CN105466898A - Preparation method of amino CQD (carbon quantum dot) fluorescence and 4-nitrophenol molecularly imprinted sensor - Google Patents
Preparation method of amino CQD (carbon quantum dot) fluorescence and 4-nitrophenol molecularly imprinted sensor Download PDFInfo
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- CN105466898A CN105466898A CN201510866335.6A CN201510866335A CN105466898A CN 105466898 A CN105466898 A CN 105466898A CN 201510866335 A CN201510866335 A CN 201510866335A CN 105466898 A CN105466898 A CN 105466898A
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The invention relates to a preparation method of an amino CQD (carbon quantum dot) fluorescence and 4-nitrophenol molecularly imprinted sensor and belongs to the technical field of environment function materials. According to the method, firstly, citric acid and polyethyleneimine are added to water and dissolved, and a transparent solution is obtained; the transparent solution is transferred to a hydrothermal reaction kettle, is heated, reacts and is cooled, and an amino CQD dispersion liquid is obtained; the dispersion liquid is centrifuged, and an amino CQD solution is obtained; the amino CQD solution and ethanol are added to a flask, 4-nitrophenol, AM (acrylamide), EGDMA (ethylene dimethacrylate) and AIBN (2,2'-azobis(2-methylpropionitrile)) are added, N2 is introduced for oxygen removal, after two steps of polymerization, a product is washed with water and ethanol, unreacted substances are removed, and the product is dried in a vacuum drying oven; 4-nitrophenol as a template molecule is eluted by an eluent, and the CQD fluorescence molecularly imprinted polymer is obtained. The fluorescence molecularly imprinted polymer has better optical stability and can rapidly recognize and optically detect 4-nitrophenol.
Description
Technical field
The present invention relates to a kind of preparation method of amino-carbon quantum dot fluorescence p-nitrophenol trace sensor, belong to technical field of environment function material preparation.
Background technology
In recent years, fluorescent carbon applications to nanostructures receives increasing concern, and carbon quantum dot is as novel fluorescence carbon nanomaterial, and the fluorescent characteristic relying on self desirable and biocompatibility excite people's interest widely.Carbon quantum dot had both had desirable anti-light bleaching and flicker free optical characteristics, also there are no cytotoxicity, biological chemistry inertia, thermal stability and the easy metabolic of biosome, therefore, carbon quantum dot can become the fabulous selection replacing traditional quantum dot and organic molecule dyestuff, and multiple field can be widely used in, for this reason, the fundamental research carrying out fluorescent carbon quantum dot has important theory significance and using value, becomes study hotspot in recent years.At present, carbon quantum dot prepare approach and application aspect research has had obvious lifting, the research that carbon quantum dot is used for sensing assays as fluorescence probe is increased year by year, simultaneously along with the preparation of high performance carbon quantum dot and the gradual perfection of surface modification technology are with ripe, the detectability of carbon quantum dot in fluorescence analysis is greatly improved.But the specific selectivity of quantum dot need to improve, its selectivity of mensuration especially for stuctures and properties analog is also not obvious.
Molecular imprinting (Molecularimprintingtechnology, MIT) be preparation has single-minded recognition capability polymkeric substance process to a certain specific molecular, the polymkeric substance of preparation is called molecularly imprinted polymer (Molecularlyimprintedpolymers, MIPs).General first the interaction with selected function monomer by template molecule of the preparation process of MIPs forms supramolecular complex, polymkeric substance is formed again under crosslinking chemical effect, after finally removing template molecule by certain means, in the MIPs of acquisition, just leave binding site template molecule to specific recognition.In recent years, much more more and more the specific recognition of MIPs and extensive practicality have attracted interest and the favor of scientific worker, have many research work to be incorporated in molecular imprinting by fluorescent material quantum dot, prepare compound fluorescence molecule imprinted material.The preparation of compound fluorescence molecule imprinted material makes MIPs be further expanded in the range of application analyzed in detection and using method, and the selectivity of MIPs also makes the sensitivity of compound fluorescence probe and selectivity be significantly improved simultaneously.
