CN105717089A - Sensor for detecting phosphorus containing pesticides and manufacture and use methods thereof - Google Patents
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- 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
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- C07C309/43—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
The invention discloses a super-molecule assembled carbon quantum dot nano sensor for detecting phosphorus containing pesticides and manufacture and use methods thereof. The fluorescent nano sensor takes alkyl ammonium carbon quantum dots assembled at the surfaces of nano particles of sulfonatocalixarene as a substrate, and terbium ions are coordinated on the surface of the nano particles in situ. When the sensor is used for detection, whether a detected pesticide contains phosphorus can be determined according to the change of characteristic emission peaks of terbium ions in a detection result. The sensor has the advantages of being low in cost and simple in detection operation, is free of any toxicity as excellent water soluble matter, and is high in detection sensitivity.
Description
Technical field
The present invention relates to the preparation method of a kind of nano-sensor and this sensor and using method, the present invention relates to the carbon quantum dot nano-sensor of a kind of Supramolecular Assembling detecting phosphorous pesticide and preparation and using method exactly.
Background technology
Pesticide refers to the chemical substance of the harmful organism for agriculture forest and husbandry yield of eliminating the effects of the act, and pesticide can also regulate the growth of plant.In agricultural production, the pesticide of some classification is widely used, such as organic phosphates, carbamates, organochlorine class and pyrethroid pesticide.But the health caused because of the residual of pesticide and food-safety problem are the major issues of society's general concern.The management lack of standardization of pesticide and use, serious threat food and Agriculture Ecological Environment Security, exist potentially hazardous to the health of the mankind, and Pesticide Residue increasingly causes concern and the attention of people's height.The various com-parison and analysis complexity making pesticide residues of pesticide variety, Detection task is very arduous.Therefore, developing quick, convenient, efficient and practical pesticide residue analysis method, the detection particularly detecting phosphorous pesticide is current research focus, and this work has important theoretical and practical significance to preserving the ecological environment and implementing food safety strategy.
In commercial production and environmental monitoring, phosphorous pesticide carries out detecting typically by gas chromatography or liquid chromatography.These common methods generally require the processing procedure of complexity and expensive instrument, therefore largely limit its approach quickly detected.Therefore, environmental area is had great significance by a kind of cheap quick phosphorous Pesticides Testing method of invention.
Summary of the invention
The present invention provides a kind of nano fluorescent sensor that can be used for phosphorous Pesticides Testing, provides preparation method and the using method of this sensor simultaneously.
The nano fluorescent sensor for phosphorous Pesticides Testing of the present invention is as what formula 1 was shown assembles with Sulfonated calixarenes
Alkylammonium carbon quantum dot in nanoparticle surface is substrate, has terbium ion in nanoparticle surface complexed in situ.
The substrate of the present invention nano fluorescent sensor for preparing described phosphorous Pesticides Testing is the alkylammonium carbon quantum dot that Sulfonated calixarenes is assembled in nanoparticle surface.
The present invention for preparing the preparation method of the substrate of the nano fluorescent sensor of phosphorous Pesticides Testing is: by soluble in water for alkylammonium carbon quantum dot; preferably it is dissolved in 50mL water by 20mg alkylammonium carbon quantum dot; add Sulfonated calixarenes under agitation; under inert gas shielding, sufficiently conducted ultrasonic reaction processes; again reaction solution is sufficiently stirred for; then the supernatant 1000Da bag filter dialysis treatment extracted reaction solution, obtained solution is the substrate of the nano fluorescent sensor for preparing phosphorous Pesticides Testing.
The preparation method of the nano fluorescent sensor of the phosphorous Pesticides Testing of the present invention is: first add the buffer of not phosphoric acid in its substrate, then adds terbium ion more wherein.
Alkylammonium carbon quantum dot preparation method involved in the present invention is: be dissolved in 5mL water by 1.5g beet alkali hydrochlorate, afterwards 1.2g trishydroxymethylaminomethane (Tris) is joined in alkali solution of beet, until solution becomes clarification, adding excessive isopropanol more wherein makes the organic salt presoma of generation precipitate out, excessive presoma is removed with washed with isopropyl alcohol precipitate, 250 DEG C are reheated after the solid drying obtained being processed again, then it is incubated, make trishydroxymethylaminomethane carburizing temperature, ensure the integrity of the glycine betaine unit of outside simultaneously, after aforementioned heat treatment, handy water extraction goes out solid, then through removing bulky grain thing therein, adding substantial amounts of acetone in filtrate makes carbon quantum dot precipitate out from solution, the carbon quantum dot being isolated to.
The user of the nano fluorescent sensor of the phosphorous Pesticides Testing of the present invention is: added by determinand in the nano fluorescent sensor of phosphorous Pesticides Testing, the fluorescence of system is measured, according to whether phosphorous the change at the characteristic emission peak of terbium ion in testing result judges in tested pesticide with 270-300nm excitation wavelength.Currently preferred excitation wavelength is 275nm.
