CN106496117B - A kind of mercury ion Ratiometric fluorescent probe of 8-hydroxyquinoline class and preparation method thereof - Google Patents
A kind of mercury ion Ratiometric fluorescent probe of 8-hydroxyquinoline class and preparation method thereof Download PDFInfo
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- CN106496117B CN106496117B CN201610920911.5A CN201610920911A CN106496117B CN 106496117 B CN106496117 B CN 106496117B CN 201610920911 A CN201610920911 A CN 201610920911A CN 106496117 B CN106496117 B CN 106496117B
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention belongs to metal ion probe fields more particularly to a kind of mercury ion Ratiometric fluorescent probe of 8 hydroxyquinoline class and preparation method thereof.The present invention provides a kind of 8 8-hydroxyquinoline derivatives, the molecular formula of 8 8-hydroxyquinoline derivative is：C20H15ClFNO；The present invention also provides a kind of preparation methods of above-mentioned 8 8-hydroxyquinoline derivative；Meanwhile the product obtained the present invention also provides above-mentioned 8 8-hydroxyquinoline derivative or above-mentioned preparation method is in Hg2+Application in detection.Through experimental tests can obtain, and the compound obtained by technical solution provided by the invention is as fluorescence probe in use, only to Hg2+Response, high specificity；For the Hg of various concentration2+When being detected, good linear relationship is presented, can be applied to Hg2+Quantitative detection；For Hg2+Detection have high sensitivity, remove Hg2+Outer other metal ions interfere very little, detection method reliable and stable measurement result.It solves in the prior art, the detection of mercury ion has the response time long and the sensitive low technological deficiency of detection.
Description
Technical field
The invention belongs to metal ion probe field more particularly to a kind of mercury ion Ratio-type fluorescence of 8-hydroxyquinoline class
Probe and preparation method thereof.
Background technology
It is well known that mercury is one of hypertoxic metal, the problem of mercury pollution, has grown into a global problem, to people
Class and natural environment for the survival of mankind constitute serious threat.Wherein, Hg2+Pollution as most common mercury pollution
Object is distributed widely in sky gas and water and soil, and the generation of pollution is from coal burning plant, thermometer, mercury lamp etc..Food
Chain has very strong enrichment for mercury, and the mercury in environment is passively plants enriched, becomes toxicity after biotransformation
Stronger organic mercury threatens human life's one of strongest heavy metal element safely to become.Therefore, it realizes in environment
Trace Hg detection is particularly important.
Currently used for detecting the chemical sensor of mercury ion, since the presence of other competitive metal ions is to its mercury ion
It measures and generates interference, mercury ion detecting is caused to have the response time long and the sensitive low technological deficiency of detection.
Therefore, a kind of mercury ion Ratiometric fluorescent probe of 8-hydroxyquinoline class and preparation method thereof is developed, for solving
Certainly in the prior art, the detection of mercury ion has the response time long and the sensitive low technological deficiency of detection, becomes this field
Technical staff's urgent problem to be solved.
Invention content
In view of this, the present invention provides a kind of mercury ion Ratiometric fluorescent probe of 8-hydroxyquinoline class and its preparation sides
Method, for solving in the prior art, the detection of mercury ion has the response time long and the sensitive low technological deficiency of detection.
The present invention provides a kind of 8-hydroxyquinoline derivative, the structural formula of the 8-hydroxyquinoline derivative is：
The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline derivative, the preparation method is that：
Step 1: 8- hydroxyls quinaldine and the chloro- 6- fluorobenzaldehydes of 2- are dissolved in acetic anhydride, are purified after stirring, obtain the first production
Object；
Step 2: first product is dissolved in the mixed liquor of pyridine and water, purified after stirring, obtains the second product；
Step 3: second product is dissolved in acetone, K is added2CO3With 3- bromopropenes, is purified after stirring, obtain third product；
Step 4: the third product is dissolved in N-Methyl pyrrolidone, is purified after stirring, obtain product.