Through finding the literature search of prior art, Zhang etc. are published in 2011 and 2012 " Molecularlyimprintedpolymeranchoredonthesurfaceofdenatur edbovineserumalbuminmodifiedCdTequantumdotsasfluorescent artificialreceptorforrecognitionoftargetprotein " and " Molecularlyimprintedpolymeranchoredonthesurfaceofdenatur edbovineserumalbuminmodifiedCdTequantumdotsasfluorescent artificialreceptorforrecognitionoftargetprotein " that " BiosensorsandBioelectronics " delivers respectively; Xu etc. are published in " DummyMolecularlyImprintedPolymers-CappedCdTeQuantumDotsf ortheFluorescentSensingof2,4,6-Trinitrotoluene " that " Appl.Mater.Interfaces. " delivers for 2013; Three sections of articles all pass through sol-gal process, utilize the hydrolysis of ethyl orthosilicate to obtain CdTe quantum fluorescence trace sensor, have good selectivity.But, utilize free radical polymerization means to synthesize carbon quantum dot fluorescence trace sensor and also do not report.Therefore, utilize radical polymerization technique synthesized high-performance carbon quantum dot fluorescence trace sensor, carry out optical analysis thus reach the residual quantifier elimination of quick, convenient detection necessitating.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of amino-carbon quantum dot fluorescence p-nitrophenol trace sensor, set up a kind of new method utilizing free radical polymerization means to synthesize carbon quantum dot fluorescence trace sensor.
First the citric acid of certain mass and polyethyleneimine are dissolved in water, after fully dissolving, obtain clear solution.Then transfer to mixed solution with in teflon-lined hydrothermal reaction kettle, reactor is placed in baking oven, temperature reaction, after several hours, is cooled to room temperature, can obtain the dispersion liquid of the amino-carbon quantum dot with high-performance photoluminescent property.By dispersion liquid centrifugal treating, supernatant is preserved.Precipitation polymerization method is utilized to synthesize with amino-carbon quantum dot for fluorescence carrier, p-nitrophenol is template molecule, acrylamide (AM) is function monomer, ethylene glycol dimethacrylate (EGDMA) is crosslinking chemical, 2,2-azoisobutyronitrile (AIBN) is initiating agent, ethanol be solvent carbon quantum dot fluorescence molecule trace sensor, and for optical detection p-nitrophenol.The carbon quantum dot fluorescence molecule trace sensor of preparation has good stability and optical property, and has the ability of Selective recognition p-nitrophenol.
the technical solution used in the present invention is:
A preparation method for amino-carbon quantum dot fluorescence p-nitrophenol trace sensor, carries out according to following steps:
(1) citric acid and polyethyleneimine are added to the water, after fully dissolving, obtain clear solution.Then transfer to mixed solution with in teflon-lined hydrothermal reaction kettle, reactor is placed in baking oven, temperature reaction, after several hours, is cooled to room temperature, can obtain the dispersion liquid of the amino-carbon quantum dot with high-performance photoluminescent property.By dispersion liquid centrifugal treating, supernatant is preserved, and obtains amino-carbon quantum dot solution.
(2) amino-carbon quantum dot solution step (1) obtained and ethanol join in single port flask, ultrasonic disperse, add p-nitrophenol, acrylamide (AM), ethylene glycol dimethacrylate (EGDMA) and 2,2-azo two fourth eyeball (AIBN) subsequently, logical N enough for a long time
2guarantee to eliminate oxygen, then sealed by flask, be positioned in water bath chader, reacted by two-stage polymerization, after reaction terminates, with water and ethanol washing several times, to remove the complete material of unreacted, product is dried in vacuum drying oven; With eluant, eluent, primary template molecule p-nitrophenol is eluted from products therefrom, wash-out three times; After removing template molecule, namely obtain carbon quantum dot fluorescence imprinted polymer (MIPs-CQDs).
