WO2013029278A1 - Procédé de préparation de nanoparticules de silicium fonctionnalisées - Google Patents

Procédé de préparation de nanoparticules de silicium fonctionnalisées Download PDF

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Publication number
WO2013029278A1
WO2013029278A1 PCT/CN2011/079304 CN2011079304W WO2013029278A1 WO 2013029278 A1 WO2013029278 A1 WO 2013029278A1 CN 2011079304 W CN2011079304 W CN 2011079304W WO 2013029278 A1 WO2013029278 A1 WO 2013029278A1
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Prior art keywords
silicon
silicon nanoparticles
carbon atoms
terminated
siqds
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PCT/CN2011/079304
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English (en)
Inventor
Shuqing SUN
Jing Wang
Fei Peng
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National Center For Nanoscience And Technology
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Priority to PCT/CN2011/079304 priority Critical patent/WO2013029278A1/fr
Publication of WO2013029278A1 publication Critical patent/WO2013029278A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00—Silicon; Compounds thereof
    • C01B33/02—Silicon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures

Definitions

  • the present invention relates to methods of producing stable surface functionalized silicon nanoparticles through microwave-assisted hydrosilylation of hydride-terminated silicon nanoparticles in the presence of various reactive compounds.
  • silicon is inert, nontoxic, abundant, low-cost and biocompatible. Elemental Silicon is of great importance to the development of industry. Bulk silicon is widely used in microelectronic, photovoltaic, and MEMS technologies. However, in contrast to its extensive use in electronic devices bulk silicon has found limited optical applications. Since silicon is an indirect bandgap semiconductor, the lowest point of the conduction band and the highest point in the valence band occur at different wave vectors in reciprocal space; therefore, the bandgap optical transition is dipole-forbidden in the infinite crystal and photo luminescence (PL) cannot occur.
  • PL photo luminescence
  • a very important property of nanoparticles is their enormous surface area to volume ratio.
  • Surface chemistry of SiQDs would open up a new venue for their study and possible applications.
  • the presence of oxygen at the surface of SiQDs has been shown to influence their PL intensity and emission wavelength. Therefore, the surface modification of SiQDs plays a key role for the synthesis of stable, oxide-free Silicon nanocrystals.
  • the surface chemistry of bulk silicon surfaces is a well-developed field of study and serves as a foundation for most functionalized SiQDs studies.
  • the silicon-carbon bond is both thermodynamically and kinetically stable owing to the high bond strength and low polarity of the bond.
  • the present invention provides a method for preparing functionalized silicon nanoparticles (i.e., functionalized SiQDs), including:
  • the microwave irradiation may have a power of 100 to 700 W and have a frequency of 300MHz to 300GHz.
  • the method of the present invention allows for the introduction of different functional groups on the surface.
  • the use of microwave irradiation has a net effect on the hydrosilylation reaction rate.
  • a remarkable advantage of using microwave-assisted passivation of SiQDs surfaces according to the present invention is the fact that the rate of hydrosilylation reaction and surface coverage increased greatly. The whole procedure may complete within 30 minutes that is more efficient than any of the existing methods.
  • This method of the present invention provides a simple and effective way to tailor the wetting properties of the surface by introducing hydrophobic or hydrophilic functional end groups.
  • the functionalized silicon nanoparticles have shown a very good stability in different aqueous and organic media.
  • the optical properties of the SiQDs have been preserved very well by the microwave-assisted chemical passivation. The photoluminescent characteristics of the material are stabilized over time.
  • This method contributes several advantages to yield high-quality SiQDs such as simple procedure, shorter reaction time, milder conditions, environmental friendliness and easy to scale-up.
  • Microwave-enhanced chemistry is based on the efficiency of interactions of molecules with waves and heating of materials by "microwave dielectric heating” effect, depending on the ability of materials to absorb microwaves and convert it into heat. In general, the created heating is believed to promote the chemical transformation. Thermal effect is thought to result from the dipolar polarization as a consequence of dipole-dipole interaction between polar molecules and the electromagnetic field.
  • the present inventors found that, because silicon contains many free conductive electrons and electronic holes, the charge space polarization can easily occur in the microwave frequency. Besides bulk silicon, silicon nanoparticles have strong absorbability of microwave energy. Therefore, the microwave irradiation is an effective technique for the thermal activated reaction between hydrogen-terminated SiQDs and various hydrosilylating agents.
