CN115058245A - Green fluorescent carbon quantum dot and application thereof in rapid detection of allura red - Google Patents
Green fluorescent carbon quantum dot and application thereof in rapid detection of allura red Download PDFInfo
- Publication number
- CN115058245A CN115058245A CN202210906072.7A CN202210906072A CN115058245A CN 115058245 A CN115058245 A CN 115058245A CN 202210906072 A CN202210906072 A CN 202210906072A CN 115058245 A CN115058245 A CN 115058245A
- Authority
- CN
- China
- Prior art keywords
- fcns
- green fluorescent
- carbon quantum
- fluorescent carbon
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000001514 detection method Methods 0.000 title claims abstract description 49
- 108010043121 Green Fluorescent Proteins Proteins 0.000 title claims abstract description 25
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 235000012741 allura red AC Nutrition 0.000 title claims abstract description 17
- 239000004191 allura red AC Substances 0.000 title claims abstract description 17
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 title claims abstract description 17
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims abstract description 11
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940018564 m-phenylenediamine Drugs 0.000 claims abstract description 6
- 229960004050 aminobenzoic acid Drugs 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 34
- 239000011259 mixed solution Substances 0.000 claims description 23
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 16
- 239000012498 ultrapure water Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000010791 quenching Methods 0.000 claims description 10
- 230000000171 quenching effect Effects 0.000 claims description 9
- 235000009508 confectionery Nutrition 0.000 claims description 7
- 235000019219 chocolate Nutrition 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 235000014214 soft drink Nutrition 0.000 claims description 5
- 239000006228 supernatant Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002301 cellulose acetate Polymers 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000000502 dialysis Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 230000001502 supplementing effect Effects 0.000 claims description 2
- 239000000523 sample Substances 0.000 abstract description 19
- 238000000034 method Methods 0.000 abstract description 18
- 230000035945 sensitivity Effects 0.000 abstract description 9
- 238000004458 analytical method Methods 0.000 abstract description 7
- 238000001027 hydrothermal synthesis Methods 0.000 abstract description 2
- 239000002243 precursor Substances 0.000 abstract description 2
- 238000011896 sensitive detection Methods 0.000 abstract description 2
- 235000013305 food Nutrition 0.000 description 12
- 230000005284 excitation Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 244000299461 Theobroma cacao Species 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000002795 fluorescence method Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000036039 immunity Effects 0.000 description 3
- 230000002452 interceptive effect Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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 2
- 239000001576 FEMA 2977 Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 238000005251 capillar electrophoresis Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 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 2
- 238000001736 differential pulse polarography Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229960003110 quinine sulfate Drugs 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011852 carbon nanoparticle Substances 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 231100000244 chromosomal damage Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000005558 fluorometry Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 229940051201 quinoline yellow Drugs 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000001040 synthetic pigment Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Images
Classifications
-
- 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
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/01—Particle morphology depicted by an image
- C01P2004/04—Particle morphology depicted by an image obtained by TEM, STEM, STM or AFM
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/30—Particle morphology extending in three dimensions
- C01P2004/32—Spheres
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/51—Particles with a specific particle size distribution
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
-
- 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 discloses a green fluorescent carbon quantum dot and application thereof in the aspect of rapid detection of allura red, wherein 4-aminobenzoic acid (PABA) and m-phenylenediamine are used as precursors, a green fluorescent carbon quantum dot (G-FCNs) is prepared by a hydrothermal synthesis method, and the green fluorescent carbon quantum dot is used as a probe for ultra-sensitive detection of AR. The invention obviously improves the sensitivity of the FCNs probe to AR detection and opens up a new way for AR rapid detection. The detection limit of the AR rapid detection method based on the G-FCNs established by the invention is as low as 23.5nM, so that the AR rapid detection method has high sensitivity. In addition, the method has the advantages of simple operation, low cost and quick analysis, and can be used for analyzing actual samples, thereby having good application and popularization values.
Description
Technical Field
The invention relates to the technical field of rapid detection of allura red, and particularly relates to a green fluorescent carbon quantum dot and application thereof in rapid detection of allura red.