Wherein, the mass ratio of the citric acid described in step (1) and polyethyleneimine is 2:1-2; Described water is secondary deionized water, is 30-40mL:2g with the volume mass ratio of citric acid; The volume of described reactor is 50mL; Described temperature of reaction is 160-200 DEG C, and the reaction time is 4-8 hour.
Wherein, the volume ratio of the amino-carbon quantum dot solution described in step (2) and ethanol is 0.5mL:55-65mL; In described mixed solution, the mol ratio of p-nitrophenol, AM and EDGMA is 1:4-8:12-20, and three's quality is less than 0.5g; Ratio between the amount of substance of p-nitrophenol and alcohol solvent volume is: 0.05mmol:55-65mL; The quality of the described AIBN of adding is 5-10mg; Described two-stage polymerization reaction is first step prepolymerization 5-7 hour under 48-52 DEG C of condition, and second step is polymerized 20-28 hour under 58-62 DEG C of condition.
The synthesis of non-molecularly imprinted polymer (NIPs-CQDs) is not except containing except template molecule, and other processes are identical with printing process.
technological merit of the present invention:
(1) the present invention adopts polyethyleneimine and citric acid as starting material, by one step hydro thermal method synthesizing amino carbon quantum dot; The material environmental protection adopted is pollution-free.Amino-carbon quantum dot combines with molecular imprinting first time by the present invention, the sensor of synthesis, and compared with single carbon quantum dot sensor, many one deck imprinted polymers, have specific recognition ability to target molecule, have obvious selectivity; And the surface of common carbon quantum dot is generally carboxyl, this method synthesis amido modified carbon quantum dot, amino can with p-nitrophenol formation effect, quencher better effects if.
(2) preparation technology's equipment of the present invention is simple, easy and simple to handle feasible, and output is large, and conversion ratio is high; Compared with other quantum dot trace sensors and preparation method thereof, because carbon quantum dot is nontoxic, so the present invention's synthesis is a kind of novel sensor of environmental protection; Maximum advantage has selectivity to target molecule exactly, and environment-protecting asepsis.
Preparation amino-carbon quantum dot not only there is higher optical property, and need not modify participate directly in precipitation polymerization reaction in; In preparation method, using amino-carbon quantum dot as fluorescent functional material, the fluorescence molecule trace sensor that utilized precipitation polymerization method to synthesize; The fluorescence molecule imprinted polymer utilizing the present invention to obtain has good optical stability, can realize the ability of identification and optical detection p-nitrophenol fast.
(3) preparation of molecular engram fluorescent optical sensor of the present invention makes MIPs be further expanded in the range of application analyzed in detection and using method, the selectivity of MIPs also makes the sensitivity of compound fluorescence probe and selectivity be significantly improved simultaneously, for the research of expanding the new field of Environmental Analytical Chemistry and environmental pollution chemistry and environment pollution control chemistry provides science reliable foundation; For be engaged in further correlation theory research and practical application as: on-the-spot, fast, Selective recognition measures water body with fluorimetric analysis, it is basic that the trace/ultratrace objectionable impurities in food and biosome establishes solid theory and practice.
Accompanying drawing explanation
Fig. 1: the transmission electron microscope picture of carbon quantum dot fluorescence trace sensor;
Fig. 2: the relative intensity linear graph after the p-nitrophenol of variable concentrations and the effect of carbon quantum dot fluorescence trace sensor;
Fig. 3: the relative intensity linear graph after the p-nitrophenol of variable concentrations and the effect of carbon quantum dot fluorescence non-trace sensor;
Fig. 4: under same concentration, (35 μm of ol/L) different aldehydes matter is to the quencher rate of carbon quantum dot fluorescence molecule trace sensor and the non-trace sensor of carbon quantum dot fluorescence molecule.