  • a radical mechanism is proposed for organic monolayer formation on hydrogen-terminated SiQDs surface using the commercially available alkenes as the hydrosilylating agent under microwave irradiation, as shown in FIG. 2.
  • Microwave heating causes the silicon hydrogen bond scission and production of surface silicon radical.
  • silyl radicals are known to react extremely rapidly with alkene group, formation of a silicon carbon bond is the next probable step.
  • the carbon-based radical can then abstract a hydrogen atom either from a neighboring Si-H group or from the allylic position of an unreacted alkene group.
  • the hydrosilylating agent may be any conventional ones.
  • the hydrosilylating agent preferably an organic compound containing one or more groups selected from alkenyl, alkynyl, triazo and halogen.
  • the alkenyl, alkynyl, triazo or halogen is capable of reacting with silyl radicals caused by the microwave.
  • the hydrosilylating agent may further contain additional functional group which would be better possessing at least one of the following properties, including: semiconductive, magnetic, radioactive, conductive, biological and luminescent properties.
  • These functional groups may be hydrophobic or hydrophilic, such as ester, carboxylic acids, alcohols, amines and N-hydroxysuccinimide ester.
  • the functionalized silicon nanoparticles can be covalently linked to other materials, such as proteins, peptides, fullerenes, polymers, nanoparticles and so on. It enables silicon nanoparticles to exhibite a wide spread application in various field.
  • silicon nanoparticles passivated with hydrophilic groups allow transport through a cell membrane.
  • the specific protein modified silicon nanoparticles can target certain cells in a living organism.
  • Conductive/semi-conductive and magnetic materials modified SiQDs may be used in photovoltaic devices and in- vivo dual imaging, respectively.
  • the amount of the hydrosilylating agent may be greatly excessive. For example, the amount by mole of the hydrosilylating agent may be excessive by 20 times or more.
  • the hydrosilylating reagent is one or more selected from alkenes, alkynes, alkyl halides, azides, unsaturated alcohols, unsaturated carboxylic acids, and the alkene-, alkyne-, alkyl halide-, or azide-terminated polymers.
  • the alkenes may have at least 3 carbon atoms, preferably 3 to 30 carbon atoms.
  • the alkenes include but are not limited to 1-octene, 1-decene, 1-dodecene.
  • the alkynes may have at least 3 carbon atoms, preferably 3 to 20 carbon atoms.
  • the alkynes include but are not limited to 1-octyne, 1-decyne, 1-dodecyne.
  • the alkyl halides may have 2 to 30 carbon atoms, preferably 2 to 20carbon atoms.
  • alkyl halides include but are not limited to 11-Bromoundecanoic acid
  • the azides may have 2 to 30carbon atoms, preferably 2 to 20 carbon atoms.
  • the azides include but are not limited to 11-azidoundecanoic acid, 5-azido-2-nitrobenzoic acid, N-5-azido-2-nitrobenzoyloxy succinimide.
  • the unsaturated alcohols have at least 3 carbon atoms, preferably 3 to 11 carbon atoms.
  • the unsaturated alcohols include but are not limited to 2-butene-l,4-diol, undecylenyl alcohol.
  • the unsaturated carboxylic acids have at least 3 carbon atoms, preferably 3 to 11 carbon atoms.
  • the unsaturated carboxylic acids include but are not limited to acrylic acid, 4-pentenoic acid, undecanoic acid.
  • the molecular weights of the alkene-, alkyne-, alkyl halide-, or azide-terminated polymers are range from 200Da to 200KDa.
  • the polymers include but are not limited to polyethylene glycol, poly(N-vinyl-2-pyrrolidone).
  • the microwave irradiation may be performed at any power capable of causing the silicon hydrogen bond scission and thus producing surface silicon radical.
  • the microwave irradiation preferably has a power of 50 to 700W, more preferably 100 to 700W, and preferably has a frequency of 300MHz to 300GHz.
  • the hydrosilylation may be performed in an inert atmosphere in an organic solvent.
  • the organic solvent may be any solvent capable of dissolving the hydrosilylating reagent.
  • the organic solvent is preferably but not limited to one or more selected from ethanol, n-hexadecane, and p-xylene.
  • the amount of the organic solution is not limited as long as the hydrosilylation agent can be completely dissolved.
  • the inert atmosphere may be nitrogen or argon.
  • the hydrosilylation may be performed in a reactor adapted for microwave heating.
  • microwave experiments were performed in a LWMC-205 reactor with an adjustable power 0-700W operating at a frequency of 2450 MHz.
  • the reactant of the microwave-assisted chemical reaction is a mixture of the hydrosilylation agent and suspended silicon nanoparticles in ethanol. All reactions are conducted in an open vessel containing the reactants under continuous nitrogen bubbling to ensure oxygen elimination. Silicon absorbs microwave energy efficiently.
