CN109485619A - A kind of vinyl ethers Hg2+Fluorescence probe and its preparation method and application - Google Patents
A kind of vinyl ethers Hg2+Fluorescence probe and its preparation method and application Download PDFInfo
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Abstract
The invention discloses a kind of vinyl ethers Hg2+Fluorescence probe and its preparation method and application belongs to chemistry, bioanalysis detection technique field.A kind of technical solution of the present invention main points are as follows: vinyl ethers Hg2+Fluorescence probe has the following structure:The invention further particularly discloses vinyl ethers Hg2+The preparation method of fluorescence probe and its in acetonitrile, tetrahydrofuran or neutrality DMF-H2Quantitative detection Hg in O system2+Application.Vinyl ethers Hg of the invention2+Fluorescence probe rapid reaction, easy to operate, raw material is cheap and easy to get and is easily purified, yield is higher and synthesis step is simple, has preferable commercial applications value.
Description
Technical field
The invention belongs to chemistry, bioanalysis detection technique field, and in particular to a kind of vinyl ethers Hg2+Fluorescence probe
And its preparation method and application.
Background technique
Mercury is that a kind of toxicity is big, Yi Liudong, volatile liquid metals, can pass through the suction on the absorption of wall and clothes
The approach such as attached cause secondary pollution and injury to environment and human body.Mercury has extensive use in industrial production and daily life
On the way, such as air gauge, pressure gauge, thermometer, fluorescent lamp.It is widely present in all kinds of surrounding mediums and has serious as one kind
The heavy metal of physiological-toxicity, mercury have biggish harm to environmental and biological materials.The related compound of mercury metal and mercury element
It is owned by similar or identical toxicity, micro mercury may cause intoxicating phenomenon.The toxicity of mercury can pass through food chain
Enrichment is finally transferred to the internal of food chain people from top, and then seriously endangers human health.Mercury ion can and human body
Interior some chemical substances react, and cause to metabolic pathways such as the synthesis of the generation of intracellular energy, protein and nucleic acid
It influences.For example, mercury ion base, to change permeability of cell membranes, can influence cell membrane in conjunction with the sulfydryl on cell membrane
Normal function.After the function of cell membrane is destroyed, the activity for the various enzymes being present on cell membrane will receive influence, thus
The function of influencing a series of biochemical reaction and cell uses, and if serious, is likely to result in meronecrosis.Therefore, quasi-
The really content of effective determination of the environment and Mercury in Biological Sample ion all has bioscience, environmental protection and medicine aspect
It is significant.
So far, mainly there are Atomic absorption emission spectrometry (AAS/AES), electrochemistry side to the detection method of mercury ion
Method and inductively coupled plasma mass spectrometry analyze (ICP-MS) method, these methods have both high sensitivity and selective good advantage,
But it is fixed in mercury ion to limit them for the problems such as generally existing detection speed of these methods is slow, instrument price is expensive, complicated for operation
Application in the detection of position.Based on this, a kind of novel detection reagent, i.e. fluorescence probe is had been developed in Modern Analytical Chemistry.Due to
It has the advantages that high efficiency, high sensitivity, can quickly to detect mercury ion etc. multiple, and is increasingly becoming detection mercury ion and exists
One of the important means of.Based on the particularity of mercury ion reaction, the compound partially with double bond, three keys can identify depositing for mercury
Vinyl ethers mercury ion probe has been synthesized in, present invention design, probe molecule hydrolytic cleavage under the catalysis of mercury ion, then
Cyclisation is changed with obtaining fluorescent coumarin.Such vinyl ethers mercury ion probe unstressed configuration itself either has weak
Fluorescence, by with HgCl2React the compound for generating and having fluorescent both, and the presence of mercury ion is identified with this, is subtracted
Few mercury ion is endangered caused by human health, however, the still not no relevant report of this aspect at present.
Present patent application has obtained state natural sciences fund (21702051), He'nan Normal University doctor starts project
(qd15108), He'nan Normal University youth science fund (2016QK10), the key research project plan of institution of higher education, Henan Province
The subsidy of (17A350006,18A150009) and Environmental Chemistry and ecological toxicology National Key Laboratory (KF2016-01) with
It supports.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of vinyl ethers Hg2+Fluorescence probe and preparation method thereof, should
Vinyl ethers Hg2+Fluorescence probe can be with HgCl2React the compound for generating and having fluorescent both, is identified with this
Hg2+Presence, be of great significance in terms of biological and chemical analysis detection.
