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A fluorescent probe for detecting trace water in 1,4-dioxane and its preparation method

A technology of dioxane and fluorescent probes, applied in the field of detection 1, can solve the problems of inability to use real-time detection, toxicity and the like, and achieve the effect of good practical value and high selectivity

Active Publication Date: 2022-03-08
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method cannot be used for real-time detection, and requires the use of expensive and toxic chemical reagents such as pyridine, imidazole, iodine, and alkyl sulfites

Method used

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  • A fluorescent probe for detecting trace water in 1,4-dioxane and its preparation method
  • A fluorescent probe for detecting trace water in 1,4-dioxane and its preparation method
  • A fluorescent probe for detecting trace water in 1,4-dioxane and its preparation method

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Experimental program
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Effect test

Embodiment 1

[0031] Preparation of 1-(3-methoxy-4-hydroxyphenyl)-9-(4-dimethylaminophenyl)nonan-1,6,8-triene-3,5 from 4-dimethylaminocinnamaldehyde - diketone boron difluoride complex, the reaction formula is:

[0032]

[0033] Specific steps are as follows:

[0034] 1) Preparation of 2,4-pentanedione boron difluoride complex

[0035] Add 3.02g of 2,4-pentanedione, 10mmol of boron trifluoride diethyl ether and 20mL of dichloromethane into a dry three-necked flask, react at 45°C for 3h, track and detect with TLC, and stop after the reaction is complete. After the reaction was completed, it was cooled to room temperature, and the reaction solution was distilled off under reduced pressure to remove dichloromethane, and then n-hexane was added for cooling and crystallization to obtain 3.13 g of light yellow 2,4-pentanedione boron difluoride complex, yield: 93 %. 1 H NMR (600MHz, DMSO-d6) δ: 6.39(s, 1H), 2.34(s, 6H); 13 C NMR (150MHz, CDCl 3 )δ: 192.48, 101.98, 101.95, 24.10. HRMS (m / z)...

Embodiment 2

[0041] 1-(3-methoxy-4-hydroxyphenyl)-9-(4-dimethylaminophenyl)nonan-1,6,8-triene-3,5-dioneboron difluoride The compound was dissolved in analytically pure dioxane to prepare 1×10- 5 For the probe solution of M concentration, different amounts of water are added into the probe solution to form a solution with a water content of 0-4.76%. Adopt the standard titration method to measure the water p-1-(3-methoxy-4-hydroxyl phenyl)-9-(4-dimethylaminophenyl) nonyl-1,6 of different content under the fluorescence spectrophotometer, The fluorescence emission spectrum of the 8-triene-3,5-dione boron difluoride complex, as figure 1 shown. The results show that in the range of 0-4.76% water content, with the continuous increase of water content in the system, the red fluorescence of the solution is quenched, which shows that the probe can detect water molecules sensitively and quantitatively.

Embodiment 3

[0043] 1-(3-methoxy-4-hydroxyphenyl)-9-(4-dimethylaminophenyl)nonan-1,6,8-triene-3,5-dioneboron difluoride The compound was dissolved in analytically pure dioxane to prepare 1×10- 5 The probe solution of M concentration, add the various organic solvents of 0.1mL respectively, adopt standard titration method to measure the different organic solvents to 1-(3-methoxy-4-hydroxyphenyl)- The fluorescence emission spectrum of 9-(4-dimethylaminophenyl)nona-1,6,8-triene-3,5-dione boron difluoride complex, as figure 2 shown. The results showed that the fluorescence was obviously quenched after adding water in the probe solution, while adding other solvents such as toluene, chloroform, ethyl acetate, dichloromethane, acetonitrile, acetone, tetrahydrofuran, methanol, dimethyl sulfoxide, N, N-dimethylformamide, n-hexane, petroleum ether, ethanol, etc., the fluorescence spectrum of the solution does not have obvious quenching phenomenon, which shows that the probe can specifically recogn...

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Abstract

The invention discloses a fluorescent probe for detecting trace water in 1,4-dioxane and a preparation method thereof. The present invention utilizes 4-dimethylaminocinnamaldehyde as a raw material, carries out aldol condensation reaction with the complex of 2,4-pentanedione and boron trifluoride ether, and then performs aldol condensation reaction with 3-methoxy-4-hydroxybenzaldehyde Condensation reaction, get fluorescent probe 1‑(3‑methoxy‑4‑hydroxyphenyl)‑9‑(4‑(dimethylaminophenyl) nonyl‑1, 6, 8‑triene‑3, 5‑ Diketone boron difluoride complex. This fluorescent probe can quickly react with traces of water in 1,4-dioxane, causing the red fluorescence of the fluorescent probe to be quenched, so it can be used to detect 1, The trace amount of water in 4-dioxane has the advantages of high sensitivity, high selectivity, quantitative and rapid detection, etc., and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a fluorescent probe for detecting trace water in 1,4-dioxane and a preparation method thereof. Background technique [0002] In the petrochemical industry, moisture can easily lead to pollution of gasoline, diesel and other fuels and lubricating oils. Moisture-containing fuels can cause engine corrosion. Fuel emulsification and phase separation can easily lead to corrosion and blockage of oil pipelines and various mechanical failures. In the chemical industry, pharmaceutical industry and other fields, some reaction systems are extremely sensitive to moisture, which can easily cause side reactions, change the chemical reaction speed, and affect the product yield. Some organometallic compounds participate in the reaction, which is extremely sensitive to water, and is prone to fire and explosion and cause accidents. In organic reaction systems, trace moisture often com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06G01N21/643C09K2211/1007C09K2211/1096G01N2021/6432
Inventor 王石发高语李明新巩帅田雪纯张燕杨益琴徐徐
Owner NANJING FORESTRY UNIV
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