CN116165106A - Method for detecting particle size of nano particles by using fluorescence signal - Google Patents
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- 239000002105 nanoparticle Substances 0.000 title claims abstract description 99
- 239000002245 particle Substances 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000012360 testing method Methods 0.000 claims abstract description 13
- 238000002189 fluorescence spectrum Methods 0.000 claims abstract description 10
- 238000001514 detection method Methods 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- XUMIQAOMRDRPMD-UHFFFAOYSA-N (6-oxo-1h-pyrimidin-2-yl)urea Chemical compound NC(=O)NC1=NC(=O)C=CN1 XUMIQAOMRDRPMD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000693 micelle Substances 0.000 claims description 3
- 238000001917 fluorescence detection Methods 0.000 abstract description 8
- 230000008859 change Effects 0.000 abstract description 5
- 239000000178 monomer Substances 0.000 abstract description 5
- 238000012512 characterization method Methods 0.000 abstract description 4
- 238000011065 in-situ storage Methods 0.000 abstract description 4
- 239000002086 nanomaterial Substances 0.000 abstract description 4
- 230000000007 visual effect Effects 0.000 abstract description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 13
- 230000036571 hydration Effects 0.000 description 7
- 238000006703 hydration reaction Methods 0.000 description 7
- -1 6- (hept-3-yl) -4-oxo-1, 4-dihydropyrimidin-2-yl Chemical group 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 238000002296 dynamic light scattering Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical group [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 238000004627 transmission electron microscopy Methods 0.000 description 2
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- 230000006978 adaptation Effects 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000000593 microemulsion method Methods 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N15/00—Investigating characteristics of particles; Investigating permeability, pore-volume or surface-area of porous materials
- G01N15/02—Investigating particle size or size distribution
- G01N15/0205—Investigating particle size or size distribution by optical means
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Abstract
The invention provides a method for detecting the particle size of nano particles by using fluorescence signals, which comprises the steps of preparing nano particles with different particle sizes, testing the fluorescence spectrum and the particle size of the nano particles, and establishing a standard curve of the relationship between the particle size and the fluorescence intensity of the nano particles. The invention realizes the quantitative detection of the particle size of the nano particles by establishing a standard curve between the fluorescence intensity and the particle size of the nano particles. Meanwhile, the fluorescence detection method is simple and convenient, and accurate quantitative detection can be realized under extremely low sample concentration. In addition, the size of the nanoparticle can be qualitatively determined by the change in fluorescence intensity of different nanoparticle samples at the same monomer concentration. The method provides a convenient, rapid, accurate, in-situ, real-time, quantitative and visual fluorescence detection method for characterizing the particle size of the nano particles. This also provides a new idea for the characterization of nanomaterials.
Description
Technical Field
The invention relates to the field of analysis and detection of nano particles, in particular to a method for detecting the particle size of nano particles by using fluorescent signals.
Background
Because of the physicochemical properties different from bulk materials, the nano particles are used as a nano material and play an important role in the fields of energy sources, catalysis, biological medicine, photoelectric equipment and the like. In particular, the particle size of the nanoparticles is a key factor in understanding and exploring the performance of nanomaterials. Nanoparticles with different particle diameters have different specific surface areas, which can cause the difference of atoms and surface energy on the surfaces of the nanoparticles, thereby affecting the catalytic activity of the nanoparticles, the delivery and treatment effects of medicines, the photoelectric performance and other properties, and therefore, the characterization of the particle diameters of the nanoparticles is very important.
So far, transmission electron microscopy, scanning electron microscopy, dynamic light scattering, atomic force microscopy, nuclear magnetism, etc. techniques have been widely used for characterization of nanoparticles. These techniques require expensive equipment, cumbersome sample preparation procedures, harsh test conditions, and high intensity testing and analysis procedures, which can increase the monetary, effort, and time costs of characterizing nanoparticle particle size. Fluorescent detection technology has become an indispensable analytical tool in the fields of chemistry, materials, biology and medicine because of its advantages such as high sensitivity, rapid response and simple technology. However, the current fluorescence detection techniques for characterizing nanoparticle particle size require the aid of fluorescence microscopy, which also requires significant costs and complex sample preparation, testing and analysis procedures.