The present invention adopts the following technical scheme that solve above-mentioned technical problem, a kind of vinyl ethers Hg2+Fluorescence probe,
It is characterized in that vinyl ethers Hg2+Fluorescence probe has the following structure:
Wherein R is
Vinyl ethers Hg of the present invention2+The preparation method of fluorescence probe, it is characterised in that specific steps are as follows:
Step S1: 4- (lignocaine) salicylide and salt of weak acid are added in the reaction vessel, and is dissolved in organic solvent, room
Temperature is added with stirring 1,2- Bromofume solution, until TLC monitors raw material fully reacting, evaporation and concentration product, collection has for reaction
Column chromatography for separation is carried out after machine phase and obtains intermediate A, and wherein salt of weak acid is calcium carbonate, potassium carbonate, sodium carbonate or sodium bicarbonate, is had
Solvent is ethyl alcohol, n-hexane, ethyl acetate or acetone；
Step S2: the malononitrile and o-amino thiophenol being added in the reaction vessel, and be dissolved in organic solvent, it is stirred at room temperature
Lower addition acidic catalyst, until TCL monitors raw material fully reacting, filtration washing product carries out weight after collecting organic phase for reaction
Crystallization and purification obtains intermediate B, and wherein organic solvent is dimethyl sulfoxide, methanol, n-butanol or acetone, acidic catalyst three
Fluoroacetic acid, glacial acetic acid, hypochlorous acid or hydrochloric acid；
Step S3: using dimethyl sulfoxide as solvent, being added intermediate A in the reaction vessel, and lower addition highly basic is stirred at room temperature
Compound, TLC monitor fully reacting, and reaction system is extracted with ethyl acetate, and progress column chromatography for separation obtains after collecting organic phase
Intermediate C, wherein strong alkali compound is potassium tert-butoxide, sodium tert-butoxide, sodium hydride, tert-butyl lithium or n-BuLi；
Step S4: using dehydrated alcohol as solvent, intermediate C and intermediate B are added in the reaction vessel, is stirred at room temperature down and adds
Enter organo-alkali compound, reaction is until TLC monitors raw material fully reacting, and progress column chromatography for separation purifies to obtain after collecting organic phase
Target product M, that is, vinyl ethers Hg2+Fluorescence probe, wherein organo-alkali compound is pyridine, diethylamine, triethylamine, three ethyl alcohol
Amine or 4-dimethylaminopyridine；
The corresponding synthetic route of preparation process are as follows:
Further preferably, the detailed process of step S1 are as follows: by 4- (lignocaine) salicylide 0.639g and potassium carbonate
0.549g is added in the round-bottomed flask of 100mL, is added to 1,2- Bromofume solution, 571 μ L with after 15mL acetone solution
It states in reaction solution, back flow reaction 48h, 1,2- Bromofume solution 2.855mL and potassium carbonate 0.54g is added in reaction process, instead
Raw material fully reacting should be monitored up to TLC, reaction solution is cooled to room temperature, is concentrated by evaporation, column chromatography for separation obtains 0.2695g Huang
Color crystalline intermediate A.
Further preferably, the molar ratio of malononitrile described in step S2 and o-amino thiophenol is 1:1, institute in step S3
The molar ratio for stating intermediate A and strong alkali compound is 1:1, and intermediate C described in step S4 and intermediate B feed intake mole
Than for 1:1.
Vinyl ethers Hg of the present invention2+Fluorescence probe is in acetonitrile, tetrahydrofuran or neutrality DMF-H2It is fixed in O system
Amount detection Hg2+Application, as vinyl ethers Hg2+R is in fluorescence probeWhen, corresponding vinyl ethers Hg2+Fluorescence
ProbeIn neutral DMF-H2Quantitative detection Hg in O system2+Application, the wherein fluorescence of system
Intensity and Hg2Concentration is 1 × 10-5-6×10-6It is in a linear relationship within the scope of mol/L.
Vinyl ethers Hg of the invention2+Fluorescence probe rapid reaction, easy to operate, raw material is cheap and easy to get and is easy to mention
It is pure, yield is higher and synthesis step is simple, have preferable commercial applications value；And vinyl ethers Hg obtained2+It is glimmering
Light probe is in acetonitrile, tetrahydrofuran or neutrality DMF-H2It can be realized Hg in O system2+Quantitative detection.
Specific embodiment
Above content of the invention is described in further details by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on above content of the present invention belong to this hair
Bright range.
Embodiment 1
Synthesis process is illustrated by taking above compound as an example:
Step S1: by 4- (lignocaine) salicylide (0.639g, 3.31mmol) and potassium carbonate (0.549g, 3.97mmol)
It is added in the round-bottomed flask of 100mL, is added to 1,2- Bromofume (571 μ L, 6.62mmol) with after 15mL acetone solution
In reaction solution, reaction solution is cooled to room temperature, is concentrated by evaporation until TLC monitoring raw material fully reacting by back flow reaction 48h, reaction,
Column chromatography for separation obtains 0.2695g yellow crystals intermediate A, yield 28%.