The present invention utilizes nano-sensor that the technology of Supramolecular Assembling prepares finishing cyclic compound calixarenes, that be substrate with carbon quantum dot.In recent years, the carbon nanomaterial such as diamond, fullerene, Graphene, fluorescent carbon nano material and carbon quantum dot shows a series of peculiar property and has attracted the extensive concern of researcher.Wherein carbon quantum dot is shown one's talent in carbon nanomaterial family due to optics and the fluorescent emission character of its uniqueness.Big quantity research shows that conventional semiconductors quantum dot has adjustable fluorescent emission character, and this characteristic makes it be applied in bio-sensing and bio-imaging field.But, semiconductor-quantum-point has some limitation, for instance being used mostly heavy metal presoma in the preparation due to semiconductor-quantum-point thus causing that it has higher bio-toxicity, therefore greatly limit semiconductor-quantum-point application in biological field.Being different from traditional semiconductor-quantum-point, carbon quantum dot except having fluorescence intensity height, launching the character such as adjustable, also has the characteristics such as hypotoxicity, good biocompatibility, low cost and chemical inertness as a kind of novel nano material simultaneously.These character compensate for the deficiency of conventional semiconductors quantum dot, makes carbon quantum dot be obtained for application in various fields.The nano-sensor that the present invention this is substrate with carbon quantum dot is not only with low cost, simple to operate, the phosphorous pesticide of identification that simultaneously can be sensitive, therefore has bigger application prospect and industrial production potential.
The sensor prepared based on carbon quantum dot of the present invention has following several respects advantage: 1) with low cost, simple to operate；Sensor of the invention is prepared by conventional compound, simultaneously also without the instrument of complex and expensive during detection, only just can realize the detection to pesticide by the change in fluorescence of tracking system.2) good water solubility, environmental friendliness；Sensor of the invention has good water solublity, therefore can realize the Pesticides Testing in pure aquatic system, and meanwhile, this material itself does not have any toxicity, has any impact thus without to environment.3) ratio sensor, susceptiveness is good；More traditional sensor is compared, and ratio sensor can overcome in environment such as pH, temperature, other factor such as material and ionic strength impacts on system sensitivity, therefore has higher sensitivity.
Accompanying drawing explanation
Fig. 1 is the assembling process schematic diagram of the nano-sensor of the present invention.
Fig. 2 is the synthesis schematic diagram of the finishing molecule sulfonation calixarenes of the present invention.
The nuclear-magnetism of Fig. 3 sulfonation cup [4] aromatic hydrocarbons characterizes collection of illustrative plates.
The carbon quantum dot that Fig. 4 is the present invention prepares schematic diagram.
The transmission electron microscope phenogram of nano-sensor under (a), (b) respectively different chi footpaths in Fig. 5, wherein the illustration in the b figure upper right corner is the lattice structure of nanoparticle under high power ultramicroscope, is used for illustrating the spacing of lattice of nano material.
Fig. 6,7,8 and 9 are the sign of nano-sensor of the present invention respectively, wherein: Fig. 6 is the change in fluorescence after carbon quantum dot, carbon quantum dot calixarenes, introducing terbium ion；Fig. 7 is the system change in fluorescence of the terbium ion introducing variable concentrations；The photoelectron spectroscopy that Fig. 8 is nano fluorescent sensor characterizes；Fig. 9 is the photoelectron spectroscopy of terbium ion.
Figure 10 is not phosphorous pesticide structure formula used in choice experiment of the present invention.
Figure 11 is the selectivity fluorogram of not phosphorous pesticide used in choice experiment of the present invention.
Figure 12 is the ratio fluorescent block diagram of different not phosphorous pesticide.
Figure 13 is phosphorous pesticide structure formula used in choice experiment of the present invention.
Figure 14 is the selectivity fluorogram of phosphorous pesticide used in choice experiment of the present invention；.
Figure 15 is the ratio fluorescent block diagram of different phosphorous pesticide
Figure 16 is the fluorescence titration spectrogram of isocarbophos.
Figure 17 is the change in fluorescence trend that after adding variable concentrations isocarbophos, 490nm and 545nm locates
The Linear Fit Chart at Figure 18 and Figure 19 respectively 545nm and 490nm place.
Detailed description of the invention
The following is embodiments of the invention.