Therefore, there is a need in the art to develop a fluorescence detection method that is rapid, accurate in results, real-time in situ, and quantitatively characterizes the particle size of nanoparticles.
The invention comprises the following steps:
the invention aims to provide a fluorescence detection method for detecting the particle size of nano particles, which is convenient, rapid, accurate in result, real-time in situ and quantitative. The local environment of the fluorescent groups inside the nano particles is different from that of the fluorescent groups on the surfaces, so that the fluorescence quantum yield of the fluorescent groups is different, and the ratio of the surfaces to the internal fluorescent groups is changed due to the change of the particle sizes of the nano particles, so that the fluorescence signal of the nano particles is changed, and the particle sizes of the nano particles can be detected by utilizing the change of the fluorescence signal.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the method for detecting the particle size of the nano particles by utilizing fluorescence signals is characterized in that the nano particles with different particle sizes are prepared, the fluorescence spectrum and the particle size of the nano particles are tested, and a standard curve of the relationship between the particle size and the fluorescence intensity of the nano particles is established. By utilizing the change of fluorescence intensity caused by the difference of aggregation behaviors of fluorescent molecules in nano particles with different particle diameters, the quantitative relation between the fluorescence intensity and the particle diameter of the nano particles is established, so that the quantitative detection of the particle diameter of the nano particles is realized.
The compound is a fluorescent molecule modified by two 2-ureido-4 [1H ] -pyrimidinone (UPy) units, and the structure of the fluorescent molecule is shown as a formula (I).
R is any fluorescent molecular skeleton.
Further R is a framework structure with a formula (II), a formula (III) and a formula (IV)
R is aggregation-induced emission fluorescent molecule 1- (6- (hept-3-yl) -4-oxo-1, 4-dihydropyrimidin-2-yl) -3- (2- (4- (2- (3- (hept-3-yl)) -4-oxo-1, 4-dihydroxypyrimidin-2-yl) ureido) ethoxy) phenyl) -2-phenyl-2- (4- (pyridin-4-yl) phenylvinyl) phenoxy) ethyl) urea with a skeleton structure of formula (II), which is abbreviated as TPEPy-UPy.
The fluorescent molecules are constructed into supermolecular polymer nano particles through quadruple hydrogen bonds formed by UPy units.
The nano particles are prepared by a microemulsion method, so that the nano particles have good water dispersion capability. The preparation process comprises the following steps: dissolving the fluorescent molecules in chloroform, injecting the chloroform solution into an aqueous solution containing a surfactant, performing ultrasonic treatment, standing and aging to obtain the required spherical nano-particles.
In the preparation process, the fluorescent molecules dissolved in chloroform form long-chain compounds through four-fold hydrogen bonds. In the standing aging process, the long-chain compound is assembled under the action of hydrophilic and hydrophobic to obtain the required spherical nano particles.
Purified water was used as water.
The volume ratio of the chloroform solution of the fluorescent molecules to the aqueous solution containing the surfactant is 1:100-1:10.
The surfactant is cetyl trimethyl ammonium bromide or sodium dodecyl sulfate;
the concentration of aqueous solution of cetyltrimethylammonium bromide was 1.1mM;
the aqueous solution of sodium dodecyl sulfate had a concentration of 10mM.
Establishing a standard curve of the fluorescent intensity-particle size relationship of the nano particles, comprising: and (3) preparing the nano particles with different particle sizes. Preparing chloroform solutions of fluorescent molecules with different concentrations, respectively injecting the chloroform solutions with the same volume into water solutions containing surfactants, performing ultrasonic treatment, standing and aging to obtain nano particles with different particle diameters.