Embodiment
Below in conjunction with concrete embodiment, the present invention will be further described.
embodiment 1:
(1) 2g citric acid and 1g polyethyleneimine are joined in 30mL deionized water, after fully dissolving, obtain clear solution.Then mixed solution being transferred to volume is in 50mL hydrothermal reaction kettle, reactor is placed in baking oven, is warming up to 160 degree DEG C, reacts after 4 hours, is cooled to room temperature, can obtain the dispersion liquid of the amino-carbon quantum dot with high-performance photoluminescent property; By dispersion liquid centrifugal treating, supernatant is preserved, and obtains amino-carbon quantum dot solution.
(2) in 100mL round-bottomed flask, add in the amino-carbon quantum dot solution and 55mL ethanol that 0.5mL step (1) obtains, ultrasonic disperse, at logical N
2condition under, add 0.05mmol p-nitrophenol, 0.2mmolAM, 0.6mmolEGDMA, 5mgAIBN, then seals flask, is positioned in water bath chader, 48 DEG C of prepolymerization 5h, 58 DEG C of polymerization 20h, after reaction terminates, wash several times with ethanol, to remove the complete material of unreacted, product is dried in vacuum drying oven.With eluant, eluent, primary template molecule p-nitrophenol is eluted from products therefrom, wash-out three times; After removing template molecule, namely obtain carbon quantum dot fluorescence imprinted polymer (MIPs-CQDs).The synthesis of non-molecular engram sensor (NIPs-CQDs) is not except containing except template molecule, and other processes are identical with printing process.
embodiment 2:
(1) 2g citric acid and 2g polyethyleneimine are joined in 40mL deionized water, after fully dissolving, obtain clear solution.Then mixed solution being transferred to volume is in 50mL hydrothermal reaction kettle, reactor is placed in baking oven, is warming up to 200 DEG C, reacts after 8 hours, is cooled to room temperature, can obtain the dispersion liquid of the amino-carbon quantum dot with high-performance photoluminescent property; By dispersion liquid centrifugal treating, supernatant is preserved, and obtains amino-carbon quantum dot solution.
(2) in 100mL round-bottomed flask, add in the amino-carbon quantum dot solution and 65mL ethanol that 0.5mL step (1) obtains, ultrasonic disperse, at logical N
2condition under, add 0.05mmol p-nitrophenol, 0.4mmolAM, 1mmolEGDMA, 10mgAIBN, then seals flask, is positioned in water bath chader, 52 DEG C of prepolymerization 7h, 62 DEG C of polymerization 28h, after reaction terminates, wash several times with ethanol, to remove the complete material of unreacted, product is dried in vacuum drying oven.With eluant, eluent, primary template molecule p-nitrophenol is eluted from products therefrom, wash-out three times; After removing template molecule, namely obtain carbon quantum dot fluorescence imprinted polymer (MIPs-CQDs).The synthesis of non-molecular engram sensor (NIPs-CQDs) is not except containing except template molecule, and other processes are identical with printing process.
embodiment 3:
(1) 2g citric acid and 1.5g polyethyleneimine are joined in 35mL deionized water, after fully dissolving, obtain clear solution.Then mixed solution being transferred to volume is in 50mL hydrothermal reaction kettle, reactor is placed in baking oven, is warming up to 180 DEG C, reacts after 6 hours, is cooled to room temperature, can obtain the dispersion liquid of the amino-carbon quantum dot with high-performance photoluminescent property.By dispersion liquid centrifugal treating, supernatant is preserved, and obtains amino-carbon quantum dot solution.
