CN112345112A - Preparation method of temperature-sensitive nano probe - Google Patents

Preparation method of temperature-sensitive nano probe Download PDF

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CN112345112A
CN112345112A CN202011133780.9A CN202011133780A CN112345112A CN 112345112 A CN112345112 A CN 112345112A CN 202011133780 A CN202011133780 A CN 202011133780A CN 112345112 A CN112345112 A CN 112345112A
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戴李宗
夏龙
毛杰
许一婷
陈婷
陈国荣
彭超华
曾碧榕
罗伟昂
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01K—MEASURING TEMPERATURE; MEASURING QUANTITY OF HEAT; THERMALLY-SENSITIVE ELEMENTS NOT OTHERWISE PROVIDED FOR
    • G01K7/00—Measuring temperature based on the use of electric or magnetic elements directly sensitive to heat ; Power supply therefor, e.g. using thermoelectric elements
    • G01K7/16—Measuring temperature based on the use of electric or magnetic elements directly sensitive to heat ; Power supply therefor, e.g. using thermoelectric elements using resistive elements
    • G01K7/22—Measuring temperature based on the use of electric or magnetic elements directly sensitive to heat ; Power supply therefor, e.g. using thermoelectric elements using resistive elements the element being a non-linear resistance, e.g. thermistor
    • G01K7/226—Measuring temperature based on the use of electric or magnetic elements directly sensitive to heat ; Power supply therefor, e.g. using thermoelectric elements using resistive elements the element being a non-linear resistance, e.g. thermistor using microstructures, e.g. silicon spreading resistance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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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
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    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/08—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing boron

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Abstract

The invention relates to a preparation method of a temperature-sensitive nano probe. Firstly, a monomer containing a catechol group is efficiently combined with the surface of a metal oxide, and then the monomer containing a phenylboronic acid group is controllably coated on the surface of the metal oxide under the drive of B-N coordination, so that a monodisperse nano probe with controllable particle size is formed. The method has the advantages of simple operation, mild reaction conditions, short period, easy post-treatment and easy control. The prepared nano probe has single and stable particle size and regular appearance. And the core/shell synergy of the metal oxide @ borate polymer is utilized, so that the hybrid nano material has the temperature-sensitive characteristic.

Description

Preparation method of temperature-sensitive nano probe
Technical Field
The invention relates to a preparation method of a temperature-sensitive nano probe.
Background
The temperature sensitive material is a material which can detect the temperature of an object, a space and the like and can give a change of an electric signal according to a change of the temperature. Has good application prospect in the fields of biology, medicine, sensor manufacturing and the like. Wu et al construct multilayer organosilicon/graphene oxide coating on the surface of combustible material, utilize the graphene oxide coating to form graphite alkene under high temperature to make the resistance of material change and carry out the early warning of fire (ACS Nano 2017,12(1),416 and give an eye-protection 424), this compares with the mode of the rescue of putting out a fire after the fire takes place, and this is the effective measure of changing "passive fire extinguishing" into "initiative fire prevention".
The common temperature sensitive materials are mainly ceramic materials, and the production of the ceramic materials needs processes such as molding, high-temperature sintering and the like, and the processes are complex and high in production cost. Therefore, it is necessary to develop a simple temperature sensitive material preparation method.
Disclosure of Invention
The invention aims to provide a method for preparing a temperature-sensitive nano probe aiming at the defects of the prior art,
the technical scheme of the invention is as follows:
a method for preparing a temperature-sensitive nanoprobe comprises the following steps:
the method comprises the following steps: preparation of phenylboronic acid/catechol group monomer:
dissolving a first polyamino compound and 4-formylphenylboronic acid in a first solvent, and stirring in a dark place for full reaction to obtain a monomer containing a phenylboronic acid group;
dissolving a second polyamino compound and 3, 4-dihydroxy benzaldehyde in a second solvent, and stirring in a dark place for full reaction to obtain a catechol group-containing monomer;
step two: preparation of nanoprobes with temperature sensitivity:
1) uniformly dispersing a metal oxide in a first solvent to obtain a metal oxide dispersion liquid;
2) dropwise adding the catechol group-containing monomer obtained in the first step with a certain concentration into the metal oxide dispersion obtained in the first step to obtain a first solution;
3) adjusting the monomer containing the phenylboronic acid group obtained in the step one to a certain concentration, slowly dropwise adding the monomer into the solution one obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature sensitive nano probe.
