CN109294143A - A kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material and preparation method and application - Google Patents
A kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material and preparation method and application Download PDFInfo
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- CN109294143A CN109294143A CN201811071551.1A CN201811071551A CN109294143A CN 109294143 A CN109294143 A CN 109294143A CN 201811071551 A CN201811071551 A CN 201811071551A CN 109294143 A CN109294143 A CN 109294143A
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- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
Abstract
The present invention relates to a kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material and preparation method and applications.The technical solution adopted is that: polymeric ionic liquid (PILs) is modified by noncovalent interaction to the surface redox graphene (rGO), then by simple electrostatic interaction in the further rhetorical function molecule beta-cyclodextrin of composite material surface (β-CD), a kind of novel β-CD/PILs-rGO composite material for having both PILs, β-CD and rGO characteristic is prepared, the composite material can be used for fluorescence detection cholesterol, have good detection performance.
Description
Technical field
The invention belongs to field of compound material more particularly to a kind of cyclodextrin-polymeric ionic liquid functionalization graphene are multiple
Condensation material and its preparation method and application.
Background technique
Cholesterol (Cholesterol) is also known as cholesterine, is the basic structure ingredient of animal cell membrane, is maintaining cell membrane
It plays an important role in complete and mobility, cholesterol is also the biosynthesis precursor of bile acid and steroid hormone.Blood
Middle cholesterol levels are excessively high, will increase the risk for suffering from vascular diseases, including coronary heart disease, hypertension and atherosclerosis.It is another
Aspect, cholesterol level deficiency are considered related to depression, cancer and the performance of cerebral hemorrhage.It follows that Blood Cholesterol
Content is an important indicator of clinical biochemistry.Up to the present, methods have been developed various cholesterol detections point
Analysis method, such as colorimetric method, electrochemical process, chromatography and fluorescence method etc..However, the high method of most of selectivity all relies on
The oxidation reaction of cholesterol oxidase, more expensive and easy inactivation.Therefore, develop and improve it is a kind of have it is highly selective,
The method of inexpensive, convenient cholesterol detection is very necessary.
In recent years, grapheme material due to its have many advantages, such as large specific surface area, good electric conductivity, high transparency and and
It is concerned, in the numerous excellent properties of grapheme material, the characteristic of large specific surface area makes it be suitable for as carrier material.Polymerization
Ionic liquid is similar to ionic liquid, has good ion exchangeable, it is compound with graphene, can not only assign graphite
The good water dispersible of alkene material, while being easy to introduce functional mass.Beta-cyclodextrin is due to hydrophilic peripheral and hydrophobic
Inner cavity can form inclusion compound, the efficient choosing that beta-cyclodextrin and its derivative are separated as structure with gas chromatography in the solution
Device, outstanding pharmaceutical carrier and the good main body of molecular recognition is selected to be widely studied.Polymeric ionic liquid can be simple, quick, high
Beta-cyclodextrin is introduced into grapheme material surface by effect ground, the unique molecular recognition performance of graphene is assigned, by the composite material
For in the cholesterol fluorescence detection application of no enzyme.
Summary of the invention
The present invention arrives polymeric ionic liquid by π-π interaction, by beta-cyclodextrin by the way that electrostatic adsorption is immobilized
Grapheme material surface, it is therefore an objective to obtain a kind of having both polymeric ionic liquid highly dissoluble, the inclusion characteristic of beta-cyclodextrin and stone
The novel cyclodextrin of black alkene material high-specific surface area characteristic-polymeric ionic liquid functionalization graphene composite material (β-CD/
PILs-rGO).The method for synthesizing composite material is simple, easy purification, has good dispersibility in water, is using fluorescent method
There is good application prospect in the fields such as cholesterol detection.
To achieve the above object, the technical solution adopted by the present invention is that: a kind of cyclodextrin-polymeric ionic liquid function fossil
Black alkene composite material, preparation method include the following steps:
1) preparation of polymeric ionic liquid modification graphite alkene compound (PILs-rGO): by graphene oxide ultrasonic disperse
In deionized water, the suspension of stable dispersion is formed, polymeric ionic liquid, magnetic agitation and ultrasound is added, is adjusted with NaOH
Hydrazine hydrate is added dropwise thereto, reacts under the conditions of 90-110 DEG C for pH value of solution, and product is centrifuged and washes and is dried in vacuo, obtains PILs-
rGO；
2) cyclodextrin-polymeric ionic liquid functionalization graphene composite material (β-CD/PILs-rGO) preparation, by sulfonic acid
Change beta-cyclodextrin ultrasonic disperse in deionized water, takes PILs-rGO aqueous dispersions to mix with sulfonated β-CD aqueous dispersions, magnetic
Power stirring, product is centrifuged and is washed, and vacuum drying obtains target product β-CD/PILs-rGO.