  • the functionalized silicon nanoparticles may be purified by centrifuge. After microwave irradiation, the reaction mixture is centrifuged to remove organic reagents and yield solid silicon nanoparticles.
  • the solid silicon nanoparticles are washed with reactive organic soluble solvents for four times to obtain dry nanoparticle products.
  • These functionalized silicon nanoparticles dispersed in water, ethanol or hexane can be redispersed in those solvents for characterization.
  • the hydrogen-terminated Silicon nanoparticles may be prepared by various methods. Methods to produce hydrogen-terminated Silicon nanoparticles include hydrofluoric (HF) acid etching from amorphous silicon oxide powders or pure silicon powders, electrochemical etching of crystalline silicon wafers, plasma synthesis, reduction of SiCl 4 with various types of reducing agents or the metathesis reaction between sodium silicide and NH 4 Br. All the hydrogen-terminated silicon nanoparticles can be further functionalized through microwave-assisted chemical reaction. Perhaps the most widely studied silicon based nanostructure is porous silicon. Therefore, the present invention includes a method of producing luminescent silicon nanoparticles by ultrasonicating porous silicon films.
  • HF hydrofluoric
  • Fig. 3 is a transmission electron microscope (TEM) image obtained of suspended silicon nanoparticles produced by ultrasonicating porous silicon for 2 hours in ethanol. As shown in Fig.
  • the nanostructures in the range of 2 to 50 nm are not individual nanoparticles, but are silicon nanoparticles domains trapped in larger pieces of the porous silicon structure.
  • the PL property of the silicon nano-fragments is the same with the original porous silicon film, and they can be used for the further functionalization step.
  • FIG. 1 is a schematic diagram that illustrates the overall procedure for production of functionalized silicon quantum dots, according to the method of the present invention.
  • FIG. 2 is a schematic diagram that illustrates the mechanism for the radical-based hydrosilylation by microwave assisted reaction on hydrogen-terminated SiQDs.
  • FIG. 3 is a transmission electron microscope (TEM) image obtained of suspended hydrogen-terminated silicon nanoparticles produced in the preparation example 1 by ultrasonicating porous silicon for 2 hours in ethanol, and wherein a number of nanostructures can be seen with sizes ranging from 2-50 nm.
  • TEM transmission electron microscope
  • Fig. 4 is the TEM image of the undecanoic acid-terminated silicon quantum dots in water and inset showing a high-resolution TEM image of an individual silicon nanocrystal.
  • Fig. 5 is the TEM image of the polyacrylic acid-terminated silicon quantum dots.
  • Fig. 6 is the FTIR spectrum of n-decane-passivated silicon nanoparticles.
  • Fig. 7 is the FTIR spectrum of diol-passivated silicon nanoparticles.
  • Fig. 8 is the FTIR spectra of silicon nanoparticles capped with (a) polyacrylic acid, (b) pentanoic acid, and (c) undecanoic acid.
  • Fig. 9 is the UV (a) and PL (b, nm) spectra of undecanoic acid terminated-silicon nanoparticles in water.
  • Fig. 10 is the photograph of decane, PAA and pentanoic acid capped silicon quantum dots dispersed in hexane and water, respectively. Under UV light excitation the silicon nanoparticles retain their PL in different solvent media.
  • 1-decene, 2-butene-l ,4-diol, acrylic acid, 4-pentenoic acid and 10-undecenoic acid are used as the hydrosilylation agent, respectively, so as to obtain luminescent silicon nanoparticles functionalized with decane, diol, polyacrylic acid (PAA), pentanoic acid, and undecanoic acid, respectively.
  • 1-Decene, 2-butene-l ,4-diol, acrylic acid, 4-pentenoic acid and 10-undecenoic acid were purchased from Alfa Aesar. All chemicals were used as-received without additional purification.
  • the silicon quantum dots were achieved in an etching process with a current density of 130 mA/cm 2 for 10 min, and were well dispersed in 20 ml ethanol solution by ultrasonic treatment. Afterwards, the precipitates after ultrasonification were removed using a poly(tetrafluoroethylene) (PTFE) syringe filter (pore size 0.22 ⁇ ). The purified SiQDs ethanol solution was then utilized for the further functionalization.
  • PTFE poly(tetrafluoroethylene)
  • Microwave-irradiation was performed in a LWMC-205 reactor with an adjustable power 0-700 W operating at a frequency of 2450 MHz.
  • the reactants of the microwave-assisted chemical reaction are a mixture of 1-decene (10 ml) and suspended silicon nanoparticles (2 mg) in ethanol (5ml). All reactions are conducted in an open vessel with a refluxing condenser and containing the reactants under continuous nitrogen bubbling to ensure oxygen elimination.
  • the power of the microwave irradiation was 400 W, and the reactions time was 15 min.
  • reaction mixture was centrifuged to remove the excess organic reagents and yield solid silicon nanoparticles. Especially, decane-terminated SiQDs were washed with hexane for four times.
