CN102061160A - Synthesis process of fluorescent probe for detecting mercury ions - Google Patents
Synthesis process of fluorescent probe for detecting mercury ions Download PDFInfo
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- CN102061160A CN102061160A CN2009102197757A CN200910219775A CN102061160A CN 102061160 A CN102061160 A CN 102061160A CN 2009102197757 A CN2009102197757 A CN 2009102197757A CN 200910219775 A CN200910219775 A CN 200910219775A CN 102061160 A CN102061160 A CN 102061160A
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Abstract
The invention discloses a synthesis process of a fluorescent probe for detecting mercury ions and relates to the synthesis process of the fluorescent probe, in particular to the synthesis process of the fluorescent probe for detecting the mercury ions. The invention provides the synthesis process of the fluorescent probe for detecting the mercury ions, which has high selectivity, relatively high sensitivity and high anti-jamming capability and can be further applied in an organism and an environment. The invention adopts the following technical scheme that the process comprises the following technical steps of: synthesizing an intermediate 2; synthesizing R-E; and synthesizing a probe R-A.
Description
Technical field:
The present invention relates to a kind of synthesis technique of fluorescent probe, more particularly, relate to a kind of synthesis technique that is used to detect the fluorescent probe of mercury ion.
Background technology:
Mercury is a kind of toxic chemical substance of serious physiology that has, because it has persistence, easily transport property and biomagnification highly, makes it become one of the most noticeable environmental pollutant in the present whole world; On the other hand, mercury and mercury salt use very extensively in industry again.For these reasons, the detection of mercury causes people's very big concern in the organism or in the environment.
Recently decades, reported multiple Hg
2+Analytical procedure.Such as, ultraviolet spectrophotometry, high performance liquid chromatography, atomic absorption/emission spectrometry, inductively coupled plasma mass spectrometry (ICPMS), chemoluminescence method, electrochemical process (polarography and voltammetry) etc., but the detection method that these are traditional, often very high to the requirement of plant and instrument, cost an arm and a leg, also requiring has a large amount of samples, and does not allow continuous detecting.And the fluorescent spectrometry of recent findings is highly sensitive because of having, selectivity good, low cost and other advantages receives much concern.
Most Hg
2+No matter fluorescent probe is response type or solvay-type, and their recognition group mostly contains sulfide group, but some important factors have limited them in environment and biological intravital application:
(1) as other heavy metal elements, by enhanced spin orbital coupling (heavy atoms effect), Hg2+ can cause the reduction of performance index such as the fluorescence quantum yield of dyestuff and molar extinction coefficient;
(2) relatively poor water-soluble feasible application is very difficult;
(3) be used for complexing Hg
2+With part through regular meeting to other as Zn
2+, Pb
2+And Ag
+Deng also certain complex ability is arranged, therefore cause the selectivity of probe to reduce;
(4) disturbed by other metal ions or negatively charged ion cancellation, the immunity from interference of probe is not strong.
Summary of the invention:
The present invention is exactly at the problems referred to above, provide a kind of and had good selectivity, than high sensitive, immunity from interference strong and can be further in vivo and being used to of using in the environment detect the synthesis technique of the fluorescent probe of mercury ion.
