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Synthesis and application of a fluorescent probe for simultaneously distinguishing between gold ions au3+ and palladium

A fluorescent probe, gold ion technology, applied in the field of analytical chemistry

Active Publication Date: 2022-06-07
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some have been reported for the detection of gold ions (Au 3 + ) or palladium species (Pd 0 , Pd 2+ , Pd 4+ ) fluorescent probes, but at the same time distinguish and detect gold ions (Au 3+ ) and palladium species (Pd 0 , Pd 2+ , Pd 4+ ) bifunctional fluorescent probes have not been reported yet

Method used

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  • Synthesis and application of a fluorescent probe for simultaneously distinguishing between gold ions au3+ and palladium
  • Synthesis and application of a fluorescent probe for simultaneously distinguishing between gold ions au3+ and palladium
  • Synthesis and application of a fluorescent probe for simultaneously distinguishing between gold ions au3+ and palladium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1. Synthesis of 5-ethyl-8-methoxy-1,2,3,3a,4,5-hexahydropyrrololo (1,2-a) quinoxaline

[0028] a. 30g (175.31mmol) 3-fluoro-4-nitroanisole and 37.5g (227.9mmol) L-proline methyl ester hydrochloride was added to 200mL anhydrous acetonitrile, and then added 73mL (525.9mmol) triethylamine heated reflux reaction for 6 hours, filtered to remove triethylamine hydrochloride, spin-drying solution,

[0029] b. Dissolve the drying solution with 300mL methanol, slowly add 46.76g (874.13mmol) ammonium chloride and 57.15g (874.13mmol) zinc powder, stir overnight at room temperature, and then filter to remove the zinc powder, spin out the solvent, add the solid to the water, filter the green solid,

[0030] c. The green solid was dissolved with 400 mL anhydrous tetrahydrofuran, 36.4 g (962.17 mmol) sodium borohydride and 122 mL (962.17 mmol) boron trifluoride diethyl ether were added, the reaction was completed for 12 hours, after the reaction was complete, slowly poured into the...

Embodiment 2

[0032] Example 2. Synthesis of 5-ethyl-8-hydroxy-1,2,3,3a,4,5-hexahydropyrrole [1,2-a]quinoxaline-7-carboxaldehyde

[0033] I. Under nitrogen protection conditions, an appropriate amount of drying and re-distilled 10mL N, N-dimethylformamide (DMF) was slowly added to 10mL (64.22mmol) phosphorus chloride (POCl). 3) in, stirred at 20-50 ° C for 30-60 minutes to give a yellow solution, 10g (35.68mmol) 5-ethyl-8-methoxy-1,2,3a,4,5-hexahydropyrrole (1,2-a) quinoxaline dissolved in 40mL N, N-dimethylformamide (DMF), dropwise added to the yellow mixed solution, the mixture continued under nitrogen protection at 60 °C stirring reaction for 12 hours; After the reaction is complete, the reaction solution is poured into an appropriate amount of ice water, adjust the pH to 5 to 6 with 20% NaOH solution, and then extracted with ethyl acetate, the organic layer is dried to give a yellow solution,

[0034] II. 621.8mg (23.05mmol) aluminum and 5.85g (23.05mmol) iodine added to 15mL of anhydrous a...

Embodiment 3

[0035] Example 3. Synthesis of 2- ((5-ethyl-8-(propyl-2-ayn-1-yloxy)-1,2,3,3a,4,5-hexahydropyrrolofa [1,2-a]quinoxa-7-yl) methylene) malonitrile

[0036] i. 200mg (811.9 μmol) 5-ethyl-8-hydroxy-1,2,3,3a,4,5-hexahydropyrrole [1,2-a]quinoxaline-7-carboxaldehyde and 289mg (2.44mmol) acryloyl chloride was added to 8mL of anhydrous dichloromethane, and then 246.5mg (2.44mmol) was added to re-distill triethylamine, and the reaction at room temperature was 3 hours, and the cyan solid was obtained by the column 140mg, with a yield of 60.63%;

[0037] ii. 140mg (492.3 μmol) solid and 39.02mg (590.80 μmol) malonitrile in step i was added to 8 mL ethanol, reacted overnight at room temperature, filtered to obtain the fluorescent molecular probe 2- (5-ethyl-8-(prop-2-alkyn-1-yloxy) -1,2,3a,4,5-hexahydropyrrole [1,2-a] quinoxaline-7-yl) methylene) malonitrile 101mg, yield 61.72%.

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Abstract

The invention discloses a method for simultaneously distinguishing gold ions (Au 3+ ) and palladium species (Pd 0 , Pd 2+ , Pd 4+ ) bifunctional fluorescent probe, the chemical structure of the fluorescent probe is as follows: the fluorescent probe can be combined with gold ions (Au 3+ ) and palladium species (Pd 0 , Pd 2+ , Pd 4+ ) undergo different chemical reactions to generate products with different optical properties, and the probes and gold ions (Au 3+ ) after the reaction emits 484nm blue light at an excitation wavelength of 422nm, and palladium species (Pd 0 , Pd 2+ , Pd 4+ ) after the reaction, the red light of 606nm is emitted at the excitation wavelength of 472nm, thereby realizing the simultaneous distinction of gold ions (Au 3+ ) and palladium species (Pd 0 , Pd 2+ , Pd 4+ )the goal of. The fluorescent molecular probe disclosed by the present invention can be used for gold ions (Au 3+ ) and palladium species (Pd 0 , Pd 2+ , Pd 4+ ) quantification and gold ion (Au 3+ ) and palladium species (Pd 0 , Pd 2+ , Pd 4+ ) simultaneous fluorescence imaging analysis, has great application prospects in the technical fields such as environment and life sciences.

Description

Technical field [0001] The present invention belongs to the field of analytical chemistry techniques, specifically relates to a kind of au can be simultaneously distinguished gold ions 3+ With palladium (Pd 0 ，Pd 2+ ，Pd 4+ Synthesis of a fluorescent probe, and the quantitative detection of gold ions Au in the environment by this probe 3+ With palladium (Pd 0 ， Pd 2+ ，Pd 4 + ), simultaneously distinguish imaging gold ions in living cells 3+ and palladium (Pd 0 ，Pd 2+ ，Pd 4+ ) of the application. Background [0002] Fluorescent probes have the characteristics of high sensitivity, visualization, easy operation, low cost, etc., in recent decades, all kinds of fluorescent probes are widely used in the detection of various metal ions. The fluorescent molecular probe designed for synthesis of multi-signal and multi-detection is used for the detection and quantification of a variety of metal ions, and has high application value in the fields of analytical chemistry and environmental pol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09K11/06G01N21/64
CPCC07D487/04C09K11/06G01N21/643C09K2211/1044Y02P10/20
Inventor 尹鹏陈洁甘亚兵尹国兴李海涛
Owner HUNAN NORMAL UNIVERSITY
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