CN113372538A - Poly 3, 4-ethylenedioxythiophene nano-particles and preparation method thereof - Google Patents

Poly 3, 4-ethylenedioxythiophene nano-particles and preparation method thereof Download PDF

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CN113372538A
CN113372538A CN202110762589.9A CN202110762589A CN113372538A CN 113372538 A CN113372538 A CN 113372538A CN 202110762589 A CN202110762589 A CN 202110762589A CN 113372538 A CN113372538 A CN 113372538A
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ethylenedioxythiophene
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CN113372538B (en
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田颜清
曹戈
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/11—Homopolymers
    • C—CHEMISTRY; METALLURGY
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08G2261/40—Polymerisation processes
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Abstract

The invention relates to a poly 3, 4-ethylenedioxythiophene nanoparticle and a preparation method thereof, wherein the preparation method of the poly 3, 4-ethylenedioxythiophene nanoparticle comprises the following steps: and carrying out oxidation polymerization reaction on the 3, 4-ethylenedioxythiophene in a mixed solvent of dichloromethane and acetonitrile to obtain the poly 3, 4-ethylenedioxythiophene nano-particles. The method can prepare the water-based poly 3, 4-ethylenedioxythiophene nanoparticles which are regular in morphology, good in water dispersibility, high in conductivity and excellent in suspension performance in different solvents.

Description

Poly 3, 4-ethylenedioxythiophene nano-particles and preparation method thereof
Technical Field
The invention relates to the technical field of conductive materials, in particular to a poly (3, 4-ethylenedioxythiophene) nanoparticle and a preparation method thereof.
Background
The conjugated conductive polymers are conjugated polymers, mainly refer to polymers with large conjugated delocalized pi bonds, and due to the properties of relatively low monomer cost, excellent chemical stability, easy synthesis, high conductivity and the like, a great deal of research interest is brought, and the potential of the conjugated conductive polymers can be used in the aspects of sensors, photovoltaics, supercapacitors, thermoelectric devices, field effect transistor electrostatic coating technologies and the like.
However, the conjugated polymer does not achieve both the excellent electrical properties of the optical metal and the processability thereof. To the extent that their conductivity and processability, mutually repel each other, a certain balance needs to be made between these two characteristics. In general, the processability problem of conjugated polymers is generally undesirable and insoluble in most organic dispersant media due to their highly conjugated molecular structure (highly planar and strongly interacting pi-conjugation). To overcome these obstacles, and to improve solubility, various methods have been proposed, such as introducing large counterions to reduce interchain interactions, attaching pendant groups/chains to a rigid backbone, preparing colloidally dispersed forms, such as water-based latexes, and exploring novel monomer derivatives.
Poly (3, 4-ethylenedioxythiophene) (PEDOT) is one of the most studied materials among conductive polymers, which has many advantages such as thermal stability, good film forming characteristics, low oxidation potential, excellent transparency of dopants and tunable conductivity state. Doping with polystyrene sulfonate (PSS) generally plays a crucial role in improving the solubility and electrical properties of PEDOT. Experiments have shown that PSS does not contribute directly to the transport of charge carriers, but acts as a template at the dissociated sulfonate group to compensate the charge of the cationic PEDOT by forming a stable salt. Thus, aqueous solutions of PEDOT can be formed using PSS as a dispersant.
However, the use of PSS or other dispersants may reduce the lifetime of PEDOT because PSS containing sulfonic acid groups is strongly hygroscopic and can readily absorb moisture from the surrounding atmosphere, resulting in poor and sustained deterioration of the performance of organic devices. In addition, PEDOT doped with PSS cannot be dispersed in other organic solvents, limiting its applicability.
Therefore, there is a need in the art to prepare a PEDOT material that does not require doping PSS and is capable of dispersing various organic solvents, so as to continue to advance the development of its applications.
Disclosure of Invention
In view of the defects of the prior art, an object of the present invention is to provide a method for preparing poly-3, 4-ethylenedioxythiophene (PEDOT) nanoparticles, particularly to provide a method for preparing high-polarity anhydrous poly-3, 4-ethylenedioxythiophene nanoparticles, and particularly to provide a method for preparing poly-3, 4-ethylenedioxythiophene (PEDOT) nanoparticles not doped with PSS, wherein the poly-3, 4-ethylenedioxythiophene nanoparticles prepared by the preparation method have regular shapes, good water dispersibility, high conductivity, and excellent suspension performance in different solvents.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a preparation method of poly 3, 4-ethylenedioxythiophene nanoparticles, which comprises the following steps: and carrying out oxidation polymerization reaction on the 3, 4-ethylenedioxythiophene in a mixed solvent of dichloromethane and acetonitrile to obtain the poly 3, 4-ethylenedioxythiophene nano-particles.
