CN115609001B - Method for preparing functionalized gold nanoparticles by using alkyne compounds - Google Patents
Method for preparing functionalized gold nanoparticles by using alkyne compounds Download PDFInfo
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- CN115609001B CN115609001B CN202210856343.2A CN202210856343A CN115609001B CN 115609001 B CN115609001 B CN 115609001B CN 202210856343 A CN202210856343 A CN 202210856343A CN 115609001 B CN115609001 B CN 115609001B
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B22F9/00—Making metallic powder or suspensions thereof
- B22F9/16—Making metallic powder or suspensions thereof using chemical processes
- B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
- B22F9/24—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds starting from liquid metal compounds, e.g. solutions
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- B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
- B22F1/05—Metallic powder characterised by the size or surface area of the particles
- B22F1/054—Nanosized particles
- B22F1/056—Submicron particles having a size above 100 nm up to 300 nm
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- B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
- B22F1/10—Metallic powder containing lubricating or binding agents; Metallic powder containing organic material
- B22F1/102—Metallic powder coated with organic material
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- 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
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- 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
Abstract
The invention relates to gold trichloride is reduced by alkyne compounds, and small molecule modified gold nanoparticles are rapidly synthesized in one step under normal temperature conditions, so that the synthesis and modification processes of the gold nanoparticles are greatly simplified. The preparation method is simplified and the reaction time is shortened. Taking the change value of fluorescence luminescence response after gold trichloride (100 mu M) is reduced by alkynyl-containing metal compound 4 (10 mu M) to generate gold nanoparticles as a reference, the larger the change value is, the more efficient the generation is proved, the change of fluorescence luminescence response values in different solutions (figure 3A), different pH values (figure 3B) and buffer solutions (figure 3C) with different concentrations is examined respectively, and the result shows that the process is applicable to various solutions and is irrelevant to the concentration of the buffer solution, the nanoparticles can be well formed under neutral and alkaline conditions, and the changed process is not simple and can be determined.
Description
Technical Field
The invention belongs to a synthesis method of gold nanoparticles, and relates to a method for preparing functionalized gold nanoparticles by using alkyne compounds.
Background
To date, various gold nanoparticle synthesis methods, such as chemical, have been developedChemical reduction (chem. Phys. Letters, 2008,463,145), biosynthesis (Nanomed.Nanotechnol.Biol.Med., 2010,6,257;Carbohydr.Polym. 2017,72,169), sonochemistry (Mater. Letters, 2007,61,3429), photochemical reduction (J. Urol.,2008,179,748) and irradiation (radiation. Phys. Chem.,2009,78,251). Most of these methods require severe reaction conditions (e.g., high temperature), specialized technicians, and specific instrumentation, which add difficulty to the synthesis of gold nanoparticles, and synthesis of unmodified gold nanoparticles, e.g., chemical reduction is typically accomplished by reduction of tetrachloroauric acid (HAuCl) using a certain reducing agent 4 ) To produce gold nanoparticles, the basic idea is to first dissolve HAuCl 4 Then the solution is stirred rapidly and simultaneously with the addition of the reducing agent to drive the Au 3+ The reduction of ions to neutral gold ions has the disadvantage that generally after multiple steps of operation monodisperse spherical gold nanoparticles of a certain size can be produced in solution and that their monodispersity is lost when large-size gold nanoparticles are produced. In addition, part of the method needs heating, the chemical synthesis method has strict requirements on the proportioning concentration of various solutions, reducing agents and stabilizing agents, and common reagents comprise sodium borohydride NaBH 4 (acc. Chem. Res.,2008,41,1721), sodium citrate Na 3 C 6 O 5 H 7 (J.am.chem.Soc., 2010,132,4678) and formaldehyde CH 2 O (j. Control. Release,2009,139,239). The biosynthesis method is to biocatalytically synthesize gold nanoparticles in (cancer) cells without using any other chemical reagents, and such gold nanoparticles have a high degree of biocompatibility, which is disadvantageous: the cells need to be cultured, the operation is performed at the cell level, and other separation means need to be used for separating the nanoparticles. The ultrasonic chemical method generally uses an ultrasonic generator in a constant temperature water bath, gold ions can be reduced by ultrasonic assistance in the presence of 2-propanol, and the ultrasonic chemical method is an environment-friendly and rapid synthesis method, but has the defects of poor reproducibility and adjustability, generally uses various stabilizers in the synthesis process, and requires special personnel to operate the ultrasonic generator. The irradiation method can synthesize gold nanoparticles with diameter of 2-40 nm by using ultraviolet radiation with different wavelengths, and uses natural polysaccharide alginate solution or bovine serum albumin as stabilizerThe preferred method of gold nanoparticles with controllable and high purity, however, requires an instrument for generating gamma rays, and is complicated to operate. In addition, the stabilizer bovine serum albumin belongs to biological products, and the change of serum is easy to cause poor repeatability.