In order to realize above-mentioned purpose of the present invention, the present invention adopts following technical scheme, and processing step of the present invention is:
1. intermediate 2 is synthetic
0.48g (0.02mol) Na is joined in the 10ml dehydrated alcohol, treat that Na dissolves fully after, restir 0.5h; Drip ethyl thioglycolate then, n (ethyl thioglycolate): n (Na)=1.0: 1～1.2: 1, after stirring 3h under the room temperature, drip 4-(N, the N-Dichloroethyl) the DMF solution 5ml of aminobenzaldehyde, n (4-(N, N-Dichloroethyl) aminobenzaldehyde): n (Na)=9: 20～12: 20 stirs 3h down at 40～45 ℃; After outstanding the desolventizing, add less water, use dichloromethane extraction, after the anhydrous sodium sulfate drying organic phase, remove solvent, silica gel chromatography separates;
Reaction equation is:
2.R-E synthetic
With mol ratio is that 2.5: 1～1.5: 1 2-(N, N-diethyl) amino-phenol and intermediate 2 joins in the single port flask that fills the 20ml propionic acid, adds the 30mg p-methyl benzenesulfonic acid again, 60～70 ℃ of reaction 18h down; Reaction finishes postcooling to room temperature, pours in the frozen water, regulates pH to neutral with NaOH solution, uses dichloromethane extraction then, uses the anhydrous sodium sulfate drying organic phase, and after outstanding the desolventizing, silica gel chromatography separates;
Reaction equation is:
3. probe R-A's is synthetic
70mg (0.1mmol) R-E is dissolved into MeOH and the THF (V: V=1.0: 1.0～1.5: 1.0), add LiOH again, n (LiOH): n (R-E)=1.0: 1～1.5: 1, nitrogen protection, 0 ℃ of following 24h that stirs of 10ml; After removing solvent, add less water, transfer to pH=5.0～6.0 with dilute hydrochloric acid, use dichloromethane extraction again, after the anhydrous sodium sulfate drying organic phase, remove solvent, silica gel chromatography separates.
Reaction equation is:
Beneficial effect of the present invention:
1. synthetic R-A probe of the present invention shows higher selectivity to mercury ion in HEPES buffered soln, be not subjected to the interference of other metal ions;
2. synthetic R-A probe of the present invention and mercury ion have stronger complex ability, are not subjected to multiple anionic influence the in the environment, and micromole's level detects the mercury ion of aqueous phase again;
3. after synthetic R-A probe of the present invention enters viable cell, can detect mercury ion;
4. productive rate of the present invention is 80.7%.
Embodiment:
Processing step of the present invention is:
1. intermediate 2 is synthetic
0.48g (0.02mol) Na is joined in the 10ml dehydrated alcohol, treat that Na dissolves fully after, restir 0.5h; Drip ethyl thioglycolate then, n (ethyl thioglycolate): n (Na)=1.0: 1～1.2: 1, after stirring 3h under the room temperature, drip 4-(N, the N-Dichloroethyl) the DMF solution 5ml of aminobenzaldehyde, n (4-(N, N-Dichloroethyl) aminobenzaldehyde): n (Na)=9: 20～12: 20 stirs 3h down at 40～45 ℃; After outstanding the desolventizing, add less water, use dichloromethane extraction, after the anhydrous sodium sulfate drying organic phase, remove solvent, silica gel chromatography separates;
Reaction equation is:
2.R-E synthetic
With mol ratio is that 2.5: 1～1.5: 1 2-(N, N-diethyl) amino-phenol and intermediate 2 joins in the single port flask that fills the 20ml propionic acid, adds the 30mg p-methyl benzenesulfonic acid again, 60～70 ℃ of reaction 18h down; Reaction finishes postcooling to room temperature, pours in the frozen water, regulates pH to neutral with NaOH solution, uses dichloromethane extraction then, uses the anhydrous sodium sulfate drying organic phase, and after outstanding the desolventizing, silica gel chromatography separates;
Reaction equation is:
3. probe R-A's is synthetic
70mg (0.1mmol) R-E is dissolved into MeOH and the THF (V: V=1.0: 1.0～1.5: 1.0), add LiOH again, n (LiOH): n (R-E)=1.0: 1～1.5: 1, nitrogen protection, 0 ℃ of following 24h that stirs of 10ml; After removing solvent, add less water, transfer to pH=5.0～6.0 with dilute hydrochloric acid, use dichloromethane extraction again, after the anhydrous sodium sulfate drying organic phase, remove solvent, silica gel chromatography separates.
Reaction equation is:
The structure of intermediate 2, R-E, R-A has obtained the affirmation of nuclear magnetic spectrogram and mass spectrum.