1H NMR(CDCl3, 400MHz): δ 10.2 (s, 1H), 7.7 (d, J=9.2Hz, 1H), 6.3 (dd, J=9.2,
1.6Hz, 1H), 6.0 (d, J=2Hz, 1H), 6.0 (d, J=2Hz, 1H), 4.4 (t, J=6Hz, 2H), 3.7 (t, J=6Hz,
2H), 3.4 (q, J=7.2Hz, 4H), 1.2 (t, J=6.8Hz, 6H)；13C NMR(CDCl3,400MHz):δ187.0,162.8,
153.8,130.3,114.4,105.1,93.7,68.2,44.8,29.1,12.6。
Step S2: malononitrile (0.66g, 10mmol) and o-amino thiophenol (1.1mL, 10mmol) are added to 100mL's
It in round-bottomed flask, is dissolved with 10mL methanol, is stirred at room temperature lower dropwises addition 0.57mL glacial acetic acid, raw material is monitored by TLC after reaction 13h
Reaction solution filtration washing is obtained yellow crystals by fully reacting, and it is solid then to obtain 1.26g yellow with dehydrated alcohol recrystallization purification
Body intermediate B, yield 72%.
1H NMR(CDCl3, 400MHz) and δ 8.04 (d, J=7.8Hz, 1H), 7.89 (d, J=7.8Hz, 1H), 7.53 (t, J
=7.8Hz, 1H), 7.53 (t, J=7.8Hz, 1H), 7.44 (t, J=7.8Hz, 1H), 4.24 (s, 2H)；13C NMR(CDCl3,
400MHz)δ160.4,152.2,135.0,126.4,125.5,122.5,122.2,116.4,22.3。
Step S3: intermediate A (0.4334g, 1.445mmol) is added in the round-bottomed flask of 100mL, with 5mL diformazan
Base sulfoxide (DMSO) dissolution, be stirred at room temperature it is lower potassium tert-butoxide (0.168g, 1.455mmol) is added in reaction solution, react 1h
TLC monitors raw material fully reacting afterwards, and system carries out washing with distilled water (20mL × 3) and ethyl acetate extracts, and organic phase is used
It is concentrated in vacuo after anhydrous sodium sulfate is dry, product obtains 0.2367g yellowish-brown oily intermediate C through pillar layer separation, and yield is
75%.
1H NMR(CDCl3, 400MHz): δ 10.1 (s, 1H), 7.7 (d, J=9.0Hz, 1H), 6.7 (dd, J=13.7,
6.1Hz, 1H), 6.4 (dd, J=9.0,2.3Hz, 1H), 6.1 (d, J=2.3Hz, 1H), 4.8 (dd, J=13.8,1.7Hz,
1H), 4.5 (dd, J=6.0,1.8Hz, 1H), 3.4 (q, J=7.1Hz, 4H), 1.2 (t, J=7.1Hz, 6H)；13C NMR
(CDCl3,400MHz):δ186.7,161.4,153.6,148.1,130.3,115.0,106.8,98.0,96.4,44.8,
12.5。
Step S4: intermediate C (0.200g, 0.913mmol) and intermediate B (0.160g, 0.913mmol) are added to
It in 25mL round-bottomed flask, is dissolved with 0.1mL triethylamine and 5mL dehydrated alcohol, mixed liquor is stirred at room temperature, after reacting 3h
TLC monitors raw material fully reacting, and product purifies to obtain 0.186g yellow solid target compound M through column chromatography for separation, and yield is
55%.
1HNMR(CDCl3,400MHz):δ8.46(d,1H),8.44(s,1H),8.00(d,1H),7.84(d,1H),0.30
(s, 6H), 1.11 (s, 9H), 1.21-1.25 (t, J=7.2Hz, 6H), 3.39-3.44 (d, J=7.2Hz, 4H), 6.08 (s,
1H), 6.42 (s, 1H), 7.32-7.36 (m, J=7.2Hz, 1H), 7.44-7.47 (t, J=12.8Hz, 1H)13CNMR
(CDCl3,400MHz):δ12.69,18.40,25.89,44.89,100.91,106.32,109.79,111.33,121.23,
122.97,124.87,126.31,130.32,134.32,141.87,152.31,153.96,158.44,165.76。
Embodiment 2
Pass through the acquired part of compounds structure of the above method
Embodiment 3
The fluorescence activity data of part of compounds Preliminary Determination are analyzed
The compound of all synthesis is characterized using ultraviolet and fluorescence.The results show that acetonitrile, tetrahydrofuran or in
Property DMF-H2Hg is added in O system2+The fluorescence intensity of fluorescent probe molecule can be made to greatly enhance, when in fluorescent probe molecule
R isWhen, system fluorescence enhancement is maximum, especially in neutral DMF-H2In O system, the fluorescence intensity change of system and
Hg2+Concentration is 1 × 10-5-6×10-6It is in a linear relationship within the scope of mol/L, therefore vinyl ethers Hg2+Fluorescence probe may be implemented
In neutral DMF-H2To Hg in O system2+Quantitative detection.