  • Functionalized silicon nanoparticles were obtained using the same method as Example 1, except that 1-decene was replaced with 2-butene-l,4-diol, and during purification of functionalized SiQDs, hexane was replaced with ethanol.
  • Functionalized silicon nanoparticles were obtained using the same method as Example 1, except that 1-decene was replaced with acrylic acid, and the power of the microwave irradiation was 150 W, and during purification of functionalized SiQDs, hexane was replaced with ethanol.
  • Example 4 Functionalized silicon nanoparticles were obtained using the same method as Example 1, except that 1-decene was replaced with 4-pentenoic acid, and the power of the microwave irradiation was 200 W, and during purification of functionalized SiQDs, hexane was replaced with ethanol.
  • Functionalized silicon nanoparticles were obtained using the same method as Example 1, except that 1-decene was replaced with 10-undecenoic acid, and the power of the microwave irradiation was 200W, and during purification of functionalized SiQDs, hexane was replaced with ethanol.
  • Fig. 4 displays the TEM image of the undecanoic acid-terminated silicon quantum dots and inset showing a high-resolution TEM image of an individual silicon nanocrystal. Due to the thermal effect of the microwave irradiation, silicon nano-fragments separate into silicon nanoparticles, which have an average diameter of 4 ⁇ 0.5 nm.
  • the diol, PAA (polyacrylic acid), pentanoic acid, and undecanoic acid-terminated silicon nanoparticles are water soluble. Their TEM images are similar except PAA-terminated silicon nanoparticles.
  • the acrylic acid monomers adequately react with the Si-H bond of the surface under microwave irradiation, and then initiate free radical polymerization.
  • Fig. 5 shows the TEM image of silicon nanoparticles capped with PAA. After purification, the PAA-terminated silicon nanoparticles have good water dispersibility. In the present invention, the FTIR results of functionalized silicon nanoparticles have shown these functional groups are very stable under microwave irradiation. For analysis, the nanoparticles were purified through centrifugation, dried under vacuum, and then dispersed in chloroform. A KBr pellet was prepared by grinding powder KBr and a drop of each silicon nanoparticle dispersion.
  • Fig. 6 shows the FTIR spectrum of n-decane-passivated silicon nanoparticles.
  • the peaks around 2854 and 2921 cm “1 represent alkane C-H stretching.
  • Two peaks observed at 1461 and 1261 cm “1 are attributed to the vibrational scissoring and symmetric bending of Si-CH 2 , respectively, confirming that the 1-decene is indeed bound covalently to the surface of the particles.
  • Fig. 7 the peak corresponding to an O-H stretching of an alcohol group can be observed at 3350 cm "1 .
  • Fig.8 shows FTIR spectra of the PAA (spectrum a), pentanoic acid (spectrum b), and undecanoic acid (spectrum c) capped silicon nanoparticles.
  • Characteristic carboxylic acid C 0 and C-H features arising from surface-tethered organic acids appear at 1715 and 2850-2980 cm “1 , respectively. Peaks observed at 1456 and 1258 cm “1 are attributed to Si-CH 2 vibrational scissoring and symmetric bending.
  • the spectrum c of PAA functionalized silicon nanoparticles also displays -OH stretching around 3500 cm "1 , which is owing to residual water in the polymer.
  • Fig.9a UV-visible
  • PL photoluminescence
  • Fig.9b The optical properties of undecanoic acid-terminated silicon nanocrystals were investigated using UV-visible (Fig.9a) and photoluminescence (PL) spectroscopy (Fig.9b).
  • the Uv-vis spectrum of the silicon nanoparticles dispersed in water gives a broad absorption band, with a shoulder at 320 nm characteristic of silicon nanoparticles.
  • the fluorescence emission spectrum of undecanoic acid-terminated silicon nanocrystals in water reveal a red luminescence centered at 680 nm, which was excited at 365 nm.
  • Fig. 10 shows the photograph of decane, PAA and pentanoic acid capped silicon quantum dots dispersed in hexane and water, respectively. Under UV light excitation the silicon nanoparticles retain their PL in different media.
  • the present inventors have demonstrated herein that their reported method for the producing stable surface functionalized silicon quantum dots through microwave-assisted hydrosilylation of hydrogen-terminated Si nanoparticles is not limited merely to alkenes, but in fact is also effective with alkynes, alkyl halides and azides.
  • Functionalization of hydrogen-terminated silicon nanoparticles under microwave irradiation has been performed to produce nanoparticles with reactive surface functionalities such as diols and carboxylic acids. These nanoparticles exhibit luminescence under UV excitation and show a very good stability in different aqueous and organic media. Establishing this efficient microwave assisted functionalization method as being flexible to various functionalities serves to increase its potential applications.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Silicon Compounds (AREA)

