KR101251334B1 - Polydiacetylne-magnetic nano composite, preparation thereof and use thereof - Google Patents

Abstract

The present invention relates to a magnetic nanocomposite having a structure in which polydiacetylene and magnetic nanoparticles are combined, a method for preparing the same, and a use thereof. The polydiacetylene magnetic nanocomposite according to the present invention is a complex of a structure in which polydiacetylene and magnetic nanoparticles are combined with changes in color and fluorescence by recognizing a change in the external environment, and a polydie in which color changes according to the environment. It possesses both the properties of acetylene and the magnetic properties of magnetic nanoparticles, which can be applied to various applications such as sensor material separation and biosensors.

Description

Polydiacetylene magnetic nanocomposite, preparation method thereof and use thereof {POLYDIACETYLNE-MAGNETIC NANO COMPOSITE, PREPARATION THEREOF AND USE THEREOF}

The present invention relates to a polydiacetylene magnetic nanocomposite, and more particularly, to a magnetic nanocomposite having a new structure in which a polydiacetylene conjugated polymer and magnetic nanoparticles are combined with changes in color and fluorescence by recognizing changes in the external environment. The present invention relates to a preparation method and an application thereof.

The present invention relates to a complex of polydiacetylene conjugated polymer and magnetic nanoparticles, a method for preparing the same, a sensor application using the same, and an application to a sensor material separation system. More specifically, the present invention relates to a method of preparing a magnetic nanocomposite by combining polydiacetylene dispersed in an aqueous solution with magnetic magnetite particles, and then applying the same to a sensor and a sensor material separation system.

Polydiacetylene is a polymer of diacetylene monomers. When a double bond and a triple bond exist alternately in a molecule in the polymer main chain, and the diacetylene monomers are in close proximity to have a crystalline or semi-crystalline structure. It is a conjugated polymer (conjugated polymer) having a characteristic made by irradiation with ultraviolet or gamma rays. Under suitable conditions, polydiacetylene dispersed in an aqueous solution or prepared in a thin film form on a solid substrate has a blue color showing a maximum absorption wavelength at about 650 nm. The blue polydiacetylene is changed into a red solution having a maximum absorption wavelength at about 550 nm according to a change in a certain external environment (for example, heating, pH, molecular recognition, etc.). Due to the color change under these specific conditions, studies are being actively made to use polydiacetylene as various kinds of sensors.

A currently known document related to a composite of polydiacetylene and magnetic nanoparticles is Korean Patent Application No. 2007-0092522, which discloses a magnetic nanoparticle having a polydiacetylene coating layer. In order to increase stability, polydiacetylene is used as a coating layer.

In order to separate the polydiacetylene combined with the sensor material in the aqueous solution, polydiacetylene combined with the sensor material may be obtained through a method such as dialysis, centrifugation, or lypophilization. However, these methods have the disadvantage of requiring a large amount of sample and taking several days to several tens of days to separate.

The present inventors have a problem that can occur in the method of separating polydiacetylene combined with the sensor material in the above-described conventional aqueous solution, for example, excessive sample consumption, separation time of several days or tens of days, separated polydiacetylene As a result of researches to solve the problem of not being able to redisperse in the aqueous solution, the polydiacetylene combined with the sensor material using the magnet can be separated within a few minutes or several hours with only a small amount of sample. The present invention has been completed by developing a complex of polydiacetylene and magnetic nanoparticles having a new structure that can easily remove particles.

An object of the present invention can be applied as a sensor, a polydiacetylene magnetic nanocomposite, a method of manufacturing the same, and the application thereof, which can separate the polydiacetylene combined with the sensor material in a short time with a small amount of sample in a short time. The present invention provides a method for separating sensor materials used.

In order to achieve the above object, the present invention provides a magnetic nanocomposite in which polydiacetylene and magnetic nanoparticles are combined.

