CN111286321B - Preparation method and application of flavonoid fluorescent nano material - Google Patents
Preparation method and application of flavonoid fluorescent nano material Download PDFInfo
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- 229930003935 flavonoid Natural products 0.000 title claims abstract description 59
- 235000017173 flavonoids Nutrition 0.000 title claims abstract description 59
- 239000002086 nanomaterial Substances 0.000 title claims abstract description 57
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000001514 detection method Methods 0.000 claims abstract description 9
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- 230000035484 reaction time Effects 0.000 claims abstract description 3
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- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 125000003916 ethylene diamine group Chemical group 0.000 claims description 2
- 238000001471 micro-filtration Methods 0.000 claims description 2
- 238000005374 membrane filtration Methods 0.000 claims 1
- 238000006862 quantum yield reaction Methods 0.000 abstract description 9
- 238000012360 testing method Methods 0.000 abstract description 8
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract description 5
- 229910021645 metal ion Inorganic materials 0.000 abstract description 5
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- AKYHKWQPZHDOBW-UHFFFAOYSA-N (5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl)-(6-methoxyquinolin-4-yl)methanol Chemical compound OS(O)(=O)=O.C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 AKYHKWQPZHDOBW-UHFFFAOYSA-N 0.000 description 1
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- 239000001576 FEMA 2977 Substances 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
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- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
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- 238000000295 emission spectrum Methods 0.000 description 1
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- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229960003110 quinine sulfate Drugs 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
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- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0063—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres
- A61K49/0065—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the luminescent/fluorescent agent having itself a special physical form, e.g. gold nanoparticle
- A61K49/0067—Preparation for luminescence or biological staining characterised by a special physical or galenical form, e.g. emulsions, microspheres the luminescent/fluorescent agent having itself a special physical form, e.g. gold nanoparticle quantum dots, fluorescent nanocrystals
-
- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses a preparation method and application of a flavonoid fluorescent nano material. The optimized reaction conditions of the invention are that 60 percent or 70 percent ethanol solution is controlled to be 1:5-1:10 (g/mL), the volume ratio of the concentrated extract to the high purity water was controlled to 10:5-13, controlling the final concentration of the dopant in the reaction system at 0-0.36mol/L, controlling the reaction temperature at 180-200 ℃ and controlling the reaction time at 3-6h. Through test result screening, the reaction system doped with the ethylenediamine can prepare the flavonoid fluorescent nano material with stronger fluorescence quantum yield, strong light stability and yellow-green light fluorescence emission, and Hg 2+ Can effectively quench the fluorescence intensity of the flavonoid nano material and realize the detection of harmful metal ions.
Description
Technical Field
The invention belongs to the technical development field of nanometer functional materials, and particularly relates to a preparation method and application of a flavonoid fluorescent nanometer material.
Background
The fluorescent nano material is widely applied to detection of harmful metal ions and pesticides due to good optical performance. In recent years, designing and developing more fluorescent nanomaterials with excellent optical properties is one of the hot spots of research, wherein flavonoids are the main targets of design and development. The flavonoids are widely present in fruits, vegetables and plants, and are natural substances with antibacterial and anticancer activities. But the research on preparing the fluorescent nano material by taking the flavonoid compound as the raw material is few at present.
The defects of toxic reagents, expensive raw materials, harsh synthesis conditions and the like exist in the conventional synthesis process of the fluorescent nano material, and most of prepared fluorescent quantum dots have the defects of low fluorescent quantum yield, poor stability, blue light emission and the like, so that the research and development of the flavonoid fluorescent nano material with strong fluorescent quantum yield and strong light stability have important significance in the research of potential functions of the flavonoid fluorescent nano material in the aspects of harmful metal ion detection, pesticide detection, biological imaging and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method and application of a flavonoid fluorescent nano material.
In order to achieve the above object, one of the technical solutions of the present invention is to provide:
a preparation method of a flavonoid fluorescent nano material comprises the following steps:
(1) Peeling and pulping kiwi fruits to prepare a sample, weighing a certain mass of the sample, adding 60% or 70% ethanol solution, performing ultrasonic treatment in water bath, centrifuging, removing residues, and taking supernatant to obtain an extracting solution;
(2) Concentrating the extracting solution, then adding high-purity water and dopant, heating for reaction, cooling to room temperature, centrifuging, filtering, and freeze-drying to obtain the flavonoid fluorescent nano material.
The mass-to-volume ratio of the weighed sample to the 60% or 70% ethanol solution is 1g:5-10mL.
The temperature of the water bath ultrasound is 50-60 deg.C, and the time is 40-60min.
The rotation speed of the centrifugation is 6000-10000rpm, and the time is 10-15min.
The volume of the concentrated extractive solution is 1/8-1/4 of the volume before concentration.
The volume ratio of the concentrated extracting solution to the high-purity water is 10:5-13.
The adulterant is ethylenediamine or triethylamine; the final concentration of the dopant is 0-0.36mol/L.
The heating reaction temperature is 180-200 ℃, and the time is 3-6h.