Preferably, the rate of charge of the 8- hydroxyls quinaldine, the chloro- 6- fluorobenzaldehydes of 2- and acetic anhydride is 9.43mmol:
(11.32~12) mmol:(10~15) mL.
Preferably, the temperature stirred described in step 1 be 140~145 DEG C, the time stirred described in step 1 be 18~
22h。
Preferably, the rate of charge of first product, pyridine and water is 6.2mmol:10mL:(5~10) mL.
Preferably, the temperature stirred described in step 2 is 130~140 DEG C, and the time stirred described in step 2 is 3~4h.
Preferably, second product, K2CO3, 3- bromopropenes and acetone rate of charge be 5.1mmol:8mmol:(1~
1.5)mL:(30~35) mL.
Preferably, the temperature stirred described in step 3 is 60~65 DEG C, and the time stirred described in step 3 is 4~5h.
Preferably, the rate of charge 4.5mmol of the third product and N-Methyl pyrrolidone:(10~15) mL；
The temperature stirred described in step 4 is 210~220 DEG C, and the time stirred described in step 4 is 3~4h.
The present invention also provides one preparation methods of a kind of above-mentioned 8-hydroxyquinoline derivative or any of the above to obtain
Product in Hg2+Application in detection.
In conclusion the present invention provides a kind of 8-hydroxyquinoline derivative, the molecule of the 8-hydroxyquinoline derivative
Formula is：C20H15ClFNO；The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline derivative；Meanwhile the present invention
It additionally provides above-mentioned 8-hydroxyquinoline derivative or product that above-mentioned preparation method obtains is in Hg2+Application in detection.Through experiment
Detection can obtain, and the compound obtained by technical solution provided by the invention is as fluorescence probe in use, only to Hg2+Response, it is special
It is anisotropic strong；For various concentration Hg2+When being detected, good linear relationship is presented, can be applied to Hg2+Quantitative detection；
For detection have high sensitivity, remove Hg2+Other metal ions interfere very little, detection method reliably steady measurement result
It is fixed.It solves in the prior art, the detection of mercury ion has the response time long and the sensitive low technological deficiency of detection.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
The embodiment of invention for those of ordinary skill in the art without creative efforts, can also basis
The attached drawing of offer obtains other attached drawings.
Fig. 1 is 8-hydroxyquinoline derivative made from 1~embodiment of embodiment 3 in technical solution provided by the invention1H-NMR collection of illustrative plates；
Fig. 2 is 8-hydroxyquinoline derivative produced by the present invention, is to be measured for Hg at 351nm in wavelength2+Selectivity
Measurement result；
Fig. 3 is 8-hydroxyquinoline derivative produced by the present invention, is to measure that Hg is added at 351nm in wavelength2+Front and back is glimmering
Light spectroscopic assay result；
Fig. 4 is 8-hydroxyquinoline derivative produced by the present invention, Hg2+Concentration and 8-hydroxyquinoline derivatives fluorescent intensity ratio
Value I506/I428Relationship；
Fig. 5 is 8-hydroxyquinoline derivative produced by the present invention, is added before and after different metal ions, and 8-hydroxyquinoline derives
Fluorescence peak intensity rate I at 506nm and at 428nm506/I428The block diagram of variation.
Specific implementation mode
The present invention provides a kind of mercury ion Ratiometric fluorescent probes of 8-hydroxyquinoline class and preparation method thereof, for solving
Certainly in the prior art, the detection of mercury ion has the response time long and the sensitive low technological deficiency of detection.
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
The every other embodiment that technical staff is obtained without making creative work belongs to the model that the present invention protects
It encloses.
In order to which the present invention is described in more detail, with reference to embodiment to a kind of mercury of 8-hydroxyquinoline class provided by the invention
Ion Ratiometric fluorescent probe and preparation method thereof, is specifically described.
The synthetic route of preparation method provided by the present invention is as follows：
Embodiment 1
The present embodiment is to prepare C according to above-mentioned preparation method20H15The specific embodiment of ClFNO.
The chloro- 6- fluorobenzaldehydes of the 2- of the 8- hydroxyls quinaldine of 9.43mmol and 11.32mmol are dissolved in 10ml acetic anhydrides to mix
It closes, in 140 DEG C of heating stirrings, condensing reflux is reacted 18 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is petroleum ether/second
Acetoacetic ester isolates brown solid, is the first product 1.
5ml water agitating and heatings are added in 130 DEG C of heating stirrings in the first products of 6.2mmol 1 and 10ml pyridinium dissolutions, after
Continuous condensing reflux reacts 4 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is petrol ether/ethyl acetate, isolated ash
White solid, as the second product 1.
By the second products of 5.1mmol 1 and 30ml acetone, the 3- bromopropenes of 1ml and 8mmol K2CO3Mixing is heated at 60 DEG C
Stirring, condensing reflux are reacted 4 hours, are cooled to room temperature.Column chromatography purifies, and eluant, eluent is dichloromethane, isolated yellow green
Mucus, as third product 1.
The N-Methyl pyrrolidone of 4.5mmol third products 1 and 10ml are dissolved, in 210 DEG C of heating stirrings, condensing reflux
Reaction 3 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is dichloromethane, detaches to obtain yellow-brown solid, as product 1.
Product 1 is C through Structural Identification20H15ClFNO。
Embodiment 2
The present embodiment is to prepare C according to above-mentioned preparation method20H15The specific embodiment of ClFNO.
The chloro- 6- fluorobenzaldehydes of the 2- of the 8- hydroxyls quinaldine of 9.43mmol and 11.32mmol are dissolved in 10ml acetic anhydrides to mix
It closes, in 145 DEG C of heating stirrings, condensing reflux is reacted 20 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is petroleum ether/second
Acetoacetic ester isolates brown solid, is the first product 2.
10ml water agitating and heatings are added in 135 DEG C of heating stirrings in the first products of 6.2mmol 2 and 10ml pyridinium dissolutions,
Condensing reflux reacts 4 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is petrol ether/ethyl acetate, isolated greyish white
Color solid, as the second product 2.
By the 3- bromopropenes and 8mmolK of the second products of 5.1mmol 2 and 30ml acetone, 1ml2CO3Mixing is heated at 65 DEG C
Stirring, condensing reflux are reacted 4 hours, are cooled to room temperature.Column chromatography purifies, and eluant, eluent is dichloromethane, isolated yellow green
Mucus, as third product 2.
The N-Methyl pyrrolidone of 4.5mmol third products 2 and 10ml are dissolved, in 220 DEG C of heating stirrings, condensing reflux
Reaction 3 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is dichloromethane, detaches to obtain yellow-brown solid, as product 2.
Product 2 is C through Structural Identification20H15ClFNO。
Embodiment 3
The present embodiment is to prepare C according to above-mentioned preparation method20H15The specific embodiment of ClFNO.
The chloro- 6- fluorobenzaldehydes of the 2- of the 8- hydroxyls quinaldine of 9.43mmol and 12mmol are dissolved in 15ml acetic anhydrides to mix,
In 145 DEG C of heating stirrings, condensing reflux is reacted 22 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is petroleum ether/acetic acid
Ethyl ester isolates brown solid, is the first product 3.
5ml water agitating and heatings are added in 140 DEG C of heating stirrings in the first products of 6.2mmol 3 and 10ml pyridinium dissolutions, it is cold
Solidifying back flow reaction 3 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is petrol ether/ethyl acetate, isolated canescence
Solid, as the second product 3.
By the 3- bromopropenes and 8mmolK of the second products of 5.1mmol 3 and 35ml acetone, 1.5ml2CO3Mixing adds at 65 DEG C
Thermal agitation, condensing reflux are reacted 5 hours, are cooled to room temperature.Column chromatography purifies, and eluant, eluent is dichloromethane, isolated yellowish green
Color mucus, as third product 3.
The N-Methyl pyrrolidone of 4.5mmol third products 3 and 15ml are dissolved, in 220 DEG C of heating stirrings, condensing reflux
Reaction 4 hours, is cooled to room temperature.Column chromatography purifies, and eluant, eluent is dichloromethane, detaches to obtain yellow-brown solid, as product 3.
Product 3 is C through Structural Identification20H15ClFNO。
Embodiment 4
The present embodiment is C made from 1~embodiment of embodiment 320H15ClFNO is as fluorescence probe to Hg2+Selectivity.
It is 1 in volume ratio:In 1 methanol-water mixed solution, after 10 μM of 8-hydroxyquinoline class fluorescence probe is added, then
It is separately added into the Li of one times of equivalent+、Na+、K+、Mg2+、Ca2+、Ba2+、La3+、Fe2+、Fe3+、Co2+、Ni2+、Cu2+、Ag+、Zn2+、
Cd2+、Hg2+And Al3+Ion, the fluorescence spectrum of ion fore-and-aft architecture is added with wavelength for the excitation light measurement of 351nm, and gained is surveyed
It is fixed that the results are shown in Figure 2.
As shown in Figure 2, Hg is only added2+Afterwards, occur stronger new emission peak, explanation at 506nm：Embodiment 1~
C made from embodiment 320H15ClFNO is a kind of to Hg2+The Ratiometric fluorescent probe of response.
Embodiment 5
The present embodiment is C made from 1~embodiment of embodiment 320H15ClFNO is as fluorescence probe, to various concentration Hg2+
Fluoroscopic examination.
It is 1 in volume ratio:In 1 methanol-water mixed solution, after 10 μM of 8-hydroxyquinoline class fluorescence probe is added, then
Add respectively according to a concentration of 0 μM, 1 μM, 2 μM, 3 μM, 4 μM, 5 μM, 6 μM, 7 μM, 8 μM, 9 μM, 10 μM, 12 μM, 15 μM and 20 μM
Enter Hg2+, it is the exciting light of 351nm with wavelength, measures and Hg is added2+The fluorescence spectrum of front and back 8-hydroxyquinoline class fluorescence probe, knot
Fruit is as shown in Figure 3.
From figure 3, it can be seen that with Hg2+The increase of ion concentration, 8-hydroxyquinoline class fluorescence probe is at 506nm
Fluorescence intensity gradually increases, and the fluorescence intensity change at 428nm is little.
Fluorescence peak intensity rate I506/I428 is as ordinate, c (c Hg using at 506nm and at 428nm2+It is mole dense
Degree) it works curve as abscissa, working curve is shown in Fig. 4, according to Fig. 4 as can be seen that Hg2+For 1 equivalent when fluorescence intensity reach
To saturation, meanwhile, working curve also clearly shows that 8-hydroxyquinoline class fluorescence probe and Hg2+Combination ratio be 1:1, work as Hg2+
When concentration range is in 0~10 μM, I506/I428Good linear relationship is presented with c, calcium is：
I506/I428=0.25832*c+0.03364, (R2=0.96836).
The present embodiment experimental results show that the 8-hydroxyquinoline class fluorescence probe can be used for quantitative detection Hg2+,
Good linear relationship, high sensitivity is presented in I506/I428 and c.
Embodiment 6
The present embodiment is C made from 1~embodiment of embodiment 320H15ClFNO is as fluorescence probe, other common metals
Example is for Hg2+Fluoroscopic examination interference experiment measure.
It is 1 in volume ratio:After 10 μM of 8-hydroxyquinoline class fluorescence probe is added in 1 methanol-water mixed solution, respectively
The Hg of one times of equivalent is all added2+Afterwards, then it is separately added into the Li of equimolar amounts+、Na+、K+、Mg2+、Ca2+、Ba2+、La3+、Fe2+、Fe3 +、Co2+、Ni2+、Cu2+、Ag+、Zn2+、Cd2+、Hg2+And Al3+Ion is the exciting light of 351nm with wavelength, measures and Hg is added2+From
The fluorescence spectrum of 8-hydroxyquinoline class fluorescence probe before and after son, the fluorescence peak intensity rate at 506nm and at 428nm by record
I506/I428Change with different metal ions is turned into block diagram, and acquired results are as shown in Figure 5.
It is obtained by the present embodiment the experimental results showed that, the 8-hydroxyquinoline class fluorescence probe is right in methanol-water mixture
Hg2+There is high sensitivity, the presence of other metal ions in solution to interfere its measurement result less, detection for the detection of ion
As a result reliable and stable.
In conclusion the present invention provides a kind of 8-hydroxyquinoline derivative, the molecule of the 8-hydroxyquinoline derivative
Formula is：C20H15ClFNO；The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline derivative；Meanwhile the present invention
It additionally provides above-mentioned 8-hydroxyquinoline derivative or product that above-mentioned preparation method obtains is in Hg2+Application in detection.Through experiment
Detection can obtain, and the compound obtained by technical solution provided by the invention is as fluorescence probe in use, only to Hg2+Response, it is special
It is anisotropic strong；For various concentration Hg2+When being detected, good linear relationship is presented, can be applied to Hg2+Quantitative detection；
For detection have high sensitivity, remove Hg2+Other metal ions interfere very little, detection method reliably steady measurement result
It is fixed.It solves in the prior art, the detection of mercury ion has the response time long and the sensitive low technological deficiency of detection.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (8)
1. a kind of preparation method of 8-hydroxyquinoline derivative, which is characterized in that the structural formula of the 8-hydroxyquinoline derivative
For：
The preparation method is that：
Step 1: 8- hydroxyls quinaldine and the chloro- 6- fluorobenzaldehydes of 2- are dissolved in acetic anhydride, are purified after stirring, obtain the first product；
Step 2: first product is dissolved in the mixed liquor of pyridine and water, purified after stirring, obtains the second product；
Step 3: second product is dissolved in acetone, K is added2CO3With 3- bromopropenes, is purified after stirring, obtain third product；
Step 4: the third product is dissolved in N-Methyl pyrrolidone, is purified after stirring, obtain product.
2. preparation method according to claim 1, which is characterized in that the 8- hydroxyls quinaldine, the chloro- 6- fluorobenzaldehydes of 2-
Rate of charge with acetic anhydride is 9.43mmol:(11.32~12) mmol:(10~15) mL.
3. preparation method according to claim 1, which is characterized in that the temperature stirred described in step 1 is 140~145
DEG C, the time stirred described in step 1 is 18~22h.
4. preparation method according to claim 1, which is characterized in that the rate of charge of first product, pyridine and water is
6.2mmol:10mL:(5~10) mL.
5. preparation method according to claim 1, which is characterized in that the temperature stirred described in step 2 is 130~140
DEG C, the time stirred described in step 2 is 3~4h.
6. preparation method according to claim 1, which is characterized in that second product, K2CO3, 3- bromopropenes and acetone
Rate of charge be 5.1mmol:8mmol:(1~1.5) mL:(30~35) mL.
7. preparation method according to claim 1, which is characterized in that the temperature stirred described in step 3 is 60~65 DEG C,
The time stirred described in step 3 is 4~5h.
8. preparation method according to claim 1, which is characterized in that the throwing of the third product and N-Methyl pyrrolidone
Material is than being 4.5mmol:(10~15) mL；
The temperature stirred described in step 4 is 210~220 DEG C, and the time stirred described in step 4 is 3~4h.
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