CN105236383A - Wavelength adjustable carbon quantum dots, preparation method and applications thereof - Google Patents
Wavelength adjustable carbon quantum dots, preparation method and applications thereof Download PDFInfo
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Abstract
The present invention belongs to the technical field of nanometer materials, and particularly relates to wavelength adjustable carbon quantum dots, a preparation method and applications thereof. According to the present invention, the one-pot method (reaction kettle) is used to synthesize, the method has characteristics of simpleness, green environmental protection and low raw material prices, the reaction temperature is 140-200 DEG C, and the great industrial production prospects are provided; according to the synthesized carbon quantum dots, the inner core has a graphitized crystal lattice structure, the outer shell is a layer of amorphous carbon and contains a lot of hydrophilic functional groups, and the carbon quantum dots has good solubility and good stability in a polar solvent, and has diameter distribution of 1.5-4 nm; the fluorescence redshift of the carbon quantum dots is generated by the change of the surface functional groups; and the wavelength adjustable carbon quantum dots adopted as the novel light-emitting material has characteristics of low production cost, low biological toxicity, high light emitting efficiency, good stability, and good application prospects in optoelectronic devices and biotechnology.
Description
Technical field
The invention belongs to technical field of nano material, be specifically related to a kind of carbon quantum dot and its preparation method and application.
Background technology
In recent years, fluorescence semiconductor quantum dots core-shell structure nanometer particle of being correlated with as CdSe, ZnS and CdSe etc. has attracted everybody interest widely because of the optical property of its uniqueness and huge biomedical applications prospect.Its luminescence mechanism is due to the transition of exciton between valence band and conduction band.Semiconductor-quantum-point is repeatedly used in fluorescence imaging experiments, in tumor vascular system, on tumour distinctive barrier film antigen, mark lymphoglandula in had successful application.But, such quantum dot all includes heavy metal Cd, also has suitable toxicity, thus bring huge health and environmental hazard to the mankind even if use under extremely low concentration conditions, therefore which limits the application prospect of semiconductor-quantum-point, particularly application clinically.So, find a kind of completely newly, there is better optical property, that hypotoxic quantum dot carrys out alternative above-mentioned semiconductor-quantum-point is just necessary.Since carbon quantum dot was found first in 2004, it just promptly grows into a nova of field of nanometer material technology.This is that a class is new, the carbon nanomaterial of size of particles below 10 nanometers, and there is the advantageous property that strong stability of photoluminescence and other semiconductor-quantum-points such as biologically inert, good bio-compatibility do not possess, and be considered to be the best replacer of other semiconductor-quantum-points.What special needs proposed is, carbon nano-particles has low-down toxicity, even if toxicity is still very little under the concentration of mg/ml rank, and carbon atom is as organic main skeleton, the modification of the surface group of carbon is become be more prone to, range of choice is wider.These outstanding advantages make carbon nano-particles have application prospect more widely in biomarker, bio-identification, bio-imaging etc.Logical development in a few years, the synthetic method of carbon quantum dot is in the news a lot, specifically have hydrothermal method, Microwave Digestion, laser ablation, calcination method and acid hydrolyzation etc., various method has its corresponding feature, also can accomplish that size of particles is adjustable in certain limit.But, the luminescence mechanism of carbon nano-particles is very unclear, the phenomenon of the red shift along with the increase of excitation wavelength of the emission wavelength in its fluorescence spectrum is not also explained, the carbon quantum dot of major part synthesis sends blue light and green glow, almost seldom have at ruddiness or near-infrared luminous, and corresponding quantum yield is all lower than 5%.As everyone knows, near infrared light has better biological tissue penetrativity, very large application prospect and meaning is had in vivo in bio-nanotechnology, the carbon point transmitting reported at present mainly concentrates on blue light and green wavelength, this bottleneck limits its biologic applications, particularly small animal imaging in biology.So it is necessary for preparing the fluorescent carbon point that can have the sub-productive rate of higher amount in red light district.The multi-color marking performance of carbon point on the other hand.The carbon point of major part report can by changing excitation wavelength thus realize multi-color marking, but also cannot realize single wavelength and excite the red four kinds of color marks of lower bluish-green Huang.This application being carbon point brings more opportunity.
Quantum dot, in biomedical application, requires that quantum dot must possess water-soluble preferably, good luminescent properties, suitable size, good biocompatibility and can to carry out biology crosslinked.