In a magnetic nanocomposite having a structure in which a polydiacetylene and magnetic nanoparticles are bonded to each other according to the present invention, a polydiacetylene forms a core, and the magnetic nanoparticles have a structure bonded to a terminal of the polydiacetylene core. The hydrophilic group of the diacetylene monomer used to prepare the polydiacetylene according to the present invention acts as a ligand capable of binding to the surface of the magnetic nanoparticles, and FIG. 1 shows a schematic diagram thereof. Carboxylic acids, amines, alcohols and the like on the polydiacetylene surface form covalent bonds with the magnetic nanoparticle surface or some seem to bind by physical adsorption.

Polydiacetylene magnetic nanocomposite according to the present invention

Polymerizing the diacetylene monomer in a solvent to prepare a polydiacetylene solution;

Mixing the polydiacetylene solution with the magnetic nanoparticles;

And ultrasonically treating the mixture of polydiacetylene and magnetic nanoparticles.

At this time, the poly acetylene is composed of the structure of formula (1).

[Formula 1]

In Formula 1, d + g is 0, 1 or 2, e + f is an integer of 2 to 50, e and f is an integer greater than 1, A and B is a methyl group, amine group, carboxyl group, hydroxy group, A maleimide group, a biotin group, an N-hydroxysuccinimide group, a benzoic acid group or an activated ester group, L ₁ and L ₂ are the same or different from each other, an alkyl group having 2 or more carbon atoms, at least one ethylene oxide Group, amine group, amide group, ester group or carbonyl group.

In one embodiment of the present invention, the diacetylene monomer is PCDA (10,12-pentacosadiynoic acid) represented by the following formula (2), PCDA-EDEA (N- (2- (2- ( 2-aminoethoxy) ethoxy) ethyl) pentacosa-10,12-diynamide), PCDA-AEE (N- (2- (2-hydroxyethoxy) ethyl) pentacosa-10,12-diynamide) represented by Formula 4 below, PCDA-mHPBA (3- (pentacosa-10,12-diynoyloxy) phenylboronic acid) represented by 5, PCDA-mBzA (3-pentacosa-10,12-diynamidobenzoic acid) represented by Formula 6 below, PCDA-IPA (5-pentacosa-10,12-diynamidoisophthalic acid) to be represented, DCDDA-mCPE (3- (10,12-d ° C.osadiynoyloxy) diphenylphenylic acid) represented by the following Chemical Formula 8 may be used.

[Formula 2]

CH _3- (CH ₂ ) ₁₁ -C≡CC≡C- (CH ₂ ) ₈ -COOH

(3)

CH _3- (CH ₂ ) ₁₁ -C≡CC≡C- (CH ₂ ) ₈ -CONH- (CH ₂ CH ₂ O) ₂ -CH ₂ CH ₂ -NH ₂

[Formula 4]

CH _3- (CH ₂ ) ₁₁ -C≡CC≡C- (CH ₂ ) ₅ -CONH-CH ₂ CH ₂ O-CH ₂ CH ₂ -OH

[Chemical Formula 5]

CH _3- (CH ₂ ) ₁₁ -C≡CC≡C- (CH ₂ ) ₅ -COO-C ₆ H ₄ -B- (OH) ₂

[Formula 6]

CH _3- (CH ₂ ) ₁₁ -C≡CC≡C- (CH ₂ ) ₅ -CONH-C ₆ H ₄ -COOH

[Formula 7]

CH _3- (CH ₂ ) ₁₁ -C≡CC≡C- (CH ₂ ) ₅ -CONH-C ₆ H _3- (COOH) ₂

[Formula 8]

HO ℃ -C ₆ H ₄ -COO- (CH ₂ ) ₈ -C≡CC≡C- (CH ₂ ) ₈ -COO-C ₆ H _4- COOH

The production of the polydiacetylene solution may use water or an organic solvent, the organic solvent is not particularly limited, dimethylformamide (DMF), dimethylsuloxide (DMSO), chloroform, dichloromethane, hexane, tetra Preference is given to selecting among tetrahydrofuran (THF), acetone and alcohols.