One, the hybridized nanometer biosensor matrix preparation method of the present invention is as follows:
(1) preparation of Sulfonated calixarenes
A. the synthesis to tert-butyl group p tertButylcalixarene
20g p-t-butyl phenol, 0.24g sodium hydroxide and 12.5mL(37%) formaldehyde joins in 500mL round-bottomed flask, add water knockout drum, reaction temperature 110-120 DEG C, with fraction water device water-dividing, reaction 2-3h, treat that solution becomes thick, stop heating, it is cooled to room temperature, add 200mL diphenyl ether, and it is added thereto to 40mL ethyl acetate, reaction temperature rises to about 140 DEG C, divide water 0.5-1h, then reaction is risen to 260 DEG C, backflow 2-3h, stopped reaction, it is cooled to room temperature, add 150mL ethyl acetate, stirring 0.5h, solid is had to precipitate out, with 20mL ethyl acetate drip washing twice, 20mL glacial acetic acid and 20mL washing, dry, with 180 DEG C of re crystallization from toluene, obtain tert-butyl group p tertButylcalixarene.Productivity: 65%.
B. the synthesis to the de-tert-butyl group of tert-butyl group p tertButylcalixarene
250mL there-necked flask adds 13.3g previous step product, 9.0g (96mmol) virtue phenol and 14.0g(105mmol) aluminum trichloride (anhydrous).It is eventually adding 125mL dry toluene, ambient temperature under nitrogen protection stirring reaction 1h, it is subsequently poured in the flask equipped with 250mL0.2mol/L hydrochloric acid solution, stirring, stratification.By mixture separatory, it is transferred in round-bottomed flask after obtaining organic facies and revolves steaming, sucking filtration after addition methanol, use chloroform-methanol recrystallization after drying.Productivity: 69%.
C. the synthesis of Sulfonated calixarenes
5g upper step product adds 50mL98% concentrated sulphuric acid and heats in oil bath, control reaction 80-90 DEG C, reaction 4h, water solublity experiment is without stopping heating after insoluble matter, it is cooled to room temperature, dropwise adds in 100mL saturated aqueous common salt under cryosel bath, after dripping, putting in refrigerator after being heated to reflux 5min cooling and filter, sucking filtration obtains the thick product of white.Finally obtain white crystal with distilled water recrystallization.Productivity: 78%.Its preparation process is referring to accompanying drawing 2.
Nucleus magnetic hydrogen spectrum characterization result (accompanying drawing 3):1HNMR(400MHz,D2O,25°C)δ:4.01(s,8H,CH2), 7.57 (s, 8H, ArH).The result obtained is consistent with the result of report, illustrates to obtain the sterling of this compound.
(2) preparation of alkylammonium carbon quantum dot
Alkylammonium carbon quantum dot is prepared by literature procedure (A.W.Zhu, Q.Qu, X.L.Shao, B.Kong, Y.Tian, Angew.Chem.Int.Ed.2012,51,7185.).First, 1.5g beet alkali hydrochlorate is dissolved in 5mL water, obtains a kind of acid solution.Joining in alkali solution of beet by 1.2g trishydroxymethylaminomethane (Tris) afterwards, until solution becomes clarification, simultaneously pH value of solution gradually becomes neutral along with the addition of Tris.This water miscible organic salt can pass through to add excessive isopropanol (100mL) makes it precipitate out.The syrupy material 100mL washed with isopropyl alcohol of class obtained three times.Whole process repeats to remove excessive presoma for more than twice.The solid obtained 80 DEG C is dry 1-3 days, is then warmed up to 250 DEG C in tube furnace 2 hours.This temperature reaches the carburizing temperature of Tris, can ensure that again the integrity of the glycine betaine unit of outside simultaneously.Brown solid is obtained after heat treatment.Going out solid with 25mL water extraction, 13000 leave the heart 15 minutes, remove bulky grain thing, filtrate adds substantial amounts of acetone after taking out, and such as the volume ratio acetone more than 10:1, makes carbon quantum dot precipitate out from solution, the carbon quantum dot drying for standby obtained after centrifugal, obtained product is referring to Fig. 7.
(3) assembling of hybridized nanometer sensor (i.e. the substrate of the present invention)
First the alkylammonium carbon quantum dot of 5mg is dissolved in 20mL ultra-pure water, under stirring condition, adds 2mg/mL Sulfonated calixarenes aqueous solution, under Ar gas shielded ultrasonic 30 minutes.The reaction solution obtained at room temperature stirs 12 hours.The brown solution 10000 obtained leaves the heart 30 minutes to remove bigger reaction particles, takes supernatant 1000Da bag filter dialysis 72h, and the solution obtained is stand-by substrate, and its Spectroscopic Characterization is shown in accompanying drawing 8-Figure 11, and preparation process is referring to accompanying drawing 1.
Two, for the nano fluorescent transducer production method of phosphorous Pesticides Testing
The matrix solution taking the 100 above-mentioned gained of μ L joins in 2mLHEPES buffer solution, then adds 5mL10 wherein-2Terbium chloride (the TbCl of M3) aqueous solution, react the nano fluorescent sensor for phosphorous Pesticides Testing obtaining the present invention for five minutes.Preparation process is referring to accompanying drawing 1.