Summary of the invention
The object of the present invention is to provide that a kind of production cost is low, bio-toxicity is little, luminous efficiency is high, good biocompatibility, there is adjustable carbon quantum dot of the wavelength (color) of intense fluorescence (being called for short carbon point) and its preparation method and application.
The carbon quantum dot of the Wavelength tunable that the invention provides out, its kernel has graphited crystalline network, and shell is the unbodied carbon of one deck and containing a large amount of hydrophilic functional groups, in common polar solvent, has good solubleness and stability; Diameter Distribution is between 1.5-4 nanometer; The fluorescence red shift of carbon quantum dot is produced by the change of surface functional group.
The preparation method of the carbon quantum dot of the Wavelength tunable that the invention provides out, concrete steps are as follows:
(1) mixing solutions of one kettle way preparation containing various fluorescent carbon point
Measuring 5 milliliters of ethanol puts in the centrifuge tube of 50 milliliters, weigh a certain amount of urea (0.1-0.2 gram) more respectively and a certain amount of Ursol D (0.1-0.3 gram) joins in centrifuge tube, concussion is until dissolve completely, add a certain amount of deionized water (20-45 milliliter) again, mix, mixed solution is transferred in autoclave; After first high temperature oven being preheated to certain temperature (140-200 degree Celsius), then reactor is put into baking oven, react several hours (6-18 hour), react complete, turn off baking oven, naturally cool to room temperature;
(2) be separated mixing solutions, be purified into the carbon point sample that fluorescence color is different
The mixed solution obtained in step (1) is carried out revolving and steams to residual 3-5 milliliters of liquid, add 6-8 gram of silica gel (100-200 order), stir, again revolve and steam to dry, preserve; Meanwhile, dry method is adopted to carry out dress post (300-400 order silica gel); Roll-out on pillar, the mixture be spin-dried for is dispersed in above silicagel column, then add the Na of 9-11 gram (preferably 10 grams) in the above
2cO
3; Be eluent with the mixed solution (volume ratio is (18-25): 1, and preferred volume ratio is 20:1) of ethanol and ethyl acetate, be separated; In the process be separated, the solution flowed out with ultra violet lamp, collects the solution component launching identical fluorescence together, carries out revolving steaming, be again distributed in water, finally obtain the carbon quantum dot aqueous solution of the different fluorescence of multiple transmitting.
The present invention have collected the carbon point of eight kinds of different glow colors, and their fluorescence peak position is respectively: 440, and 458,517,553,566,580,594,625 nanometers, quantum yield respectively is: 21.23%, and 13.18%, 8.53%, 19.64%, 27.5%, 35.14%, 29.62%, 23.81%.These eight kinds of carbon points have similar particle dia, are approximately 2.5 nanometers, but the different functional group in surface result in different photoluminescent properties.
The present invention, in the process of preparation eight kinds of fluorescent carbon points, have employed one kettle way (reactor), and its synthetic method is simple, environmental protection, and the raw material of use is cheap, and temperature of reaction, at 140-200 degree Celsius, has very large industrial production prospect.Meanwhile, in the process of reaction, do not use any poisonous reagent (water, urea and Ursol D), be Green Chemistry completely.Only need to carry out at normal temperatures in the process of purifying, only need to use more cheap organic reagent (ethanol and ethyl acetate), though the amount used larger be through simple distillation afterwards these reagent can use further, this just can the expense of very large reduction production process.
The carbon point that fluorescence prepared by the present invention is adjustable does not have any difference on pattern, and its difference is mainly reflected on surface functional group.Along with the red shift of fluorescence, the oxygen-containing functional group on carbon point surface increases, and namely degree of oxidation rises.These carbon points are due to containing a large amount of hydrophilic functional groups, so good solubleness can be had in aqueous systems, in the scope of pH value 3-12, fluorescence can not change substantially, in the solution system of high ionic strength, fluorescence intensity is substantially unattenuated, and these test conditions all prove that it very has prospect in the application of biological field.In addition, these carbon points can be dissolved in the organic solvent such as ethanol, ethyl acetate, and have higher quantum yield, and these phenomenons also show that carbon point prepared by this method also can have wide practical use in the field such as photoelectric device, catalysis further.
The preparation method that the present invention proposes is not only Green Chemistry, and is with low cost, easy to operate.