The filtration is a 0.22 μm microfiltration membrane.
One of the technical schemes of the invention is to provide: a flavonoid fluorescent nano material in Hg 2+ Application in detection.
The invention has the beneficial effects that:
1. in order to solve the defects of toxic reagents, expensive raw materials, harsh synthesis conditions and the like in the process of synthesizing the fluorescent nano material, the invention provides a green and mild synthesis method, which selects kiwi fruits as the raw materials, uses 60 percent or 70 percent ethanol solution to extract flavonoid compounds in the kiwi fruits, centrifuges to obtain supernatant, and adopts aqueous solution as a solvent to prepare the fluorescent nano material by a hydrothermal synthesis method.
2. In order to overcome the defects of low fluorescence quantum yield, poor stability, blue light emission and the like of the fluorescence quantum dots, the flavonoid fluorescent nano material with strong fluorescence quantum yield and strong light stability is prepared by selecting flavonoid extracts in kiwi fruits as raw materials and debugging reaction conditions, wherein the reaction conditions are optimized, namely 60% or 70% ethanol solution is controlled to be 1:5-1:10 (g/mL), the volume ratio of the concentrated extract to the high purity water was controlled to 10:5-13, controlling the final concentration of a dopant (ethylenediamine or triethylamine) in the reaction system at 0-0.36mol/L, controlling the reaction temperature at 180-200 ℃ and the reaction time at 3-6h, and screening the nano material prepared by the ethylenediamine doping reaction to have stronger fluorescence quantum yield and strong light stability.
3. The flavonoid fluorescent nano material designed and developed by the invention firstly has the flavonoid in the oxidation-reduction intermediate state,the flavone has weak acidity, and nitrogen atoms have lone pair electrons as nucleophilic reagent to produce addition reaction with ketone to form compound containing C = N double bond, which is favorable to doping nitrogen atoms. Through test result screening, the reaction system doped with the ethylenediamine can prepare the flavonoid fluorescent nano material with stronger fluorescence quantum yield, strong light stability and yellow-green light fluorescence emission, and Hg 2+ Can effectively quench the fluorescence intensity of the flavonoid nano material and realize the detection of harmful metal ions.
Drawings
FIG. 1 shows the ultraviolet absorption spectrum of the flavonoid fluorescent nanomaterial prepared in example 1 and the fluorescence emission spectrum thereof under excitation light of 340nm (a) and 700nm (b).
FIG. 2 is a fluorescence emission spectrum of the flavonoid fluorescent nanomaterial prepared in example 1 under different excitation lights.
Fig. 3 is a photostability test of the flavonoid fluorescent nanomaterial prepared in example 1.
FIG. 4 shows the flavonoid fluorescent nanomaterial prepared in example 1 and Hg with different concentrations 2+ Fluorescence response spectrum.
Detailed Description
The following examples are provided to further illustrate the embodiments of the present invention.
Example 1
A preparation method of a flavonoid fluorescent nano material comprises the following steps:
(1) Peeling and pulping kiwi fruits to prepare a sample, and weighing 8g of the sample and placing the sample in a centrifugal tube; then adding 40mL of 70% (v/v) ethanol solution into a centrifuge tube, performing ultrasonic treatment in 55 ℃ water bath for 1h to extract flavonoid compounds in the kiwi fruit, centrifuging at 6000rpm for 10min, removing residues, taking supernatant, and placing in a beaker to obtain an extracting solution;
(2) Concentrating the extracting solution to 10mL, adding high-purity water to 23mL, transferring to a reaction kettle, adding 250 mu L of ethylenediamine into the reaction kettle, and uniformly mixing;
(3) And (3) placing the reaction kettle in a blast type oven, heating to react for 4 hours at 200 ℃, cooling to room temperature, centrifuging at 6000rpm for 15min, filtering with a 0.22-micron microporous filter membrane, and freeze-drying to obtain the flavonoid fluorescent nano material.
Example 2
A preparation method of a flavonoid fluorescent nano material comprises the following steps:
(1) Peeling and pulping kiwi fruits to prepare a sample, and weighing 6g of the sample and placing the sample in a centrifugal tube; then adding 40mL of 70% (v/v) ethanol solution into the centrifuge tube, performing ultrasonic treatment in water bath at 60 ℃ for 40min to extract flavonoid compounds in the kiwi fruit, centrifuging at 6000rpm for 10min, removing residues, taking supernatant, and placing in a beaker to obtain an extracting solution;
(2) Concentrating the extracting solution to 10mL, adding high-purity water to 20mL, transferring to a reaction kettle, adding 100 mu L triethylamine into the reaction kettle, and uniformly mixing;
(3) And (3) placing the reaction kettle in a blast type oven, heating to react for 6h at 190 ℃, cooling to room temperature, centrifuging at 10000rpm for 15min, filtering with a 0.22 mu m microporous filter membrane, and freeze-drying to obtain the flavonoid fluorescent nano material.
