CN103382389A - Fluorescent carbon quantum dot, its light-emitting polymer based composite material and preparation method - Google Patents
Fluorescent carbon quantum dot, its light-emitting polymer based composite material and preparation method Download PDFInfo
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Abstract
The invention discloses a fluorescent carbon quantum dot, its light-emitting polymer based composite material and a preparation method thereof. More specifically, the invention provides a method for preparation of the fluorescent carbon quantum dot and its light-emitting polymer based composite material by taking a small molecule compound as a carbon source and an organosilicone monomer as a catalyst and stabilizer. By means of the combined action of the polymerizable organosilicone monomer and the small molecule carbon source, the carbon quantum dot can be formed in one step. Without purification, the reaction product only needs solvent removal to undergo further reaction so as to form a carbon quantum dot-organosilicone resin composite material. The organosilicone monomer involved in the invention can promote formation of the carbon quantum dot, and can play a role of stabilizing the carbon quantum dot, and also can be used as a polymer matrix monomer. Therefore, the obtained carbon quantum dot has stable luminescent properties, is well compatible with the polymer matrix and keeps the original luminescent properties. The method disclosed in the invention has a simple process and is easy to implement, and can be widely applied in the fields of solar cells and LED devices.
Description
Technical field
The present invention relates to field of functional polymer composites, be specifically related to a kind of fluorescent carbon quantum dot and luminescence polymer based composites and preparation method.
Background technology
Fluorescent carbon quantum dot (CDs) is the important nano-carbon material of another class after carbon nanotube, Nano diamond, soccerballene and Graphene, quantum dot has excellent optics and electric property, compare with traditional semiconductor-quantum-point, CDs has low toxicity, inexpensive, good light stability, the advantages such as good biocompatibility, so CDs has a wide range of applications in fields such as bio-imaging, bio-sensing and probe, photochemical catalysis, fluorescent ink, LED device and solar cells.since CDs in 2004 is by reported first, the method for preparing CDs is constantly emerged in large numbers, such as laser ablation, high temperature pyrolytic cracking (HTP), combustion method, hydrothermal method, template, the electrochemical etching method, ultrasonic and microwave assisting method etc., although it is a lot of to prepare the method for CDs, but they exist different defectives, such as the product of preparation need to be through complicated sepn process, yield poorly, the preparation process complexity is difficult for realizing industrialization etc., serious fluorescent quenching appears in carbon quantum dot that the more important thing is present most of method preparation under dry state, thereby limited the application of CDs in solid unit.
Summary of the invention
One of purpose of the present invention is to provide a kind of fluorescent carbon quantum dot.
Two of purpose of the present invention is to provide the luminescence polymer based composites based on this fluorescent carbon quantum dot.
Three of purpose of the present invention is to provide the preparation method of this fluorescent carbon quantum dot.
Four of purpose of the present invention is to provide the preparation method of this luminescence polymer based composites.
Invention is achieved through the following technical solutions above-mentioned purpose:
Invention provides a kind of fluorescent carbon quantum dot or its luminescence polymer based composites, is prepared by following raw material:
The small molecules carbon source;
Organosilane monomer;
Described small molecules carbon source is one or more in L-AA (L-AA), citric acid (CA), folic acid, glucose; Described organosilane monomer is one or more in N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane (KH792), γ aminopropyltriethoxy silane (KH550), γ-glycidyl ether oxygen propyl trimethoxy silicane (KH560), γ-methacryloxypropyl trimethoxy silane (KH570).
Preferably, the mol ratio of described small molecules carbon source and organosilane monomer is 1:0.5～10.
Invention provides the preparation method of this fluorescent carbon quantum dot simultaneously: small molecules carbon source and organosilane monomer are generated fluorescent carbon quantum dot in the solvent neutralization reaction.
Preferably, described solvent is the mixing solutions of second alcohol and water, and the volume ratio of second alcohol and water is 1:0.2～1.
Preferably, in above-mentioned reaction process, the reaction density of described small molecules carbon source is 0.05～0.5 mol/L.
Preferably, temperature of reaction is 80～95 ℃; Reaction times is 5～24h.
Invention provides the preparation method of this luminescence polymer based composites simultaneously, is that fluorescent carbon quantum dot reaction product obtained above is further removed solvent, solidifies to obtain the luminescence polymer based composites.
Preferably, curing reaction temperature is 60～100 ℃; The curing reaction time is 5～72h.
Small molecules carbon source of the present invention is the necessary reaction raw materials of Formed quantum dot.The existence of organosilane monomer can promote the carbon formation of quantum dots, and utilizes organosilane monomer to the surface modification effect of carbon quantum dot, can play the effect of Stable Carbon quantum dot, prevents its reunion.On the other hand, organosilane monomer can be used as the monomer of polymeric matrix, not only make the carbon quantum dot have satisfactory stability and higher fluorescence property in solution, can form polymer matrix composite after solvent is removed, still can keep original fluorescence property.This shows, the main advantage that the small molecules carbon source combines with organosilicon is to take full advantage of the multiple effect of organosilane monomer, intercept the reunion between the carbon quantum dot, and original position forms polymkeric substance after desolventizing, make the carbon quantum dot that good dispersion be arranged in polymeric matrix, thereby obtain the luminescence polymer matrix material, reach carbon quantum dot and polymeric matrix consistency well and keep the purpose of original characteristics of luminescence.If do not use organosilane monomer, the luminescent properties of the carbon quantum dot that generates is relatively poor, and after the removal solvent, serious fluorescent quenching appears in the carbon quantum dot under dry state, is difficult to be employed.