The method comprises the steps of firstly utilizing the high-efficiency combination of the monomer containing the catechol group and the surface of the metal oxide, and then carrying out controllable coating on the surface of the metal oxide under the drive of B-N coordination with the monomer containing the phenylboronic acid group, thereby forming the monodisperse nano probe with controllable particle size. And then, the core/shell synergy of the metal oxide semiconductor nanocrystal @ borate polymer is utilized to endow the hybrid nanomaterial with good carrier generation capacity and carrier stability, so that the temperature-sensitive nanoprobe is prepared.
The invention has the following advantages:
(1) the method has the advantages of simple operation, mild reaction conditions, short period, easy post-treatment and easy control.
(2) According to the invention, the controllable coating of the metal oxide is carried out by using the efficient combination of catechol-inorganic surface and B-N coordination to cooperatively drive the borate polymer, and the synthesized nano probe has single and stable particle size and regular appearance.
(3) According to the invention, elements such as boron, nitrogen, phosphorus and the like can be introduced into the monomer through organic synthesis design, and the high-temperature conductivity of the nano probe can be adjusted by adjusting the thickness of the borate polymer coating.
Drawings
The invention is further illustrated by the following figures and examples.
FIG. 1 shows Fe in example 12O3@ borate polymer, borate polymer and Fe2O3Infrared spectrum of
FIG. 2 shows TiO in example 62@ borate polymer, borate polymer and TiO2Infrared spectrum of
FIG. 3 shows Fe in example 12O3Transmission electron microscope photograph of @ borate polymer
FIG. 4 shows Fe in example 22O3Transmission electron microscope photograph of @ borate polymer
FIG. 5 shows Fe in example 32O3Transmission electron microscope photograph of @ borate polymer
FIG. 6 is a transmission electron micrograph of the TiO2@ borate polymer of example 7.
Detailed Description
A method for preparing a nanoprobe with temperature sensitivity comprises the following steps:
1) preparation of monomer containing phenylboronic acid/catechol group:
1-1) dissolving a first polyamino compound and 4-formylphenylboronic acid in a first solvent, and stirring and reacting for 24 hours at 20 ℃ in the absence of light to obtain a monomer containing phenylboronic acid groups;
1-2) dissolving a second polyamino compound and 3, 4-dihydroxy benzaldehyde in a second solvent, and stirring and reacting for 12 hours at 20 ℃ in the dark to obtain a catechol group-containing monomer;
the first polyamino compound may be ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, di-N-butylamine, 1, 6-hexanediamine, p-phenylenediamine, tris- (4-aminophenyl), 4 '-diaminodiphenylmethane, hexa (4-aminophenoxy) cyclotriphosphazene, 1,3, 5-tris (4-aminophenyl) benzene, 2,4, 6-tris (N,4' -aminophenyl) -1,3, 5-triazine.
Wherein the molar ratio of the first polyamino compound to 4-formylphenylboronic acid is 1: 2 to 6
The second polyamino compound may be ethylenediamine, diethylenetriamine, triethylenetetramine, di-N-butylamine, 1, 6-hexamethylenediamine, p-phenylenediamine, tris- (4-aminophenyl), 4 '-diaminodiphenylmethane, hexa (4-aminophenoxy) cyclotriphosphazene, 1,3, 5-tris (4-aminophenyl) benzene, 2,4, 6-tris (N,4' -aminophenyl) -1,3, 5-triazine.
Wherein the molar ratio of the second polyamino compound to 3, 4-dihydroxybenzaldehyde is 1: 2 to 6
Wherein the first polyamino compound and the second polyamino compound may be the same or different.
