CN116730324B - Near-infrared AIE carbon dot, preparation method thereof and application thereof in triple anti-counterfeiting and aluminum ion detection - Google Patents
Near-infrared AIE carbon dot, preparation method thereof and application thereof in triple anti-counterfeiting and aluminum ion detection Download PDFInfo
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 49
- 229910052782 aluminium Inorganic materials 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 238000001514 detection method Methods 0.000 title claims abstract description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 104
- -1 flavonoid compounds Chemical class 0.000 claims abstract description 56
- 238000012360 testing method Methods 0.000 claims abstract description 31
- 229930003935 flavonoid Natural products 0.000 claims abstract description 14
- 235000017173 flavonoids Nutrition 0.000 claims abstract description 14
- 238000004729 solvothermal method Methods 0.000 claims abstract description 13
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- 238000004220 aggregation Methods 0.000 claims abstract description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
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- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 claims description 6
- KZNIFHPLKGYRTM-UHFFFAOYSA-N apigenin Chemical compound C1=CC(O)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 KZNIFHPLKGYRTM-UHFFFAOYSA-N 0.000 claims description 6
- XADJWCRESPGUTB-UHFFFAOYSA-N apigenin Natural products C1=CC(O)=CC=C1C1=CC(=O)C2=CC(O)=C(O)C=C2O1 XADJWCRESPGUTB-UHFFFAOYSA-N 0.000 claims description 6
- 229940117893 apigenin Drugs 0.000 claims description 6
- 235000008714 apigenin Nutrition 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 claims description 5
- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 claims description 5
- 229940117954 naringenin Drugs 0.000 claims description 5
- 235000007625 naringenin Nutrition 0.000 claims description 5
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 4
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 4
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 4
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 4
- 229960001285 quercetin Drugs 0.000 claims description 4
- 235000005875 quercetin Nutrition 0.000 claims description 4
- MNFZZNNFORDXSV-UHFFFAOYSA-N 4-(diethylamino)benzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C=C1 MNFZZNNFORDXSV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002215 flavonoids Chemical class 0.000 claims description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 17
- 239000006185 dispersion Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000000034 method Methods 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 230000005284 excitation Effects 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 9
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- 238000004440 column chromatography Methods 0.000 description 6
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- 150000002500 ions Chemical class 0.000 description 5
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- 239000000047 product Substances 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- 238000000862 absorption spectrum Methods 0.000 description 3
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- 230000002860 competitive effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
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- 230000007613 environmental effect Effects 0.000 description 1
- 238000002284 excitation--emission spectrum Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 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
- C09K11/08—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
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- 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
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- 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
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- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biophysics (AREA)
- Optics & Photonics (AREA)
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Abstract
The invention provides a preparation method of near-infrared AIE carbon dots, which takes flavonoid compounds and carbonyl-containing compounds as raw materials, adopts a solvothermal method to prepare the near-infrared AIE carbon dots, has simple preparation steps, low raw material cost and high preparation yield, and is expected to be used for industrialization; the near infrared AIE carbon dot has the AIE property of double emission, the double emission peaks respectively emit cyan fluorescence of 480nm and 676nm in a dispersion state, and near infrared fluorescence of 676nm in an aggregation state, so that the near infrared AIE carbon dot is applicable to more application scenes; the near infrared AIE carbon point can emit phosphorescence on filter paper, and fluorescent ink capable of being used for triple anti-counterfeiting is prepared by utilizing the double emission, AIE and phosphorescence properties of the near infrared AIE carbon point; the cyan carbon dots obtained after the near infrared AIE carbon dots are purified can respond to aluminum ions, and the aluminum ion test paper for on-site detection of the aluminum ions is prepared.
Description
Technical Field
The invention relates to the technical field of carbon dots, in particular to a near infrared AIE carbon dot, a preparation method thereof and application thereof in triple anti-counterfeiting and aluminum ion detection.
Background
Carbon dots are a class of zero-dimensional nanomaterials with dimensions less than 10nm, which have attracted considerable attention since 2004 was reported. The carbon dots are composed of dispersed spheroidal carbon particles composed of sp2 hybridized carbon cores and various functional groups such as hydroxyl, carboxyl, amino, etc., which provide abundant modification sites and ensure the water solubility of the carbon dots. The special structure of the carbon dots enables the dye to have excellent optical properties, such as emission dependence on excitation, up-conversion luminescence, photo-bleaching resistance, photo-scintillation resistance and the like, and the dye is simpler to prepare and better in stability than the traditional organic dye. Therefore, carbon dots are widely used in the fields of anti-counterfeiting, biological imaging, drug transport, optical devices, and the like.