In addition, the magnetic nanoparticles to be used may be a composite or a pulverized product as iron oxide, for example, nanoparticles having a diameter of 20nm to 30nm, including magnetite (F ₂ O ₃ ) can be used. The smaller the size of the magnetic nanoparticles, the more magnetic particles are bound to the polydiacetylene surface, and the larger the number of binding is smaller. Since the synthesized magnetic nanoparticles can be made larger or smaller depending on the reaction conditions, the size of the desired magnetic particles can be used.

The magnetic nanoparticles in the preparation of the nanocomposite may be prepared in a solution phase, in particular an aqueous phase. The nanoparticle solution can be prepared at all pH conditions, and in particular, in order to prepare a complex by adding a small amount of magnetic nanoparticles, it is preferable that the conditions are an acid solution of pH 2.0 to 4.5 or a basic solution of pH 11.0 to 12.5.

The polydiacetylene solution and the magnetic nanoparticle solution are preferably mixed at a ratio of 0.2-1 mol of magnetic nanoparticles per mol of polydiacetylene. If the magnetic nanoparticles are less than 0.2 mole, the magnetism of the polydiacetylene magnetic nanocomposite may be weak and not attracted to the magnet. have.

The manufacturing method according to an embodiment of the composite of polydiacetylene conjugated polymer and magnetic nanoparticles according to the present invention is as follows.

The diacetylene monomer is directly mixed with water or mixed with an organic solvent, and then ultrasonically treated with a mixture of the diacetylene monomer and water to disperse the diacetylene monomer. The diacetylene monomer is polymerized by exposing ultraviolet light to a mixture of dispersed diacetylene monomer and water, and magnetic nanoparticles in a solution or powder state are mixed with the polymerized polydiacetylene and water mixture. Ultrasonic treatment is performed on a mixture of polydiacetylene, water and magnetic nanoparticles to bind the magnetic nanoparticles to polydiacetylene to prepare a polydiacetylene magnetic nanocomposite according to the present invention. In this case, the ultraviolet exposure is not particularly limited thereto, but preferably, irradiation is performed for 1 to 10 minutes with ultraviolet rays of 220 to 330 nm.

The polydiacetylene magnetic nanocomposite according to the present invention was prepared by dispersing in aqueous solution because most of the various sensor materials are detected in water, but can be prepared in an organic solvent as well as aqueous solution.

The complex of polydiacetylene conjugated polymer and magnetic nanoparticles according to the present invention may be prepared in a form in which magnetic nanoparticles are bonded to the core as well as a structure bonded to the outside of the polydiacetylene. Method for producing a magnetic nanoparticle composite according to this embodiment is as follows.

Magnetic nanoparticles are mixed in water or in an organic solvent, and the magnetic nanoparticles are dispersed by ultrasonication in the magnetic nanoparticle mixture. In addition, the diacetylene monomer is directly mixed with water or mixed with an organic solvent, and then mixed with a magnetic nanoparticle solution, followed by sonication. A polydiacetylene magnetic nanocomposite according to the present invention is prepared by polymerizing a diacetylene monomer by exposing ultraviolet rays to a magnetic nanocomposite having magnetic nanoparticles in a core dispersed in water. In this case, the ultraviolet exposure is not particularly limited thereto, and may be performed by irradiating an ultraviolet ray of 220 to 330 nm for 1 to 10 minutes.

The polydiacetylene magnetic nanocomposites according to the present invention can be used as biosensors and material separation sensors. In another aspect, the present invention comprises the steps of mixing the complex according to the present invention with a sensing target material to form a magnetic nanocomposite to which the sensing target material is bound; And separating a magnetic nanocomposite to which a sensing target material is bound by applying a magnetic material to the outside of the container containing the complex.

This is possible when the magnet is fixed to the side of the container containing the aqueous solution of the magnetic nanocomposite according to the present invention, while the magnetic field is formed around the magnet, the blue magnetic nanocomposite can be obtained by the magnetic force where the magnet is fixed. .