Preferably, above-mentioned a kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material, the polymerization from
Sub- liquid is made by 1- vinyl -3- imidazole-butyl bromide salt monomer.
Preferably, above-mentioned a kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material, the polymerization from
Sub- liquid the preparation method comprises the following steps: 1- vinyl -3- imidazole-butyl bromide salt monomer and azodiisobutyronitrile are dissolved in chloroform, be passed through
Nitrogen, flow back 3h under 70 DEG C of oil baths, three times with chloroform by product, is dried in vacuo to get target product.
Preferably, above-mentioned a kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material, step 1) is middle to be adjusted
Solution ph is 10.
Preferably, above-mentioned a kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material, the ring paste
Essence-polymeric ionic liquid functionalization graphene composite material is the laminated structure of ultrathin transparent.
A kind of above-mentioned cyclodextrin-polymeric ionic liquid functionalization graphene composite material answering in cholesterol detection
With.Method is as follows: weigh above-mentioned cyclodextrin-polymeric ionic liquid functionalization graphene composite material, ultrasonic disperse in water,
Cyclodextrin-polymeric ionic liquid functionalization graphene aqueous nancomposite dispersion liquid, fluorescent material are added in phosphate buffer solution,
Magnetic agitation 30min stands 10min, and the solution containing cholesterol is added, and stirring is transferred in cuvette, carries out fluorescence inspection
It surveys.
Preferably, the cyclodextrin-polymeric ionic liquid functionalization graphene aqueous nancomposite dispersion liquid concentration is
2mg/mL。
Preferably, the fluorescent material is rhodamine B, and concentration is 2 μm of ol/L.
The beneficial effects of the present invention are:
1, the present invention has obtained a kind of novel cyclodextrin-polymeric ionic liquid functionalization graphene composite material, preparation letter
It is single, at low cost.
2, the composite material prepared by the present invention has both good water dispersible, large specific surface area and inclusion characteristic.
3, the present invention prepared by composite material can be used for cholesterol detection, have the characteristics that it is highly selective, easy to detect,
There is good application prospect in cholesterol detection field.
Detailed description of the invention
Fig. 1 is the TEM figure of β-CD/PILs-rGO.
Fig. 2 is that the ultraviolet-visible of β-CD (a), PILs-rGO (b), GO (c) and β-CD/PILs-rGO (d) aqueous dispersions is inhaled
Receive spectrum.
Fig. 3 is the XRD diagram of GO (a), PILs-rGO (b) and β-CD/PILs-rGO (c).
Fig. 4 is rhodamine B (RB) aqueous dispersions (a)；RB+PILs-rGO mix moisture dispersion liquid (b)；RB+β-CD/PILs-
The fluorescence spectra of rGO+ cholesterol mix moisture dispersion liquid (c) and RB+ β-CD/PILs-rGO (d) mix moisture dispersion liquid.
Fluorescence curve when Fig. 5 A is the cholesterol solution addition β-CD/PILs-rGO-RB system of various concentration, a-y points
Not corresponding to cholesterol concentration is 0,0.01,0.02,0.03,0.04,0.05,0.1,0.2,0.3,1,2,3,4,5,10,20,30,
40,50,100,150,200,300,400,500 μm of olL-1When fluorescence curve.
Fig. 5 B is the curve that peak fluorescence intensity changes with cholesterol concentration.
Fig. 5 C is that cholesterol concentration is 0.01-5.0 μm of olL-1Range inner cholesterol concentration/peak fluorescence intensity is solid with gallbladder
The linear relationship chart of determining alcohol variation.
Fig. 5 D is that cholesterol concentration is 5.0-500 μm of olL-1Range inner cholesterol concentration/peak fluorescence intensity is solid with gallbladder
The linear relationship chart of determining alcohol variation.