Different small molecules carbon sources, the activity of its reaction is difference to some extent.And different organosilane monomers, active group on its molecular structure is different, therefore with the reaction of the active group on carbon quantum dot surface difference to some extent, and brings different stabilising effects.As most preferred scheme, comparatively speaking, L-AA has higher reactive behavior, more easily obtains the carbon quantum dot, and the carbon quantum dot that obtains also has better luminescent properties.The amino of KH791 is easier to carry out amidate action with the carboxyl on carbon quantum dot surface, can more effectively play the effect of passivation carbon quantum dot, improves the luminescent properties of carbon quantum dot.
Compared with prior art, the present invention has following beneficial effect:
The present invention goes on foot by polymerisable organosilane monomer and small molecules carbon source acting in conjunction one and forms the carbon quantum dot, and reaction product need not to purify only needs desolventizing just can further react formation carbon quantum dot and silicone resin matrix material.Organosilane monomer in the present invention can promote the carbon formation of quantum dots, and can play the effect of Stable Carbon quantum dot, simultaneously as the monomer of polymeric matrix, the carbon quantum dot light emitting stable performance that therefore obtains, good and keep original characteristics of luminescence with the polymeric matrix consistency.The inventive method technique is simple, and is easy to implement, can be widely used in solar cell and LED devices field.
Description of drawings
Fig. 1 is UV, visible light absorption, fluorescence spectrum and the digital photograph under the 365nm ultraviolet lamp of the fluorescent carbon quantum dot solution for preparing of the embodiment of the present invention 1 and Comparative Examples 1;
Fig. 2 is the transmission electron microscope photo of the fluorescent carbon quantum dot for preparing of the embodiment of the present invention 1;
Fig. 3 is the UV, visible light Absorption and fluorescence spectrum of the luminescence polymer based composites for preparing of the embodiment of the present invention 1;
Fig. 4 is the fluorescence spectrum of the fluorescent carbon quantum dot solution for preparing of the embodiment of the present invention 10;
Fig. 5 is fluorescent carbon quantum dot solution or the digital photograph of luminescence polymer based composites under UV-light that different embodiments of the invention obtain; Wherein
5a, 5b are respectively the digital photograph of fluorescent carbon quantum dot solution under visible light and 365nm ultraviolet lamp that the embodiment of the present invention 1 prepares;
5c, 5d are respectively the digital photograph of luminescence polymer based composites under visible light and 365nm ultraviolet lamp that the embodiment of the present invention 1 prepares;
5e, 5f are respectively the digital photograph of luminescence polymer based composites under visible light and 365nm ultraviolet lamp that the embodiment of the present invention 9 prepares;
5g, 5h are respectively fluorescent carbon quantum dot digital photograph under visible light and 365nm ultraviolet lamp after drying on filter paper that the embodiment of the present invention 1 prepares.
Embodiment
Below further illustrate technical scheme of the present invention by specific embodiment.
Embodiment 1
(1) 0.528g(3mmol) L-AA is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:1), add 7.92g(30mmol) N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), then react 24h under magnetic agitation in 95 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 13.5%(table 1), its fluorescence spectrum and UV, visible light absorb as Fig. 1, transmission electron microscope photo such as Fig. 2, its digital photograph such as Fig. 5 a under visible light and 365nm UV-light, 5b, it is at dry rear digital photograph such as Fig. 5 g under visible light and 365nm ultraviolet lamp on filter paper, 5h.
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then be spin-coated on quartz plate, solidify 48h in 80 ℃ of baking ovens, obtain the luminescence polymer based composites, its fluorescence spectrum and UV, visible light absorb as Fig. 3, its digital photograph such as Fig. 5 c, 5d under visible light and 365nm UV-light.
Embodiment 2
(1) 1.584g(9mmol) L-AA is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:0.8), add 2.124g(9mmol) γ-glycidyl ether oxygen propyl trimethoxy silicane (KH560), then react 12h under magnetic agitation in 80 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 12.7%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then is spin-coated on quartz plate, solidifies 5h in 100 ℃ of baking ovens, obtains the luminescence polymer based composites.
Embodiment 3
(1) 5.28g(30mmol) L-AA is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:0.5), add 3.39g(15mmol) N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane (KH792), then react 5h under magnetic agitation in 90 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 10.3%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then is spin-coated on quartz plate, solidifies 48h in 80 ℃ of baking ovens, obtains the luminescence polymer based composites.