Background
The synthetic pigment has the advantages of bright color, low cost and strong dyeing power, and is widely used in the food industry to change the appearance of food, thereby improving appetite. Allure Red (AR) belongs to synthetic azo dyes, has the advantages of low cost and high stability, and is widely used in various foods, such as candies, jellies, juices, dairy products, beverages and the like. Despite its wide application, its toxicity and pathogenicity are not negligible due to its unique structure with azo functional groups and aromatic rings. It has been reported that excessive use of AR may cause various diseases such as respiratory and digestive problems, hyperactivity, insomnia, asthma, allergy, chromosome damage, lymphoma, and the like. To prevent AR abuse, regulations are enacted in many countries. For example, in the united states, germany, norway, denmark, france, sweden, switzerland, belgium, austria and indian AR are classified as illegal food colorants and are completely prohibited from use. China specifies the maximum permitted usage of AR in different types of food, for example, the maximum permitted usage of AR in soft drinks is 0.1g kg -1 The maximum allowable usage limit of the candies and the chocolate is 0.3g kg -1 . Therefore, there is a need to develop a simple, rapid and convenient analytical method for accurately determining the AR content in food.
Currently, researchers have established a variety of analytical methods to accurately detect AR, including Thin Layer Chromatography (TLC), Differential Pulse Polarography (DPP), electrochemical sensing, Capillary Electrophoresis (CE), High Performance Liquid Chromatography (HPLC), and the like. While these methods have proven useful for AR detection, they typically suffer from expensive, cumbersome sample preparation procedures and long time consuming instrumentation. Therefore, the fluorescence method based on the functionalized carbon quantum dots (FCNs) has the advantages of rapidness, simplicity in operation, low cost, good selectivity, high sensitivity and the like, and shows a good application prospect in the aspect of overcoming the difficulties.
Carbon quantum dots(FCNs) generally refer to oxygen-enriched carbon nanoparticles having a particle size of less than 10nm, with pronounced fluorescence (PL) properties. FCNs have excellent photostability, adjustable emission, water solubility, biocompatibility, and low cytotoxicity. Based on these advantages, FCNs have occupied a niche in food testing. Research shows that the FCNs-based sensing system has higher sensitivity in the aspect of detecting food additives such as lemon yellow, citric acid, malachite green, carmine, glutathione and the like. However, to date, research into AR detection using FCNs as nanoprobes is still rare and only two reports have been found. Vijeata et al prepared three FCNs probes for AR detection using fruit shell, pulp and gum mixtures with detection limits of 0.260, 0.607 and 0.166. mu. mol L, respectively -1 . In another study, Gunjal et al prepared FCNs probes for AR detection from sawmill waste as a raw material with an obtained detection limit of 0.91. mu. mol L -1 (0.45μg mL -1 ). These two studies demonstrate the feasibility of using FCNs as nanoprobes for AR detection. However, both of these works are based on FCNs that fluoresce in the blue at short wavelengths, and are susceptible to interference from solvent scattering spectra or lack of large stokes shifts limiting the sensitivity of detection. To further improve the analytical performance of FCNs-based fluorescence methods, it is essential to develop FCNs probes based on long-wavelength fluorescence for AR detection.
Disclosure of Invention
Aiming at the problem of insufficient sensitivity of the existing AR detection technology based on short-wavelength blue fluorescent FCNs, the invention develops a rapid detection method based on green fluorescent G-FCNs for AR detection, and the sensitivity of the rapid detection method is far higher than that of any existing fluorescent probe based on FCNs. In addition, the method has the advantages of simple operation, low cost and quick detection, and can be used for AR detection in actual food matrixes.
The invention adopts the following technical scheme:
a preparation method of green fluorescent carbon quantum dots comprises the following steps:
(1) dissolving 0.13g of 4-aminobenzoic acid and 0.10g of m-phenylenediamine in 20.0mL of a mixed solution of ultrapure water and absolute ethyl alcohol at an equal volume ratio; transferring the mixture solution into a polytetrafluoroethylene-lined autoclave, and heating at a constant temperature of 180 ℃ for 12 hours;
(2) the reaction product was allowed to stand to cool to room temperature and then transferred to a 50.0mL centrifuge tube. After centrifugation at 12000rpm/min for 15 minutes, the supernatant was collected;
(3) redissolving the obtained supernatant in ultrapure water, and purifying in a 1.0L beaker through a dialysis membrane for 3 days, and supplementing fresh ultrapure water every 24 h; and (4) freeze-drying the purified solution containing the G-FCNs to obtain dried G-FCNs powder, and storing the dried G-FCNs powder in a drying box for a long time.