The poly 3, 4-ethylenedioxythiophene nanoparticles are innovatively prepared in the mixed solvent of dichloromethane and acetonitrile, water-dispersible poly 3, 4-ethylenedioxythiophene nanoparticles with regular shapes can be obtained, and the nanoparticles have high conductivity and excellent suspension performance in various solvents (such as methanol, ethanol, 1, 4-dioxane, ethyl acetate, 4-methyl-2-pentanone, diethyl ether or n-hexane and the like), and the regular nanoparticles can promote the dispersing capacity.
The poly 3, 4-ethylenedioxythiophene nano particles which can be highly dispersed and prepared by the method can be positioned between the micron silver sheets in the conductive adhesive and form conductive interconnection, so that the contact resistance of the conductive adhesive is minimized, the conductive performance is further improved, and the poly 3, 4-ethylenedioxythiophene nano particles have a good application prospect in the conductive adhesive.
The poly 3, 4-ethylenedioxythiophene nano particles prepared by the method have excellent solubility and electrical properties even if the PSS is not doped.
Preferably, the volume ratio of dichloromethane and acetonitrile is (1-4):1, e.g., 1:1, 2:1, 3:1, etc.
According to the invention, the volume ratio of dichloromethane to acetonitrile is preferably (1-4):1, and the volume ratio is controlled within the ratio, so that the prepared poly 3, 4-ethylenedioxythiophene nano particles have more regular shapes, the conductivity and the suspension performance are further improved, and if more dichloromethane or more acetonitrile is used, the conductivity is reduced.
Preferably, the oxidative polymerization reaction is carried out in the presence of an oxidizing agent.
Preferably, the oxidizing agent comprises anhydrous ferric chloride and/or cupric chloride, preferably anhydrous ferric chloride.
Preferably, the time for the oxidative polymerization reaction is 20-30h, such as 21h, 22h, 23h, 24h, 25h, 26h, 27h, 28h, 29h, etc., preferably 24 h.
Preferably, the temperature of the oxidized polymer reaction is-5 to 5 deg.C, such as-4 deg.C, -3 deg.C, -2 deg.C, -1 deg.C, 0 deg.C, 1 deg.C, 2 deg.C, 3 deg.C, 4 deg.C, etc., preferably 0 deg.C.
Preferably, the preparation method specifically comprises: and mixing a dichloromethane solution containing 3, 4-ethylenedioxythiophene with an acetonitrile solution containing an oxidant, stirring, and carrying out oxidative polymerization reaction to obtain the poly 3, 4-ethylenedioxythiophene nano particles.
Preferably, the preparation method further comprises: after the oxidative polymerization, the product is filtered and washed.
Preferably, the washing is specifically rinsing with a hydrochloric acid solution.
Preferably, the preparation method specifically comprises the following steps: mixing a dichloromethane solution containing 3, 4-ethylenedioxythiophene with an acetonitrile solution containing anhydrous ferric chloride, stirring, carrying out oxidative polymerization reaction at 0 ℃ for 20-30h, filtering, and washing to obtain the poly 3, 4-ethylenedioxythiophene nanoparticles;
the volume ratio of the dichloromethane to the acetonitrile is (1-4) to 1.
Preferably, the yield of the poly 3, 4-ethylenedioxythiophene nanoparticles is greater than or equal to 70%, such as 71%, 72%, 73%, 74%, 75%, 76%, 77%, 78%, 79%, 80%, and the like.
Illustratively, the synthesis route of the poly 3, 4-ethylenedioxythiophene nanoparticles provided by the invention is as follows:
Figure BDA0003150515110000041
wherein RT represents room temperature.
The second object of the present invention is to provide poly (3, 4-ethylenedioxythiophene) nanoparticles obtained by the preparation method of the first object.
Preferably, the conductivity of the poly 3, 4-ethylenedioxythiophene nano particles is more than or equal to 220S/cm, such as 225S/cm, 230S/cm, 235S/cm, 240S/cm, 245S/cm, 250S/cm and the like.
Preferably, the particle size of the poly 3, 4-ethylenedioxythiophene nanoparticles is 40-60nm, such as 42nm, 43nm, 44nm, 45nm, 46nm, 47nm, 48nm, 49nm, 50nm, 52nm, 54nm, 56nm, 58nm and the like, preferably 50 nm.
