmental problems. Therefore, the detection of heavy metals has received more and more attention in recent years. Due to the high toxicity of mercury in biology and its wide application in industry, the heavy metal pollution caused by mercury ions has always been concerned. Therefore, the highly sensitive detection of mercury ions is one of the urgent problems to be solved in the field of analytical chemistry. . There are many fluorescent probes for heavy metal detection that have been discovered so far, mainly through metal comple...

Claims

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Application Information

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IPC IPC(8): C08G65/333C08G65/334C09K11/06G01N21/64
CPCC08G65/33396C08G65/3346C09K11/06G01N21/643C09K2211/1475C09K2211/1466G01N2021/6439
Inventor 彭媛媛张安林赵思纯
Owner 湖南华腾制药有限公司
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