(2) in 100mL round-bottomed flask, add in the amino-carbon quantum dot solution and 60mL ethanol that 0.5mL step (1) obtains, ultrasonic disperse, at logical N
2condition under, add 0.05mmol p-nitrophenol, 0.3mmolAM, 0.8mmolEGDMA, 8mgAIBN, then seals flask, is positioned in water bath chader, 50 DEG C of prepolymerization 6h, 60 DEG C of polymerization 24h, after reaction terminates, wash several times with ethanol, to remove the complete material of unreacted, product is dried in vacuum drying oven.With eluant, eluent, primary template molecule p-nitrophenol is eluted from products therefrom, wash-out three times; After removing template molecule, namely obtain carbon quantum dot fluorescence imprinted polymer (MIPs-CQDs).The synthesis of non-molecular engram sensor (NIPs-CQDs) is not except containing except template molecule, and other processes are identical with printing process.
Fig. 1 is the transmission electron microscope picture of carbon quantum dot fluorescence trace sensor prepared by the inventive method; Can reflect that from figure carbon quantum dot fluorescence trace sensor successfully synthesizes, carbon quantum dot, by polymer overmold, defines compound material.
The application of carbon quantum dot fluorescence trace sensor in p-nitrophenol detects of preparation:
Carbon quantum dot fluorescence trace sensor (100mg/L) of preparation and object p-nitrophenol to be measured (5mmol/L) are mixed with storing solution respectively.The carbon quantum dot fluorescence trace sensor solution getting 100 μ L joins in testing tube, and p-nitrophenol storing solution is added in pipe, be mixed with standard model 6-10 that p-nitrophenol concentration is 0-35 μM, measure fluorescence spectrum, along with the increase of p-nitrophenol concentration, on fluorescence spectrum, fluorescent emission peak intensity reduces gradually, according to Stern-Volmerequation (
f 0 / F=1+K sv [c]) with concentration [c] for horizontal ordinate, relative intensity of fluorescence (
f 0 / F)for ordinate draws fluorescence response curve.Select several aldehydes matter (2,4-chlorophenesic acid, 2,6-chlorophenesic acid, 2,4,5-trichlorophenol), material as a comparison, participate in the research of carbon quantum dot fluorescence trace sensor recognition performance.
Concrete operations are as follows:
Test example 1: carbon quantum dot fluorescence trace sensor the present invention prepared and the non-trace sensor of carbon quantum dot fluorescence are configured to the sensor aqueous solution of 100mg/L, and phenols object is configured as the ethanolic solution of 5mmol/L.The ethanolic solution of the sensor aqueous solution and 0-0.035mL p-nitrophenol of getting 100 μ L joins in 5mL color comparison tube, and use water constant volume, in color comparison tube test fluid, p-nitrophenol concentration is respectively 0,1,2,5,10,15,25,35 μm of ol/L, 20 minutes are left standstill after test fluid shaken at room temperature, detect the impact of p-nitrophenol on carbon quantum dot fluorescence trace sensor and carbon quantum dot fluorescence non-trace sensor fluorescence intensity of variable concentrations, result shows, along with the increase of p-nitrophenol concentration, on fluorescence spectrum, fluorescent emission peak intensity reduces gradually.According to Stern-Volmerequation (
f 0 / F=1+K sv [c]) with concentration [c] for horizontal ordinate, relative intensity of fluorescence (
f 0 / F)for ordinate draws fluorescence response curve, obtain the straight line (as shown in Figures 2 and 3) that related coefficient is 0.9993 and 0.9996 respectively.Result shows, carbon quantum dot fluorescence trace sensor has the ability of good optical detection p-nitrophenol.