Abstract

L'invention concerne un procédé de préparation de nanoparticules de silicium fonctionnalisées, ledit procédé consistant à : (1) préparer des nanoparticules de silicium à terminaison hydrogène ; et (2) soumettre les nanoparticules de silicium à terminaison hydrogène à une hydrosilylation avec un réactif d'hydrosilylation en présence d'un rayonnement micro-ondes. Ce procédé apporte un certain nombre d'avantages, à savoir simplification du traitement final, temps de réaction plus court, conditions moins rigoureuses et protection de l'environnement.
PCT/CN2011/079304 2011-09-02 2011-09-02 Procédé de préparation de nanoparticules de silicium fonctionnalisées WO2013029278A1 (fr)

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WO2016054522A1 (fr) 2014-10-03 2016-04-07 Ntercept, Llc Compositions et procédés pour inhiber l'activité biologique de biomolécules solubles
WO2017176762A1 (fr) 2016-04-06 2017-10-12 Nanotics, Llc Particules comprenant des sous-particules ou des échafaudages d'acide nucléique
CN110591690A (zh) * 2019-09-20 2019-12-20 中南大学 一种可表面化学修饰的疏水性硅量子点及其制备方法和应用
US10653790B2 (en) 2015-07-29 2020-05-19 Nanotics, Llc Compositions and methods related to scavenger particles
US11065345B2 (en) 2017-01-04 2021-07-20 Nanotics, Llc Methods for assembling scavenging particles

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016054522A1 (fr) 2014-10-03 2016-04-07 Ntercept, Llc Compositions et procédés pour inhiber l'activité biologique de biomolécules solubles
US9623081B2 (en) 2014-10-03 2017-04-18 Ntercept, Llc Compositions and methods for inhibiting the biological activity of soluble biomolecules
US9907831B2 (en) 2014-10-03 2018-03-06 Nanotics, Llc Compositions and methods for inhibiting the biological activity of soluble biomolecules
US10420817B2 (en) 2014-10-03 2019-09-24 Nanotics, Llc Compositions and methods for inhibiting the biological activity of soluble biomolecules
US10888602B2 (en) 2014-10-03 2021-01-12 Nanotics, Llc Compositions and methods for inhibiting the biological activity of soluble biomolecules
US11771744B2 (en) 2014-10-03 2023-10-03 Nanotics, Llc Compositions and methods for inhibiting the biological activity of soluble biomolecules
US10653790B2 (en) 2015-07-29 2020-05-19 Nanotics, Llc Compositions and methods related to scavenger particles
WO2017176762A1 (fr) 2016-04-06 2017-10-12 Nanotics, Llc Particules comprenant des sous-particules ou des échafaudages d'acide nucléique
US11065345B2 (en) 2017-01-04 2021-07-20 Nanotics, Llc Methods for assembling scavenging particles
CN110591690A (zh) * 2019-09-20 2019-12-20 中南大学 一种可表面化学修饰的疏水性硅量子点及其制备方法和应用

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