The traditional fluorescent carbon dots have good fluorescence in a dispersion state, and in an aggregation state, fluorescence quenching is caused by excessive energy transfer and pi-pi stacking effect, so that the application of the carbon dots is limited. Based on this, researchers have prepared aggregation-induced emission carbon dots (AIE) to overcome this defect, which have attracted extensive attention from reports. The current methods for developing AIE carbon dots mainly comprise a matrix doping method and a precursor structure regulating method. The double emission means that the fluorescent material has two emission peaks, false positive is not easy to occur in detection, the current double emission AIE has fewer carbon points, and a light emitting mechanism is fuzzy, and reasonable explanation and characterization are needed. Furthermore, the reported fluorescent colors of AIE carbon dots are mostly blue and yellow, with near infrared AIE carbon dots being very rare.
Counterfeiting and counterfeiting products are a common phenomenon today that can have adverse effects on individuals and society. The anti-counterfeiting material needs to have the characteristics of easy synthesis, high yield, long-term storage, environmental protection, difficult replication and the like. The first generation of anti-counterfeiting material is created by using traditional single-emission fluorescent dye, and the fluorescent anti-counterfeiting mode is relatively single and is easy to forge. The second generation of anti-counterfeiting material is to improve the security by applying a mixture of various luminescent materials, patterns written by using a plurality of fluorophores show different fluorescent patterns at different excitation wavelengths, and the anti-counterfeiting material has higher security, however, an experienced counterfeiter can still easily imitate the material, so that the fluorescent material with higher encryption security is needed to be used for anti-counterfeiting. The carbon dots have excellent optical properties, such as emission dependence excitation, up-conversion luminescence, phosphorescence and other luminescence modes, so that counterfeiters are difficult to copy, and the carbon dots have good stability, can be stored for a long time, and have wider prospects in anti-counterfeiting application. However, the carbon dots currently have the following disadvantages in security applications: (1) The fluorescence of the traditional carbon dots is easy to quench due to pi-pi stacking effect in the aggregation state; (2) AIE carbon dots can not emit light in a dispersed state, and the application range is narrow; (3) the yield of carbon dots is low, and the method is not suitable for practical application; (4) The light-emitting mode is less and is mostly short-wavelength, and is easy to copy. These drawbacks limit the use of conventional carbon dots in security applications. Therefore, the preparation method of the multifunctional carbon dots with high yield and multiple anti-counterfeiting functions has important significance.
Disclosure of Invention
The method provided by the invention prepares near infrared AIE carbon dots (called N-CDs for short) with double emission, AIE and phosphorescence properties in high yield, prepares the near infrared AIE carbon dots (called C-CDs for short) into fluorescent ink which can be used for triple anti-counterfeiting, and the cyan carbon dots (called C-CDs for short) obtained by purifying the near infrared AIE carbon dots can respond to aluminum ions, so that the aluminum ion test paper for detecting the aluminum ions is prepared, can rapidly detect the aluminum ions, and is hopeful to be used for Al in actual samples 3+ And (5) detecting.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a preparation method of near infrared AIE carbon dots, which comprises the following steps:
and mixing the flavonoid compound, the carbonyl compound and the first organic solvent, and performing solvothermal reaction to obtain the near-infrared AIE carbon point.
Preferably, the flavonoid compound is one or more of quercetin, naringenin, apigenin and apigenin; the carbonyl-containing compound is one or more of barbituric acid, p-dimethylaminoacetophenone and p-diethylaminobenzaldehyde.
The invention also provides the near infrared AIE carbon dots prepared by the preparation method.
Preferably, the near infrared AIE carbon dots have aggregation-induced emission properties, emit cyan fluorescence at 480nm in a dispersed state, and emit near infrared fluorescence at 676nm in an aggregated state.
The invention also provides application of the near infrared AIE carbon dots in triple anti-counterfeiting.
Preferably, after the near infrared AIE carbon dots and the second organic solvent are mixed, the fluorescent ink for triple anti-counterfeiting is obtained.
Preferably, the mark formed by the fluorescent ink for triple anti-counterfeiting is blue fluorescence under the irradiation of a light source of 300-450 nm, becomes red fluorescence under the irradiation of the light source when meeting water, and can be circularly switched between the blue fluorescence and the red fluorescence, and emits green phosphorescence after the light source is turned off.
The invention also provides application of the near infrared AIE carbon dots in aluminum ion detection.
Preferably, the near infrared AIE carbon dots are purified to provide cyan carbon dots;
and mixing the cyan carbon dots with a third organic solvent to obtain a solution containing the cyan carbon dots, and dripping the solution containing the cyan carbon dots on filter paper to obtain the aluminum ion test paper for aluminum ion detection.
Preferably, the aluminum ion test paper selectively responds to Al 3+ The aluminum ion test paper encounters Al 3+ After that, its fluorescence changes from dark red to bright cyan.