Compared with the prior art, the invention has the following beneficial effects:
the water-dispersible PEDOT nano particles prepared by the method provided by the invention are simple and controllable to synthesize, have good water dispersibility and regular nano spherical morphology.
Drawings
Fig. 1 is a schematic diagram of a preparation method of PEDOT nanoparticles provided in example 1.
Figure 2a is an SEM image of PEDOT nanoparticles provided in example 1.
Figure 2b is an SEM image of PEDOT nanoparticles provided in example 1.
Fig. 3 is a distribution diagram of the particle size of PEDOT nanoparticles provided in example 1.
Figure 4 is a FT-IR characterization of PEDOT nanoparticles provided in example 1.
Figure 5 is an XRD pattern of PEDOT nanoparticles provided in example 1.
Figure 6 is a current-voltage plot of PEDOT nanoparticles provided in example 1.
Figure 7a is a graph of the suspension characteristics of PEDOT nanoparticles provided in example 1.
Fig. 7b is a graph of suspension tests of PEDOT nanoparticles provided in example 1 in different solvents.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
The embodiment provides a preparation method of poly 3, 4-ethylenedioxythiophene nanoparticles, and the preparation process is shown in fig. 1 and specifically includes the following steps:
in a 500 ml beaker, 3 g of thiophene monomer was added to 60 ml of dichloromethane. 12g of anhydrous iron (III) chloride dissolved in 30ml of acetonitrile are introduced with vigorous stirring to polymerize ETDOT. After 24 hours of reaction at 0 ℃, a blue precipitate formed, the product was filtered and washed with dilute hydrochloric acid solution until a colorless filtrate was obtained, i.e., PEDOT nanoparticles were obtained in a yield of 70%.
The following tests were carried out on PEDOT nanoparticles prepared in example 1:
(1) the morphology of the PEDOT nanoparticles obtained by SEM testing is shown in fig. 2a and 2b, and from fig. 2a and 2b, it can be seen that the PEDOT nanoparticles exhibit a nanoparticle morphology with a relatively uniform length distribution.
(2) The particle size distribution of the PEDOT nanoparticles prepared in this example, as measured by a dynamic light scattering instrument, is shown in fig. 3, which shows a diameter of about 50 nm.
(3) The chemical structure of PEDOT nanoparticles was characterized by fourier transform infrared spectroscopy (FT-IR) studies. The dominant IR band of PEDOT is observed in fig. 4, which is consistent with previous reports. At 1,515cm-1And 1,397cm-1The IR band of (a) is an asymmetric stretching mode with respect to stretching between C ═ C and the thiophene ring. 1,169, 1,136, 1,090cm-1C-O-C bending vibration due to ethylenedioxy group, 997, 840, 609 and 480cm-1The band at (B) is a characteristic band of tensile vibration of the C-S-C bond.
(4) The XRD pattern of PEDOT nanoparticles is shown in figure 5. All polymers are in
Figure BDA0003150515110000061
And
Figure BDA0003150515110000062
Figure BDA0003150515110000063
a characteristic peak is shown nearby, which can be attributed to the plane ring between PEDOT chainsAnd (4) stacking.
(5) Figure 6 shows the current-voltage curve of PEDOT granular samples. Indicating the voltammetric ohmic behavior of PEDOT polymer. PEDOT granules were pressed from 10 mg powder by applying 3500KPa pressure, while the conductance through the four probes further PETDOT was around 220S/cm at the test conductivity.
(6) The suspension characteristics of PEDOT nanoparticles are shown in fig. 7a, characterized by Zeta potential measurements. The data show that the nanorods have a high zeta potential of 33mv in water. Obviously, PEDOT nanoparticles can form stable colloidal suspensions in water, which is crucial to provide a way to process these conductive polymers in aqueous PU to prepare high performance conductive adhesive composites with biocompatible resins. Fig. 7a shows the dissolution of PEDOT nanoparticles in different organic solvents, where the solvent 1 is methanol, the solvent 2 is ethanol, the solvent 3 is 1, 4-dioxane, the solvent 4 is ethyl acetate, the solvent 5 is 4-methyl-2-pentanone, the solvent 6 is diethyl ether, and the solvent 7 is n-hexane, and it shows that the PEDOT nanoparticles can be dispersed in most polar organic solvents, which indicates that the PEDOT nanoparticles have good potential for processing various polymer composites.
Example 2
The only difference from example 1 is that the volumes of dichloromethane and acetonitrile are 20mL and 20mL (1:1), respectively, and the yield is 50%.
The PEDOT nanoparticles of this example were well dispersed in water and had an electrical conductivity of 20S/cm.