9 different nanoparticles were prepared;
the concentration of the chloroform solution of the fluorescent molecule is 3.75mg/mL, 5.00mg/mL, 8.75mg/mL, 12.50mg/mL, 20.00mg/mL, 30.00mg/mL, 40.00mg/mL, 50.00mg/mL and 60.00mg/mL;
the volume of the chloroform solution was 0.2mL;
the volume of the aqueous solution containing the surfactant is 15mL;
the shape of the nano particles is spherical.
The fluorescence intensity of the nanoparticle is obtained by fluorescence spectroscopy. The fluorescence spectrum is tested in nanoparticle aqueous solutions with the same monomer concentration;
the fluorescence spectrum was obtained by testing an aqueous nanoparticle solution with a monomer concentration of 8 μm;
the fluorescence intensity is taken from the same emission wavelength;
the size of the nanoparticles is obtained by dynamic light scattering. The particle size of the nanoparticles was tested in aqueous nanoparticle solutions below the critical micelle concentration of the surfactant.
The average hydration diameter was used for the particle size of the nanoparticles.
The standard curve of the relationship between the fluorescence intensity and the particle size of the nano particles is used for quantitatively detecting the particle size of the nano particles, and the preparation and test conditions of the detected nano particles are consistent with those of the nano particles for establishing the standard curve. Preparing chloroform solution with any concentration of the fluorescent molecules, preparing nano particles according to the method for preparing the nano particles, testing the fluorescent intensity of the nano particles under the same testing conditions, and bringing the obtained fluorescent intensity into a standard curve of the relationship between the fluorescent intensity and the particle size to realize quantitative detection of the particle size of the nano particles.
The invention provides a method for detecting the particle size of nano particles by using fluorescence signals, which realizes the quantitative detection of the particle size of the nano particles by establishing a standard curve between the fluorescence intensity and the particle size of the nano particles. Meanwhile, the fluorescence detection method is simple and convenient, and accurate quantitative detection can be realized under extremely low sample concentration. In addition, the size of the nanoparticle can be qualitatively determined by the change in fluorescence intensity of different nanoparticle samples at the same monomer concentration. The method provides a convenient, rapid, accurate, in-situ, real-time, quantitative and visual fluorescence detection method for characterizing the particle size of the nano particles. This also provides a new idea for the characterization of nanomaterials.
Drawings
FIG. 1 is a fluorescence spectrum of an aqueous solution of 9 nanoparticles of TPEPy-UPy in the examples;
FIG. 2 is a transmission electron microscope image of NP5, NP6, NP7, NP8, NP9 of TPEPy-UPy in the examples;
FIG. 3 is a distribution of hydration diameters of 9 nanoparticles of TPEPy-UPy in the examples;
FIG. 4 is a plot of fluorescence intensity versus average hydrated diameter for 9 nanoparticles of TPEPy-UPy in the examples;
FIG. 5 is a fluorescence spectrum of NP10 of TPEPy-UPy in the example, excitation wavelength 365nm, test concentration 8. Mu.M;
FIG. 6 is a distribution of hydrated diameters of NP10 of TPEPy-UPy in the example.
Detailed Description
The present invention is described in detail below by way of examples, which are necessary to be pointed out herein for further illustration only and are not to be construed as limiting the scope of the invention, as many insubstantial modifications and adaptations can be made by those skilled in the art in light of the foregoing disclosure. Embodiments of the invention and features of the embodiments may be combined with each other without conflict.
A standard curve of the relationship between the fluorescence intensity and the particle size of the nanoparticles was established using fluorescent molecules having a skeleton of formula (II), and used to detect the particle size of any nanoparticle.
The fluorescent molecule having a skeleton of formula (II) is 1- (6- (hept-3-yl) -4-oxo-1, 4-dihydropyrimidin-2-yl) -3- (2- (4- (1- (4- (2- (3- (6- (hept-3-yl)) -4-oxo-1, 4-dihydroxypyrimidin-2-yl) ureido) ethoxy) phenyl) -2-phenyl-2- (4- (pyridin-4-yl) phenylvinyl) phenoxy) ethyl) urea, abbreviated as TPEPy-UPy, structural formula:
(1) Synthetic reference methods for TPEPy-UPy (x.zhu, j. -x.wang, l. -y.niu, q. -Z.Yang, chem.Mater.2019,31, 3573-3581).