The application of the green fluorescent carbon quantum dots in the aspect of rapid detection of allura red comprises the following steps:
1) mixing ultrapure water and green fluorescent carbon quantum dots to obtain a green fluorescent carbon quantum dot solution;
2) respectively mixing and reacting the allure red with different concentrations with the green fluorescent carbon quantum dot solution to obtain mixed solutions with different allure red concentrations, respectively measuring the fluorescence intensity of the mixed solutions with different allure red concentrations, and obtaining the fluorescence quenching efficiency F 0 Linear relationship of/F and allura red concentration in the mixed solution;
3) mixing a sample to be detected with the green fluorescent carbon quantum dot solution for reaction to obtain a mixed solution of the sample to be detected, and measuring the fluorescence intensity of the mixed solution of the sample to be detected;
4) according to fluorescence quenching efficiency F 0 And obtaining the concentration of the allura red in the mixed solution of the sample to be detected through the linear relation between the concentration of the allura red in the mixed solution and the concentration of the allura red in the mixed solution.
Further, the concentration of the green fluorescent carbon quantum dot solution in the step 1) is 0.001-0.1mg mL -1 。
Further, the concentration of the green fluorescent carbon quantum dot solution in the step 1) is 0.01mg mL -1 。
Further, step 2) the fluorescence quenching efficiency F 0 The linear relationship between/F and allura red concentration in the mixed solution is: y 0.0849x + 0.9883.
Further, in the step 2) and the step 3), the pH value of the reaction system is between 2.0 and 12.0.
Further, in the step 2) and the step 3), the pH value of the reaction system is 6.5.
Further, in the step 2) and the step 3), the fluorescence intensity is measured at lambda ex Is 400nm, lambda em Measured at 493 nm.
Further, the reaction time of the step 2) and the step 3) is 1 min.
Further, in step 3), the sample to be tested is: soft drink, candy or chocolate containing AR is pulverized, dissolved or diluted, and filtered with cellulose acetate membrane injection filter with pore diameter of 0.45 μm to obtain extractive solution.
The invention has the following beneficial effects:
the invention takes 4-aminobenzoic acid (PABA) and m-phenylenediamine as precursors, prepares the green fluorescent G-FCNs by a hydrothermal synthesis method, takes the green fluorescent G-FCNs as probes for the ultra-sensitive detection of AR, has the detection limit as low as 23.5nM, and opens up new prospects for improving the detection performance of AR detection. The method also has the advantages of simple operation, low cost and quick analysis, and can be used for analyzing actual samples, thereby having good application and popularization values.
Drawings
FIG. 1 is a schematic view of the detection method of the present invention;
FIG. 2(A) UV-visible absorption spectra (solid line), fluorescence excitation spectra (dashed line) and emission spectra (dotted line) of G-FCNs; the insert picture at the upper right corner is an ultraviolet-visible absorption spectrum amplified in the range of 300-500nm, and the picture at the upper left corner is a G-FCNs aqueous solution under the irradiation of natural light (left) and ultraviolet light (right); (B) fluorescence spectra of G-FCNs at different excitation wavelengths; (C) (a) quinine sulfate and (b) a G-FCNs ultraviolet absorption intensity-fluorescence spectrum peak area integral diagram;
FIG. 3 is an (A) TEM image of G-FCNs; (B) a particle size distribution histogram; (C) an FTIR spectrogram;
FIG. 4(A) graph of the effect of pH on detecting AR; (B) a graph of the effect of G-FCNS concentration on detecting AR; (C) the influence curve of the reaction time on the detection of AR;
FIG. 5(A) contains different concentrations of AR (0.0-60.0. mu. mol L) -1 ) Solution of G-FCNs (0.01mg mL) -1 ) A fluorescence spectrum of (a); (B) f 0 A linear plot of/F versus AR concentration;
FIG. 6 is a bar graph of (A) selectivity and (B) interference immunity of G-FCNs to small molecules such as AR, anions and cations, and various amino acids.
