CN106010523A - Phosphorus-doped fluorescent carbon point with high fluorescent quantum yield as well as preparation method and application thereof - Google Patents

Phosphorus-doped fluorescent carbon point with high fluorescent quantum yield as well as preparation method and application thereof Download PDF

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CN106010523A
CN106010523A CN201610344777.9A CN201610344777A CN106010523A CN 106010523 A CN106010523 A CN 106010523A CN 201610344777 A CN201610344777 A CN 201610344777A CN 106010523 A CN106010523 A CN 106010523A
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carbon point
fluorescent carbon
phosphorus doping
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CN106010523B (en
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郭兴家
刘文静
丛臣日
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Liaoning University
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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
    • C09K11/70—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing phosphorus
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    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
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    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
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    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
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    • B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
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    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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    • 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"

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Abstract

The invention relates to a phosphorus-doped fluorescent carbon point with a high fluorescent quantum yield as well as a preparation method and application thereof. According to the technical scheme, purified carbon point solid powder is obtained by taking tannic acid and polyethylenimine (PEI), adding de-ionized water and phosphoric acid, then transferring the mixture into a hydrothermal reaction kettle, keeping the heat and reacting for 2h to 6h in a temperature range of 140 DEG C to 240 DEG C, naturally cooling at a room temprature to obtain a light brown nano carbon point crude product solution, and centrifuging, dialyzing, refining, freezing and drying. The carbon point provided by the invention can be used for cell imaging and a photodegradation treatment process of contained organic dyestuffs. The fluorescent quantum yield of the prepared fluorescent carbon point can reach 25.4 percent. After being stored in a dark place for 6 months, the carbon point still can emit bright blue fluorescent light under the illumination of a 365nm ultraviolet lamp and the carbon point has good stability at a room temperature.