Disclosure of Invention
Technical problem to be solved
In order to avoid the defects of the prior art, the invention provides a method for preparing functionalized gold nanoparticles by using alkyne compounds, which solves the defects that most of the existing gold nanoparticle synthesis methods need harsh reaction conditions (such as high temperature), professional technicians and specific instruments.
Technical proposal
A method for preparing functionalized gold nanoparticles by using alkyne compounds is characterized by comprising the following steps:
step 1, solution preparation: dissolving an alkyne compound in an organic solution to prepare an alkyne compound solution; preparing gold trichloride into an aqueous gold trichloride solution by using ultrapure water;
step 2, preparing gold nanoparticles: adding alkyne compound solution and gold trichloride aqueous solution into any aqueous phase or solution of the aqueous phase and all water-miscible organic phase, standing, and reducing gold trichloride to generate small molecule modified gold nanoparticles;
the alkyne compound is modified on the surface of the gold nanoparticle.
The alkyne compounds include, but are not limited to, compounds of the following structural formula:
the concentration of the solution after the alkyne compound is dissolved in the organic solution is 0-1.0M.
The concentration of the solution for preparing the gold trichloride by using the ultrapure water is 0-1.0M.
The organic solution is all water-miscible organic solution.
The organic phase is all water-miscible organic phase.
The standing temperature is 0-100 ℃.
And (3) observing the morphology of the gold nanoparticles generated in the step (2) by adopting a transmission electron microscope, and analyzing the diameter and potential distribution condition of the gold nanoparticles generated in the step (2) by adopting a nano-granularity and Zeta potential analyzer.
Advantageous effects
According to the method for preparing the functionalized gold nanoparticles by using the alkyne compound, gold trichloride is reduced by using the alkyne compound, so that the gold nanoparticles modified by small molecules are rapidly synthesized in one step under the normal temperature condition, and the synthesis and modification processes of the gold nanoparticles are greatly simplified. The preparation method is simplified and the reaction time is shortened.
Generating gold nanoparticles:
the feasibility of this approach was investigated using Transmission Electron Microscopy (TEM), dynamic Light Scattering (DLS) and Zeta potential. As shown in FIG. 1, a metal alkyne compound (alkyne compound 4) is firstly dissolved in DMSO solution to prepare a 5.0mM solution, 2.0 mu L and 2.0 mu L of 50.0mM gold trichloride solution are added into a buffer solution prepared by mixing 10.0mM hydroxyethyl piperazine ethylene sulfate (HEPES) solution (pH=7) and ethanol solution 1:1, the total volume is 1.0mL, the mixture is kept stand for 20 minutes at normal temperature, TEM images show that the solution contains a large number of spherical particles with uniform size, the diameter of the particle size is 233.68nm, the surface of the particles is negatively charged, and the potential value is-23.5, and the results show that the gold nano particles can be rapidly prepared by the method through the alkyne compound under the normal temperature condition in one step.
In addition, fig. 2 is an element distribution diagram of gold nanoparticles generated by reducing gold trichloride by an alkynyl-containing metal complex, wherein orange represents gold element and green represents iridium element, and fig. 2 shows that gold element and iridium element are uniformly distributed on the surfaces of the newly generated nanoparticles, so that it is proved that iridium-containing alkyne compounds are indeed subjected to chemical reaction with gold trichloride and are modified on the surfaces of the gold nanoparticles.