Specific embodiment
1 cyclodextrin of embodiment-polymeric ionic liquid functionalization graphene composite material (β-CD/PILs-rGO)
(1) preparation method
1, the synthesis of graphene oxide
Graphene oxide is prepared using Hummer method.The concentrated sulfuric acid of 67.5mL is added into three neck round bottom flask, then will
It is placed in ice-water bath, adds the high purity graphite of 2g and the NaNO of 1.6g3, after mixing evenly, at 5 DEG C hereinafter, being slowly added to
The solid KMnO of 9g4, about 1h adds, and 30min is reacted between 32-38 DEG C, has a small amount of bubble to generate.It reacts close to terminal
When, the suspension of black becomes the dope of taupe, places 5 days at room temperature.Then it is diluted with the hot water of 560mL, finally
H is added dropwise2O2Remaining high price manganese ion is restored, until solution becomes glassy yellow.Product is centrifuged 10min through 10000rpm, uses
The NaOH solution of 0.01mol/L neutralizes extra acid, is then detected into supernatant with barium salt without SO4 2-In the presence of being washed with water
It is washed twice to neutrality, then with dehydrated alcohol, vacuum drying obtains target product.
2, the synthesis of PILs-rGO composite material
The preparation of polymeric ionic liquid poly- (1- vinyl -3- butyl imidazole bromide) (PILs): by 4g 1- vinyl -3-
Imidazole-butyl bromide salt monomer and 0.08g azodiisobutyronitrile are added in round-bottomed flask, and chloroform is added, nitrogen is passed through, at 70 DEG C
Flow back 3h under oil bath, three times with chloroform by product, to get target product after vacuum drying.
The GO of 50mg is taken to be scattered in 100mL deionized water, ultrasonic 3h forms the suspension of stable dispersion.400mg is added
Polymeric ionic liquid is poly- (1- vinyl -3- butyl imidazole bromide), magnetic agitation 1h, ultrasonic 20min.It is molten with 1mol/L NaOH
PH is adjusted to 10 by liquid, and 0.53mL hydrazine hydrate is added dropwise thereto, reacts 1h under the conditions of 100 DEG C.Product is centrifuged 20min through 12000rpm
Afterwards, it is washed with water, is repeated 3 times, to remove extra hydrazine hydrate.Centrifugal solids product vacuum is dry, it obtains PILs-rGO and receives
Nano composite material.Product 20mg is taken, is ground, ultrasonic disperse is in 20mL deionized water.
3, the synthesis of β-CD/PILs-rGO composite material
Sulfonated β-the CD of 300mg is taken to be scattered in 60mL deionized water, ultrasonic 30min.Take PILs-rGO nanometers of 30mL
Aqueous nancomposite dispersion liquid, the sulfonated β-CD aqueous dispersions of 60mL are in beaker, magnetic agitation 3h.Product is centrifuged
It after (10000rpm, 8min), is washed with water, is repeated 3 times.Centrifugal solids product vacuum is dry, it is multiple to obtain β-CD/PILs-rGO
Condensation material.By β-CD/PILs-rGO composite material mortar grinder at powder, ultrasonic disperse is formed in deionized water again
Concentration is the uniform dispersion liquid of 2mg/mL.
(2) experimental result
Fig. 1 is the TEM shape appearance figure of β-CD/PILs-rGO compound, and β-CD/PILs-rGO is ultra-thin as we can see from the figure
Transparent laminated structure, edge crimp, and lateral dimension is about in several hundred nanometers to several microns.
Fig. 2 is the ultraviolet spectrogram of β-CD (a), PILs-rGO (b), GO (c) and β-CD/PILs-rGO (d) aqueous dispersions.
It is the π-π * transition of C=C on GO by curve c it is found that the characteristic peak of GO is 230nm.When GO is reduced under PILs concurrent conditions
Afterwards (b), characteristic peak red shift is at 270nm, this illustrates that the oxide group of GO is reduced, and the pi-conjugated system of π-is restored.It is basic herein
On, by being further introduced into β-CD, for β-CD within this range substantially without characteristic peak (a), compound still has suction at the place 270nm or so
It receives peak and there is (d), illustrate property of the modification without influence PILs-rGO nano-complex of β-CD.
Fig. 3 is the XRD diagram of GO (a), PILs-GP (b) and PILs-GP/ β-CD (c).The diffraction spectra of GO (a) goes out at 11.5 °
Existing graphite (001) crystallographic plane diffraction peak, it was demonstrated that graphite is oxidized completely.PILs-GP (b) and PILs-GP/ β-CD (c) are at 24.2 °
There is wider diffraction maximum in place, is graphite (002) crystallographic plane diffraction peak.