Description

A kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point and its preparation method and application
Technical field
The present invention relates to carbon nanomaterial technical field, be specifically related to a kind of in phosphoric acid medium, with tannic acid and PEI Synthesize a kind of phosphorus doping fluorescent carbon point with blue-fluorescence and application thereof.
Background technology
Carbon point (Carbon Dots) is the fluorescent carbon nano-particle that a kind of scattered class being smaller in size than 10nm is spherical, has excellent Good photoluminescence performance.Compared with traditional organic fluorescent dye, fluorescent carbon point has higher light stability and anti-light bleaching Property.Additionally, fluorescent carbon point molecular weight and particle diameter are less, good biocompatibility, toxicity is low, exciting light spectrum width and also continuously, can To realize a polynary transmitting of elementary excitation, be a kind of extraordinary fluorescent labeling and imaging agents, and be successfully applied cell with In living imaging.Fluorescent carbon point itself has some special natures so that it is in photoelectric device, organic solar batteries, photocatalysis Etc. aspect be with a wide range of applications.Although carbon point preparation method and related application research have had a large amount of report, but there is also The problems such as fluorescence quantum yield is relatively low, and preparation process is complicated, therefore find simple, and quickly preparation has good luminous performance The method of fluorescent carbon point is the most necessary.
Summary of the invention
It is an object of the invention to provide a kind of phosphorus doping fluorescent carbon point simply, effectively with relatively high-fluorescence quantum yield and Preparation method.
For realizing the purpose of the present invention, the technical solution used in the present invention is as follows: a kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon Point, preparation method is as follows: take tannic acid and PEI, is sequentially added into deionized water and phosphoric acid, after stirring and dissolving, transfer In reactor, hydro-thermal reaction 2～6h, it is cooled to room temperature, obtains crude product, through dialysis, lyophilization, obtain the phosphorus of purification Doping fluorescent carbon point.
Preferably, above-mentioned a kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point, in mass ratio, tannic acid: polyethyleneimine Ammonia=1:1～5.
Preferably, above-mentioned a kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point, every gram of tannic acid adds 15～80ml water.
Preferably, above-mentioned a kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point, every gram of tannic acid adds 1.5～5ml phosphoric acid.
Preferably, above-mentioned a kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point, hydrothermal temperature is 140～240 DEG C.
It is a further object of the present invention to provide the application in bio-imaging and catalytic degradation dyestuff of the phosphorus doping fluorescent carbon point.
The application in degradating organic dye of the above-mentioned high-fluorescence quantum yield phosphorus doping fluorescent carbon point.Method is as follows: in having Adding the tungsten trioxide photocatalyst that above-mentioned phosphorus doping fluorescent carbon point is modified in the solution of organic dye, under dark surrounds, stirring is inhaled After attached 1h, with 500W height Hg lamp irradiation；The tungsten trioxide photocatalyst that described phosphorus doping fluorescent carbon point is modified is: by upper The phosphorus doping fluorescent carbon point stated and WO3Mixing, under the conditions of 140～240 DEG C, reacting by heating 3～4h.
The invention has the beneficial effects as follows:
Preparation method the most of the present invention is simple, be easily achieved industrialized production.Use tannic acid inexpensive, that be easy to get, polymine and Phosphoric acid, with hydro-thermal reaction technology one-step synthesis fluorescent carbon point.
2. the nano fluorescent carbon point biocompatibility that prepared by the present invention is preferable, it is possible to achieve internal fluorescence imaging.
3. the nano fluorescent carbon point fluorescence quantum yield that prepared by the present invention is up to 25.4%.
4. the nano fluorescent carbon point maximum excitation that prepared by the present invention and transmitting wavelength are respectively 345nm and 469nm.In the dark preserve 6 After individual month, under the ultra violet lamp of 365nm, still send brilliant blue fluorescence.Carbon point stability at room temperature is described Well.Fluorescent carbon point water solublity prepared by the present invention is good and stable, places and undergo no deterioration for 1 year under room temperature.
Accompanying drawing explanation
Fig. 1 is the transmission electron microscope photo of fluorescent carbon point.
Fig. 2 is the X-ray diffractogram of fluorescent carbon point.
Fig. 3 is the infrared spectrogram of fluorescent carbon point.
Fig. 4 is the zeta potential diagram of fluorescent carbon point solution.
Fig. 5 is the uv-visible absorption spectra figure of fluorescent carbon point solution.
Fig. 6 is the excitation and emission spectra figure of fluorescent carbon point solution.
Fig. 7 is the fluorescence emission spectrogram that different wavelengths of light excites lower fluorescent carbon point solution.
Fig. 8 is the pH value impact (λ ex=345nm) on carbon point solution fluorescence.
Fig. 9 is the NaCl concentration impact (λ ex=345nm) on carbon point solution fluorescence.
Figure 10 is the illumination impact (λ ex=345nm) on carbon point solution fluorescence.
Figure 11 is the fluorescence microscope cell picked-up situation to carbon point.
Figure 12 is that under illumination and dark condition, methylene blue light degradation changes over curve.
Detailed description of the invention
Embodiment 1
Weigh the tannic acid of 0.2g and the PEI of 0.2g, add the deionized water of 10ml, add the phosphoric acid of 0.5ml, fully Stirring and dissolving, transfers to, in the reactor of 50ml, put in air dry oven, heats 2h in 140 DEG C, naturally cools to room Temperature, obtains dark-brown carbon point solution, is then passed through dialysis and lyophilization, finally gives phosphorus doping fluorescent carbon point (CDs) Pressed powder.Fluorescence quantum yield is 25.4%.
The transmission electron microscope photo of phosphorus doping fluorescent carbon point is as shown in Figure 1.As seen from the figure, the particle diameter of carbon point is at about 9nm.
The X-ray diffraction spectrum of phosphorus doping fluorescent carbon point is as shown in Figure 2.X-ray diffraction analysis shows, carbon point powder exists One obvious and wider diffraction maximum occurs near 2 θ=23 °, shows that carbon point is to exist in amorphous state mode.
The infrared spectrum of phosphorus doping fluorescent carbon point is as shown in Figure 3.Infrared spectrogram shows that the stretching vibration that there is-OH and-NH is inhaled Receive peak (3411cm-1), the stretching vibration absworption peak (1623cm of carbonyl-1), the stretching vibration absworption peak that the doping of P-O key produces At 1088cm-1Near, C-N stretching vibration absworption peak is at 1350cm-1Place.