(2) The preparation process of the nano particles with different particle diameters is as follows: 3.75mg/mL, 5.00mg/mL, 8.75mg/mL, 12.50mg/mL, 20.00mg/mL, 30.00mg/mL, 40.00mg/mL, 50.00mg/mL, 60.00mg/mL of a chloroform solution of TPEPy-UPy was prepared, 0.2mL of the chloroform solution was added to 15mL of an aqueous solution (1.1 mM) containing cetyltrimethylammonium bromide, the resulting mixture was sonicated for 25 minutes, and 9 different nanoparticles named NP1, NP2, NP3, NP4, NP5, NP6, NP7, NP8, NP9 were obtained after leaving it to stand and aging for 24 hours under a dark condition, respectively.
(3) Establishment of a standard curve of the relationship between fluorescence intensity and particle size of nanoparticles: the 9 nanoparticles were diluted to an aqueous solution with a monomer concentration of 8 μm (at this time, the concentration of the surfactant in the aqueous solution was far lower than the critical micelle concentration of the surfactant), and the fluorescence spectra of the 9 nanoparticles were measured at an excitation wavelength of 365nm as shown in fig. 1. As shown in fig. 2, the morphology of NP5, NP6, NP7, NP8, NP9 was observed as regular spheres by transmission electron microscopy. The particle size distribution of 9 nanoparticles obtained by dynamic light scattering test is shown in fig. 3. As shown in fig. 4, the fluorescence intensity at an emission wavelength of 500 nm was selected to establish a standard curve with an average hydration diameter, which is exponentially related to the fluorescence intensity for nanoparticles, with a correction factor of 0.994. The data for fluorescence intensity and average hydration diameter for the standard curve are shown in Table 1.
TABLE 1 fluorescence intensity and average hydration diameter of 9 nanoparticles of TPEPy-UPy at an emission wavelength of 500 nm
(4) The chloroform solution of TPEPy-UPy of 1.5mg/mL is prepared, the nano particle is named NP10 by adopting the preparation method of the nano particle, the measured fluorescence spectrum is shown as a graph in figure 5, the fluorescence intensity at 500 nanometers is 162, the average hydration diameter of the nano particle is 40 nanometers according to the fitted standard curve of figure 4, and the average hydration diameter of the nano particle passing the dynamic light scattering test is very close to 41 nanometers, which proves the accuracy of the fluorescence detection mode.
It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Claims (6)
1. The method for detecting the particle size of the nano particles by utilizing the fluorescence signal is characterized by preparing the nano particles with different particle sizes, testing the fluorescence spectrum and the particle sizes of the nano particles, establishing a standard curve of the relationship between the particle sizes of the nano particles and the fluorescence intensity, and realizing the quantitative detection of the particle sizes of the nano particles.
2. The method for detecting particle size of nanoparticles using fluorescent signal as claimed in claim 1, wherein the molecules for preparing nanoparticles are two fluorescent molecules modified by 2-ureido-4 [1h ] -pyrimidinone UPy unit; the molecular structure of the nanoparticle is shown as a formula (I):
wherein R is any fluorescent molecular skeleton.
3. The method for detecting particle size of nanoparticles using fluorescent signal as set forth in claim 1, wherein the fluorescent intensity used for creating the standard curve is the same as the fluorescent intensity at the same emission wavelength.
4. The method of claim 1, wherein the fluorescence spectrum used to establish the standard curve is measured in an aqueous solution below the critical micelle concentration of the surfactant.
5. The method for detecting particle size of nanoparticles using fluorescent signal as recited in claim 1, wherein the formed nanoparticles have a regular spherical morphology.
6. The method for detecting particle size of nanoparticles by fluorescence signal according to claim 1, wherein the standard curve of the relationship between particle size and fluorescence intensity of nanoparticles is used for quantitatively detecting particle size of nanoparticles, and the preparation and test conditions of detected nanoparticles are consistent with those of nanoparticles for establishing standard curve.
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