Embodiment above describes basic principles and main features of the invention and advantage, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe originals of the invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (6)
1. a kind of vinyl ethers Hg2+Fluorescence probe, it is characterised in that vinyl ethers Hg2+Fluorescence probe has following knot
Structure:
Wherein R is
2. a kind of vinyl ethers Hg described in claim 12+The preparation method of fluorescence probe, it is characterised in that specific steps
Are as follows:
Step S1: 4- (lignocaine) salicylide and salt of weak acid are added in the reaction vessel, and is dissolved in organic solvent, room temperature is stirred
Lower addition 1,2- Bromofume solution is mixed, until TLC monitors raw material fully reacting, evaporation and concentration product collects organic phase for reaction
Column chromatography for separation is carried out afterwards and obtains intermediate A, and wherein salt of weak acid is calcium carbonate, potassium carbonate, sodium carbonate or sodium bicarbonate, You Jirong
Agent is ethyl alcohol, n-hexane, ethyl acetate or acetone；
Step S2: the malononitrile and o-amino thiophenol being added in the reaction vessel, and be dissolved in organic solvent, it is stirred at room temperature down and adds
Enter acidic catalyst, until TCL monitors raw material fully reacting, filtration washing product is recrystallized after collecting organic phase for reaction
Purification obtains intermediate B, and wherein organic solvent is dimethyl sulfoxide, methanol, n-butanol or acetone, and acidic catalyst is trifluoro second
Acid, glacial acetic acid, hypochlorous acid or hydrochloric acid；
Step S3: using dimethyl sulfoxide as solvent, being added intermediate A in the reaction vessel, and lower addition highly basic chemical combination is stirred at room temperature
Object, TLC monitor fully reacting, and reaction system is extracted with ethyl acetate, and progress column chromatography for separation obtains centre after collecting organic phase
Body C, wherein strong alkali compound is potassium tert-butoxide, sodium tert-butoxide, sodium hydride, tert-butyl lithium or n-BuLi；
Step S4: using dehydrated alcohol as solvent, being added intermediate C and intermediate B in the reaction vessel, and lower addition, which is stirred at room temperature, to be had
Machine alkali cpd, reaction is until TLC monitors raw material fully reacting, and progress column chromatography for separation purifies to obtain target after collecting organic phase
Product M, that is, vinyl ethers Hg2+Fluorescence probe, wherein organo-alkali compound be pyridine, diethylamine, triethylamine, triethanolamine or
4-dimethylaminopyridine；
The corresponding synthetic route of preparation process are as follows:
3. vinyl ethers Hg according to claim 22+The preparation method of fluorescence probe, it is characterised in that the tool of step S1
Body process are as follows: 4- (lignocaine) salicylide 0.639g and potassium carbonate 0.549g are added in the round-bottomed flask of 100mL, used
1,2- Bromofume solution, 571 μ L is added in above-mentioned reaction solution after 15mL acetone solution, back flow reaction 48h, reaction process
In add 1,2- Bromofume solution 2.855mL and potassium carbonate 0.54g, reaction will react until TLC monitors raw material fully reacting
Liquid is cooled to room temperature, and is concentrated by evaporation, and column chromatography for separation obtains 0.2695g yellow crystals intermediate A.
4. vinyl ethers Hg according to claim 22+The preparation method of fluorescence probe, it is characterised in that institute in step S2
The molar ratio for stating malononitrile and o-amino thiophenol is 1:1, and intermediate A described in step S3 and feeding intake for strong alkali compound are rubbed
, than being 1:1, intermediate C described in step S4 and the molar ratio of intermediate B are 1:1 for you.
5. vinyl ethers Hg described in claim 12+Fluorescence probe is in acetonitrile, tetrahydrofuran or neutrality DMF-H2In O system
Quantitative detection Hg2+Application.
6. application according to claim 5, it is characterised in that: as vinyl ethers Hg2+R is in fluorescence probe
When, corresponding vinyl ethers Hg2+Fluorescence probeIn neutral DMF-H2Quantitative detection in O system
Hg2+Application, the wherein fluorescence intensity and Hg of system2Concentration is 1 × 10-5-6×10-6It is in a linear relationship within the scope of mol/L.
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