The zeta current potential of phosphorus doping fluorescent carbon point solution as shown in Figure 4, in the solution when pH=6.0, the zeta current potential of carbon point It is worth inclined negative value, shows carbon point surface slightly negative electricity.
The uv-visible absorption spectra of phosphorus doping fluorescent carbon point solution is as shown in Figure 5.As seen from the figure, carbon point solution exists Having an obvious characteristic absorption peak at 350nm, scope is extended to visual field by ultra-violet (UV) band.
The fluorescence excitation of phosphorus doping fluorescent carbon point solution and emission spectrum are as shown in Figure 6.As seen from the figure, the maximum of fluorescent carbon point swashs Send out wavelength and maximum emission wavelength is respectively 345nm and 469nm.
Under different wavelengths of light excites, the fluorescence emission spectrum of fluorescent carbon point solution is as shown in Figure 7.By figure it is found that along with Excitation wavelength increases (from 330nm to 370nm), the fluorescence emission peak of fluorescent carbon point gradually blue shift, it is indicated that prepared carbon Point has excitation wavelength dependency.
PH value affects result as shown in Figure 8 to carbon point solution fluorescence.As seen from the figure, during pH=5, fluorescence is the strongest, and works as solution When pH value is increased or decreased, carbon point fluorescence intensity all decreases, and shows that the luminescence generated by light of carbon point is had necessarily by solution acidity Impact.
The NaCl concentration impact on fluorescent carbon point solution fluorescence: be separately added into the most commensurability in the carbon point solution dilute 50 times NaCl, measures carbon point fluorescent emission intensity, has investigated the NaCl concentration impact on carbon point fluorescence intensity, and result is shown in Fig. 9.By Scheming visible, in the range of 0～2.0mol/L, the fluorescence intensity of carbon point solution has almost no change.Therefore, prepared fluorescence Carbon point has preferable saline-alkaline tolerance.
The illumination impact on carbon point solution fluorescence: the carbon point solution determining dilution 50 times respectively is continuous under 500W height mercury lamp Irradiate 0.5,1,1.5,2,3,4, fluorescence intensity after 5h.As seen from Figure 10, the fluorescence intensity of carbon point is not sent out Raw significantly change, shows carbon point good stability, anti-light bleaching.
Embodiment 2
Weigh the tannic acid of 0.2g and the PEI of 1.0g, add the deionized water of 15ml, add the phosphoric acid of 1.0ml, fully stir Mix dissolving, transfer to, in the reactor of 50ml, put in air dry oven, heat 4 hours in 180 DEG C, naturally cool to Room temperature, obtains dark-brown carbon point solution, is then passed through dialysis and obtains phosphorus doping fluorescent carbon point solution.
Embodiment 3
Weigh the tannic acid of 0.5g and the PEI of 1.2g, add the deionized water of 20ml, add the phosphoric acid of 1.5ml, fully stir Mix dissolving, transfer to, in the reactor of 50ml, put in air dry oven, heat 4 hours in 200 DEG C, naturally cool to Room temperature, obtains dark-brown carbon point solution, is then passed through dialysis and obtains phosphorus doping fluorescent carbon point solution eventually.
Embodiment 4
Weigh the tannic acid of 1.0g and the PEI of 1.2g, add the deionized water of 20ml, add the phosphoric acid of 1.5ml, fully After stirring, transfer to, in the reactor of 50ml, put in air dry oven, heat 6 hours in 180 DEG C, naturally cool to Room temperature, obtains dark-brown carbon point solution, is then passed through dialysis and obtains phosphorus doping fluorescent carbon point solution.
Embodiment 5
Weigh the tannic acid of 1.0g and the PEI of 1.2g, add the deionized water of 15ml, add the phosphoric acid of 1.5ml, fully After stirring, transfer to, in the reactor of 50ml, put in air dry oven, heat 6 hours in 180 DEG C, naturally cool to Room temperature, obtains dark-brown carbon point solution, is then passed through dialysis and obtains phosphorus doping fluorescent carbon point solution.
The application in bio-imaging agent of the embodiment 6 phosphorus doping fluorescent carbon point
It is that 100 μ g/L phosphorus doping fluorescent carbon point solution co-culture with stomach cancer cell BGC-823 at 37 DEG C by concentration, exists respectively When 6 and 24h, by the fluorescence microscope cell picked-up situation to carbon point, result is as shown in figure 11.As seen from the figure, with Time of increases, and cell is the best to carbon point picked-up effect, demonstrates good cell imaging effect.
The application in degradating organic dye of the embodiment 7 phosphorus doping fluorescent carbon point
Method: the tungsten trioxide photocatalyst (CDs-WO that phosphorus doping fluorescent carbon point is modified3): weigh 0.2g tannic acid and The PEI of 0.4g is in beaker, and adds 15ml deionized water and stir, and adds the phosphoric acid of 0.5ml, proceeds to the water of 50ml In thermal response still, add the WO of 0.5g3, in air dry oven at a temperature of 230 DEG C, react 3h.Cooling room temperature after from The heart, is dried to obtain the tungsten trioxide photocatalyst (CDs-WO that carbon point is modified3)。
Take 50ml methylene blue solution (mass concentration is 10mg/L) in beaker, add 50mg CDs-WO3, in dark Stirring and adsorbing 1h under environment so that it is reach adsorption and desorption balance, then use 500W high voltage mercury lamp radiation, every one section time Between sample, at wavelength 664nm, measured the absorbance of methylene blue solution by UV, visible light-spectrophotometer, by following The percent of decolourization of equation calculating methylene blue:
In formula: A0For the initial absorbance of the solution of methylene blue, A is the absorbance of different t methylene blue.
Comparative example 1: phosphorus doping fluorescent carbon point (CDs): weigh the tannic acid of 0.2g and the PEI of 0.4g in beaker, and add Enter 15ml deionized water to stir, add the phosphoric acid of 0.5ml, proceed in the hydrothermal reaction kettle of 50ml, at air dry oven In at 140 DEG C, react 2h.It is centrifuged after cooling room temperature, is dried to obtain phosphorus doping fluorescent carbon point.
Take 50ml methylene blue solution (mass concentration is 10mg/L) in beaker, add 50mg phosphorus doping fluorescent carbon point, Stirring and adsorbing 1h under dark surrounds so that it is reach adsorption and desorption balance, then use 500W high voltage mercury lamp radiation, every A period of time samples, and is measured the absorbance of methylene blue solution at wavelength 664nm by UV, visible light-spectrophotometer.
Comparative example 2: take 50ml methylene blue solution (mass concentration is 10mg/L) in beaker, adds 50mg nanometer WO3, stirring and adsorbing 1h under dark surrounds so that it is reach adsorption and desorption balance, then with 500W height Hg lamp irradiation, Sample at set intervals, at wavelength 664nm, measured the extinction of methylene blue solution by UV, visible light-spectrophotometer Degree.
Result is as shown in figure 12.Research shows, is used alone WO3Time, the photodegradation rate of methylene blue is 52.3%, and Adding the fluorescent carbon point that the present invention obtains in system, photodegradation rate reaches 80.7%.Illustrate that the carbon point of the present invention can promote WO3 Photodegradation to methylene blue.