The invention provides a preparation method of near infrared AIE carbon dots, which takes flavonoid compounds and carbonyl-containing compounds as raw materials, and adopts a solvothermal method to prepare near infrared AIE carbon dots with near infrared emission, double emission, aggregation-induced emission and phosphorescence emission properties, wherein the AIE properties are caused by rotatable groups formed by connecting the carbonyl-containing compounds with the carbon dots; secondly, the near infrared AIE carbon dot has double-emission AIE property, wherein the double-emission property is that the prepared carbon dot is a carbon dot mixed carbon dot, double-emission peaks respectively emit cyan fluorescence of 480nm and 676nm in a disperse state, near infrared fluorescence of 676nm is emitted in an aggregation state, fluorescence at 480nm is quenched due to excessive energy transfer and pi-pi stacking effect, meanwhile, the rotation of a surface group of the near infrared AIE carbon dot is inhibited, near infrared AIE fluorescence at 676nm appears, and the near infrared AIE carbon dot can be suitable for more application scenes due to different color fluorescence in the disperse state and the aggregation state; again, based on the confinement of the filter paper fiber to the near infrared AIE carbon sites, which can phosphorescence on the filter paper, the transition from carbon sites to excited triplet state is stabilized, the N-CDs double emission, AIE and phosphorescence properties, the preparation ofThe fluorescent ink can be used for triple anti-counterfeiting, and has a higher safety index; finally, the cyan carbon point C-CDs obtained by N-CDs purification can respond to Al 3+ It is prepared into Al 3 + Test paper with high response speed can be used for Al 3+ Is provided. The method provided by the invention has the advantages of simple preparation steps, low raw material cost and high preparation yield, and is expected to be used for industrialization. The results of the examples show that the method provided in example 4 of the present invention produces near infrared AIE carbon dots in yields as high as 83.2%; the rabbit dripped with the fluorescent ink for triple anti-counterfeiting prepared in the application example (4) has different fluorescence under different environments, can realize triple anti-counterfeiting by utilizing various spectral properties of N-CDs, is difficult to copy, and has higher safety; the aluminum ion test paper for aluminum ion detection prepared in application example 7 can be used for selectively detecting Al 3+ The addition of other ions does not affect the Al of the C-CDs pair 3+ And the response proves that the probe has good anti-interference performance.
Drawings
FIG. 1 is a normalized ultraviolet absorption, excitation and emission diagram of a fluorescent ink for triple anti-counterfeiting prepared in application example 4 of the present invention in water;
FIG. 2 is a fluorescence chart and a fluorescence spectrum chart of N-CDs prepared in example 12 of the invention at different water contents (0% -99%), wherein A in FIG. 2 is a fluorescence chart in a cuvette, and B in FIG. 2 and C in FIG. 2 are fluorescence emission charts of N-CDs prepared in example 12 at 480nm and 676nm with increasing water content, respectively;
FIG. 3 is a graph showing the ultraviolet absorption, excitation and emission normalization of C-CDs prepared in application example 7 in water and an X-ray diffraction chart, wherein A in FIG. 3 is a graph showing the ultraviolet absorption, excitation and emission normalization of C-CDs prepared in application example 7 in water; wherein B in FIG. 3 is an X-ray diffraction pattern of the C-CDs prepared in application example 7;
FIG. 4 is a diagram showing the real object of the C-CDs prepared in application example 7 of the present invention under ultraviolet lamps with different water contents;
FIG. 5 is a diagram of the fluorescent ink for triple anti-counterfeiting prepared in application example 4 of the present invention applied in triple anti-counterfeiting;
FIG. 6 shows C-CDs-responsive Al prepared in application example 7 of the present invention 3+ Fluorescence spectrum of concentration;
FIG. 7 is a graphical representation of the results of the selectivity and competition experiments for the aluminum ion test paper prepared from the C-CDs prepared in application example 7, wherein A in FIG. 7 is a graphical representation of the results of the selectivity and B in FIG. 7 is a graphical representation of the results of the competition experiments.
Detailed Description
The invention provides a preparation method of near infrared AIE carbon dots, which comprises the following steps:
and mixing the flavonoid compound, the carbonyl compound and the first organic solvent, and performing solvothermal reaction to obtain the near-infrared AIE carbon point.
In the present invention, the raw materials used are all conventional commercial products in the art unless otherwise specified.
In the invention, the flavonoid compound is preferably one or more of quercetin, naringenin and apigenin. In the invention, the carbonyl-containing compound is one or more of barbituric acid, p-dimethylaminoacetophenone and p-diethylaminobenzaldehyde.
In the present invention, the first organic solvent is preferably one or more of ethanol, methanol, acetic acid, and N, N-dimethylformamide.
