Schiff base fluorescent probe and synthesis method and application thereof

A technique for fluorescent probes and synthesis methods, applied in the field of Schiff base fluorescent probes and their synthesis and application, capable of solving problems such as limited application range, long response time, and poor selectivity, achieving clear and recognizable results and low detection costs , Simple and convenient operation

Inactive Publication Date: 2017-08-04
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently reported methods for the detection of copper ions have disadvantages such as complex synthesis, only suitable for organic solvent detection, long response time and poor selectivity, and the scope of application is limited.

Method used

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  • Schiff base fluorescent probe and synthesis method and application thereof
  • Schiff base fluorescent probe and synthesis method and application thereof
  • Schiff base fluorescent probe and synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthesis of embodiment 1 Schiff base fluorescent probe L

[0033] 4-phenyl-3-thiosemicarbazide (0.167g, 1mmol) was dissolved in ethanol (5ml); take 8-hydroxyjulonidine-9-formaldehyde (0.217g, 1mmol) in a three-necked flask, add 5ml EtOH, heating to reflux, the solution turns into a yellow clear solution at 50°C; at this time, add the ethanol solution of 4-phenyl-3-thiosemicarbazide to the ethanol solution of 8-hydroxyjulonidine-9-formaldehyde, and keep the temperature The reaction was continued at 80° C. After 24 hours, a large amount of yellow solid was produced, which was filtered by suction and dried to obtain the Schiff base fluorescent probe L (0.242 g, yield: 66%). 1 HNMR(DMSO-d6)δ:11.385(s,1H,-OH),9.903(s,1H,-NH-),9.297(s,1H,-NH-),8.156(s,1H,-HC=N ),7.498(d,2H,-ArH),7.339(t,2H,-ArH),7.166(t,1H,-ArH),3.159(m,4H,-CH 2 ),2.593(m,4H,-CH 2 ),1.852(m,4H,-CH 2 ), HRMS (ESI): C 20 h 22 N 4 OS(M+H) calculated value 367.1514, experimental value 367.1587.

Embodiment 2

[0034] Embodiment 2 Schiff base fluorescent probe L is used for the fluorescence spectrometry of trace water

[0035] Take 20 μL of probe L stock solution and add it to a clean colorimetric tube, then add 12 μL of Al 3+ Finally, dilute to 5mL with methanol, shake the solution, take 2.5mL into a clean cuvette, and detect it on a fluorescence spectrophotometer. With the addition of a small amount of water, the solution gradually changes from orange to yellow. It is yellow, and the emission peak at 570nm gradually weakens, and a blue shift occurs, moving from 570nm to 540nm. For the fluorescence spectrum, see figure 1 .

Embodiment 3

[0036] Embodiment 3 Schiff base fluorescent probe L measures the linear relationship of trace water

[0037] Take 20 μL of probe L stock solution and add it to a clean colorimetric tube, then add 12 μL of Al 3+ Methanol solution, finally dilute to 5mL with methanol, shake the solution evenly, take 2.5mL into a clean cuvette, and detect it on a fluorescence spectrophotometer. With the addition of a small amount of water, the solution gradually changes from orange to yellow. Yellow, and the emission peak at 570nm gradually weakens, and a blue shift occurs, moving from 570nm to 540nm. The amount of gradually adding trace water is 0%-3%, and the fluorescence intensity F of the system and the content of trace water present a good linear relationship in the scope of 0.1%-1.4% (R 2 = 0.986). Take the trace water content as the abscissa, and take the fluorescence intensity F as the ordinate to plot, and obtain a linear equation: F=957.15-520.35 [H 2 O]. See the working line diagra...

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Abstract

The invention provides a schiff base fluorescent probe and a synthesis method and application thereof. The preparation method of the probe comprises the following steps: heating and refluxing 8-hydroxyl julolidine-9-formaldehyde and 4-phenyl-3-thiosemicarbazide which are reactants in ethanol for 20-24 hours; after reaction is finished, carrying out suction filtration; and washing to obtain yellow solid which is the schiff base fluorescent probe. The fluorescent probe can be used for detecting trace water and copper ions. Detection of the trace water is realized on the basis of a complex formed by the schiff base fluorescent probe and Al3+. Detection of the copper ions is realized by making schiff base probe into schiff base test paper. The detecting method is high in sensitivity, simple to operate, convenient, rapid and practical.

Description

technical field [0001] The invention relates to a fluorescent probe and its detection method for trace water and copper ions, in particular to a synthesis method of a Schiff base fluorescent probe and the application of the Schiff base fluorescent probe in detecting trace water and copper ions. Background technique [0002] The detection and quantitative analysis of trace amounts of water in organic solvents is of great significance in chemical analysis and also has important applications in industrial processes, food processing, biomedicine, and environmental monitoring. The currently recognized method for detecting trace water is the Karl Fischer method, which can detect trace water down to 1ppm, but it has many disadvantages, that is, it needs to use complicated instruments and needs to contact toxic reagents (i.e. imidazole, I 2 and SO 2 ), time-consuming and susceptible to interference from other substances. There is an urgent need to develop methods that can detect t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/04C09K11/06G01N21/64
CPCC07D455/04C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 王煜秦丽媛邵秀清
Owner SHANXI UNIV
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