CN115609001A - Method for preparing functionalized gold nanoparticles by using acetylene compounds - Google Patents
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Abstract
The invention relates to a method for rapidly synthesizing small-molecule modified gold nanoparticles in one step at normal temperature by reducing gold trichloride through acetylene compounds, which greatly simplifies the synthesis and modification processes of the gold nanoparticles. The invention simplifies the preparation method and shortens the reaction time. The fluorescence luminescence response change value after the metal compound 4 (10 mu M) containing alkynyl reduces gold trichloride (100 mu M) to generate gold nanoparticles is taken as a reference, the higher the change value is, the higher the generation efficiency is, the changes of the fluorescence luminescence response value in different solutions (figure 3A), different pH values (figure 3B) and different concentrations of buffer solutions (figure 3C) are respectively considered, and the result shows that the process disclosed by the invention is suitable for various solutions and has no relation with the concentration of the buffer solutions, and the nanoparticles can be well formed under neutral and alkaline conditions.
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 have been developed, such as chemical reduction methods (chem.phys.lett., 2008,463, 145), biosynthesis methods (nanomed.nanotechnol.biol.med., 2010,6, 257. Most of these methods require harsh reaction conditions (such as high temperature), skilled technicians and special equipment, which increases difficulty in synthesizing gold nanoparticles, and the synthesized gold nanoparticles are unmodified, for example, chemical reduction methods generally use some kind of reducing agent through reduction of tetrachloroauric acid (HAuCl) 4 ) To produce gold nanoparticles, the basic idea is to first dissolve HAuCl 4 Then rapidly stirring the solution while adding a reducing agent to add Au 3+ The reduction of ions to neutral gold ions has the disadvantage that monodisperse spherical gold nanoparticles of a certain size can be produced in solution after generally multiple operations are required, and the monodispersity is lost when producing gold nanoparticles of large size. 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 synthesize gold nanoparticles in a (cancer) cell in a biocatalytic manner without using any other chemical reagent, and the gold nanoparticles have high biocompatibility and have the disadvantages that: cells need to be cultured, operations need to be carried out at the cell level, and other separation means need to be adopted to separate the nanoparticles. The ultrasonic wave generator is generally used in a constant-temperature water bath in the ultrasonic chemistry method, gold ions can be reduced by ultrasonic assistance in the presence of 2-propanol, and the method is an environment-friendly and rapid synthesis method, but has the defects of poor reproducibility and adjustability, and is generally used in the synthesis processA stabilizer and a specially-assigned person to operate the ultrasonic transmitter. The irradiation method needs ultraviolet radiation with different wavelengths to synthesize gold nanoparticles with the diameter of 2-40 nm, and the use of natural polysaccharide alginate solution or bovine serum albumin as a stabilizer is a preferred method for synthesizing the gold nanoparticles with controllable size and high purity, but needs an instrument for generating gamma rays and has complex operation. In addition, the stabilizer bovine serum albumin belongs to biological products, and the change of serum easily causes 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 acetylene compounds, which solves the defects that the existing gold nanoparticle synthesis method mostly needs harsh reaction conditions (such as high temperature), professional technicians and specific instruments and equipment.
Technical scheme
A method for preparing functionalized gold nanoparticles by using acetylene compounds is characterized by comprising the following steps:
the alkyne compound is modified on the surface of the gold nanoparticle.
The acetylenic compounds include, but are not limited to, compounds of the following structural formula:
the concentration of the solution of the alkyne compound dissolved in the organic solution is 0-1.0M.
The concentration of the ultrapure water preparation solution for gold trichloride is 0-1.0M.
The organic solution is all water-miscible organic solutions.
The organic phases are all water-miscible organic phases.
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 using a nano-particle size and Zeta potential analyzer.
Advantageous effects
According to the method for preparing the functionalized gold nanoparticles by using the acetylene compounds, disclosed by the invention, gold trichloride is reduced by using the acetylene compounds, so that the micromolecule modified gold nanoparticles are quickly synthesized in one step at normal temperature, 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 the method 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 first dissolved in DMSO solution to prepare a 5.0mM solution, 2.0 μ L and 2.0 μ L of a 50.0mM gold trichloride solution are added to a buffer prepared by mixing a 10.0mM hydroxyethylpiperazine ethanethiosulfonic acid (HEPES) solution (pH = 7) with ethanol solution 1, the total volume is 1.0mL, the solution is left standing at normal temperature for 20 minutes, 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 as detected by dynamic light scattering, the surface of the particle is negatively charged, and the potential value is-23.5, and these results show that the method can prepare gold nanoparticles rapidly in one step by using the alkyne compound at normal temperature.