In the invention, the ratio of the mass of the flavonoid, the mass of the carbonyl-containing compound and the volume of the first organic solvent is 1g: (0.5-2) g:50mL.
In the present invention, the temperature of the solvothermal reaction is preferably 170 to 250 ℃, more preferably 180 to 230 ℃. In the present invention, the time of the solvothermal reaction is 5 to 8 hours, more preferably 6 hours. The method controls the temperature and time of the solvothermal reaction in the range so as to synthesize the carbon dot with higher yield and stable luminous property, has better economy, and avoids the influence of the excessive temperature or the excessive reaction time on the luminous property of the carbon dot.
After the solvothermal reaction, the invention preferably carries out rotary evaporation and drying on the product of the solvothermal reaction in sequence to obtain near-infrared AIE carbon points.
The method of the present invention is not particularly limited, and the solvent may be removed. In the present invention, the drying temperature is preferably 45 to 55 ℃, more preferably 50 ℃. The drying time is not particularly limited, and the solvent remained after rotary evaporation can be removed.
In the present invention, the near infrared AIE carbon dots are preferably stored at 5℃for use.
The invention also provides the near infrared AIE carbon dots prepared by the preparation method.
In the present invention, the carbon dots preferably have a dual emission property, and fluorescence emission wavelengths thereof are 480nm and 676nm, respectively.
In the present invention, the near infrared AIE carbon dot preferably has aggregation-induced emission property, emits cyan fluorescence of 480nm in a dispersed state, and emits near infrared fluorescence of 676nm in an aggregated state.
In the present invention, the near infrared AIE carbon dots preferably emit bright green phosphorescence on dry filter paper.
The invention also provides application of the near infrared AIE carbon dots in triple anti-counterfeiting.
The invention preferably mixes the near infrared AIE carbon dots and the second organic solvent to obtain the fluorescent ink for triple anti-counterfeiting.
In the present invention, the second organic solvent is preferably one or more of ethanol, methanol, and acetone.
In the invention, the concentration of near infrared AIE carbon dots in the fluorescent ink for triple anti-counterfeiting is preferably 1.0-3.0 mg/mL.
In the invention, the mark formed by the fluorescent ink for triple anti-counterfeiting is blue fluorescence under the irradiation of a light source of 300-450, and becomes red fluorescence under the irradiation of the light source when meeting water, and the blue fluorescence and the red fluorescence can be circularly switched, and green phosphorescence is emitted after the light source is turned off; the wavelength of the light source is more preferably 365nm.
The preparation method of the triple anti-counterfeiting fluorescent ink provided by the invention is simple to operate, mild in reaction condition and suitable for large-scale production.
The invention also provides application of the near infrared AIE carbon dots in aluminum ion detection.
The near infrared AIE carbon point is preferably purified to obtain a cyan carbon point; mixing the cyan carbon dots with a third organic solvent to obtain a solution containing the cyan carbon dots; and (3) dripping the solution containing the cyan carbon dots on filter paper to obtain the aluminum ion test paper for detecting aluminum ions.
In the present invention, the purification means is preferably column chromatography. In the present invention, the column chromatography is preferably gradient elution; the eluent used for gradient elution is a mixed solvent of methanol and dichloromethane; the volume ratio of the methanol to the dichloromethane is preferably 200:1 gradually transitions to 10:1.
after column chromatography, the invention preferably carries out rotary evaporation and drying on the column chromatography product in sequence to obtain the near infrared AIE carbon point.
The method of the present invention is not particularly limited, and the solvent may be removed. In the present invention, the drying temperature is preferably 45 to 55 ℃, more preferably 50 ℃. The drying time is not particularly limited, and the solvent remained after rotary evaporation can be removed.
In the present invention, the solvent in the solution of the cyan carbon dot is preferably at least one of ethanol, methanol, and acetone; the concentration of the cyan carbon dots in the solution of the cyan carbon dots is preferably 3.0 to 7.0mg/mL. .
In the invention, the aluminum ion test paper preferably selectively responds to Al 3+ The method comprises the steps of carrying out a first treatment on the surface of the The aluminum ion test paper preferably encounters Al 3+ After that, its fluorescence changes from dark red to bright cyan.
In the invention, the Al ion test paper detects Al 3+ The concentration of (C) is preferably 0.0 to 14.0. Mu.g/mL.
The preparation method of the aluminum ion test paper provided by the invention is simple to operate, mild in reaction condition, suitable for large-scale production, high in response speed and applicable to Al 3+ Is provided.