Claims (8)

1. a high-fluorescence quantum yield phosphorus doping fluorescent carbon point, it is characterised in that preparation method is as follows: take tannic acid and polyethyleneimine Ammonia, is sequentially added into deionized water and phosphoric acid, after stirring and dissolving, transfers in reactor, hydro-thermal reaction 2～6h, cooling To room temperature, obtain crude product, through dialysis, lyophilization, obtain high-fluorescence quantum yield phosphorus doping fluorescent carbon point.
A kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point the most according to claim 1, it is characterised in that: in mass ratio, Tannic acid: PEI=1:1～5.
A kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point the most according to claim 1, it is characterised in that: every gram of tannic acid Add 15～80ml water.
A kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point the most according to claim 1, it is characterised in that: every gram of tannic acid Add 1.5～5ml phosphoric acid.
A kind of high-fluorescence quantum yield phosphorus doping fluorescent carbon point the most according to claim 1, it is characterised in that: hydro-thermal reaction temperature Degree is 140～240 DEG C.
6. the application in bio-imaging of the high-fluorescence quantum yield phosphorus doping fluorescent carbon point described in claim 1.
7. the application in degradating organic dye of the high-fluorescence quantum yield phosphorus doping fluorescent carbon point described in claim 1.
Application the most according to claim 7, it is characterised in that: method is as follows: add power in the solution containing organic dyestuff Profit requires the tungsten trioxide photocatalyst that the phosphorus doping fluorescent carbon point described in 1 is modified, stirring and adsorbing 1h under dark surrounds Afterwards, 500W high voltage mercury lamp radiation is used；The tungsten trioxide photocatalyst that described phosphorus doping fluorescent carbon point is modified is: will Phosphorus doping fluorescent carbon point described in claim 1 and WO3Mixing, under the conditions of 140～240 DEG C, reacting by heating 3～4h.
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CN106974659A (en) * 2017-05-20 2017-07-25 复旦大学 A kind of latent fingerprint detection method based on red fluorescence carbon point material
CN111849102A (en) * 2020-07-28 2020-10-30 南宁师范大学 Polyvinyl alcohol/N, P-CDs flame-retardant film and preparation method thereof
CN111879746A (en) * 2020-08-20 2020-11-03 西南石油大学 Fluorescent chemical sensor and preparation method and application thereof
CN115893374A (en) * 2021-09-30 2023-04-04 北京服装学院 Preparation and application of carbon dots by using polyamide as precursor
CN116395672A (en) * 2023-03-31 2023-07-07 西南交通大学 Preparation method of fluorescent carbon dots, antibacterial material and method for inhibiting gram bacteria

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106974659A (en) * 2017-05-20 2017-07-25 复旦大学 A kind of latent fingerprint detection method based on red fluorescence carbon point material
CN111849102A (en) * 2020-07-28 2020-10-30 南宁师范大学 Polyvinyl alcohol/N, P-CDs flame-retardant film and preparation method thereof
CN111849102B (en) * 2020-07-28 2022-10-18 南宁师范大学 Polyvinyl alcohol/N, P-CDs flame-retardant film and preparation method thereof
CN111879746A (en) * 2020-08-20 2020-11-03 西南石油大学 Fluorescent chemical sensor and preparation method and application thereof
CN111879746B (en) * 2020-08-20 2022-02-01 西南石油大学 Fluorescent chemical sensor and preparation method and application thereof
CN115893374A (en) * 2021-09-30 2023-04-04 北京服装学院 Preparation and application of carbon dots by using polyamide as precursor
CN116395672A (en) * 2023-03-31 2023-07-07 西南交通大学 Preparation method of fluorescent carbon dots, antibacterial material and method for inhibiting gram bacteria

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