Wherein the first solvent and the second solvent are at least one of methanol and ethanol
2) Preparation of nanoprobes with temperature sensitivity:
2-1) uniformly dispersing the metal oxide in a first solvent;
2-2) dropwise adding a monomer containing a catechol group obtained in the step 1-2) into the metal oxide dispersion liquid obtained in the step 2-1) at a certain concentration;
2-3) adjusting the monomer containing the phenylboronic acid group obtained in the step 1-1) to a certain concentration, slowly dropwise adding 10ml of the monomer into the reaction system obtained in the step 2-2), and reacting at normal temperature after dropwise adding;
2-4) after the reaction, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe.
Wherein in the step 2-1), the metal oxide particles may be Fe2O3、TiO2。
Wherein in the step 2-1), the concentration of the metal oxide particles is controlled to be 0.5-1 mg/ml.
Wherein in the step 2-2), the volume ratio of the metal oxide dispersion liquid to the solution of the catechol group-containing monomer is 4-10: 1;
wherein in the step 2-2), the concentration of the catechol group-containing monomer is 0.1-1 mg/ml.
Wherein in the step 2-3), the concentration of the monomer containing the phenylboronic acid group is 0.1-1 mg/ml.
The temperature-sensitive nanoprobes designed according to the present invention will be described in detail with reference to the following examples, but the embodiments of the present invention are not limited thereto, and the examples should not be construed as limiting the present invention.
Example 1
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of 4,4' -diaminodiphenylmethane and 2.2mmol of 4-formylphenylboronic acid in 40ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24 hours to obtain a monomer containing phenylboronic acid groups;
2) dissolving 1mmol of tri- (4-aminophenyl) amine and 3.3mmol of 3, 4-dihydroxybenzaldehyde in 40ml of methanol, and stirring for reaction at 20 ℃ in the dark for 12 hours to obtain a monomer containing a catechol group;
preparation of nanoprobes with temperature sensitivity:
1) mixing 25mg of spindle type Fe2O3Uniformly dispersing in 50ml of methanol;
2) to the shuttle type Fe obtained in step 1)2O3Dropwise adding 10ml of 0.1mg/ml methanol solution containing catechol group monomer into the dispersion liquid;
3) adjusting the concentration of 10ml of methanol solution containing the phenylboronic acid group monomer to 0.1mg/ml, slowly dropwise adding 10ml of methanol solution into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
Example 2
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of 4,4' -diaminodiphenylmethane and 2.4mmol of 4-formylphenylboronic acid in 40ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24h to obtain a monomer containing phenylboronic acid groups;
2) dissolving 1mmol of tri- (4-aminophenyl) amine and 3.6mmol of 3, 4-dihydroxy benzaldehyde in 40ml of methanol, and stirring for reaction at 20 ℃ in the dark for 12 hours to obtain a monomer containing a catechol group;
preparation of nanoprobes with temperature sensitivity:
1) 35mg of spindle type Fe2O3Uniformly dispersing in 50ml of methanol;
2) to the shuttle type Fe obtained in step 1)2O3Adding dropwise into the dispersionAdding 10ml of 0.5mg/ml methanol solution containing catechol group monomer;
3) adjusting the concentration of 10ml of methanol solution containing the phenylboronic acid group monomer to 0.5mg/ml, slowly dropwise adding 10ml of methanol solution into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
Example 3
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of 4,4' -diaminodiphenylmethane and 2.8mmol of 4-formylphenylboronic acid in 40ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24 hours to obtain a monomer containing a phenylboronic acid group;
2) dissolving 1mmol of 1,3, 5-tri (4-aminophenyl) benzene and 4.2mmol of 3, 4-dihydroxy benzaldehyde in 40ml of methanol, and stirring for reaction at 20 ℃ in the dark for 12h to obtain a catechol group-containing monomer;
preparation of nanoprobes with temperature sensitivity:
1) 50mg of spindle type Fe2O3Uniformly dispersing in 50ml of methanol;
2) to the shuttle type Fe obtained in step 1)2O3Dropwise adding 10ml of methanol solution containing catechol group monomer with the concentration of 1mg/ml into the dispersion liquid;
3) regulating the concentration of 10ml of methanol solution containing the phenylboronic acid group monomer to 1mg/ml, slowly dropwise adding 10ml of methanol solution into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding is finished;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
Example 4
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of 1,3, 5-tri (4-aminophenyl) benzene and 3.6mmol of 4-formylphenylboronic acid in 60ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24 hours to obtain a monomer containing phenylboronic acid groups;