When the magnetic nanocomposite aqueous solution according to the present invention is heated to a certain temperature, the color of the solution is changed from blue to red due to the color transfer characteristics of the polydiacetylene. When the magnet is fixed to the side of the container containing the red magnetic nanocomposite aqueous solution, a magnetic field is formed around the magnet, and the red magnetic nanocomposite can be obtained where the magnet is fixed by the magnetic force. In addition, when the magnetic nanocomposite aqueous solution combining polydiacetylene and magnetite having a reversible color transition property is heated to a temperature of 100 ° C. or higher, the color of the solution changes from blue to red, and when cooled to room temperature, the color returns to blue again. The magnetic nanocomposite aqueous solution exhibiting such reversible color transfer characteristics can be obtained by using a magnet.

After applying the magnetic nanocomposite according to the present invention to the sensor material, the magnetic nanocomposite combined with the sensor material may be obtained using a magnet and separated from the unbound sensor material. The magnet that can be used in the present invention is not particularly limited, and the stronger the magnet, the more preferable it is to obtain the magnetic nanocomposite in a short time.

One embodiment of the separation of the sensing material according to the present invention is as follows. When the alpha-cyclodextrin is added to the aqueous magnetic nanocomposite solution prepared according to the present invention, the color of the solution changes from blue to red. When the magnet is fixed to the side of the container containing the aqueous solution of the red magnetic nanocomposite combined with the alpha-cyclodextrin, a magnetic field is formed around the magnet, and the magnet is fixed to the red magnetic nanocomposite combined with the alpha-cyclodextrin by magnetic force. Where it can be obtained. This method allows for easy separation of polydiacetylene combined with sensor material without the use of complex methods such as centrifugation and dialysis. This principle can be applied to various fields, and can be used for the detection and separation of various sensor materials such as DNA, protein, heavy metal ions, poisons, as well as the separation of the cyclodextrin.

The present invention provides a complex of polydiacetylene conjugated polymer and magnetic nanoparticles with a change in color and fluorescence by recognizing changes in the external environment, wherein the complex of polydiacetylene conjugated polymer and magnetic nanoparticles is polydiacetylene conjugated. By retaining the properties of the polymer and the magnetic properties of the magnetic nanoparticles, it is expected to be applied to sensor material separation, biosensor, drug delivery system, and the like.

Figure 1A is a schematic diagram (a) showing the structure of the polydiacetylene magnetic nanocomposite according to the present invention, and a partial enlarged view of the polydiacetylene magnetic nanocomposite structure when the magnetic nanoparticles are iron oxide (Fe ₃ O ₄ ) (B).
Figure 1B is an enlarged structural formula of the polydiacetylene magnetic iron oxide composite structure in the polydiacetylene magnetic nanocomposite structure according to the present invention.
2 is a TEM picture of the magnetite, (b) a SEM picture of the polydiacetylene, (c) a SEM picture of the polydiacetylene magnetite complex obtained in accordance with an embodiment of the present invention, (d) a polydiacetylene magnetite complex Tem picture.
3 is a SEM photograph of (a) a polydiacetylene fiber obtained according to an embodiment of the present invention, (b) a SEM photograph of a composite in which magnetite is bonded to the polydiacetylene fiber, and (c) a TEM photograph.
Figure 4 is a photograph showing the process and the result of the separation by applying a magnetic field to the polydiacetylene magnetic nanocomposite prepared according to the present invention.
Figure 5 is a photograph showing that the color change by heating the polydiacetylene magnetic nanocomposite prepared according to the present invention.
6 is a photograph showing a process and a result of separating a polydiacetylene magnetic nanocomposite prepared according to the present invention by applying a magnetic field after the color change by heating.
7 is a photograph showing a reversible color change in the process of cooling the polydiacetylene magnetic nanocomposite prepared according to the present invention at room temperature after heating and a process of separating and adding a magnetic field thereto and the result.
FIG. 8 is a photograph showing a process of changing a color to red by reacting a polyacetylene magnetic nanocomposite prepared in accordance with the present invention with alpha-cyclodextrin, and separating a red magnetic nanocomposite by applying a magnetic field.
9 is a schematic diagram showing a form in which a polydiacetylene magnetic nanocomposite and alpha-cyclodextrin are combined.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the present invention. Such variations and modifications are intended to be within the scope of the appended claims.