According to the invention, gold trichloride is reduced by using the alkyne compound for the first time, and the gold nanoparticles modified by small molecules are rapidly synthesized in one step under the normal temperature condition by using the alkyne compound, so that the synthesis and modification processes of the gold nanoparticles are greatly simplified. The preparation method is simplified and the reaction time is shortened.
Performance test of gold nanoparticles generated:
taking the change value of fluorescence luminescence response after gold trichloride (100 mu M) is reduced by alkynyl-containing metal compound 4 (10 mu M) to generate gold nanoparticles as a reference, the larger the change value is, the more efficient the generation is proved, the change of fluorescence luminescence response values in different solutions (figure 3A), different pH values (figure 3B) and buffer solutions (figure 3C) with different concentrations is examined respectively, and the result shows that the process is applicable to various solutions and is irrelevant to the concentration of the buffer solution, the nanoparticles can be well formed under neutral and alkaline conditions, and the changed process is not simple and can be determined.
Drawings
Fig. 1: (A) Adding gold trichloride to generate a TEM result of gold nanoparticles; (B) DLS results of gold nanoparticles were generated after addition of gold trichloride.
Fig. 2: gold trichloride is reduced by the metal complex containing alkynyl to generate an element distribution spectrum of gold nano-particles (orange represents gold element; green represents iridium element).
Fig. 3: the change in luminescence response of fluorescence after gold trichloride (100. Mu.M) was reduced by alkynyl-containing metal complex 4 (10. Mu.M) to gold nanoparticles (the greater the change, the more efficient the formation was demonstrated). The results of response change values under the conditions of different buffer systems (A), pH values (B) and HEPES concentrations (C) show that the compound is applicable to various buffers and is irrelevant to the concentrations of the buffer systems, is less influenced by the pH values, and can well form nano particles under neutral and alkaline conditions.
Detailed Description
The invention will now be further described with reference to examples, figures:
example one: DLS and Zeta potentials were used to investigate the ability of alkynyl-containing aliphatic hydrocarbon compounds to reduce gold trichloride to gold nanoparticles. Firstly, propargylamine (alkyne compound 1) is dissolved in DMSO solution to prepare 5.0mM solution, 2.0 mu L of 5.0mM 1 solution and 2.0 mu L of 50.0mM gold trichloride solution are added into buffer solution prepared by mixing 10.0mM hydroxyethylpiperazine ethylsulfuric acid (HEPES) solution (pH=7) and ethanol solution 1:1, the total volume is 1.0mL, the mixture is kept stand for 20 minutes at normal temperature, gold nano particles are generated, the diameter of the particle size monitored by DLS is 136.00nm, the surface of the particles is positively charged, and the potential value is 11.96.
Example two: DLS and Zeta potentials were used to investigate the ability of alkynyl-containing aliphatic hydrocarbon compounds to reduce gold trichloride to gold nanoparticles. Firstly, boc-amino-propyne (alkyne compound 2) is dissolved in DMSO solution to prepare 5.0mM solution, 2.0 mu L of 5.0mM 2 solution and 2.0 mu L of 50.0mM gold trichloride solution are added into buffer solution prepared by mixing 10.0mM hydroxyethylpiperazine ethylene sulfonic acid (HEPES) solution (pH=7) and ethanol solution 1:1, the total volume is 1.0mL, the mixture is kept stand for 20 minutes at normal temperature, gold nano particles are generated, the diameter of the particle size monitored by DLS is 165.44nm, the surface of the particles is positively charged, and the potential value is 30.6.
Example three: DLS and Zeta potentials are adopted to study the capability of an alkynyl-containing aromatic hydrocarbon compound to reduce gold trichloride to generate gold nano-particles. Firstly, dissolving 4-ethynyl-benzaldehyde (acetylenic compound 3) into a DMSO solution to prepare a 5.0mM solution, taking 2.0 mu L of the 5.0mM 3 solution and 2.0 mu L of 50.0mM gold trichloride solution, adding the solution into a buffer solution prepared by mixing 10.0mM hydroxyethylpiperazine ethylene sulfonic acid (HEPES) solution (pH=7) and ethanol solution 1:1, and standing for 20 minutes at normal temperature to prepare gold nanoparticles, wherein the diameter of the particle size monitored by DLS is 125.9nm, the surface of the particles is positively charged, and the potential value is 29.91.