The application of 2 cyclodextrin of embodiment-polymeric ionic liquid functionalization graphene composite material (β-CD/PILs-rGO)
(1) cyclodextrin-application of the polymeric ionic liquid functionalization graphene composite material in terms of cholesterol detection
2 μm of ol/L rhodamine B (RB) solution of 0.06mL are taken, are diluted to 3.00mL with the phosphate buffer solution that pH is 7.4,
It stirs evenly, surveys fluorescence spectra with sepectrophotofluorometer.
2 μm of 0.02mL 2mg/mL PILs-rGO aqueous dispersions, 0.06mL ol/L rhodamine B solutions are taken, are 7.4 with pH
Phosphate buffer solution be diluted to 3.00mL, stir evenly, with sepectrophotofluorometer survey fluorescence spectra.
2 μm of 0.20mL 2mg/mL β-CD/PILs-rGO aqueous dispersions, 0.06mL ol/L rhodamine B solutions are taken, are with pH
7.4 phosphate buffer solution is diluted to 3.00mL, magnetic agitation 30min, and 3 μ L 0.5mol/L cholesterol solutions, stirring is added
3min surveys fluorescence spectra with sepectrophotofluorometer.
2 μm of 0.20mL 2mg/mL β-CD/PILs-rGO aqueous dispersions, 0.06mL ol/L rhodamine B solutions are taken, are with pH
7.4 phosphate buffer solution is diluted to 3.00mL, magnetic agitation 30min, surveys fluorescence spectra with sepectrophotofluorometer.
Fig. 4 is rhodamine B aqueous dispersions (a), RB+PILs-rGO mix moisture dispersion liquid (b), RB+ β-CD/PILs-rGO+
The fluorescence spectra of cholesterol mix moisture dispersion liquid (c) and RB+ β-CD/PILs-rGO mix moisture dispersion liquid (d).Rhodamine B with
The fluorescence intensity (b) of PILs-rGO mixed liquor is more much higher than rhodamine B and the fluorescence intensity of β-CD/PILs-rGO (d) mixed liquor,
This shows that the variation of fluorescence intensity is mainly as caused by the effect between rhodamine B and β-CD.When cholesterol be added rhodamine B with
After the mixed liquor (c) of β-CD/PILs-rGO, fluorescence intensity is increased, illustrate cholesterol instead of rhodamine B, therefore the detection system
System can be used for cholesterol detection, and have good sensibility to the detection of cholesterol.
(2) detection performance of the cyclodextrin-polymeric ionic liquid functionalization graphene composite material to various concentration cholesterol
Take cyclodextrin prepared by 25 parts of embodiments 1 (one)-polymeric ionic liquid functionalization graphene aqueous nancomposite
Dispersion liquid, every part of 0.20mL are separately added into 0.06mL (2 μm of ol/L) rhodamine B solution in every part, the phosphoric acid buffer for being 7.4 with pH
Solution is diluted to 3.00mL.Stand 10min after magnetic agitation 30min, be added the cholesterol solution of various concentration, cholesterol it is dense
Degree is respectively as follows: 0,0.01,0.02,0.03,0.04,0.05,0.1,0.2,0.3,1,2,3,4,5,10,20,30,40,50,100,
150,200,300,400,500 μm of olL-1, stir 3min.Fluorescence spectra is surveyed with sepectrophotofluorometer.
Fluorescence curve when Fig. 5 A is the cholesterol solution addition β-CD/PILs-rGO-RB system of various concentration.Fluorescence is surveyed
Surely selected excitation wavelength is 420nm, and launch wavelength range is 500-730nm, and exciting slit width is 10nm, transmite slit width
For 5nm, peak fluorescence intensity corresponding wavelength is about 579nm.As seen from the figure, curve a is fluorescence curve when cholesterol not being added,
It is 10 μm of olL when 3 μ L concentration are added-1Cholesterol solution when, fluorescence signal enhancing, be curve b.With the cholesterol of addition
Concentration be gradually increased, fluorescence signal gradually increases.The peak value of every group of curve fluorescence intensity is changed with cholesterol concentration and is mapped,
Obtain Fig. 5 B.Fig. 5 C and Fig. 5 D are the line that various concentration range inner cholesterol concentration/peak fluorescence intensity changes with cholesterol concentration
Sexual intercourse figure.It is 0.01-5.0 μm of olL that curve, which is the range of linearity of cholesterol concentration detection, in Fig. 5 C-1, linear equation y=
0.111x+0.006, R2Value is 0.999.It is 5.0-500 μm of olL that curve, which is the range of linearity of cholesterol concentration detection, in Fig. 5 D-1, linear equation y=0.030x+0.865, R2Value is 0.998.