≪ Example 1 >

(1-1) Magnetite (Fe ₃ O ₄ Aqueous Solution Preparation

4.87 g of iron chloride (FeCl ₃ · 6H ₂ O) and 3.37 g of iron sulfate (FeSO ₄ · 7H ₂ O) were dissolved in 130 ml of water, and 25 g of polyethylene glycol was added thereto and heated to 78 ° C. . 10 ml of 25% aqueous ammonia was added to the heated solution, followed by stirring for one day, and the precipitated magnetite (Fe ₃ O ₄ ) was filtered. 20 ml of water was added to 9.26 mg of the obtained magnetite and sonicated for 20 minutes to disperse. Subsequently, hydrochloric acid (HCl) was added to make p H 2 of the aqueous solution of magnetite, thereby preparing a solution of magnetite. The TEM photograph of the prepared magnetite is shown in FIG. 2 (a).

(1-2) Preparation of polydiacetylene aqueous solution

7.5 mg of PCDA was dissolved in 0.2 ml DMSO, then 20 ml of water was added and sonicated for 15 minutes to disperse. The solution in which PCDA was dispersed was filtered using a 0.8 μm filter and cooled at 4 ° C. for 4 hours. Subsequently, an aqueous solution in which PCDA was dispersed was exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to obtain a blue polydiacetylene solution. The SEM photograph of the obtained polydiacetylene aqueous solution is shown in FIG.

(1-3) Preparation of Polydiacetylene Magnetic Nanocomposite

The polydiacetylene magnetic material of Example 1 was prepared by mixing the magnetite solution prepared in (1-1) and the polydiacetylene solution prepared in (1-2) in a molar ratio of 0.5: 1, and then ultrasonically treating for 3 minutes. Nanocomposites were obtained. SEM photographs and TEM photographs of the obtained polydiacetylene magnetic nanocomposites are shown in (c) and (d) of FIG. 2.

<Example 2>

(2-1) Magnetite (Fe ₃ O ₄ Aqueous Solution Preparation

4.87 g of iron chloride (FeCl _{3 ·} H ₂ O) and 3.37 g of iron sulfate (FeSO _{4 ·} H ₂ O) were dissolved in 130 ml of water, and then 25 g of polyethylene glycol was added thereto and heated to 78 ° C. . 10 ml of 25% aqueous ammonia was added to the heated solution, followed by stirring for one day, and the precipitated magnetite (Fe ₃ O ₄ ) was filtered. 20 ml of water was added to 9.26 mg of the obtained magnetite and sonicated for 20 minutes to disperse. Subsequently, sodium hydroxide (NaOH) was added so that the magnetite aqueous solution had a pH of 13 to prepare a magnetite aqueous solution.

(2-2) Preparation of Polydiacetylene Aqueous Solution

10.0 mg of PCDA-EDEA was dissolved in 1 ml CHCl ₃ and then 20 ml of water was added and sonicated for 15 minutes to disperse. The PCD-EDEA dispersed solution was filtered using a 0.8 mm filter and cooled at 4 ° C. for 4 hours. Subsequently, an aqueous solution in which PCDA-EDEA was dispersed was exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to obtain a blue polydiacetylene solution.

(2-3) Preparation of Polydiacetylene Magnetic Nanocomposite

The polydiacetylene magnetic nanocomposite of Example 2 was prepared by mixing the magnetite solution prepared in (2-1) and the polydiacetylene solution prepared in (2-2) in a molar ratio of 0.5: 1, and then sonicating for 3 minutes. Prepared.

<Example 3>

(3-1) Preparation of polydiacetylene aqueous solution

9.2 mg of PCDA-AEE was dissolved in DMSO and then 20 ml of water was added and sonicated for 15 minutes to disperse. The PCDA-AEE dispersed solution was filtered using a 0.8 μm filter and cooled at 4 ° C. for 4 hours. Subsequently, an aqueous solution in which PCDA-AEE was dispersed was exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to obtain a blue polydiacetylene solution.