Detailed Description
In order to more clearly illustrate the technical solution of the present invention, the following examples are given. The starting materials, the reactions and the work-up procedures present in the examples are, unless otherwise stated, commercially available starting materials and techniques known to those skilled in the art.
As shown in FIG. 1, G-FCNs were prepared by hydrothermal heating of 4-aminobenzoic acid (PABA) and m-phenylenediamine. AR effectively reduces the fluorescence intensity of G-FCNs in a concentration-dependent manner through electrostatic adsorption, Internal Filter Effect (IFE) and dynamic quenching. Therefore, a fluorescence method based on G-FCNs is proposed to detect AR. The influence of detection conditions such as G-FCNs concentration, pH value and reaction time on the analysis performance is studied in detail. The method is thoroughly verified by researching the linear range, the detection limit, the selectivity and the anti-interference capability of the method. Finally, the method is used for determining AR in food to evaluate the feasibility of practical application. The method has ultrahigh sensitivity, good selectivity, low cost and easy operability, and provides a convenient and reliable analysis strategy for AR monitoring.
Synthesis of G-FCNs:
0.13g of PABA and 0.10g of m-phenylenediamine were dissolved in 20.0mL of a mixed solution of ultrapure water and absolute ethanol (1:1v: v). The mixture solution was transferred to a polytetrafluoroethylene-lined autoclave and heated at a constant temperature of 180 ℃ for 12 hours. The reaction product was allowed to stand to cool to room temperature and then transferred to a 50.0mL centrifuge tube. After centrifugation at 12000rpm (revolutions per minute) for 15 minutes, the supernatant was collected, redissolved in ultrapure water, and purified by dialysis membrane (MWCO ═ 500-. The purified solution containing the G-FCNs is lyophilized to obtain dried G-FCNs powder, which is stored in a drying oven for a long time.
Physical and chemical property characterization of G-FCNs:
the ultraviolet absorption properties of G-FCNs were investigated using ultraviolet-visible absorption spectroscopy (UV-Vis). FIG. 2A (solid line) shows UV-Vis spectra of G-FCNs with absorption peaks at 240, 270 and 375 nm. The peaks at 240nm are pi → pi transitions due to C ═ N bonds, while the peaks at 270 and 375nm are N → pi transitions due to C ═ O bonds.
The fluorescence properties of G-FCNs were investigated by fluorescence spectroscopy. As shown in FIG. 2A (dashed line), G-FCNs have an excitation peak at 400 nm. As shown in FIG. 2A (dotted line), the emission peak of G-FCNs at 400nm excitation was 493 nm. Aqueous solutions of G-FCNs appear brownish yellow in natural light (FIG. 2A, left of the top left inset) and bright green under UV irradiation (FIG. 2A, right of the top left inset). FIG. 2B is an emission spectrum of G-FCNs at different excitation wavelengths, which is seen to exhibit excitation wavelength dependence. As shown in FIG. 2C, the quantum yield of G-FCNs was measured to be 15.40% using quinine sulfate as a reference material.
Morphology and size of the G-FCNs were measured by TEM method. As shown in FIG. 3A, the G-FCNs are uniform in size and spherical in shape. FIG. 3B is a histogram of the particle size distribution of G-FCNs. The grain size distribution range of the G-FCNs is 0.35-6.65nm, and the average grain size is 2.5 +/-0.4 nm.
The functional groups of the G-FCNs are characterized by Fourier infrared spectroscopy. As shown in FIG. 3C, at 3426 and 3213cm -1 The absorption peak in the range is attributed to O-H/N-H stretching vibration. 2923cm -1 And 1693cm -1 The absorption peaks at (a) correspond to the stretching vibration of C-H and C ═ O, respectively. The C-N and N-H stretching vibration respectively appears at 1600cm -1 And 1496cm -1 . The C-N stretching vibration and the C-O stretching vibration respectively appear in 1313-1260cm -1 And 1170cm -1 . Thus, the hydrophilicity of G-FCNs is attributed to the unsaturated carbonaceous structure having nitrogen-and oxygen-containing functional groups on its surface.