Three, the nano fluorescent sensor using method for phosphorous Pesticides Testing of the present invention
The non-phosphorous pesticide of present invention actual measurement is: Acetamiprid, carbendazim, carbofuran, Mobucin, ethiprole bromine and Cyano chrysanthemate, its structural formula is shown in accompanying drawing 10；The phosphorous pesticide of present invention actual measurement is: chlopyrifos, Profenofos, dichlorvos, parathion, and Bayer 71628, really pleasure, isocarbophos and phosmet, its structural formula is shown in accompanying drawing 13.The nano fluorescent sensor solution being previously used for phosphorous Pesticides Testing is transferred in 1 centimetre of cuvette, determinand is separately added in different cuvettes subsequently, measures the fluorescence of this system with 275nm for excitation wavelength.The testing result of above-mentioned 6 kinds of non-phosphorous pesticide is shown in accompanying drawing 11 and Figure 12, accompanying drawing 11 and Figure 12 add the fluorescence not significantly impact on system of the non-phosphorous pesticide as seen, still can show the emission peak of carbon quantum dot and terbium ion.The testing result of aforementioned 8 kinds of phosphorous pesticide is shown in accompanying drawing 14 and Figure 15, by accompanying drawing 14 and Figure 15 as seen after adding phosphorous pesticide, the emission peak of system middle rare earth terbium ion is decreased obviously, but the fluorescence of carbon quantum dot does not significantly change, the ratio fluorescent that therefore can pass through rare earth ion and carbon quantum dot realizes the detection to phosphorous pesticide.
The detection example that the present invention one is actual is detection isocarbophos, with being calculated as follows that the concentration linear fit of detection and detection are limit:
Selecting isocarbophos is that example carries out fluorescence titration test experience, and its testing result is shown in Figure 16 and Figure 17, obtained fluorescence intensity is fitted obtain matched curve and sees Figure 18 and Figure 19, utilize formula
Detection limit=3 × S.D./slope
In formula: I0For the fluorescence intensity that 275nm excitation material is obtained；I0For the average of the obtained fluorescence intensity of 275nm excitation material, n is testing time, in the present invention n=10；
First obtain
S.D.(545nm)=0.006129
S.D.(490nm)=0.007477
Calculate obtained detection limit according to the above results and be listed in table 1.
Claims (8)
1. for the nano fluorescent sensor of phosphorous Pesticides Testing, it is characterised in that described nano fluorescent sensor be as shown in Equation 1 be assembled in the alkylammonium carbon quantum dot of nanoparticle surface for substrate with Sulfonated calixarenes,
Terbium ion is had in nanoparticle surface complexed in situ.
2. for preparing the substrate of the nano fluorescent sensor of the phosphorous Pesticides Testing described in claim 1, it is characterised in that described substrate is the alkylammonium carbon quantum dot that Sulfonated calixarenes is assembled in nanoparticle surface.
3. the preparation method of the substrate of the nano fluorescent sensor for preparing phosphorous Pesticides Testing described in claim 2; it is characterized in that soluble in water for alkylammonium carbon quantum dot; add Sulfonated calixarenes under agitation; under inert gas shielding, sufficiently conducted ultrasonic reaction processes; again reaction solution is sufficiently stirred for; then the supernatant 1000Da bag filter dialysis treatment extracted reaction solution, obtained solution is the substrate of the nano fluorescent sensor for preparing phosphorous Pesticides Testing.
4. the preparation method of the substrate of the nano fluorescent sensor for preparing phosphorous Pesticides Testing described in claim 3, it is characterised in that the alkylammonium carbon quantum dot of 5mg is dissolved in 20mL ultra-pure water, adds 2mg/mL Sulfonated calixarenes aqueous solution under stirring condition.
5. the preparation method of the nano fluorescent sensor of the phosphorous Pesticides Testing described in claim 1, it is characterised in that: first the substrate described in claim 2 adds not phosphorous buffer, then add terbium ion more wherein.
6. the preparation method of the nano fluorescent sensor of phosphorous Pesticides Testing according to claim 5, it is characterised in that: the matrix solution of 100 μ L will join in 2mLHEPES buffer solution, then add 5 milliliter 10 wherein-2The terbium chloride aqueous solution of M.
7. the using method of the nano fluorescent sensor of the phosphorous Pesticides Testing described in claim 1, it is characterized in that adding determinand in the nano fluorescent sensor of phosphorous Pesticides Testing, the fluorescence of system is measured, according to whether phosphorous the change at the characteristic emission peak of terbium ion in testing result judges in tested pesticide with 270-300nm excitation wavelength.
8. the using method of the nano fluorescent sensor of phosphorous Pesticides Testing according to claim 7, is characterized in that excitation wavelength used is 275nm.
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