(1) 0.528g(3mmol) L-AA is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:0.2), add 3.32g(15mmol) γ-aminopropyl triethoxysilane (KH550), then react 24h under magnetic agitation in 100 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 11.9%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then is spin-coated on quartz plate, solidifies 72h in 60 ℃ of baking ovens, obtains the luminescence polymer based composites.
Embodiment 5
(1) 1.056g(6mmol) L-AA is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:1), add 7.45g(30mmol) γ-methacryloxypropyl trimethoxy silane (KH570), then react 24h under magnetic agitation in 85 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 9.8%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then is spin-coated on quartz plate, solidifies 48h in 70 ℃ of baking ovens, obtains the luminescence polymer based composites.
(1) 0.576g(3mmol) citric acid is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:1), add 5.28g(20mmol) N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), then react 24h under magnetic agitation in 95 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 9.2%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then is spin-coated on quartz plate, solidifies 24h in 80 ℃ of baking ovens, obtains the luminescence polymer based composites.
Embodiment 7
(1) 1.08g(6mmol) glucose is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:1), add 3.96g(15mmol) N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), then react 12h under magnetic agitation in 90 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 8.9%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then is spin-coated on quartz plate, solidifies 48h in 100 ℃ of baking ovens, obtains the luminescence polymer based composites.
Embodiment 8
(1) 1.324g(3mmol) folic acid is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:0.5), add 7.92g(30mmol) N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), then react 12h under magnetic agitation in 80 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 9.3%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then is spin-coated on quartz plate, solidifies 48h in 70 ℃ of baking ovens, obtains the luminescence polymer based composites.
(1) 1.584g(9mmol) L-AA is dissolved in the mixing solutions (volume ratio of 180ml second alcohol and water, ethanol: water=1:0.8), add 23.76g(90mmol) N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), then react 12h under magnetic agitation in 90 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot and organosilicon preformed polymer mixing solutions, the quantum yield of purification after product is 13.2%(table 1).
(2) product with gained in (1) steams desolventizing at 50 ℃ of backspins, then pours in polypropylene molds, solidifies 72h in 80 ℃ of baking ovens, obtains the luminescence polymer based composites, its digital photograph such as Fig. 5 e, 5f under visible light and 365nm UV-light.
Embodiment 10
(1) 1.584g(9mmol) L-AA is dissolved in the mixing solutions (volume ratio of 180ml second alcohol and water, ethanol: water=1:1), add 23.76g(90mmol) N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), then react under magnetic agitation in 95 ℃ of oil baths, sampling and testing at regular intervals, its fluorescence spectrum such as Fig. 4.
Comparative Examples 1
(1) 0.528g(3mmol) L-AA is dissolved in the mixing solutions (volume ratio of 60ml second alcohol and water, ethanol: water=1:1), then react 24h under magnetic agitation in 90 ℃ of oil baths, naturally cool to room temperature, obtain fluorescent carbon quantum dot solution, the quantum yield of purification after product is 3.6%(table 1), its fluorescence spectrum and UV, visible light absorb as Fig. 1.
By Comparative Examples more as can be known, organosilane monomer can effectively improve the luminous intensity of carbon quantum dot.
The quantum yield contrast of the reaction system of table 1 embodiment and Comparative Examples, reaction conditions and carbon quantum dot product
Claims (10)
1. a fluorescent carbon quantum dot or its luminescence polymer based composites is characterized in that being prepared by following raw material:
The small molecules carbon source;
Organosilane monomer;
Described small molecules carbon source is one or more in L-AA (L-AA), citric acid (CA), folic acid, glucose;
Described organosilane monomer is one or more in N-(β-aminoethyl)-γ-aminopropyl triethoxysilane (KH791), N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane (KH792), γ aminopropyltriethoxy silane (KH550), γ-glycidyl ether oxygen propyl trimethoxy silicane (KH560), γ-methacryloxypropyl trimethoxy silane (KH570).
2. matrix material as claimed in claim 1, the mol ratio that it is characterized in that described small molecules carbon source and organosilane monomer is 1:0.5～10.
3. the preparation method of a fluorescent carbon quantum dot as claimed in claim 1, is characterized in that: small molecules carbon source and organosilane monomer are reacted the generation fluorescent carbon quantum dot in solvent.
4. preparation method as claimed in claim 3, is characterized in that described solvent is the mixing solutions of second alcohol and water, and the volume ratio of second alcohol and water is 1:0.2～1.
5. preparation method as claimed in claim 3, the concentration that it is characterized in that described small molecules carbon source is 0.05～0.5 mol/L.
6. preparation method as claimed in claim 3, is characterized in that described temperature of reaction is 80～95 ℃.
7. preparation method as claimed in claim 3, is characterized in that the described reaction times is 5～24h.
8. the preparation method of a luminescence polymer based composites as claimed in claim 1, it is characterized in that the fluorescent carbon quantum dot reaction product of the arbitrary claim gained of claim 3-7 is further removed solvent, curing obtains the luminescence polymer based composites.
9. preparation method as claimed in claim 8, is characterized in that described curing reaction temperature is 60～100 ℃.
10. preparation method as claimed in claim 8, is characterized in that the described curing reaction time is 5～72h.
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