(3-2) Preparation of Polydiacetylene Magnetic Nanocomposite

The polydiacetylene magnetic nanocomposite of Example 3 was mixed by mixing the aqueous magnetite solution prepared in (1-1) with the polydiacetylene aqueous solution prepared in (3-1) at a molar ratio of 0.5: 1 and then sonicated for 3 minutes. Prepared.

<Example 4>

(4-1) Preparation of polydiacetylene aqueous solution

9.9 mg of PCDA-mHPBA was dissolved in 0.2 ml of DMSO, then 20 ml of water was added and sonicated for 15 minutes to disperse. The PCDA-mHPBA dispersed solution was filtered using a 0.8 μm filter and cooled at 4 ° C. for 4 hours. Subsequently, an aqueous solution in which PCDA-mHPBA was dispersed was exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to obtain a blue polydiacetylene solution.

(4-2) Preparation of polydiacetylene magnetic nanocomposite

The polydiacetylene magnetic nanocomposite of Example 4 was prepared by mixing the magnetite solution prepared in (1-1) and the polydiacetylene solution prepared in (4-1) at a molar ratio of 0.5: 1, and then sonicating for 3 minutes. Prepared.

<Example 5>

(5-1) Preparation of polydiacetylene aqueous solution

9.9 mg of PCDA-mBzA was dissolved in 0.2 ml DMSO, then 20 ml of water was added and sonicated for 15 minutes to disperse. The solution in which PCD-mBzA was dispersed was filtered using a 0.8 μm filter and cooled at 4 ° C. for 4 hours. Subsequently, an aqueous solution in which PCDA-mBzA was dispersed was exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to obtain a blue polydiacetylene solution.

(5-2) Preparation of polydiacetylene magnetic nanocomposite

The polydiacetylene magnetic nanocomposite of Example 5 was mixed by mixing the aqueous magnetite solution prepared in (1-1) with the polydiacetylene solution prepared in (5-1) at a molar ratio of 0.5: 1, and then sonicated for 3 minutes. Prepared.

<Example 6>

(6-1) Preparation of polydiacetylene aqueous solution

12.0 mg of DCDDA-mCPE was dissolved in 0.2 ml of DMSO, then 20 ml of water was added and sonicated for 15 minutes to disperse. The PCDA-mHPBA dispersed solution was filtered using a 0.8 μm filter and cooled at 4 ° C. for 4 hours. Subsequently, an aqueous solution in which PCDA-mHPBA was dispersed was exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to obtain a blue polydiacetylene solution.

(6-2) Preparation of polydiacetylene magnetic nanocomposite

The polydiacetylene magnetic nanocomposite of Example 6 was mixed by mixing the magnetite solution prepared in (1-1) with the polydiacetylene solution prepared in (6-1) at a molar ratio of 0.5: 1, and then sonicated for 3 minutes. Prepared.

Example 7 Preparation of Polydiacetylene Fiber Magnetic Nanocomposite

(7-1) Polydiacetylene Fiber Production

Dissolve 10.0 mg of PCDA-IPA in 10 ml of 7 ml of Ethanol and 3 ml of H ₂ O in a ratio of 7: 3. After stirring for 20 minutes at a temperature of 60 ℃. Cooled at room temperature for 4 hours. The solution containing the dispersed PCDA-IPA fibers was then exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to obtain a blue polydiacetylene fiber solution. The SEM photograph of the obtained polydiacetylene fiber is shown in Fig. 3 (a).

(7-2) Preparation of Polydiacetylene Magnetite Composite

The polydiacetylene magnetic nanocomposite of Example 7 was mixed by mixing the magnetite solution prepared in (1-1) with the polydiacetylene solution prepared in (7-1) at a molar ratio of 0.5: 1, and then sonicated for 3 minutes. Prepared.

Magnetic nanocomposites having a structure in which magnetite was bonded to the polydiacetylene fiber according to Example 7 were obtained, and SEM and TEM images thereof are shown in FIGS. 3B and 3C.