In addition, fig. 2 is an element distribution diagram spectrum of gold nanoparticles generated by reduction of gold trichloride by the metal complex containing alkynyl, wherein orange represents a gold element, and green represents an iridium element, and fig. 2 shows that the gold element and the iridium element are uniformly distributed on the surfaces of the newly generated nanoparticles, which proves that the alkyne compound containing iridium actually performs a chemical reaction with gold trichloride and is modified on the surfaces of the gold nanoparticles.
According to the invention, the acetylene compound is used for reducing gold trichloride for the first time, and the acetylene compound is used for realizing the rapid one-step synthesis of the micromolecule modified gold nanoparticles under the normal temperature condition, so that the synthesis and modification processes of the gold nanoparticles are greatly simplified. The invention simplifies the preparation method and shortens the reaction time.
Performance test of generated gold nanoparticles:
the method takes the fluorescence luminous response change value of the metal compound 4 (10 mu M) containing alkynyl to reduce gold trichloride (100 mu M) to generate gold nanoparticles as reference, the larger the change value is, the higher the generation efficiency is, and the changes of the fluorescence luminous response value in different solutions (figure 3A), different pH values (figure 3B) and buffer solutions (figure 3C) with different concentrations are respectively considered.
Drawings
FIG. 1: (A) Adding gold trichloride to generate a TEM result of gold nanoparticles; (B) After adding gold trichloride, DLS results of the gold nanoparticles are generated.
FIG. 2: the metal complex containing alkynyl reduces gold trichloride to generate an element distribution spectrum of gold nanoparticles (orange represents a gold element; green represents an iridium element).
FIG. 3: the alkynyl group-containing metal complex 4 (10. Mu.M) reduced gold trichloride (100. Mu.M) to produce gold nanoparticles, and the fluorescence response change value was observed (the higher the change value, the higher the efficiency of the production). The results of the response change values under different conditions of (A) buffer system, (B) pH and (C) HEPES concentration respectively show that the composite is applicable to various buffers, has no relation with the concentration of the buffer system, is less influenced by the pH, and can well form nanoparticles under neutral and alkaline conditions.
Detailed Description
The invention will now be further described with reference to the following examples, and the accompanying drawings:
example one: DLS and Zeta potential are adopted to research the capability of the alkynyl-containing aliphatic hydrocarbon compound in reducing gold trichloride to generate gold nanoparticles. Firstly, propargylamine (acetylene compound 1) is dissolved in DMSO (dimethyl sulfoxide) 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 a buffer solution prepared by mixing 10.0mM hydroxyethylpiperazine ethanethiosulfonic acid (HEPES) solution (pH = 7) and ethanol solution 1, the total volume is 1.0mL, the mixture is kept still at normal temperature for 20 minutes, gold nanoparticles are generated, the diameter of the particle diameter monitored by DLS is 136.00nm, the surface of the particle is positively charged, and the potential value is 11.96.
Example two: DLS and Zeta potential are adopted to research the capability of the alkynyl-containing aliphatic hydrocarbon compound in reducing gold trichloride to generate gold nanoparticles. First, boc-amino-propyne (acetylene compound 2) was dissolved in DMSO solution to prepare a 5.0mM solution, 2.0 μ L of 5.0mM 2 solution and 2.0 μ L of 50.0mM gold trichloride solution were added to a buffer prepared by mixing 10.0mM hydroxyethylpiperazinethiesulfonic acid (HEPES) solution (pH = 7) with ethanol solution 1, in a total volume of 1.0mL, and left to stand at room temperature for 20 minutes, to generate gold nanoparticles, which were monitored to have a particle diameter of 165.44nm by DLS, a positive charge on the surface of the particles, and a potential value of 30.6.
Example three: DLS and Zeta potential are adopted to research the capability of aromatic hydrocarbon compounds containing alkynyl to reduce gold trichloride to generate gold nanoparticles. First, 4-ethynyl-benzaldehyde (acetylenic compound 3) was dissolved in DMSO solution to prepare a 5.0mM solution, 2.0 μ L of 5.0mM 3 solution and 2.0 μ L of 50.0mM gold trichloride solution were added to a buffer prepared by mixing 10.0mM hydroxyethylpiperazine ethanethiosulfonic acid (HEPES) solution (pH = 7) with ethanol solution 1.