Claims (1)
1. synthesis technique that is used to detect the fluorescent probe of mercury ion is characterized in that processing step of the present invention is:
(1) intermediate 2 is synthetic
0.48g (0.02mol) Na is joined in the 10ml dehydrated alcohol, treat that Na dissolves fully after, restir 0.5h; Drip ethyl thioglycolate then, n (ethyl thioglycolate): n (Na)=1.0: 1～1.2: 1, after stirring 3h under the room temperature, drip 4-(N, the N-Dichloroethyl) the DMF solution 5ml of aminobenzaldehyde, n (4-(N, N-Dichloroethyl) aminobenzaldehyde): n (Na)=9: 20～12: 20 stirs 3h down at 40～45 ℃; After outstanding the desolventizing, add less water, use dichloromethane extraction, after the anhydrous sodium sulfate drying organic phase, remove solvent, silica gel chromatography separates;
Reaction equation is:
(2) R-E's is synthetic
With mol ratio is that 2.5: 1～1.5: 1 2-(N, N-diethyl) amino-phenol and intermediate 2 joins in the single port flask that fills the 20ml propionic acid, adds the 30mg p-methyl benzenesulfonic acid again, 60～70 ℃ of reaction 18h down; Reaction finishes postcooling to room temperature, pours in the frozen water, regulates pH to neutral with NaOH solution, uses dichloromethane extraction then, uses the anhydrous sodium sulfate drying organic phase, and after outstanding the desolventizing, silica gel chromatography separates;
Reaction equation is:
(3) probe R-A's is synthetic
70mg (0.1mmol) R-E is dissolved into MeOH and the THF (V: V=1.0: 1.0～1.5: 1.0), add LiOH again, n (LiOH): n (R-E)=1.0: 1～1.5: 1, nitrogen protection, 0 ℃ of following 24h that stirs of 10ml; After removing solvent, add less water, transfer to pH=5.0～6.0 with dilute hydrochloric acid, use dichloromethane extraction again, after the anhydrous sodium sulfate drying organic phase, remove solvent, silica gel chromatography separates;
Reaction equation is:
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|---|---|---|---|
| CN2009102197757A CN102061160A (en) | 2009-11-11 | 2009-11-11 | Synthesis process of fluorescent probe for detecting mercury ions |
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| CN2009102197757A CN102061160A (en) | 2009-11-11 | 2009-11-11 | Synthesis process of fluorescent probe for detecting mercury ions |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103254128A (en) * | 2013-03-25 | 2013-08-21 | 中南大学 | Water-soluble fluorescent probe for naked eye and light enhancement detection of mercury ions and synthesis and application thereof |
| CN104845612A (en) * | 2015-04-29 | 2015-08-19 | 南华大学 | Polystyrene mercury ion fluorescence recognition materials and preparation method thereof |
| CN107090002A (en) * | 2017-05-25 | 2017-08-25 | 河南牧业经济学院 | A kind of response type naphthalimide fluorescence probe for detecting mercury ion and preparation method and application |
| CN108863911A (en) * | 2018-07-18 | 2018-11-23 | 山西大学 | A kind of preparation method and application of turn-on type mercury ion fluorescence probe |
-
2009
- 2009-11-11 CN CN2009102197757A patent/CN102061160A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103254128A (en) * | 2013-03-25 | 2013-08-21 | 中南大学 | Water-soluble fluorescent probe for naked eye and light enhancement detection of mercury ions and synthesis and application thereof |
| CN103254128B (en) * | 2013-03-25 | 2018-08-24 | 中南大学 | It is a kind of water solubility bore hole and light enhancing detection mercury ion fluorescence probe and its synthesis and application |
| CN104845612A (en) * | 2015-04-29 | 2015-08-19 | 南华大学 | Polystyrene mercury ion fluorescence recognition materials and preparation method thereof |
| CN104845612B (en) * | 2015-04-29 | 2017-05-03 | 南华大学 | Polystyrene mercury ion fluorescence recognition materials and preparation method thereof |
| CN107090002A (en) * | 2017-05-25 | 2017-08-25 | 河南牧业经济学院 | A kind of response type naphthalimide fluorescence probe for detecting mercury ion and preparation method and application |
| CN108863911A (en) * | 2018-07-18 | 2018-11-23 | 山西大学 | A kind of preparation method and application of turn-on type mercury ion fluorescence probe |
| CN108863911B (en) * | 2018-07-18 | 2020-07-10 | 山西大学 | Preparation method and application of turn-on type mercury ion fluorescent probe |
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Application publication date: 20110518 |