3. Optimization of experimental conditions
In order to obtain the best detection performance, main working parameters of the sensing platform are optimized, wherein the main working parameters comprise the pH of a reaction system, the concentration of the G-FCNs solution and the reaction.
3.1 Effect of pH on the assay
As shown in FIG. 4A, pH value(PBS solution, 10.0mM) varying between 2.0 and 12.0 results in a fluorescence quenching efficiency, F 0 /F (wherein F) 0 And F respectively refer to fluorescence intensities of G-FCNs before and after mixing with AR), and the highest value was obtained at pH 6.5 (ultrapure water). Therefore, the optimum pH was selected to be 6.5. In order to simplify the steps, ultrapure water is adopted as a solution in the subsequent detection work.
Effect of 3.2G-FCNs concentration on detection
As shown in FIG. 4B, the concentration of G-FCNs increased from 0.001 to 0.01mg mL -1 Time of day, F of the sensing system 0 the/F increased significantly, in the higher concentration range (0.01-0.1mg mL) -1 ) Inner F 0 the/F drops sharply. Therefore, 0.01mg mL was selected -1 The optimum concentration of G-FCNs is obtained.
3.3 Effect of reaction time on the assay
As shown in FIG. 4C, F 0 the/F sharply increases within 1.0min and tends to be constant along with the time extension, which indicates that the sensing system has high reaction speed and can complete the reaction only within 1.0min, therefore, 1.0min is adopted as the optimal reaction time in the subsequent detection work.
4. Analytical method validation
4.1 Linear Range
To investigate the effect of AR on the fluorescence intensity of G-FCNs, a concentration of 0.01mg mL was prepared using ultrapure water -1 Then adding AR with different concentrations into the prepared G-FCNs solution, reacting for 1.0min, and recording the fluorescence intensity of the mixed solution under the excitation of 400nm and the emission of 493 nm.
As shown in FIG. 5A, in a solution of G-FCNs (0.01mg mL) -1 ) After addition of different concentrations of AR, a gradual decrease in the fluorescence intensity of the G-FCNs was observed with increasing AR concentration. When the AR concentration reaches 60.0 mu mol L -1 At this time, the fluorescence of G-FCNs was quenched by approximately 95.87%. Indicating that AR can effectively quench the fluorescence intensity of G-FCNs. As shown in FIG. 5B, fluorescence quenching efficiency F 0 The dependence of/F on AR concentration is linear. The corresponding regression equation is 0.0849x + 0.9883. The detection limit was calculated to be 23.5nmol L -1 . The detection limits of the present detection method were compared to reported fluorescent methods based on FCNs, as shown in Table 1As shown, the sensitivity of the present detection method is much higher than that of any existing FCNs-based fluorescence detection method.
TABLE 1 detection Performance of FCNs-based AR fluorometry
4.2 Selectivity
This work investigated the selectivity of G-FCNs over AR. Mixing AR with different kinds of interfering substances including cation (K) + 、Na + 、Fe 2+ 、Ba 2+ 、Pb 2+ 、Cd 2+ And Mg 2+ ) Anion (Br) - 、H 2 PO 4 2- 、S 2 O 3 2- 、Cl - 、NO 3 - 、NO 2 - And F - ) Pigments (amaranth, indigo and quinoline yellow) and other small molecules (serine, tyrosine, glycine, tryptophan, glucose, D-fructose and sucrose) were dissolved in ultrapure water to a final concentration of 0.1mmol L -1 . 2.0. mu.L of each was added to a series of 5.0mL solutions containing 2.0mL of G-FCNs (0.01mg mL of each solution) -1 ) In the centrifuge tube. After thorough mixing, the maximum fluorescence intensity of the mixed solution at 493nm was recorded at an excitation wavelength of 400 nm.
As shown in fig. 6A, the introduction of AR resulted in a sharp decrease in the fluorescence intensity of G-FCNs, while other interfering substances that may be present had little significant effect on the fluorescence intensity of G-FCNs, indicating that the detection method proposed in this work has excellent selectivity for AR detection.