2) dissolving 1mmol of p-phenylenediamine and 2.4mmol of 3, 4-dihydroxy benzaldehyde in 40ml of ethanol, and stirring and reacting at 20 ℃ in the dark for 12 hours to obtain a monomer containing a catechol group;
preparation of nanoprobes with temperature sensitivity:
1) 50mg of spindle type Fe2O3Uniformly dispersing in 50ml of methanol;
2) to the shuttle type Fe obtained in step 1)2O3Dropwise adding 10ml of 0.5mg/ml methanol solution containing catechol group monomer into the dispersion liquid;
3) adjusting the concentration of 10ml of methanol solution containing the phenylboronic acid group monomer to 0.5mg/ml, slowly dropwise adding 10ml of methanol solution into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
Example 5
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of 1,3, 5-tri (4-aminophenyl) benzene and 3.6mmol of 4-formylphenylboronic acid in 60ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24 hours to obtain a monomer containing phenylboronic acid groups;
2) dissolving 1mmol of tri- (4-aminophenyl) amine and 3.6mmol of 3, 4-dihydroxybenzaldehyde in 60ml of methanol, and stirring for reaction at 20 ℃ in the dark for 12 hours to obtain a monomer containing a catechol group;
preparation of nanoprobes with temperature sensitivity:
1) 50mg of spindle type Fe2O3Uniformly dispersing in 50ml of methanol;
2) to the shuttle type Fe obtained in step 1)2O3Dropwise adding 10ml of 0.5mg/ml methanol solution containing catechol group monomer into the dispersion liquid;
3) adjusting the concentration of 10ml of methanol solution containing the phenylboronic acid group monomer to 0.5mg/ml, slowly dropwise adding 10ml of methanol solution into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
Example 6
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of 1,3, 5-tri (4-aminophenyl) benzene and 3.6mmol of 4-formylphenylboronic acid in 60ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24 hours to obtain a monomer containing phenylboronic acid groups;
2) dissolving 1mmol of tri- (4-aminophenyl) amine and 3.6mmol of 3, 4-dihydroxy benzaldehyde in 60ml of methanol, and stirring for reaction at 20 ℃ in the dark for 12h to obtain a monomer containing a catechol group;
preparation of nanoprobes with temperature sensitivity:
1) 25mg of TiO2Uniformly dispersing in 50ml ethanol;
2) to the TiO obtained in step 1)2Dropwise adding 10ml of 0.1mg/ml ethanol solution containing catechol group monomer into the dispersion liquid;
3) adjusting the concentration of 10ml of an ethanol solution containing a phenylboronic acid group monomer to 0.1mg/ml, slowly dropwise adding 10ml into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
Example 7
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of p-phenylenediamine and 2.4mmol of 4-formylphenylboronic acid in 40ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24 hours to obtain a monomer containing phenylboronic acid groups;
2) dissolving 1mmol of tri- (4-aminophenyl) amine and 3.6mmol of 3, 4-dihydroxy benzaldehyde in 60ml of methanol, and stirring for reaction at 20 ℃ in the dark for 12h to obtain a monomer containing a catechol group;
preparation of nanoprobes with temperature sensitivity:
1) 25mg of TiO2Uniformly dispersing in 50ml of methanol;
2) to the TiO obtained in step 1)2Dropwise adding 10ml of 0.5mg/ml methanol solution containing catechol group monomer into the dispersion liquid;
3) adjusting the concentration of 10ml of methanol solution containing the phenylboronic acid group monomer to 0.5mg/ml, slowly dropwise adding 10ml of methanol solution into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
Example 8
Preparation of monomer containing phenylboronic acid/catechol group:
1) dissolving 1mmol of ethylenediamine and 2.6mmol of 4-formylphenylboronic acid in 40ml of ethanol, and stirring for reaction at 20 ℃ in the dark for 24 hours to obtain a monomer containing phenylboronic acid groups;
2) dissolving 1mmol of p-phenylenediamine and 2.6mmol of 3, 4-dihydroxy benzaldehyde in 40ml of ethanol, and stirring and reacting at 20 ℃ in the dark for 12h to obtain a monomer containing a catechol group;
preparation of nanoprobes with temperature sensitivity:
1) 25mg of TiO2Uniformly dispersing in 50ml of methanol;
2) to the TiO obtained in step 1)2Dropwise adding 10ml of methanol solution containing catechol group monomer with the concentration of 1mg/ml into the dispersion liquid;
3) regulating the concentration of 10ml of methanol solution containing the phenylboronic acid group monomer to 1mg/ml, slowly dropwise adding 10ml of methanol solution into the reaction system obtained in the step 2), and reacting at normal temperature after dropwise adding is finished;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature-sensitive nano probe. The relationship between the resistance and the temperature is shown in Table 1.