Example four: DLS and Zeta potential are adopted to research the capability of the metal complex containing alkynyl to reduce gold trichloride to generate gold nanoparticles. Firstly, dissolving a metal alkyne compound (alkyne compound 5) in a DMSO solution to prepare a solution with the concentration of 5.0mM, adding 2.0 mu L and 2.0 mu L of a 50.0mM gold trichloride solution into a buffer solution prepared by mixing a 10.0mM hydroxyethylpiperazine ethanethiosulfonic acid (HEPES) solution (pH = 7) and an ethanol solution 1, wherein the total volume is 1.0mL, standing at normal temperature for 20 minutes to generate gold nanoparticles, and DLS monitors that the diameter of the particle diameter is 222.64nm, the surface of the particle is positively charged and the potential value is-26.85. The element distribution spectrum of the TEM shows that the iridium element and the gold element are highly overlapped at the distribution positions, which shows that the iridium complex and the gold nanoparticles are formed and simultaneously decorated on the surfaces of the nanoparticles to form the functionalized gold nanoparticles.
Example five (counterexample): DLS and Zeta potential are adopted to study whether the complex (control compound) without alkynyl can reduce gold trichloride to generate gold nanoparticles. First, the compound (non-acetylene compound 6) was dissolved in DMSO solution to prepare a 5.0mM solution, 2.0 μ L of 5.0mM 6 and 2.0 μ L of 50.0mM gold trichloride solution were added to a buffer prepared by mixing 10.0mM hydroxyethylpiperazine ethanethiosulfonic acid (HEPES) solution (pH = 7) with ethanol solution 1, and the total volume was 1.0mL, and the mixture was left to stand at room temperature for 20 minutes without formation of gold nanoparticles, and no particle size formation was observed in DLS. The alkynyl is shown to have a decisive role in forming gold nanoparticles.
Example six (counterexample): DLS and Zeta potential were used to study the ability of metal complexes without alkynyl groups (control compounds) to reduce gold trichloride to gold nanoparticles. First, a metal compound (non-acetylene compound 7) was dissolved in a DMSO solution to prepare a 5.0mM solution, 2.0 μ L of 5.0mM 7 and 2.0 μ L of 50.0mM gold trichloride solution were added to a buffer prepared by mixing a 10.0mM hydroxyethylpiperazine ethanethiosulfonic acid (HEPES) solution (pH = 7) with an ethanol solution 1, and the total volume was 1.0mL, and the mixture was left to stand at room temperature for 20 minutes without formation of gold nanoparticles, and formation of a particle size of DLS was not detected. The alkynyl is shown to have a decisive role in forming gold nanoparticles.
Claims (7)
1. A method for preparing functionalized gold nanoparticles by using acetylene compounds is characterized by comprising the following steps:
step 1, solution preparation: dissolving an acetylene compound in an organic solution to prepare an acetylene compound solution; preparing gold trichloride into a gold trichloride aqueous solution by using ultrapure water;
step 2, preparing gold nanoparticles: adding an acetylene compound solution and a gold trichloride aqueous solution into any aqueous phase or a solution in which the aqueous phase and all water-soluble organic phases are mixed, standing, and reducing gold trichloride to generate micromolecule modified gold nanoparticles;
the alkyne compound is modified on the surface of the gold nanoparticle.
3. the method for preparing functionalized gold nanoparticles from acetylenic compounds according to claim 1 wherein: the concentration of the solution of the alkyne compound dissolved in the organic solution is 0-1.0M.
4. The method for preparing functionalized gold nanoparticles from acetylenic compounds according to claim 1 wherein: the concentration of the ultrapure water preparation solution for gold trichloride is 0-1.0M.
5. The method for preparing functionalized gold nanoparticles from acetylenic compounds according to claim 1 wherein: the organic solution is all water-miscible organic solutions.
6. The method for preparing functionalized gold nanoparticles from acetylenic compounds according to claim 1 wherein: the organic phases are all water-miscible organic phases.
7. The method for preparing functionalized gold nanoparticles from acetylenic compounds according to claim 1 wherein: the standing temperature is 0-100 ℃.
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