4.3 interference immunity
This work examined the interference immunity of G-FCNs to AR detection. A series of 20.0. mu.L AR solutions (10.0mmol L) -1 ) Added to a solution containing 2.0mL of G-FCNs (0.01mg mL) -1 ) In a 5.0mL centrifuge tube. Then, 2.0. mu.L of each of the above-mentioned interfering substances was added to a final concentration of 0.1mmol L -1 . Similar to the selectivity study, the fluorescence intensity at 493nm under excitation at 400nm of the mixture solution was recorded.
As shown in FIG. 6B, the fluorescence of the G-FCNs/AR system is not interfered by the foreign substances, which shows that the method has good anti-interference capability. Therefore, the proposed method has the potential to be used for AR determination in real food samples.
5. Actual sample testing
Different kinds of food samples, such as AR-containing soft drinks, candies and chocolates, were purchased from local markets. For beverage samples, they were first boiled to remove dissolved CO 2 Then, 2.0mL of the sample was transferred to a centrifuge tube and diluted with 10.0mL of ultrapure water. For candies and sugar coated chocolates, they were first pulverized into fine powders, 0.1g of each sample powder was dissolved in 10.0mL of ultrapure water and sonicated for 10.0 min. Finally, the sample extract was filtered through a cellulose acetate membrane syringe filter having a pore size of 0.45 μm. A solution of G-FCNs (0.01mg mL) -1 ) Transfer to 5.0mL centrifuge tubes each containing 2.0mL of G-FCNs solution. Mixing with 20.0 μ L of each sample extractive solution, and measuring the fluorescence intensity of G-FCNs (i.e. F) at 493nm before and after adding the sample extractive solution at excitation wavelength of 400nm 0 And F).
TABLE 2 detection of AR in food samples
As shown in Table 2, the AR contents in the above food samples were 0.30, 0.71, 0.22, 0.42 and 0.51. mu. mol L, respectively -1 Corresponding to 0.14, 0.34, 0.11, 0.20 and 0.24mg kg, respectively -1 All below the maximum limit allowed for AR use in soft drinks, candies and chocolate samples in our country and therefore can be safely consumed. Sample recovery tests showed recoveries in the range of 97.4-104.8% with Relative Standard Deviation (RSD) less than 3.58%. In addition, by comparison of HPLC analysis, it was observed that the detection results of the two methods were consistent, indicating that the proposed detection method had high accuracy.
Furthermore, it should be understood that although the present specification describes embodiments, not every embodiment includes only a single embodiment, and such description is for clarity purposes only, and it is to be understood that all embodiments may be combined as appropriate by one of ordinary skill in the art to form other embodiments as will be apparent to those of skill in the art from the description herein.
Claims (10)
1. A preparation method of green fluorescent carbon quantum dots is characterized by comprising the following steps:
(1) dissolving 0.13g of 4-aminobenzoic acid and 0.10g of m-phenylenediamine in 20.0mL of a mixed solution of ultrapure water and absolute ethanol in an equal volume ratio; transferring the mixture solution into a polytetrafluoroethylene-lined autoclave, and heating at a constant temperature of 180 ℃ for 12 hours;
(2) the reaction product was allowed to stand to cool to room temperature and then transferred to a 50.0mL centrifuge tube. After centrifugation at 12000rpm/min for 15 minutes, the supernatant was collected;
(3) redissolving the obtained supernatant in ultrapure water, and purifying in a 1.0L beaker through a dialysis membrane for 3 days, and supplementing fresh ultrapure water every 24 h; the purified solution containing the G-FCNs is lyophilized to obtain dried G-FCNs powder, which is stored in a drying oven for a long time.
2. The application of the green fluorescent carbon quantum dots in the aspect of rapid detection of allura red as claimed in claim 1, is characterized by comprising the following steps:
1) mixing ultrapure water and green fluorescent carbon quantum dots to obtain a green fluorescent carbon quantum dot solution;
2) respectively mixing and reacting the allure red with different concentrations with the green fluorescent carbon quantum dot solution to obtain mixed solutions with different allure red concentrations, respectively measuring the fluorescence intensity of the mixed solutions with different allure red concentrations, and obtaining the fluorescence quenching efficiency F 0 Linear relationship of/F and allura red concentration in the mixed solution;
3) mixing a sample to be detected with the green fluorescent carbon quantum dot solution for reaction to obtain a mixed solution of the sample to be detected, and measuring the fluorescence intensity of the mixed solution of the sample to be detected;
4) according to fluorescence quenching efficiency F 0 And obtaining the concentration of the allura red in the mixed solution of the sample to be detected through the linear relation between the concentration of the allura red in the mixed solution and the concentration of the allura red in the mixed solution.