The technical solutions of the present invention will be clearly and completely described in the following in connection with the embodiments of the present invention. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The preparation method of the near infrared AIE carbon point comprises the following steps:
weighing 100.0mg of quercetin and 0.5 equivalent of barbituric acid in a polytetrafluoroethylene liner, transferring 10.0mL of first organic solvent ethanol to dissolve the substances by using a pipette, performing solvothermal reaction for 6 hours at 200 ℃ to obtain a solvothermal reaction product which is a brownish red clear solution, removing the solvent by using a rotary evaporator, drying in an oven at 50 ℃ to obtain a near infrared AIE carbon point with the yield of 75.7%, recording as N-CDs1, and placing in a refrigerator at 5 ℃ for standby.
Example 2
Near infrared AIE carbon dots were prepared according to the method of example 1, except that the first organic solvent was methanol, and the yield of the near infrared AIE carbon dots was obtained at 68.3%.
Example 3
Near infrared AIE carbon dots were prepared according to the method of example 1, except that the first organic solvent was acetic acid, and the yield of near infrared AIE carbon dots was 53.7%.
Application example 1
The preparation method of the fluorescent ink for triple anti-counterfeiting comprises the following steps: 10.0mg of N-CDs1 prepared in example 1 was dissolved in 5.0mL of ethanol to prepare 2.0mg/mL of N-CDs1 solution, which was used as a triple anti-counterfeit fluorescent ink.
The self-made carbon dot fluorescent ink is sucked by a pen, and is dripped on a rabbit cut out of filter paper, and the fluorescent phenomenon is observed under a 365nm ultraviolet lamp.
Example 4
A near-infrared AIE carbon spot was prepared as in example 1, except that 0.5 equivalent of p-dimethylaminoacetophenone was used as a carbonyl compound-containing raw material, and the obtained near-infrared AIE carbon spot was abbreviated as N-CDs2 in a yield of 83.2%.
Example 5
Near infrared AIE carbon dots were prepared according to the method of example 4, except that the first organic solvent was methanol, and the yield of near infrared AIE carbon dots was 72.2%.
Example 6
Near infrared AIE carbon dots were prepared according to the method of example 4, except that the first organic solvent was acetic acid, and the yield of near infrared AIE carbon dots was 59.8%.
Example 7
Near infrared AIE carbon dots were prepared according to the method of example 4, except that the first organic solvent was N, N-dimethylformamide, and the yield of near infrared AIE carbon dots was 63.5%.
Application example 2
The preparation method of the fluorescent ink for triple forgery prevention was performed in accordance with the method of application example 1, except that N-CDs2 prepared in example 4 was used as a raw material.
Example 8
A near-infrared AIE carbon point was prepared in the same manner as in example 1 except that 100.0mg of naringenin was used as a raw material of flavonoid compounds, and the obtained near-infrared AIE carbon point was abbreviated as N-CDs3 in a yield of 53.1%.
Example 9
Near infrared AIE carbon dots were prepared according to the method of example 8, except that the first organic solvent was methanol, and the yield of near infrared AIE carbon dots was 47.3%.
Example 10
Near infrared AIE carbon dots were prepared according to the method of example 8, except that the first organic solvent was acetic acid, and the yield of near infrared AIE carbon dots was 49.7%.
Example 11
Near infrared AIE carbon dots were prepared according to the method of example 8, except that the first organic solvent was N, N-dimethylformamide, and the yield of near infrared AIE carbon dots was 68.3%.
Application example 3
The preparation method of the fluorescent ink for triple forgery prevention was performed in accordance with the method of application example 1, except that N-CDs3 prepared in example 8 was used as a raw material.
Example 12
A near-infrared AIE carbon spot was prepared in the same manner as in example 1 except that 100.0mg of naringenin was used as a flavonoid compound raw material, 0.5 equivalent of p-dimethylaminoacetophenone was used as a carbonyl compound-containing raw material, and the obtained near-infrared AIE carbon spot was abbreviated as N-CDs4 in a yield of 76.2%.
Example 13
Near infrared AIE carbon dots were prepared according to the method of example 12, except that the first organic solvent was methanol, and the yield of near infrared AIE carbon dots was 69.5%.
Example 14
Near infrared AIE carbon dots were prepared according to the method of example 12, except that acetic acid was used as the first organic solvent, and the yield of near infrared AIE carbon dots was 81.3%.
Example 15
Near infrared AIE carbon dots were prepared according to the method of example 12, except that the first organic solvent was N, N-dimethylformamide, and the yield of near infrared AIE carbon dots was 69.5%.
Application example 4
The preparation method of the fluorescent ink for triple forgery prevention was performed in accordance with the method of application example 1, except that N-CDs4 prepared in example 12 was used as a raw material.
Example 16
A near-infrared AIE carbon spot was prepared as in example 1, except that 100.0mg of apigenin was used as a raw material for flavonoid compounds, and the obtained near-infrared AIE carbon spot was abbreviated as N-CDs5 in a yield of 56.6%.