Example four: DLS and Zeta potentials were used to investigate the ability of alkynyl-containing metal complexes to reduce gold trichloride to gold nanoparticles. Firstly, dissolving a metal alkyne compound (alkyne compound 5) in a DMSO solution to prepare a 5.0mM solution, adding 2.0 mu L and 2.0 mu L of 50.0mM gold trichloride solution into a buffer solution prepared by mixing 10.0mM hydroxyethylpiperazine ethyl sulfate (HEPES) solution (pH=7) and ethanol solution 1:1, wherein the total volume is 1.0mL, standing for 20 minutes at normal temperature, gold nanoparticles are generated, the diameter of the particle diameter monitored by DLS is 222.64nm, the surface of the particles is positively charged, and the potential value is-26.85. The element distribution spectrum of TEM shows that iridium element and gold element are highly overlapped on the distribution position, which shows that iridium complex is modified on the surface of nanoparticle while gold nanoparticle is formed, and a functionalized gold nanoparticle is formed.
Example five (counter): DLS and Zeta potentials were used to investigate whether complexes containing no alkynyl groups (control compounds) could reduce gold trichloride to gold nanoparticles. Firstly, a compound (non-acetylenic compound 6) is dissolved in a DMSO solution to prepare a 5.0mM solution, 2.0 mu L of 5.0mM 6 and 2.0 mu L of 50.0mM gold trichloride solution are added into a buffer solution prepared by mixing 10.0mM hydroxyethylpiperazine ethylsulfuric acid (HEPES) solution (pH=7) and ethanol solution 1:1, the total volume is 1.0mL, the mixture is left to stand at normal temperature for 20 minutes, no gold nanoparticles are generated, and no particle size generation is detected by DLS. It is illustrated that alkynyl groups have a decisive effect on the formation of gold nanoparticles.
Example six (counter): DLS and Zeta potentials were used to investigate the ability of alkynyl-free metal complexes (control compounds) to reduce gold trichloride to gold nanoparticles. Firstly, a metal compound (non-alkyne compound 7) is dissolved in a DMSO solution to prepare a 5.0mM solution, 2.0 mu L of 5.0mM 7 and 2.0 mu L of 50.0mM gold trichloride solution are added into a buffer solution prepared by mixing 10.0mM hydroxyethylpiperazine ethyl sulfate (HEPES) solution (pH=7) and ethanol solution 1:1, the total volume is 1.0mL, the solution is left to stand at normal temperature for 20 minutes, no gold nanoparticles are generated, and no particle size generation is detected by DLS. It is illustrated that alkynyl groups have a decisive effect on the formation of gold nanoparticles.
Claims (4)
1. A method for preparing functionalized gold nanoparticles by using alkyne compounds is characterized by comprising the following steps:
step 1, solution preparation: dissolving an alkyne compound in an organic solution to prepare an alkyne compound solution; preparing gold trichloride into an aqueous gold trichloride solution by using ultrapure water;
step 2, preparing gold nanoparticles: adding alkyne compound solution and gold trichloride aqueous solution into any aqueous phase or solution of the aqueous phase and all water-miscible organic phase, standing at normal temperature, and reducing gold trichloride to generate small molecule modified gold nanoparticles;
the alkyne compound is modified on the surface of the gold nanoparticle;
the alkyne compound comprises a compound with the following structural formula:
2. the method for preparing functionalized gold nanoparticles with acetylenic compounds according to claim 1, characterized in that: the concentration of the solution after the alkyne compound is dissolved in the organic solution is 0-1.0M.
3. The method for preparing functionalized gold nanoparticles with acetylenic compounds according to claim 1, characterized in that: the concentration of the solution for preparing the gold trichloride by using the ultrapure water is 0-1.0M.
4. The method for preparing functionalized gold nanoparticles with acetylenic compounds according to claim 1, characterized in that: the organic solution is all organic solutions which are mutually soluble with water.
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