The eight kinds of fluorescent carbon points obtained according to above-mentioned preparation method all show as and are made up of the decolorizing carbon two portions on graphited nucleus and surface on pattern.Its nanoparticle mean radius is all at 2.5 ran.These nanoparticles contain a large amount of hydrophilic functional groups at surf zone, comprise-NH ,-OH ,-COOH etc., can ensure that they are water-soluble preferably.Meanwhile.These are containing the functional group, particularly carboxyl of oxygen, and along with the red shift of fluorescence, content rises.
Eight kinds of fluorescent carbon points prepared by the present invention have higher quantum yield in the aqueous solution, wherein, ruddiness can reach 23.81%, be also that at present report is the highest.In other organic solvents, such as ethanol or ethyl acetate, quantum yield can up to 50%.These carbon points show the transmitting not relying on and excite, and 625 nanometers can be adjusted to from 440 in the position of fluorescence peak.Under the ultra violet lamp condition of hour, these carbon points still show negligible fluorescence decay substantially, confirm that these carbon points have very strong fluorescent stability.
Eight kinds of fluorescent carbon points prepared by the present invention have low-down toxicity.Be 1.8-2.0 mg/ml to the toxic limit medium dose of human cervical cancer cell, more than 3 orders of magnitude will be exceeded than the corresponding toxicities of the semiconductor-quantum-point (CdSe and CdTe) of report at present.Therefore, even if carbon point prepared by this kind of method is when concentration is higher, growth and the form of cell is not still affected.In addition, a large amount of organo-functional groups that surface is contained can provide the foundation, for the application extension of carbon point provides the foundation for the further functionalization of carbon point.
The carbon point that the present invention obtains can be used in cells in vitro imaging.When after itself and cell cultures for some time, under the exciting of single wavelength 405 nanometer, can find that carbon point mainly concentrates in the middle of tenuigenin, and send obvious indigo plant, green, yellow and red four kinds of fluorescence, so this nanoparticle can come with labeled cell thus carry out the process of growth of observation of cell, multi-color marking also can be used for.
The quantum yield that carbon point prepared by the present invention is higher because red light district has, thus can small animal imaging be used successfully to.After intravenous injection and subcutaneous injection, the fluorescence of red fluorescence carbon point can through the skin of nude mice and tissue, and this also further demonstrates the lower bio-toxicity of carbon point that we prepare.
Accompanying drawing explanation
Fig. 1 is the photo of solution under ultraviolet lamp of eight kinds of samples of embodiment 1.
Fig. 2 is the fluorescence spectrum of eight kinds of samples of embodiment 1.
Fig. 3 is the transmission electron microscope photo of four kinds of representational carbon points (bluish-green Huang is red) in embodiment 1.
Fig. 4 is four kinds of representational carbon points optical imagery photo in vitro and ruddiness carbon point optical imagery photo in vivo in embodiment 1.
Embodiment
In order to understand content of the present invention better, further illustrate the present invention below in conjunction with specific embodiment and accompanying drawing.
embodiment 1
(1) mixing solutions of preparation containing various fluorescent carbon point
First measure 5 milliliters of ethanol to put in the centrifuge tube of 50 milliliters, then weigh 0.2 gram of urea and 0.2 gram respectively and do not have oxidized Ursol D to join rapidly in centrifuge tube, concussion, until dissolve completely, forms the solution of reddish-brown.Add 45 ml deionized water again, mix, transferred to by mixed solution in autoclave (150 milliliters), sealing is preserved.After first high temperature oven being preheated to 160 degrees Celsius, then reactor is put into baking oven reaction 10 hours, react complete, turn off baking oven, open baking ovens, naturally cool to room temperature;
(2) purifying contains the mixing solutions of various fluorescent carbon point
The mixed solution obtained in step (1) is carried out revolve steaming (water-bath, 65 degrees Celsius) to residual 3-5 milliliters of liquid, add 6-8 gram of silica gel (100-200 order), stir, again revolve and steam to dry, preserve.Meanwhile, dry method is adopted to carry out dress post (300-400 order silica gel), (pillar height 12 centimetres is roll-outed on pillar, plane is neat and well spaced), the mixture be spin-dried for is dispersed in above silicagel column with dividing equally by feed hopper, again mixture surface is knocked well-balanced, then added the Na of about 10 grams in the above by feed hopper
2cO3 (be used for shock absorption).Finally, be first that eluent washes away yellow impurity with methylene dichloride, be that blue and green fluorescent carbon point isolated by eluent again with ethyl acetate, finally with the mixed solution (volume ratio is for 20:1) of ethanol and ethyl acetate for eluent, isolate yellow and red fluorescent carbon point.In the process be separated, carry out irradiations solution with ultraviolet lamp, when solution launches identical fluorescence and intensity is close constantly, we collect together, carry out concentrated by rotary evaporation, are again distributed in water, finally, we obtain the carbon quantum dot aqueous solution of the different fluorescence of multiple transmitting.It should be noted that when solution fluorescence in transition time, we will slow down the speed of solution drips, increase fluorescence color detect number of times, so just can better isolate the comparatively pure fluorescent carbon point with solid color.
The fluorescence of carbon point prepared by the method can adjust to redness from blueness, reaction is 440 to 625 nanometers on wavelength. in order to study material rate and reaction conditions to the impact of the formation of carbon point, we have selected wherein four kinds of most representative carbon points (bluish-green Huang is red) and have carried out careful sign.Carbon point order out when being separated be according to nanoparticle surface functional group polarity from small to large.The fluorescence being exactly carbon point is specifically because the surface functional group polarity increase of carbon point causes from indigo plant to red change.Show that the distribution of sizes formula of the carbon point with different glow color is similar by concrete structural characterization, mainly concentrate on 2.5 ran (as shown in Figure 3), but their content of surface oxygen (degree of oxidation) rises along with the red shift of carbon point fluorescence,-NH is comprised in addition containing other a large amount of functional groups,-OH,-COOH etc., ensure that these carbon points can be dissolved in most of polar solvent.Accurately measure the red four kinds of carbon points of bluish-green Huang quantum yield in aqueous by integrating sphere, its numerical value is respectively 21, and 9,35,24%.Therefore these materials all have broad application prospects at optics and biological field.
embodiment 2
Preparation method is identical with embodiment 1, but temperature of reaction changes 180 DEG C into, and other conditions are constant, and the emission wavelength of these the four kinds of fluorescent carbon points finally obtained is 434,512,564,609 nanometers, the concrete quantum yield calculated by integrating sphere is respectively: 33,12,18,6%.
embodiment 3
Preparation method is identical with embodiment 1, but temperature of reaction changes 140 degrees Celsius into, and other conditions are constant, and the emission wavelength of these the four kinds of fluorescent carbon points finally obtained is 452,525,571,630 nanometers, the concrete quantum yield calculated by integrating sphere is respectively: 11,8,5,2%.From the results of view, temperature has remarkably influenced to emission wavelength and quantum yield, and particularly to quantum yield, this may be because temperature plays key effect in the forming process of carbon point.
embodiment 4
Preparation method is identical with embodiment 1, but the ratio of feed change ratio and urea and Ursol D is 0:1.Now obtaining emission wavelength is 0,0,589 and 610 nanometer, and corresponding quantum yield is: 0,0,7 and 28%.As can be seen here when raw material urea is not by use, blue light and green glow are non-existent, and the change of raw material can have influence on emission wavelength and quantum yield significantly.Therefore it is necessary for studying the impact of material rate on luminosity.
embodiment 5
Preparation method is identical with embodiment 1, but the ratio of feed change ratio and urea and Ursol D is 1:10.Now obtaining emission wavelength is 445,518,580 and 608 nanometers, and corresponding quantum yield is: 3,4,15,23%.As can be seen here when the ratio shared by raw material urea is very low, although blue light and green glow also can be detected, the quantum yield of correspondence is very low.Also be very crucial from the formation of urea to blue light and green glow carbon point also can be found out here.
embodiment 6
Preparation method is identical with embodiment 1, but the ratio of feed change ratio and urea and Ursol D is 3:10.Now obtaining emission wavelength is 443,514,585 and 612 nanometers, and corresponding quantum yield is: 10,5,21 and 25%.As can be seen here when the ratio shared by raw material urea rises, the quantum yield of blue light and green glow also can rise, and the wavelength of fluorescence of the carbon point of gold-tinted and ruddiness has certain Red Shift Phenomena.
embodiment 7
Preparation method is identical with embodiment 1, but the ratio of feed change ratio and urea and Ursol D is 3:5.Now obtaining emission wavelength is 443,516,587 and 618 nanometers, and corresponding quantum yield is: 14,8,28 and 20%.As can be seen here when the ratio shared by raw material urea continues to rise, blue light and quantum yield that is yellow and ruddiness also can continue to rise, and the wavelength of fluorescence of the carbon point of gold-tinted and ruddiness also has certain Red Shift Phenomena.
embodiment 8
Preparation method is identical with embodiment 1, but the ratio of feed change ratio and urea and Ursol D is 4:5.Now obtaining emission wavelength is 441,514,570 and 624 nanometers, and corresponding quantum yield is: 18,11,27 and 17%.As can be seen here when the ratio shared by raw material urea continues to rise, the quantum yield of blue light and green glow also can continue to rise, but only has the wavelength of fluorescence of the carbon of ruddiness point to continue there is certain Red Shift Phenomena, and bluish-green yellow three kinds of colors have a small amount of blue shift.
embodiment 9
Preparation method is identical with embodiment 1, but the ratio of feed change ratio and urea and Ursol D is 5:6.Now obtaining emission wavelength is 438,518,566 and 612 nanometers, and corresponding quantum yield is: 32,29,23 and 9%.As can be seen here when the ratio shared by raw material urea continues to rise, the quantum yield of blue light and green glow also can continue to rise, but but the declining of gold-tinted and ruddiness.On wavelength, blue light, green glow, gold-tinted and ruddiness all show a small amount of blue shift, but ruddiness blue shift is relatively obvious.Time this shows that the amount of urea exceedes Ursol D, be maximum on impact on the wavelength of ruddiness.
embodiment 10
Preparation method is identical with embodiment 1, but the ratio of feed change ratio and urea and Ursol D is 2:3.Now obtaining emission wavelength is 437,514,562 and 607 nanometers, and corresponding quantum yield is: 44,35,27 and 6%.As can be seen here when the quality of raw material urea exceedes the half of Ursol D time, the quantum yield of blue light and green glow can continue to rise, and the quantum yield of ruddiness can continue to decline.In wavelength, blue light does not move substantially, but green glow, gold-tinted and ruddiness still blue shift a little a little.
Embodiment above can be summarized as form below:
Claims (5)
1. a preparation method for the carbon quantum dot of Wavelength tunable, is characterized in that concrete steps are as follows:
(1) mixing solutions of one kettle way preparation containing various fluorescent carbon point
Measure 5 milliliters of ethanol to put in the centrifuge tube of 50 milliliters, then weigh the urea of 0.1-0.2 gram and the Ursol D of 0.1-0.3 gram respectively, join in centrifuge tube, concussion until dissolve completely, then adds the deionized water of 20-45 milliliter, mixes; Mixed solution is transferred in autoclave; High temperature oven is preheated to 140-200 degree Celsius, then reactor is put into baking oven stoichiometric number 6-18 hour, react complete, naturally cool to room temperature;
(2) be separated mixing solutions, be purified into the carbon point sample that fluorescence color is different;
The mixed solution obtained in step (1) is revolved and steams to residual 3-5 milliliters of liquid, add 100-200 object 6-8 gram silica gel, stir, again revolve and steam to dry, preserve; Meanwhile, dry method equipment 300-400 object silicagel column is adopted; Then the mixture be spin-dried for is dispersed in above silicagel column, then adds the Na of 9-11 gram in the above
2cO
3; With the mixed solution of ethanol and ethyl acetate for eluent, be separated; In the process be separated, the solution flowed out with ultra violet lamp, collects the solution component launching identical fluorescence together, carries out revolving steaming, be again distributed in water, finally obtain the carbon quantum dot aqueous solution of the different fluorescence of multiple transmitting.
2. preparation method according to claim 1, it is characterized in that the carbon point of collection eight kinds of different glow colors, their fluorescence peak position is respectively: 440,458,517,553,566,580,594,625 nanometers, quantum yield is followed successively by: 21.23%, and 13.18%, 8.53%, 19.64%, 27.5%, 35.14%, 29.62%, 23.81%.
3. the carbon quantum dot of the Color tunable prepared by preparation method described in claim 1, its kernel has graphited crystalline network, shell is the unbodied carbon of one deck and containing a large amount of hydrophilic functional groups, has good solubleness and stability in polar solvent; Diameter Distribution is between 1.5-4 nanometer; The fluorescence red shift of carbon quantum dot is produced by the change of surface functional group.
4. the application of carbon quantum dot in cells in vitro imaging of Color tunable as claimed in claim 3.
5. application according to claim 4, wherein the red four kinds of carbon quantum dot of bluish-green Huang are used for multi-color marking in HeLa cell.
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