Example 17
Near infrared AIE carbon dots were prepared according to the method of example 16, except that the first organic solvent was methanol, and the yield of near infrared AIE carbon dots was 47.8%.
Example 18
Near infrared AIE carbon dots were prepared according to the method of example 16, except that the first organic solvent was acetic acid, and the yield of near infrared AIE carbon dots was 45.3%.
Example 19
Near infrared AIE carbon dots were prepared according to the method of example 16, except that the first organic solvent was N, N-dimethylformamide, and the yield of near infrared AIE carbon dots was 58.2%.
Application example 5
The preparation method of the fluorescent ink for triple forgery prevention was performed in the same manner as in application example 1, except that N-CDs5 prepared in example 16 was used as a raw material.
Example 20
A near-infrared AIE carbon spot was prepared as in example 1, except that 100.0mg of apigenin was used as a flavonoid raw material, 0.5 equivalent of p-dimethylaminoacetophenone was used as a carbonyl compound-containing raw material, and the obtained near-infrared AIE carbon spot was abbreviated as N-CDs6 in a yield of 79.5%.
Example 21
Near infrared AIE carbon dots were prepared according to the method of example 20, except that the first organic solvent was methanol, and the yield of near infrared AIE carbon dots was 68.2%.
Example 22
Near infrared AIE carbon dots were prepared according to the method of example 20, except that acetic acid was used as the first organic solvent, and the yield of near infrared AIE carbon dots was 56.4%.
Example 23
Near infrared AIE carbon dots were prepared according to the method of example 20, except that the first organic solvent was N, N-dimethylformamide, and the yield of near infrared AIE carbon dots was 61.4%.
Application example 6
The preparation method of the fluorescent ink for triple forgery prevention was performed in accordance with the method of application example 1, except that N-CDs6 prepared in example 20 was used as a raw material.
Application example 7
The preparation method of the aluminum ion test paper for aluminum ion detection comprises the following steps:
after the near infrared AIE carbon dots prepared in the example (12) are dissolved by methylene dichloride, the near infrared AIE carbon dots are purified by column chromatography, gradient elution is adopted, the eluent is a mixed solvent of methanol and methylene dichloride, and the volume ratio of the methanol to the methylene dichloride is 200:1 gradually transitions to 10:1, removing solvent from the column chromatography product by using a rotary evaporator, and drying in an oven at 50 ℃ to obtain cyan carbon point C-CDs powder with the yield of 39.7%;
and mixing the prepared cyan carbon dots C-CDs with ethanol to obtain 5.0mg/mL of solution containing the C-CDs, and sucking 100.0 mu L of solution containing the C-CDs to drop on filter paper cut into a rectangle shape to obtain the aluminum ion test paper for aluminum ion detection.
The normalized ultraviolet absorption, excitation and emission patterns and the X-ray diffraction patterns of the cyan carbon dots prepared in application example 7 in water are shown in FIG. 3, wherein A in FIG. 3 is the normalized ultraviolet absorption, excitation and emission patterns of the C-CDs prepared in application example 7 in water, and B in FIG. 3 is the X-ray diffraction pattern of the C-CDs prepared in application example 7. As can be seen from FIG. 3, the cyan carbon dots prepared in application example 7 show a broad peak at 21 degrees, which indicates the existence of graphite lattice structure.
1. Spectral Property testing of N-CDs
50.0 mu L of the fluorescent ink for triple anti-counterfeiting prepared in application example 4 is removed, and after the fluorescent ink is dissolved by 4.0mL of distilled water, the ultraviolet absorption spectrum, the excitation spectrum and the emission spectrum of the fluorescent ink are measured, so that an ultraviolet absorption, excitation and emission normalization chart of the fluorescent ink for triple anti-counterfeiting prepared in application example 4 in water is shown in figure 1, and as can be seen from figure 1, the maximum emission wavelength of N-CDs prepared in example 12 is 676nm, and near infrared is achieved.
In addition, the dual emission behavior and AIE properties of N-CDs prepared in example 12 were studied, 50.0. Mu.L of the fluorescent ink for triple forgery prevention prepared in application example 4 was removed, placed in a 15mL cuvette, and added with different volume ratios (0% -99%) The volume of the mixed solvent of water and ethanol is fixed to 5.0mL, and the mixed solvent is shown in lambda ex The fluorescence spectrum was examined at 405nm to obtain a fluorescence chart and a fluorescence spectrum chart of N-CDs prepared in example 12 at different water contents (0% -99%) as shown in FIG. 2, wherein A in FIG. 2 is a fluorescence chart in a cuvette, B in FIG. 2 and C in FIG. 2 are fluorescence emission charts of N-CDs prepared in example 12 at 480nm and 676nm, respectively, with an increase in water content, and as seen in FIG. 2, N-CDs prepared in example 12 showed cyan fluorescence in ethanol, while with an increase in water content, the color of N-CDs prepared in example 12 gradually became red, indicating that N-CDs prepared in example 12 had AIE properties, and the results of B in FIG. 2 and C in FIG. 2 were consistent with those of A in FIG. 2.