Claims (9)
1. a kind of cyclodextrin-polymeric ionic liquid functionalization graphene composite material, it is characterised in that: preparation method includes as follows
Step:
1) preparation of polymeric ionic liquid modification graphite alkene compound (PILs-rGO): by graphene oxide (GO) ultrasonic disperse
In deionized water, the suspension of stable dispersion is formed, polymeric ionic liquid, magnetic agitation and ultrasound is added, is adjusted with NaOH
Hydrazine hydrate is added dropwise thereto, reacts under the conditions of 90-110 DEG C for pH value of solution, and product is centrifuged and washes and is dried in vacuo, obtains PILs-
rGO；
2) cyclodextrin-polymeric ionic liquid functionalization graphene composite material (β-CD/PILs-rGO) preparation: by sulfonated β-
Cyclodextrin ultrasonic disperse takes PILs-rGO aqueous dispersions to mix with sulfonated β-CD aqueous dispersions, magnetic force stirs in deionized water
It mixes, product is centrifuged and is washed, vacuum drying obtains target product β-CD/PILs-rGO.
2. a kind of cyclodextrin according to claim 1-polymeric ionic liquid functionalization graphene composite material, feature exist
In: the polymeric ionic liquid is made by 1- vinyl -3- imidazole-butyl bromide salt monomer.
3. a kind of cyclodextrin according to claim 2-polymeric ionic liquid functionalization graphene composite material, feature exist
In: polymeric ionic liquid the preparation method comprises the following steps: 1- vinyl -3- imidazole-butyl bromide salt monomer and azodiisobutyronitrile are dissolved in chlorine
In imitative, it is passed through nitrogen, flow back 3h under 70 DEG C of oil baths, three times with chloroform by product, is dried in vacuo to get target product.
4. a kind of cyclodextrin according to claim 1-polymeric ionic liquid functionalization graphene composite material, feature exist
In: it is 10 that solution ph is adjusted in step 1).
5. a kind of cyclodextrin according to claim 1-polymeric ionic liquid functionalization graphene composite material, feature exist
In: the cyclodextrin-polymeric ionic liquid functionalization graphene composite material is the laminated structure of ultrathin transparent.
6. a kind of cyclodextrin described in claim 1-polymeric ionic liquid functionalization graphene composite material is in cholesterol detection
In application.
7. application according to claim 6, which is characterized in that method is as follows: weighing cyclodextrin-described in claim 1
Polymeric ionic liquid functionalization graphene composite material, ultrasonic disperse is in water, by cyclodextrin-polymeric ionic liquid function fossil
Black alkene aqueous nancomposite dispersion liquid, fluorescent material are added in phosphate buffer solution, and magnetic agitation 30min stands 10min, are added
Solution containing cholesterol, stirring, is transferred in cuvette, carries out fluorescence detection.
8. application according to claim 7, it is characterised in that: the cyclodextrin-polymeric ionic liquid function graphite
Alkene aqueous nancomposite dispersion liquid concentration is 2mg/mL.
9. application according to claim 7, it is characterised in that: the fluorescent material is rhodamine B, and concentration is 2 μm of ol/
L。
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110514712A (en) * | 2019-09-24 | 2019-11-29 | 辽宁大学 | A kind of polymeric ionic liquid modification MXene nanocomposite and its preparation method and application |
| CN110836920A (en) * | 2019-11-20 | 2020-02-25 | 山西大学 | Copper nanowire-molybdenum disulfide-graphene compound and preparation method and application thereof |
| CN113244900A (en) * | 2021-06-04 | 2021-08-13 | 中国农业大学 | Preparation method and application of functionalized magnetic beta-cyclodextrin polymer magnetic solid-phase extraction material |
-
2018
- 2018-09-14 CN CN201811071551.1A patent/CN109294143B/en active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110514712A (en) * | 2019-09-24 | 2019-11-29 | 辽宁大学 | A kind of polymeric ionic liquid modification MXene nanocomposite and its preparation method and application |
| CN110836920A (en) * | 2019-11-20 | 2020-02-25 | 山西大学 | Copper nanowire-molybdenum disulfide-graphene compound and preparation method and application thereof |
| CN110836920B (en) * | 2019-11-20 | 2021-07-02 | 山西大学 | Copper nanowire-molybdenum disulfide-graphene compound and preparation method and application thereof |
| CN113244900A (en) * | 2021-06-04 | 2021-08-13 | 中国农业大学 | Preparation method and application of functionalized magnetic beta-cyclodextrin polymer magnetic solid-phase extraction material |
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