3. The use of claim 2, wherein the concentration of the green fluorescent carbon quantum dot solution in the step 1) is 0.001-0.1mg mL -1 。
4. The use of claim 2, wherein the concentration of the green fluorescent carbon quantum dot solution in the step 1) is 0.01mg mL -1 。
5. The use of claim 2, wherein the fluorescence quenching efficiency F of step 2) is 0 The linear relationship between/F and allura red concentration in the mixed solution is as follows: y 0.0849x + 0.9883.
6. The use according to claim 2, wherein in step 2) and step 3), the reaction system has a pH between 2.0 and 12.0.
7. The use according to claim 2, wherein in step 2) and step 3), the reaction system has a pH of 6.5.
8. The use according to claim 2, wherein in step 2) and step 3) the fluorescence intensity is measured at λ ex Is 400nm, lambda em Measured at 493 nm.
9. The use of claim 2, wherein the reaction time in step 2) and step 3) is 1 min.
10. The use of claim 2, wherein the sample to be tested in step 3) is: soft drink, candy or chocolate containing AR is pulverized, dissolved or diluted, and filtered with cellulose acetate membrane injection filter with pore diameter of 0.45 μm to obtain extractive solution.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210906072.7A CN115058245B (en) | 2022-07-29 | 2022-07-29 | Green fluorescent carbon quantum dot and application thereof in rapid detection of allure red |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210906072.7A CN115058245B (en) | 2022-07-29 | 2022-07-29 | Green fluorescent carbon quantum dot and application thereof in rapid detection of allure red |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115058245A true CN115058245A (en) | 2022-09-16 |
CN115058245B CN115058245B (en) | 2023-11-21 |
Family
ID=83207510
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210906072.7A Active CN115058245B (en) | 2022-07-29 | 2022-07-29 | Green fluorescent carbon quantum dot and application thereof in rapid detection of allure red |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115058245B (en) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01305069A (en) * | 1988-05-31 | 1989-12-08 | Shionogi & Co Ltd | Benzotriazole derivative and fluorescent light emitting reagent containing the same derivative |
CN102313808A (en) * | 2011-02-01 | 2012-01-11 | 天津百鸥瑞达生物科技有限公司 | Method for detecting allura red and enzyme linked immunosorbent assay (ELISA) kit |
CN106596666A (en) * | 2016-11-18 | 2017-04-26 | 常州大学 | Methods for immobilization of bis-terpyridyl ruthenium and electrochemical luminescence detection of allura red |
CN109935713A (en) * | 2017-12-15 | 2019-06-25 | Tcl集团股份有限公司 | Quantum dot film and preparation method thereof, QLED device and preparation method thereof |
CN112461807A (en) * | 2020-11-26 | 2021-03-09 | 山西大学 | Application of carbon quantum dots in targeted nucleolus wash-free imaging |
CN114196392A (en) * | 2021-11-02 | 2022-03-18 | 山西大学 | Dual-mode ratiometric optical probe for detecting adriamycin based on sulfydryl functionalized carbon dots and preparation method and application thereof |
JP2022046118A (en) * | 2020-09-10 | 2022-03-23 | 日東電工株式会社 | Substance-permeable membrane, method for inspecting substance-permeable membrane, and membrane separation system |
-
2022
- 2022-07-29 CN CN202210906072.7A patent/CN115058245B/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01305069A (en) * | 1988-05-31 | 1989-12-08 | Shionogi & Co Ltd | Benzotriazole derivative and fluorescent light emitting reagent containing the same derivative |
CN102313808A (en) * | 2011-02-01 | 2012-01-11 | 天津百鸥瑞达生物科技有限公司 | Method for detecting allura red and enzyme linked immunosorbent assay (ELISA) kit |
CN106596666A (en) * | 2016-11-18 | 2017-04-26 | 常州大学 | Methods for immobilization of bis-terpyridyl ruthenium and electrochemical luminescence detection of allura red |
CN109935713A (en) * | 2017-12-15 | 2019-06-25 | Tcl集团股份有限公司 | Quantum dot film and preparation method thereof, QLED device and preparation method thereof |