Example 3
A preparation method of a flavonoid fluorescent nano material comprises the following steps:
(1) Peeling and pulping kiwi fruits to prepare a sample, and weighing 4g of the sample to be placed in a centrifuge tube; then adding 40mL of 60% (v/v) ethanol solution into the centrifuge tube, performing water bath ultrasound at 50 ℃ for 1h to extract flavonoid compounds in the kiwi fruit, centrifuging at 6000rpm for 15min, removing residues, taking supernatant, and placing in a beaker to obtain an extracting solution;
(2) Concentrating the extracting solution to 10mL, adding high-purity water to 15mL, transferring the mixture into a reaction kettle, and uniformly mixing;
(3) And (3) placing the reaction kettle in a blast type oven, heating to react for 3h at 180 ℃, cooling to room temperature, centrifuging at 8000rpm for 15min, filtering with a 0.22-micron microporous filter membrane, and freeze-drying to obtain the flavonoid fluorescent nano material.
Example 4
Ultraviolet spectrum test is carried out on the flavonoid fluorescent nano material prepared in the example 1, and the ultraviolet absorption spectrum (figure 1) of the flavonoid fluorescent nano material has stronger absorption peaks at 227nm and 333nm respectively, wherein the former is sp 2 Of a regionPi-pi transition, the latter due to n-pi transition. Testing the flavonoid fluorescent nano material to collect the strongest emission spectrum at 433nm under 340nm exciting light by using a fluorescence spectrophotometer (figure 1 a); and under the excitation light of 700nm, the maximum fluorescence emission intensity at 438nm is collected, which shows excellent up-conversion fluorescence (fig. 1 b), and the flavonoid fluorescent nanomaterial has good excitation light dependence (fig. 2). Under the irradiation of 365 hand-held ultraviolet lamp, the fluorescence of the flavonoid fluorescent nano material solution is yellow green.
Example 5
The fluorescence quantum yield of the flavonoid fluorescent nano material prepared in example 1 was measured, and the fluorescence quantum yield of the flavonoid fluorescent nano material in water was measured to be 7.7% by taking quinine sulfate as a standard. In order to determine the light stability performance of the flavonoid fluorescent nano material (figure 3), 340nm exciting light is used as a stable exciting light source, an optical signal of the flavonoid fluorescent nano material at 433nm is collected, the testing time is 10min, and experimental data show that the flavonoid fluorescent nano material has strong light stability.
Example 6
Hg was performed on the flavonoid fluorescent nanomaterial prepared in example 1 2+ Fluorescence response test, the test concentration of the used flavonoid fluorescent nano material is 0.67 mug/mL, and Hg with the concentration of 1mmol/L of mother liquor with different volumes is added into a fluorescence cuvette step by step 2+ Fluorescence spectroscopy experiments found to follow Hg 2+ The addition of the concentration has obvious quenching effect on the flavonoid fluorescent nano material (figure 4), hg in the experiment 2+ The detection concentration range of the fluorescent nano-material is 0-41.5 mu mol/L, thus realizing the detection of the flavonoid fluorescent nano-material on the harmful metal ions.
Claims (9)
1. The preparation method of the flavonoid fluorescent nano material is characterized by comprising the following steps of:
(1) Peeling and pulping kiwi fruits to prepare a sample, weighing a certain mass of the sample, adding 60% or 70% ethanol solution, performing water bath ultrasound, centrifuging, removing residues, and taking supernatant to obtain an extracting solution;
(2) Concentrating the extracting solution, adding high-purity water and dopants, heating at 180-200 ℃ for reaction, cooling to room temperature, centrifuging, filtering, and freeze-drying to obtain the flavonoid fluorescent nano material;
the dopant is ethylenediamine; the final concentration of the dopant is 0-0.36mol/L.
2. The method for preparing a flavonoid fluorescent nano material according to claim 1, wherein the mass volume ratio of the weighed sample to a 60% or 70% ethanol solution is 1g:5-10mL.
3. The method for preparing flavonoid fluorescent nano material according to claim 1, wherein the temperature of water bath ultrasound is 50-60 ℃ and the time is 40-60min.
4. The method for preparing flavonoid fluorescent nanomaterial according to claim 1, wherein the rotation speed of centrifugation is 6000-10000rpm, and the time is 10-15min.
5. The method for preparing a flavonoid fluorescent nanomaterial according to claim 1, wherein the volume of the extract after concentration is 1/8-1/4 of the volume before concentration.
6. The method for preparing flavonoid fluorescent nanomaterial according to claim 1, wherein the volume ratio of the concentrated extract to the high-purity water is 10:5-13.
7. The method for preparing flavonoid fluorescent nanomaterial according to any one of claims 1 to 6, wherein the heating reaction time is 3 to 6 hours.
8. The method for preparing flavonoid fluorescent nanomaterial according to claim 7, wherein the filtration is 0.22 μm microfiltration membrane filtration.
9. Flavonoid fluorescence prepared by the method of claim 1Preparation of Hg from nano material 2+ Application in detection reagents.
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