TABLE 1 relationship of nanoprobe resistance to temperature
Figure BDA0002736003620000091

Claims (10)

1. A method for preparing a temperature-sensitive nanoprobe comprises the following steps:
the method comprises the following steps: preparation of phenylboronic acid/catechol group monomer:
dissolving a first polyamino compound and 4-formylphenylboronic acid in a first solvent, and stirring in a dark place for full reaction to obtain a monomer containing a phenylboronic acid group;
dissolving a second polyamino compound and 3, 4-dihydroxy benzaldehyde in a second solvent, and stirring in a dark place for full reaction to obtain a catechol group-containing monomer;
step two: preparation of nanoprobes with temperature sensitivity:
1) uniformly dispersing a metal oxide in a first solvent to obtain a metal oxide dispersion liquid;
2) dropwise adding the catechol group-containing monomer obtained in the first step with a certain concentration into the metal oxide dispersion obtained in the first step to obtain a first solution;
3) adjusting the monomer containing the phenylboronic acid group obtained in the step one to a certain concentration, slowly dropwise adding the monomer into the solution one obtained in the step 2), and reacting at normal temperature after dropwise adding;
4) and (3) after the reaction is finished, carrying out solid-liquid separation, and drying the solid part to obtain the temperature sensitive nano probe.
2. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: the first polyamino compound is at least one of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, di-N-butylamine, 1, 6-hexanediamine, p-phenylenediamine, 4 '-diaminodiphenylmethane, hexa (4-aminophenoxy) cyclotriphosphazene and 2,4, 6-tris (N,4' -aminophenyl) -1,3, 5-triazine.
3. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: the molar ratio of the first polyamino compound to 4-formylphenylboronic acid is 1: 2-6.
4. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: the second polyamino compound is at least one of ethylenediamine, diethylenetriamine, triethylene tetramine, tetraethylenepentamine, di-N-butylamine, 1, 6-hexanediamine, p-phenylenediamine, 4 '-diaminodiphenylmethane hexa (4-aminophenoxy) cyclotriphosphazene and 2,4, 6-tris (N,4' -aminophenyl) -1,3, 5-triazine.
5. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: the molar ratio of the second polyamino compound to 3, 4-dihydroxybenzaldehyde is 1: 2-6.
6. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: the first solvent and the second solvent are respectively at least one of methanol and ethanol.
7. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: in step two, 1), the metal oxide particles are Fe2O3、TiO2At least one of; the concentration of the metal oxide particles is controlled to be 0.5-1 mg/ml.
8. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: in the step 2), the concentration of the monomer containing the catechol group is 0.1-1 mg/ml.
9. The method for preparing a temperature-sensitive nanoprobe according to claim 1, wherein: in the step two, 3), the concentration of the monomer containing the phenylboronic acid group is 0.1-1 mg/ml.
10. The temperature-sensitive nanoprobe prepared by the preparation method according to any one of claims 1 to 9.
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