JP2022046118A (en) * | 2020-09-10 | 2022-03-23 | 日東電工株式会社 | Substance-permeable membrane, method for inspecting substance-permeable membrane, and membrane separation system |
CN112461807A (en) * | 2020-11-26 | 2021-03-09 | 山西大学 | Application of carbon quantum dots in targeted nucleolus wash-free imaging |
CN114196392A (en) * | 2021-11-02 | 2022-03-18 | 山西大学 | Dual-mode ratiometric optical probe for detecting adriamycin based on sulfydryl functionalized carbon dots and preparation method and application thereof |
Non-Patent Citations (1)
Title |
---|
孙文通;康勇;王仕兴;: "食品中偶氮类色素检测方法的研究进展", 食品安全质量检测学报, no. 06 * |
Also Published As
Publication number | Publication date |
---|---|
CN115058245B (en) | 2023-11-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Leona et al. | Application of surface‐enhanced Raman scattering techniques to the ultrasensitive identification of natural dyes in works of art | |
Van Leeuw et al. | Antioxidant capacity and phenolic composition of red wines from various grape varieties: Specificity of Pinot Noir | |
US9890286B2 (en) | Colorant compounds derived from genipin or genipin containing materials | |
Singleton et al. | Anthocyanin-tannin interactions explaining differences in polymeric phenols between white and red wines | |
Gambuti et al. | Partial dealcoholisation of red wines by membrane contactor technique: influence on colour, phenolic compounds and saliva precipitation index | |
Wang et al. | Interaction of protein isolate with anthocyanin extracted from black soybean and its effect on the anthocyanin stability | |
CN111122524B (en) | Fluorescent probe for rapidly detecting morin based on fluorescence quenching method and preparation method and application thereof | |
Staško et al. | A comparative study on the antioxidant properties of Slovakian and Austrian wines | |
CN109456761B (en) | Quantitative detection of vitamin B based on carbon quantum dot fluorescence quenching method12Fluorescent probe and preparation method and application thereof | |
López et al. | Industrial vinegar clarification by cross-flow microfiltration: effect on colour and polyphenol content | |
CN113201336A (en) | Preparation method based on nitrogen-phosphorus doped carbon quantum dots and application of preparation method in rapid detection of tartrazine | |
CN113234443A (en) | Preparation method based on nitrogen, sulfur, phosphorus and chlorine co-doped carbon quantum dots and application of carbon quantum dots in rapid detection of carmine | |
CN114854407B (en) | Preparation method of L-arginine-based carbon dot and application of L-arginine-based carbon dot in lemon yellow detection | |
Widmer et al. | Methods for determining the adulteration of citrus juices | |
CN115058245B (en) | Green fluorescent carbon quantum dot and application thereof in rapid detection of allure red | |
CN115368891B (en) | Fluorescent carbon quantum dot and application thereof in rapid chlorogenic acid detection | |
CN110186886A (en) | The inversion method of Microcystins in Water MC-LR concentration | |
Sikorska | Fluorescence spectroscopy and chemometrics in analysis of beverages | |
Liu et al. | Effect of changing the melanoidins by decoction on the release of volatiles in Zhenjiang aromatic vinegar | |
Duan et al. | Accurate ethanol determination in Chinese Baijiu based on red-emitted carbon quantum dots (CQDs) and a simple pH correction | |
US5512488A (en) | Colorimetric assay for bioactive polysaccharide | |
Naidis et al. | Study of the dyeing properties of saffron and ultrafiltrated saffron powders, as colourants for natural and synthetic fibres | |
CN115232616A (en) | Preparation method and application of ratiometric fluorescent probe based on fangchinoline carbon dots | |
Hu et al. | Ultrasensitive determination of allura red in food samples based on green-emissive carbon nanodots | |
KR100651248B1 (en) | A preparation method of beverages, jam and sauce for softening meat using immature fruit and mature fruit of BOKBOONJA |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |