CN103232845B - Preparation and application for silicon quantum dots - Google Patents
Preparation and application for silicon quantum dots Download PDFInfo
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- CN103232845B CN103232845B CN201310167186.5A CN201310167186A CN103232845B CN 103232845 B CN103232845 B CN 103232845B CN 201310167186 A CN201310167186 A CN 201310167186A CN 103232845 B CN103232845 B CN 103232845B
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Abstract
The invention discloses preparation for silicon quantum dots, and a fluorescence labelling method for dopamine molecules by virtue of the silicon quantum dots, which belong to the field of nanotechnology. The method comprises the following steps of: preparing porous silicon at first, obtaining a silicon quantum dot precursor via chemical etching, and obtaining the silicon quantum dots after ultrasonic treatment, wherein the silicon quantum dot precursor can be reacted with hydrofluoric acid to generate surface Si-H, and then sequentially reacted with undecylenic acid, N-hydroxysuccinimide and dopamine, and finally ultrasonically treated to obtain the dopamine molecules which are fluorescence-labelled by the silicon quantum dots. Compared with the prior art, in the method disclosed by the invention, silicon slices are used as raw materials, and a chemical etching method is adopted, so that fluorescence labelling for the dopamine molecules by the silicon quantum dots can be realized at a low temperature and under the normal pressure; and because a chemical modification reaction is performed on the surface of the silicon quantum dot precursor, separation between the product and reactants can be realized via solvent soaking and washing, thus simplifying the separation operation. The method can also be used for fluorescence labelling for other biomolecules containing primary amine group by the silicon quantum dots.
Description
Technical field
The invention belongs to field of nanometer technology, be specifically related to a kind of preparation of silicon quantum dot and the silicon quantum dot fluorescence labeling method to Dopamine HCL molecule thereof.
Background technology
Quantum dot typically refers to the semiconductor material of size below 10nm, has obvious quantum size effect, and quantum dot fluorescence can be controlled according to the size that changes quantum dot.Therefore, quantum dot is with a wide range of applications in fields such as solar cell, luminescent device and optical bio marks.Silicon quantum dot is as the typical semiconductor nano material of one, and than other quantum dot, its exclusive surface modificability, nontoxicity and biocompatibility, have potential application at biological, medical field, attracted a lot of scholars' concern.
Zhenhui Kang etc. has reported taking graphite as anode, silicon chip is negative electrode, ethanol, hydrofluoric acid, hydrogen peroxide and heteropolyacid catalyst mixing solutions are electrolyte solution, constantly oxidized with the silicon chip of anodic bonding, under the effect of etching agent, be consumed and enter solution, so produce a large amount of nano level silicon island at silicon chip surface, thereby obtain silicon quantum dot.Control current density at 20～50mA/cm
2in scope, prepared median size and be about 1,2,3 and the silicon quantum dot of 4nm, corresponding fluorescent emission wavelength is 450,520,640 and 720nm.(Zhenhui Kang, Chi Him A.Tsang, Zhendong Zhang, Mingliang Zhang, Ning-bew Wong, J.Antonio Zapien, Yueyue Shan, Shuit-Tong Lee.A Polyoxometalate-Assisted Electrochemical Method for Silicon Nanostructures Preparation:From Quantum Dots to Nanowires. (heteropoly acid catalysis electrochemical method is prepared silicon nanocrystal: from quantum dot to silicon nanowires) Journal of the American Chemical Society.2007, 129, 5326-5327.).
The patent No. be 201010518438.0 patent also by galvanic corrosion, obtaining surface growth has the silicon chip of silicon quantum dot, and silicon chip is ultrasonic and mix with vinylformic acid in ethanol, then prepares the fluorescence silicon quantum dot of finishing with ultraviolet radiation mixing solutions.This method and the former is similar.
Shuqing Sun etc. utilizes galvanic corrosion N-shaped monocrystalline silicon piece method to prepare silicon nanometer fragment equally, and by itself and decene, undecylenic acid and undecylenyl alcohol under microwave condition, react prepare respectively fuel-displaced molten and water-soluble and there is the silicon quantum dot of red fluorescence, simultaneous verification this silicon quantum dot in living things system, there is fluorescent characteristic (the Jing Wang of stability and high efficiency, Yuexian Liu, Fei Peng, Chunying Chen, Yonghong He, Hui Ma, Lixin Cao, and Shuqing Sun.A General Route to Efficient Functionalization of Silicon Quantum Dots for High-Performance Fluorescent Probes. (a kind of functionalized silicon quantum dot is applied to high-efficiency fluorescence probe) Small.2012, 15:2430-2435.).
Keisuke Sato etc. has reported a kind of taking silicon powder as raw material, hydrofluoric acid and nitric acid are the method that etching agent is prepared fluorescence silicon quantum dot, can obtain fluorescence silicon quantum dot (the Keisuke Sato of different-grain diameter by changing the concentration ratio of hydrofluoric acid and nitric acid, Hiroaki Tsuji, Kenji Hirakuri, Naoki Fukata and Yusuke Yamauchi.Controlled chemical etching for silicon nanocrystals with wavelength tunable photoluminescence. (chemical etching method is prepared the controlled silicon nanocrystal of wavelength of fluorescence) Chemical Communications.2009, 3759-3761.).
Paras N.Prasad etc. is also raw material with silicon powder, and hydrofluoric acid and nitric acid are the fluorescence silicon quantum dot that etching agent has been prepared multiple color.Then pentenoic acid is modified to silicon quantum dot surface, and the silicon quantum dot of modification is applied to biological study, further verify silicon quantum dot being suitable in living things system, nontoxic and cell imaging characteristic (Folarin Erogbogbo, Ken-Tye Yong, Indrajit Roy, Rui Hu, Wing-Cheung Law, Weiwei Zhao, Hong Ding, Fang Wu, Rajiv Kumar, Mark T.Swihart and Paras N.Prasad.In Vivo Targeted Cancer Imaging, (biocompatible silicon nanocrystal is for the target cancer cell imaging in organism for Sentinel Lymph Node Mapping and Multi-Channel Imaging with Biocompatible Silicon Nanocrystals., sentinel lymph node mapping and multi-spectral imaging) ACS Nano.2011, 5 (1): 413-423.).
The employing silicon tetrachlorides such as Todd Emrick are raw material, under four octyl group brometo de amonios exist, prepare the silicon quantum dot that median size is about 2nm with Lithium Aluminium Hydride reduction, and in finishing the chain structure of end polyoxyethylene glycol.Such silicon quantum dot can be dispersed in a lot of solvents, and can preserve (P.K.Sudeep with solid form, Zachariah Page and Todd Emrick.PEGylated silicon nanoparticles:synthesis and characterization. (the synthetic and sign of Pegylation nano silicon particles) Chemical Communications.2008,6126-6127.).
Jonathan G.C.Veinot etc. has reported taking silsesquioxane as raw material, in the hydrofluoric acid solution of different concns, prepare the fluorescence silicon nanocrystal of different-grain diameter by photochemistry etching method, and studied impact (the Jose R.Rodr í guez of etching time on silicon nanocrystal fluorescence
joel A.Kelly, Eric J.Henderson, and Jonathan G.C.Veinot.Wavelength-Controlled Etching of Silicon Nanocrystals. (the wavelength controlled etching of silicon nanocrystal) Chemistry of Materials.2012,24:346-352.).
In sum, the method of preparing at present fluorescence silicon quantum dot mainly contains three major types, the one, taking silicon chip as anode, adopt the method for galvanic corrosion to obtain silicon quantum dot, the silicon quantum dot that this method obtains easily comes off and enters solution from silicon chip surface, is unfavorable for follow-up chemically modified and the labeled reactant to biomolecules; The 2nd, as silicon source (as silicon tetrachloride or Silicon bromide), adopt chemical reduction method to prepare fluorescence silicon quantum dot using silicon-containing inorganic compound, this compounds is very easily hydrolyzed, and reaction is difficult to be well controlled, and raw materials cost is higher; The 3rd, taking silicon powder or silicon nanometer fragment as raw material, adopt the method for chemical etching to prepare fluorescence silicon quantum dot, although some can accomplish that particle diameter is controlled, but silicon quantum dot obtain and after subsequent chemistry modification reaction finishes, product is comparatively difficult with separating of reactant, this is because the particle diameter of silicon quantum dot is too little, is difficult to be realized effectively and being separated by the method such as filter, centrifugal.
Summary of the invention
The present invention overcomes prior art deficiency provides a kind of reaction conditions gentleness, the simple silicon quantum dot preparation method of preparation process; And this silicon quantum dot is easily realized the fluorescent mark to Dopamine HCL molecule.
In order to solve above technical problem, the present invention is achieved by the following technical programs.
A preparation method for silicon quantum dot, comprises the following steps:
(1) clean plane silicon chip is immersed in 5.0M hydrofluoric acid and 0.005M Silver Nitrate mixed aqueous solution, carry out chemical etching reaction, control temperature of reaction at 50 DEG C, the reaction times is 60min;
(2) take out the silicon chip that obtains of step (1), put into 33% aqueous nitric acid and soak 20min, after taking out, use a large amount of deionized water rinsings, and dry up acquisition porous silicon with nitrogen;
(3) porous silicon step (2) being obtained immerses in the mixed aqueous solution of 1～8M hydrofluoric acid and 1M nitric acid composition, control temperature of reaction at 30～60 DEG C, reaction times is 30～180min, obtains silicon quantum dot presoma, can obtain silicon quantum dot through supersound process.
The method of above-mentioned silicon quantum dot to Dopamine HCL molecular fluorescence mark, comprises the steps:
(1) the silicon quantum dot presoma that prepared by claim 1 immerses in 5M hydrofluoric acid, controls temperature at 50 DEG C, and time length 5min, prepares the silicon quantum dot presoma that contains Si-H key in surface;
(2) the surface silicon quantum dot presoma alcohol flushing that contains Si-H key that step (1) obtains also dries up with nitrogen, under nitrogen protection, react with undecylenic acid, and control temperature of reaction is at 140 DEG C, and the reaction times is 4h;
(3) step (2) products therefrom, fully soaks with ethanol, removes the undecylenic acid being attached on silicon chip, and nitrogen dries up the rear silicon quantum dot presoma of surface with carboxyl that obtain;
(4) surface of step (3) acquisition is with the silicon quantum dot presoma of carboxyl under dicyclohexylcarbodiimide catalysis, and with N-maloyl imine reaction, controlling temperature of reaction is 40 DEG C, and the reaction times is 4h;
(5) the silicon quantum dot presoma that step (4) obtains reacts with the Dopamine HCL that is dissolved in pH=7.4 phosphate buffer solution, controlling temperature of reaction is 36 DEG C, reaction times is 4h, and product, through fully cleaning ultrasonic in water, obtains the fluorescently-labeled Dopamine HCL molecule of silicon quantum dot.
Above-mentioned silicon quantum dot also can carry out fluorescent mark containing primary amine groups biomolecules to other except Dopamine HCL molecule.
With respect to prior art, the present invention has following technique effect:
1, provide a gentle technological line of preparing silicon quantum dot, on plane silicon chip surface, prepared silicon quantum dot presoma, through supersound process, obtained silicon quantum dot;
2, silicon source required for the present invention is plane silicon chip, the method for preparing silicon quantum dot with respect to other, and raw material is relatively cheap;
3, after obtaining silicon quantum dot presoma, utilize the chemical property of element silicon itself, through some step chemical reactions, can realize the silicon quantum dot fluorescent mark to Dopamine HCL molecule;
4, occur in the surface of solid due to these chemical reactions, can realize easily separating of product and reactant, improved the efficiency that each step reaction product separates; As by simple operationss such as immersions, flushing, just can realize separating of modified outcome and reactant.
Brief description of the drawings
Fig. 1 is the preparation of a kind of silicon quantum dot of the present invention and the silicon quantum dot fluorescence labeling method schematic diagram to Dopamine HCL molecule thereof.
As shown in the figure, first silicon chip clean surface is immersed in hydrofluoric acid and Silver Nitrate mixed aqueous solution, carry out etching reaction, obtain porous silicon; Then remove remaining Ag particle with nitric acid, carry out chemical etching reaction with hydrofluoric acid-nitric acid mixing etching agent again, owing to there being different crystal faces in porous silicon chip, the reaction process of each crystal face and HF is not quite similar, for example Si (111) easily produces Si-H, and Si (100) easily produces Si-H
2and Si-H
3, different crystal faces should be different from the speed of HF reaction, and etching agent carries out chemical etching with different etch rates, so can go out a large amount of grooves in the surface etch of porous silicon, becomes the presoma of silicon quantum dot, and process is as shown in Fig. 1 (1); Under the irradiation of Portable ultraviolet lamp (365nm), silicon quantum dot presoma sends strong red fluorescence, and they can fragment into silicon quantum dot under ultrasonication, also can stably be retained in the surface of silicon chip, under the effect of HF, easily produce a large amount of Si-H on its surface
x(x=1,2 or 3) key, as shown in Fig. 1 (2); Si-H
xthere is good chemically reactive, can react with the organism containing end group C=C, react with undecylenic acid (UA), N-maloyl imines (NHS) and Dopamine HCL (DA) successively, realize the covalent coupling of Dopamine HCL molecule on silicon quantum dot presoma surface, respectively as shown in Fig. 1 (3)～(5); Finally, through ultrasonication, silicon quantum dot departs from silicon base, realizes the silicon quantum dot fluorescent mark to DA molecule.
Fig. 2 is the infrared spectrogram that silicon quantum dot presoma reacts with undecylenic acid, N-maloyl imines and Dopamine HCL successively.
Fig. 2 (a) is the infrared spectrum of silicon quantum dot presoma finishing undecylenic acid, 2923,2854cm
-1in the corresponding undecylenic acid chain of difference-CH
2-unsymmetrically and symmetrical stretching vibration, 1712cm
-1the stretching vibration of C=O in respective ends carboxyl, illustrates that undecylenic acid has been modified at silicon quantum dot presoma surface, and Fig. 2 (b) is terminal carboxyl(group) and the reacted infrared spectrogram of N-maloyl imines (NHS), 1712cm
-1peak disappears, and has generated the triplet of NHS ester, 1740cm
-1(v (C=O)) asymmetrical stretching vibration in corresponding O=C-N-C=O, 1784cm
-1the symmetrical stretching vibration of (v (C=O)) in corresponding O=C-N-C=O, 1815cm
-1in the corresponding ester group generating, the stretching vibration of C=O, illustrates that terminal carboxyl(group) is activated by NHS, and Fig. 2 (c) is the infrared spectrum that Dopamine HCL molecule reacts with NHS ester, can it is evident that the generation of amido linkage in figure, 1650,1549cm
-1corresponding acid amides I(v (C=O)) and acid amides II(δ (NH)+v (CN)), 1454cm
-1the stretching vibration of C-N in corresponding amido linkage, this feature has absolutely proved that Dopamine HCL has been marked on silicon quantum dot.Fig. 2 (c) also demonstrates NHS ester not to be had completely and Dopamine HCL molecular reaction, and this may be due to sterically hindered reason.
Fig. 3 is fluorescence spectrum figure and the uv absorption spectra of silicon quantum dot fluorescent mark Dopamine HCL molecular solution.
The silicon quantum dot presoma that surface is modified through Dopamine HCL enters the aqueous solution through supersound process, Fig. 3 (a) is its fluorescence spectrum figure, can find that it has fluorescence peak at 630nm place, under hand-held ultraviolet lamp irradiates (365nm), solution presents bright-coloured redness, and this is consistent with fluorescence spectrum figure; Fig. 3 (b) shows that it has the uv-absorbing of 250nm left and right.
Fig. 4 is the transmission electron microscope image of silicon quantum dot fluorescent mark Dopamine HCL molecular solution.
As shown in the figure, can find out that silicon quantum dot particle diameter is below 10nm.
Embodiment
Below by embodiment, the present invention is described further.But the present invention is not limited to the following example.
Embodiment 1:
(1) planar silicon is cleaned to rear 5.0M hydrofluoric acid and the 0.005M Silver Nitrate mixed aqueous solution of immersing, carry out chemical etching reaction, control temperature of reaction at 50 DEG C, the reaction times is 60min;
(2) take out the product that obtains of step (1), put into 33% aqueous nitric acid and soak 20min, to remove remaining Ag, use a large amount of deionized water rinsings, and dry up acquisition porous silicon with nitrogen;
(3) porous silicon step (2) being obtained immerses 1M hydrofluoric acid and reacts with the mixed aqueous solution of 1M nitric acid composition, controls temperature of reaction at 60 DEG C, and the reaction times is 180min, obtains silicon quantum dot presoma;
(4) the silicon quantum dot presoma that step (3) obtains immerses in 5M hydrofluoric acid, controls temperature at 50 DEG C, and the reaction times is 5min, prepares the silicon quantum dot presoma that contains Si-H key in surface;
(5) step (4) obtains surface and dries up with a large amount of alcohol flushings of the silicon quantum dot presoma of Si-H key and with nitrogen, reacts with undecylenic acid, and control temperature of reaction is at 140 DEG C, and the reaction times is 4h;
(6) step (5) products therefrom, fully soaks with ethanol, removes the undecylenic acid being attached on silicon chip, and nitrogen dries up the rear silicon quantum dot presoma of surface with carboxyl that obtain;
(7) surface of step (6) acquisition is with the silicon quantum dot presoma of carboxyl under dicyclohexylcarbodiimide catalysis, and with N-maloyl imine reaction, controlling temperature of reaction is 40 DEG C, and the reaction times is 4h;
(8) the silicon quantum dot presoma that step (7) obtains reacts with the Dopamine HCL that is dissolved in pH=7.4 phosphate buffer solution, controlling temperature of reaction is 36 DEG C, reaction times is 4h, and product, through fully cleaning ultrasonic in water, obtains the fluorescently-labeled Dopamine HCL molecule of silicon quantum dot.
Embodiment 2:
(1) with embodiment 1 step (1);
(2) with embodiment 1 step (2);
(3) porous silicon step (2) being obtained immerses 4M hydrofluoric acid and reacts with the mixed aqueous solution of 1M nitric acid composition, controls temperature of reaction at 50 DEG C, and the reaction times is 90min, obtains silicon quantum dot presoma;
(4) with embodiment 1 step (4);
(5) with embodiment 1 step (5);
(6) with embodiment 1 step (6);
(7) with embodiment 1 step (7);
(8) with embodiment 1 step (8).
Embodiment 3:
(1) with embodiment 1 step (1);
(2) with embodiment 1 step (2);
(3) porous silicon step (2) being obtained immerses 8M hydrofluoric acid and reacts with the mixed aqueous solution of 1M nitric acid composition, controls temperature of reaction at 30 DEG C, and the reaction times is 30min, obtains silicon quantum dot presoma;
(4) with embodiment 1 step (4);
(5) with embodiment 1 step (5);
(6) with embodiment 1 step (6);
(7) with embodiment 1 step (7);
(8) with embodiment 1 step (8).
The comparatively cheap silicon chip of utilization of the present invention is made raw material, adopts chemical etching method, first prepares porous silicon, on at the bottom of silicon wafer-based, prepare silicon quantum dot presoma again, etching reaction carries out under low temperature (being no more than 60 DEG C), normal pressure, through supersound process, just can obtain silicon quantum dot.Can carry out appropriate chemically modified to the presoma of above-mentioned silicon quantum dot, Dopamine HCL molecule covalency is bundled in to the surface of silicon quantum dot presoma, because silicon quantum dot connects by covalent linkage with Dopamine HCL molecule, ultrasonication can not destroy the Chemical bond between them, finally by ultrasonication, silicon quantum dot is separated with silicon base, thereby realize the mark of silicon quantum dot to Dopamine HCL molecule.Although the inventive method only relates to Dopamine HCL molecule, clearly it is also applicable to other reaction of silicon quantum dot fluorescent mark containing primary amine groups biomolecules.
Claims (2)
1. a preparation method for silicon quantum dot, is characterized in that comprising the following steps:
(1) clean plane silicon chip is immersed in 5.0M hydrofluoric acid and 0.005M Silver Nitrate mixed aqueous solution, carry out chemical etching reaction, control temperature of reaction at 50 DEG C, the reaction times is 60min;
(2) take out the silicon chip that obtains of step (1), put into 33% aqueous nitric acid and soak 20min, after taking out, use a large amount of deionized water rinsings, and dry up acquisition porous silicon with nitrogen;
(3) porous silicon step (2) being obtained immerses in the mixed aqueous solution of 1～8M hydrofluoric acid and 1M nitric acid composition, control temperature of reaction at 30～60 DEG C, reaction times is 30～180min, obtains silicon quantum dot presoma, can obtain silicon quantum dot through supersound process.
2. the method for silicon quantum dot as claimed in claim 1 to Dopamine HCL molecular fluorescence mark, is characterized in that comprising the steps:
(1) the silicon quantum dot presoma that prepared by claim 1 immerses in 5M hydrofluoric acid, controls temperature at 50 DEG C, and time length 5min, prepares the silicon quantum dot presoma that contains Si-H key in surface;
(2) the surface silicon quantum dot presoma alcohol flushing that contains Si-H key that step (1) obtains also dries up with nitrogen, under nitrogen protection, react with undecylenic acid, and control temperature of reaction is at 140 DEG C, and the reaction times is 4h;
(3) step (2) products therefrom, fully soaks with ethanol, removes the undecylenic acid being attached on silicon chip, and nitrogen dries up the rear silicon quantum dot presoma of surface with carboxyl that obtain;
(4) surface of step (3) acquisition is with the silicon quantum dot presoma of carboxyl under dicyclohexylcarbodiimide catalysis, and with N-maloyl imine reaction, controlling temperature of reaction is 40 DEG C, and the reaction times is 4h;
(5) the silicon quantum dot presoma that step (4) obtains reacts with the Dopamine HCL that is dissolved in pH=7.4 phosphate buffer solution, controlling temperature of reaction is 36 DEG C, reaction times is 4h, and product, through fully cleaning ultrasonic in water, obtains the fluorescently-labeled Dopamine HCL molecule of silicon quantum dot.
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| CN103754880A (en) * | 2014-01-20 | 2014-04-30 | 复旦大学 | Large-scale production method of silicon quantum dots |
| CN104181135B (en) * | 2014-08-19 | 2016-11-02 | 东南大学 | The application in dopamine detects of the water-soluble silicon quantum dot |
| CN104974748A (en) * | 2015-06-23 | 2015-10-14 | 南昌航空大学 | Synthetic method of silicon quantum dots |
| KR101764005B1 (en) | 2015-07-10 | 2017-08-02 | 가천대학교 산학협력단 | Method for Detecting Dopamine |
| CN111718711A (en) * | 2019-03-19 | 2020-09-29 | Tcl集团股份有限公司 | Composite material and preparation method thereof |
| CN110554203B (en) * | 2019-09-17 | 2022-10-21 | 浙江大学山东工业技术研究院 | High density lipoprotein cholesterol test paper |
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