Test example 2: carbon quantum dot fluorescence trace sensor the present invention prepared is configured to the sensor aqueous solution of 100mg/L, select p-nitrophenol, 2,4-chlorophenesic acid, 2,6-chlorophenesic acid and 2,4,5-trichlorophenol four kinds of objects, are configured as the ethanolic solution of 5mmol/L by above several aldehydes matter.The ethanolic solution getting the sensor aqueous solution of 100 μ L and the aldehydes matter of 0.035mL joins in 5mL color comparison tube, uses water constant volume, leaves standstill 20 minutes after test fluid shaken at room temperature, then detects the fluorescence intensity of solution with fluorospectrophotometer.As shown in Figure 4, the quencher amount of p-nitrophenol to carbon quantum dot fluorescence trace sensor is maximum for result, illustrates that carbon quantum dot fluorescence trace sensor has specific recognition capability to template molecule p-nitrophenol.Result shows, carbon quantum dot fluorescence trace sensor prepared by the present invention has obvious specific recognition ability to p-nitrophenol, and quencher effect is higher than other aldehydes matter.
Claims (8)
1. an amino-carbon quantum dot fluorescence p-nitrophenol trace sensor, is characterized in that, described sensor is with amino-carbon quantum dot for fluorescence carrier, is combined is prepared from molecular imprinting, has the ability of Selective recognition p-nitrophenol.
2. a preparation method for amino-carbon quantum dot fluorescence p-nitrophenol trace sensor, is characterized in that, carries out according to following steps:
(1) citric acid and polyethyleneimine are added to the water, after fully dissolving, obtain clear solution; Then mixed solution is transferred to in teflon-lined hydrothermal reaction kettle, reactor is placed in baking oven, after temperature reaction, be cooled to room temperature, the dispersion liquid of the amino-carbon quantum dot with high-performance photoluminescent property can be obtained; By dispersion liquid centrifugal treating, supernatant is preserved, and obtains amino-carbon quantum dot solution.
Amino-carbon quantum dot solution 3.(2) step (1) obtained and ethanol join in single port flask, ultrasonic disperse, add p-nitrophenol, acrylamide, ethylene glycol dimethacrylate and 2,2-azo two fourth eyeball subsequently, logical N
2to eliminate oxygen, then sealed by flask, be positioned in water bath chader, reacted by two-stage polymerization, after reaction terminates, wash with water and ethanol to remove the complete material of unreacted, product is dried in vacuum drying oven; With eluant, eluent, primary template molecule p-nitrophenol is eluted from products therefrom; After removing template molecule, namely obtain carbon quantum dot fluorescence imprinted polymer (MIPs-CQDs).
4. the preparation method of a kind of amino-carbon quantum dot fluorescence p-nitrophenol trace sensor according to claim 2, it is characterized in that, the mass ratio of the citric acid described in step (1) and polyethyleneimine is 2:1-2; Described water is secondary deionized water, is 30-40mL:2g with the volume mass ratio of citric acid;
The preparation method of a kind of amino-carbon quantum dot fluorescence p-nitrophenol trace sensor according to claim 2, it is characterized in that, described in step (1), temperature reaction temperature is 160-200 DEG C, and the reaction time is 4-8 hour.
5. the preparation method of a kind of amino-carbon quantum dot fluorescence p-nitrophenol trace sensor according to claim 2, it is characterized in that, the volume ratio of the amino-carbon quantum dot solution described in step (2) and ethanol is 0.5:55-65.
6. the preparation method of a kind of amino-carbon quantum dot fluorescence p-nitrophenol trace sensor according to claim 2, it is characterized in that, the mol ratio of p-nitrophenol, acrylamide and the ethylene glycol dimethacrylate described in step (2) is 1:4-8:12-20, and three's quality is less than 0.5g; The ratio of p-nitrophenol and ethanol is: 0.05mmol:55-65mL; The quality of the described AIBN of adding is 5-10mg.
7. the preparation method of a kind of amino-carbon quantum dot fluorescence p-nitrophenol trace sensor according to claim 2, it is characterized in that, two-stage polymerization reaction described in step (2) is first step prepolymerization 5-7 hour under 48-52 DEG C of condition, and second step is polymerized 20-28 hour under 58-62 DEG C of condition.
8. an amino-carbon quantum dot fluorescence p-nitrophenol trace sensor is in the application identified fast and in optical detection p-nitrophenol.
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