Example 8 Preparation of Polydiacetylene Magnetic Nanocomposite with Magnetic Particles Formed in a Core

(8-1) Preparation of Polydiacetylene Magnetite Composite with Magnetic Particles in the Core

The aqueous solution of magnetite prepared in (1-1) was calculated in a molar ratio of 0.2: 1 and diluted in cican. In this solution, a solution of 7.5 mg of PCDA dissolved in 2 ml DMSO was added dropwise to the magnetite solution. Sonicate for 15 minutes to disperse. The solution in which PCDA was dispersed was filtered using a 5 μm filter and cooled at 4 ° C. for 4 hours. Subsequently, an aqueous solution containing PCDA dispersed therein was exposed to ultraviolet rays at 254 nm for 10 minutes (1 mW / cm ² ) to form a polydiacetylene magnetic nanoparticle composite having magnetic nanoparticles in the core. Obtained.

<Experimental Example 1>

Magnetic Separation of Polydiacetylene Magnetic Nanocomposites

A magnet was applied to the side of the container containing the magnetic nanocomposite aqueous solution prepared in (1-3) (FIG. 4A) (FIG. 4B) and fixed for 4 hours. As a result, as the magnetic field was formed around the magnet, it was confirmed that the blue magnetic nanocomposite could be obtained by the magnetic force (FIG. 4C) of the magnet.

A blue magnetic nanocomposite aqueous solution (FIG. 5A) was heated to a temperature of 100 ° C. or higher to cause color transition to red (FIG. 5B). A magnet was applied to the side of the container containing the red magnetic nanocomposite aqueous solution ((6a) of FIG. 6) ((6b) of FIG. 6) and fixed for 4 hours. It was confirmed that the red magnetic nanocomposite can be obtained where the magnet is fixed (FIG. 6 (6c)).

<Experimental Example 2>

Magnetic Separation of Polydiacetylene Magnetic Nanocomposites (Reversible Color Transition)

The blue magnetic nanocomposite aqueous solution prepared in Example 2 ((7a) of FIG. 7) was heated to a temperature of 100 ° C. or more to generate a color transition from blue to red ((7b) of FIG. 7), and then cooled to room temperature. It returns to blue again (7c of FIG. 7). A magnet was applied to the side of the container containing the magnetic nanocomposite aqueous solution having reversible characteristics (FIG. 7 (d) of FIG. 7) and fixed for 4 hours. As a result, it was confirmed that the magnetic nanocomposite can be obtained where the magnet is fixed ((7e) of FIG. 7).

<Experimental Example 3>

Cyclodextrin Detection Using Polydiacetylene Magnetic Nanocomposites

Alpha-cyclodextrin aqueous solution was mixed with the aqueous solution of magnetic nanocomposite prepared in Example 2 ((8a) of FIG. 8) such that the final molar ratio was 1:10, and polydiacetylene and alpha-cyclodextrin reacted to produce magnetic nanoparticles. The color of the complex changed from blue to red (FIG. 8B). The magnet was applied to the side of the container containing the red magnetic nanocomposite combined with alpha-cyclodextrin (FIG. 8 (8c)) and fixed for 4 hours. It was confirmed that the red magnetic nanocomposite combined with alpha-cyclodextrin can be obtained where the magnet is fixed (FIG. 8D).

The color change according to the molecular structure before and after the application of cyclodextrin is shown schematically in FIG. 9. From the experimental results of polydiacetylene and alpha-cyclodextrin, it could be confirmed that when polydiacetylene combined with magnetic nanoparticles is applied to a sensor, detection and separation of molecular recognition reactions can be easily performed. Using this principle, the polydiacetylene magnetic nanocomposite according to the present invention can be used for the detection and separation of various sensor materials such as DNA, proteins, heavy metal ions, poisons and the like.