2. Spectral Property testing of C-CDs
The ultraviolet absorption spectrum, excitation spectrum and emission spectrum of the C-CDs prepared in application example 7 were measured by removing 50.0. Mu.L of 5.0mg/mL of the C-CDs-containing solution prepared in application example 7, dissolving the solution in 4.0mL of distilled water, and obtaining a normalized graph of ultraviolet absorption, excitation and emission of the C-CDs in water prepared in application example 7 as shown in FIG. 3A, wherein the absorption peak of the C-CDs prepared in application example 7 corresponds to the absorption spectrum of carbon dots, and an absorption peak at 440nm corresponds to the excitation spectrum at 440nm, and the emission peak wavelength is 480nm. Transferring 50.0 mu L of the solution containing C-CDs prepared in application example 7, placing the solution in a 15mL colorimetric tube, adding mixed solvents of water and ethanol with different volume ratios (0% -99%) to a volume of 5.0mL, and standing at lambda ex The fluorescence spectrum was examined at 380nm to give a physical image of the C-CDs prepared in application example 7 under ultraviolet light at different water contents as shown in FIG. 4. As can be seen from FIG. 4, the C-CDs prepared in application example 7 showed cyan fluorescence in ethanol, whereas the C-CDs prepared in application example 7 gradually became red in color with increasing water content, indicating that the C-CDs prepared in application example 7 had AIE properties.
3. Application of N-CDs in triple anti-counterfeiting
The fluorescent ink for triple anti-counterfeiting prepared in application example 4 is sucked by a pen and is dripped on a 'rabbit' cut by filter paper, fluorescence of the 'rabbit' dripped with the fluorescent ink for triple anti-counterfeiting prepared in application example 4 under different environments is observed, a physical diagram of the application of the fluorescent ink for triple anti-counterfeiting prepared in application example 4 in triple anti-counterfeiting is shown in fig. 5, and after an ultraviolet lamp is turned on, the 'rabbit' dripped with the fluorescent ink for triple anti-counterfeiting prepared in application example 4 emits blue fluorescence first, which is probably due to the fact that green fluorescence is changed into blue fluorescence due to interaction of the filter paper and N-CDs in the fluorescent ink for triple anti-counterfeiting, and the fluorescent ink for triple anti-counterfeiting is the first heavy anti-counterfeiting; after the ultraviolet lamp is turned off, the blue fluorescence of N-CDs in the triple anti-counterfeiting fluorescent ink is quenched due to aggregation, and meanwhile, the red fluorescence is turned on due to the limitation of non-radiative transition, so that the rabbit is changed into red fluorescence, and the double anti-counterfeiting fluorescent ink is second anti-counterfeiting; finally, as the filter paper limits the movement of N-CDs in the fluorescent ink for triple anti-counterfeiting, the ultraviolet lamp is turned off to see that the rabbit emits green phosphorescence, so that the triple anti-counterfeiting is realized; therefore, by utilizing various spectral properties of N-CDs, triple anti-counterfeiting can be realized, the copy is difficult, and the security is high.
4. C-CDs fluorescence spectrum with Al 3+ Concentration variation
Sucking 50.0 mu L of the solution containing C-CDs prepared in application example 7 to 5.0mg/mL, adding Al with different concentrations (0-14 mu M) into a 15mL colorimetric tube 3+ Constant volume to 5.0mL with double distilled water at lambda ex Scanning fluorescence spectrum at 380nm to obtain C-CDs response Al prepared in application example 7 3+ As shown in FIG. 6, the fluorescence spectrum of the concentration is shown in FIG. 6, and it is understood that the concentration of Al follows that of Al 3+ The concentration is increased from 0 to 14.0 mu M, the fluorescence of the system is gradually increased, and Al is realized 3+ Based on this, detectable Al was prepared using C-CDs 3 + And (5) test paper.
