CN104645938B - A kind of preparation method of dyefunctionalized magnetic Nano material and its application of fluorescence sense and Magneto separate TNT - Google Patents
A kind of preparation method of dyefunctionalized magnetic Nano material and its application of fluorescence sense and Magneto separate TNT Download PDFInfo
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- CN104645938B CN104645938B CN201510073819.5A CN201510073819A CN104645938B CN 104645938 B CN104645938 B CN 104645938B CN 201510073819 A CN201510073819 A CN 201510073819A CN 104645938 B CN104645938 B CN 104645938B
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
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- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
The invention discloses the application of a kind of preparation method of dyefunctionalized magnetic Nano material and its fluorescence sense and Magneto separate TNT it is characterised in that：First the ferriferrous oxide nanometer material obtaining Coated with Oleic Acid is reacted in Oleic acid with Oleic acid iron complex and oleyl amine；Again the ferriferrous oxide nanometer material of Coated with Oleic Acid is dispersed in the diethyl ether solution of 2 phosphoric acid ethamine and completes ligand exchange, obtain the ferriferrous oxide nanometer material of 2 phosphoric acid ethamine claddings；Last reaction with fluorescein isocyanate again obtains final product target product.The trace TNT that the dyefunctionalized magnetic Nano material of the present invention can sense and remove in pollution water sample, and there is reproducibility.
Description
Technical field
The invention belongs to technical field of nanometer material preparation, it is related to a kind of renewable fluorescence sense quick-fried with Magneto separate TNT height
The preparation method of the nano material of thing.
Background technology
Due to the biopersistence of TNT, toxicity and mutagenicity, TNT becomes one to the pollution of soil, air and subsoil water
Public topic.Report shows：Human or animal, will be to nervous system, kidney, liver and other after being exposed to for a long time in TNT atmosphere
Tissue produces major injury；Additionally, it also has, other toxic and side effects include leukocytosiss, peripheral neuritiss, heart are lost a war
With tumor of bladder etc..Therefore, develop highly sensitive method to be particularly important with removing TNT with selectivity sensing.
At present, the analysis of TNT is focused primarily on the high-sensitive method for sensing of development, the TNT's in understanding TNT contaminant water
Concrete concentration；Or development enrichment material, removes the TNT in contaminated samples.Wherein, FRET (fluorescence resonance energy transfer) or electric charge transfer
Method for quenching can in sensing sample TNT to subnanomole level.And TNT enrichment material is mainly included nano material and is polymerized with molecular engram
Thing etc..Nano material is larger because of its specific surface, has very strong absorbability, but its absorption does not have selectivity and adsorption capacity is relatively
Little；TNT imprinted polymer has good selective adsorption capacity to TNT, but most " trace cave " is located in polymer
Portion, mass transfer ability is weak, and the preparation of imprinted polymer is relatively difficult to control, and which has limited the range of application of the method.
Therefore, how simply, it is achieved at low cost sensing and the enrichment for TNT in contaminant water, remain function nano material
The a great problem of preparing technical field.
Content of the invention
It is an object of the invention to provide a kind of preparation method of dyefunctionalized magnetic Nano material and its fluorescence pass
Application in sense and Magneto separate TNT；
It is another object of the present invention to realizing dyefunctionalized magnetic Nano material after fluorescence sense with Magneto separate TNT
Regeneration.
The present invention solves technical problem, adopts the following technical scheme that：
The preparation method of the dyefunctionalized magnetic Nano material of the present invention, its feature is to carry out as follows：
(1) weigh 3～6 mmoles Oleic acid iron complexes and 20～40 milliliters of oleyl amines are added in flask, add 5～15 millis
Rise Oleic acid and be heated to 120 DEG C, stir to the dissolving of Oleic acid iron complex, obtain mixed solution；
(2) described mixed solution is warmed up to 200 DEG C, simultaneously constant temperature, after 2 hours, continues to be warmed up to 300～320 for nitrogen charging dehydration
DEG C, and constant temperature 2 hours；
(3) naturally cool to room temperature, filter to obtain precipitate, then deionized water and absolute ethanol washing gained sink successively
Starch；
(4) put the precipitate in vacuum drying oven and be dried 6 hours with 40～60 DEG C of temperature, obtain the four of Coated with Oleic Acid
Fe 3 O nano material；
(5) 2- phosphoric acid ethylamine is obtained in absolute ether the ether of the 2- phosphoric acid ethamine that mass concentration is 4～5%
Solution, the ferriferrous oxide nanometer material of described Coated with Oleic Acid is dispersed in the diethyl ether solution of described 2- phosphoric acid ethamine, ultrasonic
Under complete ligand exchange, then pass through Magneto separate, obtain 2- phosphoric acid ethamine cladding ferriferrous oxide nanometer material；
(6) fluorescein isocyanate is dissolved in the ethanol solution obtaining fluorescein isocyanate in dehydrated alcohol；By institute
The ferriferrous oxide nanometer material stating 2- phosphoric acid ethamine cladding is dispersed in dehydrated alcohol, then is added dropwise over described fluorescein isocyanide
The ethanol solution of acid esters, mechanical agitation 12 hours under room temperature under nitrogen, then separated by Magnet, gained solid product spends successively
After ionized water and absolute ethanol washing, obtain final product dyefunctionalized magnetic Nano material；
The ferriferrous oxide nanometer material of described 2- phosphoric acid ethamine cladding with the mass ratio of described fluorescein isocyanate is
100:1.
The Oleic acid iron complex that above-mentioned preparation method is used can be prepared as follows obtaining：
By FeCl3·6H2O prepares Oleic acid iron complex with enuatrol for raw material.Simply, by 5.4 grams of FeCl3·6H2O
In the mixed solution that 18.25g enuatrol is dissolved in 40 milliliters of ethanol, 30 milliliters of redistilled waters and 70 milliliters of hexane compositions,
Solution is heated to 70 DEG C and keeps 4 hours, after reaction terminates, the organic layer second distillation containing Oleic acid iron complex is washed
Wash 3 times, obtain wax-like Oleic acid iron complex after hexane is steamed.
Dyefunctionalized magnetic Nano material pattern prepared by the present invention is in spherical, and structure is homogeneous, single dispersing, and diameter is about
8～10 nanometers, there is super magnetic property and fluorescent dye can be coupled.
The dyefunctionalized magnetic Nano material of said method preparation can be used for fluorescence sense and Magneto separate TNT.Due to TNT
Upper three nitros are that strong electron-withdrawing group is rolled into a ball so that the phenyl ring of TNT is positively charged relative to short of electricity, the phenyl ring of TNT short of electricity easily with
The such as amine etc. of molecule containing lone electron pair occurs Acid-Base pairing effect to form Meisenheimer coordination compound, the absworption peak of this coordination compound
Positioned at 516 ran.When using, dyefunctionalized magnetic Nano material is dispersed in the aqueous solution containing TNT as probe
In, TNT is combined in nanometer Fe by the formation of Meisenheimer coordination compound3O4Surface, by FRET (fluorescence resonance energy transfer) side
Formula is quenched the fluorescence of fluorescein, thus reaching the purpose of TNT sensing；Due to nanometer Fe3O4Magnetic response characteristic, in externally-applied magnetic field
Under effect, can will be combined in nanometer Fe in the form of Meisenheimer coordination compound3O4On TNT from solution separate；TNT with
The combination of amine-containing compound is a kind of reversible action, will combine the Fe of TNT3O4Nanoparticle is dispersed in height and contains in amine aqueous solution,
TNT transfers to, in solution, make Fe3O4Nanoparticle is regenerated.
After the dyefunctionalized magnetic Nano material of the present invention completes fluorescence sense and the Magneto separate of TNT, in external magnetic field
Under effect by the nano material Magneto separate having adsorbed TNT out, then it is immersed in the aqueous solution of ethylenediamine that concentration is 1.0M
12 hours, again Magneto separate and with second distillation water washing so that the fluorescence of dyefunctionalized magnetic Nano material and enriching
Can be restored, realize its regeneration.
Compared with existing TNT sensing or enrichment material, the present invention has the characteristics that following and advantage：
1st, the dyefunctionalized magnetic Nano material of the present invention can sense the trace TNT in pollution water sample：The present invention's
Magnetic Nano material surface is rich in amido, and amido can pass through Acid-Base pairing effect with TNT and combine, the purple of the coordination compound being formed
Outward-visible absorbance is located at 516 nanometers, almost overlapping with 519 nanometers of the transmitting of fluorescein, thus can be turned by fluorescence resonance energy
Shifting mode senses as little as 50 nanometers in water sample of TNT.
2nd, the dyefunctionalized magnetic Nano material of the present invention can be enriched with and remove TNT in eliminating water：Due to nanometer of the present invention
Acid-Base pairing effect between the amido of material and TNT, in water sample, TNT is easily integrated in the surface of magnetic nano-particle, leads to
Cross the effect of externally-applied magnetic field, TNT can be made to separate from water sample.
3rd, the dyefunctionalized magnetic Nano material of the present invention has recyclability：It is immersed in water-soluble containing 1.0M ethylenediamine
12 hours in liquid, Magneto separate after repeatedly washing through secondary water, the fluorescence of magnetic nano-particle is restored with being enriched with performance.
4th, used in the preparation process of dyefunctionalized magnetic Nano material of the present invention, reagent is common agents, becomes
This is low, and reaction condition is easily achieved, and renovation process is convenient.
Brief description
Fig. 1 is the phenogram of the dyefunctionalized magnetic Nano material of embodiment 1 gained, and wherein left figure is the TEM figure of material,
The middle XRD figure for material, right figure is the magnetization curve of material；
Fig. 2 is that the dyefunctionalized magnetic Nano material of embodiment 1 gained is used for fluorescence sense, and wherein left figure relies on for TNT
Property fluorescence spectrum, right figure is fluorescence intensity that TNT concentration is during 1 μm of ol；
Fig. 3 is the test of the dyefunctionalized magnetic Nano material reproducibility of embodiment 1 gained, after 5 wheel experiments, fluorescence
Intensity is kept approximately constant.
Specific embodiment
Below by way of specific embodiment, description detailed complete further is made to technical scheme.Following reality
Applying example is that the present invention is further illustrated, and does not limit the scope of the invention.
Embodiment 1：
The present embodiment prepares dyefunctionalized magnetic Nano material as follows：
(1) weigh in Oleic acid iron complex 4.0 mmoles and the flask of 20 milliliters to 100 milliliters of oleyl amine, add 6 milliliters of Oleic acid
And it is heated to 120 DEG C, stir to the dissolving of Oleic acid iron complex, obtain mixed solution；
(2) mixed solution is warmed up to 200 DEG C, after nitrogen charging is dehydrated and keeps 2 hours, solution is continued to be warmed up to 300 DEG C,
And keep 2 hours；
(3) naturally cool to room temperature, filter to obtain precipitate, then deionized water and absolute ethanol washing 3～5 successively
Secondary；
(4) put the precipitate in vacuum drying oven and be dried 6 hours with 50 DEG C of temperature, obtain four oxidations of Coated with Oleic Acid
Three ferrum nano materials；
(5) by 2- phosphoric acid ethylamine obtain in absolute ether the 2- phosphoric acid ethamine that mass concentration is 5% ether molten
Liquid, the ferriferrous oxide nanometer material of Coated with Oleic Acid is dispersed in the diethyl ether solution of 2- phosphoric acid ethamine, ultrasonic under complete part
Exchange, then pass through Magneto separate, obtain the ferriferrous oxide nanometer material of 2- phosphoric acid ethamine cladding.
(6) by 1.0 milligrams of fluorescein isocyanate be dissolved in dehydrated alcohol obtain fluorescein isocyanate ethanol molten
Liquid；The ferriferrous oxide nanometer material of 100 milligrams of 2- phosphoric acid ethamine claddings is dispersed in dehydrated alcohol, then is added dropwise over fluorescence
The ethanol solution of plain isocyanates, mechanical agitation 12 hours under room temperature under nitrogen, then by Magnet separate, gained solid product according to
Secondary deionized water and absolute ethanol washing 3～5 times, obtain final product dyefunctionalized magnetic Nano material；
Fig. 1 is the phenogram of the dyefunctionalized magnetic Nano material of the present embodiment gained, and wherein left figure is the TEM of material
Figure, the middle XRD figure for material, right figure is the magnetization curve of material.From left figure it can be seen that Fe3O4The size of nanoparticle is divided
Cloth ratio is more uniform, a diameter of 8 ran.Middle figure XRD shows Fe3O4Nanoparticle is magnetic iron ore crystallographic system.Right figure shows Fe3O4
Nanoparticle does not have hysteresis loop, has super magnetic characteristic.
It is used for the property of fluorescence sense and Magneto separate TNT for the test dyefunctionalized magnetic Nano material of the present embodiment gained
Can, do following experiment：Pipetting about 3 milliliters of concentration is the dyefunctionalized magnetic Nano material solution of 1 mg/ml to cuvette
In, measure its fluorescence intensity, then continuous Deca contains 10 microlitres of the ethanol solution of 10 mmoles TNT in solution, until colorimetric
TNT concentration in ware reach 1 micro- rub, one by one measure fluorescence intensity.By the Fe in cuvette3O4Nanoparticle divides through external magnetic field
From rear, measure the TNT solubility before and after separating, the separating effect of assessment TNT with ultraviolet visible spectrophotometry.
Fig. 2 show TNT dependency fluorescence spectrum (left) of the dyefunctionalized magnetic Nano material of the present embodiment；1.0 it is micro-
The TNT rubbing result in the fluorescent quenching (right) of probe.Assessed by ultraviolet-visible spectrum, 1.0 micro- TNT that rub are attached to Fe3O4On
Ratio be 14% about, namely this part TNT can remove from solution.
For the test dyefunctionalized magnetic Nano material of the present embodiment gained after completing fluorescence sense and Magneto separate TNT
Reproducibility, makees following test：The volume of above-mentioned experiment is expanded to 50 milliliters, by detached Fe3O4Nanoparticle is immersed in and contains
12 hours in the aqueous solution of 1.0M ethylenediamine, Magneto separate after repeatedly washing through redistilled water, assess dyefunctionalized magnetic
The fluorescence of nano material and enrichment performance.
Result is as shown in figure 3, as can be seen from the figure after 5 wheel experiments, fluorescence intensity change is maintained at 5% scope
Interior it was demonstrated that the dyefunctionalized magnetic Nano material of the present embodiment has good reproducibility.
Embodiment 2：
(1) weigh in Oleic acid iron complex 6 mmoles and the flask of 40 milliliters to 100 milliliters of oleyl amine, add 15 milliliters of Oleic acid
And it is heated to 120 DEG C, stir to the dissolving of Oleic acid iron complex, obtain mixed solution；
(2) mixed solution is warmed up to 200 DEG C, after nitrogen charging is dehydrated and keeps 2 hours, solution is continued to be warmed up to 320 DEG C,
And keep 2 hours；
(3) naturally cool to room temperature, filter to obtain precipitate, then deionized water and absolute ethanol washing 3～5 successively
Secondary；
(4) put the precipitate in vacuum drying oven and be dried 6 hours with 60 DEG C of temperature, obtain four oxidations of Coated with Oleic Acid
Three ferrum nano materials；
(5) by 2- phosphoric acid ethylamine obtain in absolute ether the 2- phosphoric acid ethamine that mass concentration is 4% ether molten
Liquid, the ferriferrous oxide nanometer material of Coated with Oleic Acid is dispersed in the diethyl ether solution of 2- phosphoric acid ethamine, ultrasonic under complete part
Exchange, then pass through Magneto separate, obtain the ferriferrous oxide nanometer material of 2- phosphoric acid ethamine cladding.
(6) by 1.0 milligrams of fluorescein isocyanate be dissolved in dehydrated alcohol obtain fluorescein isocyanate ethanol molten
Liquid；The ferriferrous oxide nanometer material of 100 milligrams of 2- phosphoric acid ethamine claddings is dispersed in dehydrated alcohol, then is added dropwise over fluorescence
The ethanol solution of plain isocyanates, mechanical agitation 12 hours under room temperature under nitrogen, then by Magnet separate, gained solid product according to
Secondary deionized water and absolute ethanol washing 3～5 times, obtain final product dyefunctionalized magnetic Nano material.
Claims (2)
1. a kind of preparation method of dyefunctionalized magnetic Nano material is it is characterised in that carry out as follows：
(1) weigh 3～6 mmoles Oleic acid iron complexes and 20～40 milliliters of oleyl amines are added in flask, add 5～15 milliliters of oil
Acid is simultaneously heated to 120 DEG C, stirs to the dissolving of Oleic acid iron complex, obtains mixed solution；
(2) described mixed solution is warmed up to 200 DEG C, simultaneously constant temperature, after 2 hours, continues to be warmed up to 300～320 DEG C for nitrogen charging dehydration,
And constant temperature 2 hours；
(3) naturally cool to room temperature, filter to obtain precipitate, then deionized water and absolute ethanol washing gained precipitate successively
Thing；
(4) put the precipitate in vacuum drying oven and be dried 6 hours with 40～60 DEG C of temperature, obtain four oxidations of Coated with Oleic Acid
Three ferrum nano materials；
(5) by 2- phosphoric acid ethylamine obtain in absolute ether the 2- phosphoric acid ethamine that mass concentration is 4～5% ether molten
Liquid, the ferriferrous oxide nanometer material of described Coated with Oleic Acid is dispersed in the diethyl ether solution of described 2- phosphoric acid ethamine, ultrasonic under
Complete ligand exchange, then pass through Magneto separate, obtain the ferriferrous oxide nanometer material of 2- phosphoric acid ethamine cladding；
(6) fluorescein isocyanate is dissolved in the ethanol solution obtaining fluorescein isocyanate in dehydrated alcohol；By described 2-
The ferriferrous oxide nanometer material of phosphoric acid ethamine cladding is dispersed in dehydrated alcohol, then is added dropwise over described fluorescein isocyanate
Ethanol solution, mechanical agitation 12 hours under room temperature under nitrogen, then separated by Magnet, gained solid product uses deionization successively
After water and absolute ethanol washing, obtain final product dyefunctionalized magnetic Nano material；
The described ferriferrous oxide nanometer material of 2- phosphoric acid ethamine cladding and the mass ratio of described fluorescein isocyanate are 100:
1.
2. a kind of application of the dyefunctionalized magnetic Nano material by the method preparation described in claim 1, its feature exists
In：For fluorescence sense and Magneto separate TNT.
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