100: polydiacetylene magnetic nanocomposite
110: magnetic nanoparticles (magnetite)
120: polydiacetylene

Claims (20)

As a magnetic nanocomposite having a structure in which polydiacetylene and ferromagnetic nanoparticles are bonded,
The polydiacetylene forms a core, and the ferromagnetic nanoparticles are made of a polydiacetylene magnetic nanocomposite, characterized in that consisting of a structure bonded to the end of the core.
delete The method of claim 1,
The polydiacetylene is
The polydiacetylene magnetic nanocomposite, characterized in that made by polymerizing a diacetylene monomer represented by the formula (1).
[Formula 1]

In Chemical Formula 1,
d + g is 0,1 or 2, e + f is an integer from 2 to 50, e and f are integers greater than 1,
A and B are a methyl group, an amine group, a carboxyl group, a hydroxyl group, a maleimide group, a biotin group, an N-hydroxysuccinimide group, a benzoic acid group or an activated ester group,
L ₁ and L ₂ are the same as or different from each other and are an alkyl group having 2 or more carbon atoms, at least one ethylene oxide group, an amine group, an amide group, an ester group or a carbonyl group.
The method of claim 1,
The ferromagnetic nanoparticles are polydiacetylene magnetic nanocomposite, characterized in that the iron oxide.
5. The method of claim 4,
The iron oxide is poly acetylene magnetic nanocomposite, characterized in that 20 ~ 30nm.
The method of claim 1,
The polydiacetylene magnetic nanocomposite is a polydiacetylene magnetic nanocomposite, characterized in that dispersed in an aqueous solution.
Preparing a polydiacetylene solution by polymerizing the diacetylene monomer in one of an organic solvent, water, or a mixed solvent thereof;
Mixing the polydiacetylene solution and ferromagnetic nanoparticles; And
Sonicating the mixture of polydiacetylene and ferromagnetic nanoparticles;
Method for producing a polydiacetylene magnetic nanocomposite having a structure in which the ferromagnetic nanoparticles comprising a bond to the terminal of the polydiacetylene.
The method of claim 7, wherein
The die acetylene monomer is a manufacturing method, characterized in that represented by the following formula (1).
[Formula 1]

In Chemical Formula 1,
d + g is 0,1 or 2, e + f is an integer from 2 to 50, e and f are integers greater than 1,
A and B are a methyl group, an amine group, a carboxyl group, a hydroxyl group, a maleimide group, a biotin group, an N-hydroxysuccinimide group, a benzoic acid group or an activated ester group,
L ₁ and L ₂ are the same as or different from each other and are an alkyl group having 2 or more carbon atoms, at least one ethylene oxide group, an amine group, an amide group, an ester group or a carbonyl group.
delete The method of claim 7, wherein
The organic solvent is a solvent selected from the group consisting of dimethylformamine, dimethyl sulfoxide, chloroform, dichloromethane, hexane, tetrahydrofuran, acetone and alcohol, or a mixed solvent thereof.
The method of claim 7, wherein
The ferromagnetic nanoparticles manufacturing method, characterized in that the iron oxide.
The method of claim 11,
The iron oxide is a production method, characterized in that the composite or ground.
The method of claim 7, wherein
The ferromagnetic nanoparticles have a size of 20nm to 30nm.
The method of claim 7, wherein
The ferromagnetic nanoparticles manufacturing method characterized in that used in the preparation of a solution phase.
15. The method of claim 14,
The ferromagnetic nanoparticles solution is characterized in that the acid solution of pH 2.0 ~ 4.5.
15. The method of claim 14,
The ratio of the polydiacetylene solution and the ferromagnetic nanoparticles solution is 0.2 to 1 mole of ferromagnetic nanoparticles per mole of polydiacetylene solution.
The method of claim 7, wherein
The magnetic nanocomposite is a manufacturing method characterized in that the aqueous phase.
A biosensor comprising a polydiacetylene magnetic nanocomposite having a structure in which a polydiacetylene forms a core and a ferromagnetic nanoparticle is bonded to an end of the core.
Polydiacetylene forms a core, and a polydiacetylene magnetic nanocomposite comprising a structure consisting of a ferromagnetic nanoparticles bonded to the end of the core.
Forming a magnetic nanocomposite to which a sensing target material is bound by mixing a polydiacetylene magnetic nanocomposite having a structure in which polydiacetylene forms a core and a structure in which ferromagnetic nanoparticles are bonded to the end of the core; And
Separating the magnetic nanocomposite to which the sensing target material is bound by applying a magnetic material to the outside of the container containing the complex;
Sensing material separation method using a magnetic nanocomposite comprising a.

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