5. Performance test of aluminum ion test paper
(1) Taking 16 pieces of aluminum ion test paper for aluminum ion detection prepared in application example 7 with consistent sizes and shapes, respectively dripping 200.0 mu L of 1.0mM respectively containing ionic Al 3+ 、Ca 2+ 、Mg 2+ 、Pb 2+ 、Co 2+ 、Sn 2+ 、Ba 2+ 、Fe 2+ 、Fe 3+ 、Zn 2+ 、Cu 2+ 、Na + 、Hg 2+ 、K + 、Cu + Is used for the preparation of a solution of (a),using a blank as a control, the fluorescent color was observed under an ultraviolet lamp, and a physical diagram of the result of the selectivity experiment of the aluminum ion test paper prepared from the C-CDs prepared in application example 7 was obtained as shown in FIG. 7A, and as can be seen from FIG. 7A, no Al was added dropwise 3+ The aluminium ion test paper shows red fluorescence under an ultraviolet lamp, and Al is added dropwise 3+ The aluminum ion test paper of (C) shows bright green fluorescence, and proves that C-CDs selectively respond to Al 3+ The aluminum ion test paper for aluminum ion detection prepared in application example 7 can be used for selectively detecting Al 3+ 。
(2) Detection of other ion pairs C-CDs by competitive experiments to detect Al 3+ Taking 16 pieces of aluminum ion test paper with consistent size and shape and used for detecting aluminum ions, firstly, dripping 200.0 mu LAl on each piece of the 16 pieces of aluminum ion test paper 3+ Then 200. Mu.L of 1.0mM respectively containing ionic Al was added dropwise 3+ 、Ca 2+ 、Mg 2+ 、Pb 2+ 、Co 2+ 、Sn 2+ 、Ba 2+ 、Fe 2+ 、Fe 3+ 、Zn 2+ 、Cu 2+ 、Na + 、Hg 2+ 、K + 、Cu + A physical diagram of competitive experimental results of the aluminum ion test paper prepared from the C-CDs prepared in application example 7 is shown in FIG. 7B, and it is known from FIG. 7B that the addition of other ions does not affect the Al of the C-CDs pair by observing the fluorescent color of the filter paper under an ultraviolet lamp by using a blank as a control 3+ And the response proves that the probe has good anti-interference performance.
In summary, the method provided in example 12 of the present invention provides a near infrared AIE carbon dot yield as high as 83.2%; the rabbit dripped with the fluorescent ink for triple anti-counterfeiting prepared in application example 4 has different fluorescence under different environments, can realize triple anti-counterfeiting by utilizing various spectral properties of N-CDs, is difficult to copy, and has higher safety; the aluminum ion test paper for aluminum ion detection prepared in application example 7 can be used for selectively detecting Al 3+ The addition of other ions does not affect the Al of the C-CDs pair 3+ And the response proves that the probe has good anti-interference performance.
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.
Claims (10)
1. A preparation method of near infrared AIE carbon dots comprises the following steps:
mixing flavonoid compounds, carbonyl-containing compounds and a first organic solvent, and performing solvothermal reaction to obtain near-infrared AIE carbon points;
the carbonyl-containing compound is one or more of barbituric acid, p-dimethylaminoacetophenone and p-diethylaminobenzaldehyde;
the ratio of the mass of the flavonoid compound, the mass of the carbonyl compound and the volume of the first organic solvent is 1g: (0.5-2) g:50mL;
the temperature of the solvothermal reaction is 170-250 ℃.
2. The preparation method according to claim 1, wherein the flavonoid is one or more of quercetin, naringenin and apigenin.
3. The near infrared AIE carbon dots prepared by the preparation method of claim 1 or 2.
4. The near infrared AIE carbon dot of claim 3, wherein the near infrared AIE carbon dot has aggregation-induced emission properties, emits 480nm of cyan fluorescence in a dispersed state, and emits 676nm of near infrared fluorescence in an aggregated state.
5. The use of the near infrared AIE carbon dots of claim 4 in triple anti-counterfeiting.
6. The use according to claim 5, wherein the near infrared AIE carbon dots and the second organic solvent are mixed to obtain a fluorescent ink for triple forgery prevention.
7. The use according to claim 6, wherein the label formed by the fluorescent ink for triple anti-counterfeiting is blue fluorescence under the irradiation of a light source of 300-450 nm, red fluorescence is displayed under the irradiation of the light source after water is met, the blue fluorescence and the red fluorescence can be circularly switched, and green phosphorescence is emitted after the light source is turned off.
8. The use of the near infrared AIE carbon dot of claim 4 for the detection of aluminum ions.
9. The use according to claim 8, wherein the near infrared AIE carbon spot is purified to obtain a cyan carbon spot;
mixing the cyan carbon dots with a third organic solvent to obtain a solution containing the cyan carbon dots;
and (3) dripping the solution containing the cyan carbon dots on filter paper to obtain the aluminum ion test paper for detecting aluminum ions.
10. The use according to claim 9, wherein the aluminium ion test paper is selectively responsive to Al 3+ The aluminum ion test paper encounters Al 3+ After that, its fluorescence changes from dark red to bright cyan.
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