Example 3
The only difference from example 1 is that the volumes of dichloromethane and acetonitrile are 80mL and 20mL (4:1), respectively, and the yield is 20%.
The PEDOT nanoparticles of this example were well dispersed in water and had an electrical conductivity of 30S/cm.
Example 4
The only difference from example 1 is that the volumes of dichloromethane and acetonitrile are 10mL and 20mL (0.5:1), respectively, and the yield is 40%.
The PEDOT nanoparticles of this example had poor dispersibility in water and an electrical conductivity of less than 1S/cm.
Example 5
The only difference from example 1 is that the volumes of dichloromethane and acetonitrile are 100mL and 20mL (5:1), respectively, and the yield is 30%.
The PEDOT nanoparticles of this example had poor dispersibility in water and an electrical conductivity of about 1S/cm.
Comparative example 1
The comparative example provides a preparation method of PEDOT nanoparticles, which specifically includes the following steps:
in a 500 ml beaker, 3 g of thiophene monomer was added to water. 12g of anhydrous iron (III) chloride dissolved in 30ml of water are introduced with vigorous stirring to polymerize ETDOT. After 24 hours reaction at 0 ℃, a blue precipitate formed and the product was filtered to give 20% yield of amorphous PEDOT material.
The PEDOT material of this comparative example was not dispersible in water and had a conductivity of less than 10-4S/cm。
Comparative example 2
The comparative example provides a preparation method of PEDOT nanoparticles, which specifically includes the following steps: EDOT (0.2mL, 1.8X 10)-3mol) were added to water and the mixture was pre-emulsified for 10 minutes by magnetic stirring and then sonicated for 5 minutes using a Branson 450-D sonicator. The white dispersion obtained was transferred to a reaction flask and placed in an oil bath at a temperature of 45 ℃ under magnetic stirring. Immediately thereafter, 25mL of FeTos aqueous solution (mol/l) was added to the reaction flask. The mixture was polymerized for 24 hours. Obtaining PEDOT nanometer particles.
The PEDOT nanoparticles of this comparative example were poorly dispersible in water, with an electrical conductivity of less than 1S/cm.
The applicant states that the present invention is illustrated in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e. it is not meant that the present invention must rely on the above detailed methods for its implementation. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (10)

1. A preparation method of poly 3, 4-ethylenedioxythiophene nanoparticles is characterized by comprising the following steps: and carrying out oxidation polymerization reaction on the 3, 4-ethylenedioxythiophene in a mixed solvent of dichloromethane and acetonitrile to obtain the poly 3, 4-ethylenedioxythiophene nano-particles.
2. The method according to claim 1, wherein the volume ratio of dichloromethane to acetonitrile is (1-4): 1.
3. The production method according to claim 1 or 2, characterized in that the oxidative polymer reaction is carried out in the presence of an oxidizing agent;
preferably, the oxidizing agent comprises anhydrous ferric chloride and/or anhydrous cupric chloride.
4. The method according to any one of claims 1 to 3, wherein the time for the oxidation polymer reaction is 20 to 30 hours, preferably 24 hours;
preferably, the temperature of the oxidative polymerization reaction is-5-5 ℃, preferably 0 ℃.
5. The preparation method according to any one of claims 1 to 4, comprising in particular: and mixing a dichloromethane solution containing 3, 4-ethylenedioxythiophene with an acetonitrile solution containing an oxidant, stirring, and carrying out oxidative polymerization reaction to obtain the poly 3, 4-ethylenedioxythiophene nano particles.
6. The production method according to any one of claims 1 to 5, further comprising: filtering and washing the product after the oxidative polymerization;
preferably, the washing is specifically rinsing with a hydrochloric acid solution.
7. The preparation method according to any one of claims 1 to 6, comprising in particular the steps of: mixing a dichloromethane solution containing 3, 4-ethylenedioxythiophene with an acetonitrile solution containing anhydrous ferric chloride, stirring, carrying out oxidative polymerization reaction at 0 ℃ for 20-30h, filtering, and washing to obtain the poly 3, 4-ethylenedioxythiophene nanoparticles;
the volume ratio of the dichloromethane to the acetonitrile is (1-4) to 1.
8. The preparation method according to any one of claims 1 to 7, wherein the yield of the poly 3, 4-ethylenedioxythiophene nanoparticles is greater than or equal to 70%.
9. A poly 3, 4-ethylenedioxythiophene nanoparticle obtained by the production method according to any one of claims 1 to 8.
10. The poly 3, 4-ethylenedioxythiophene nanoparticles of claim 9, wherein the conductivity of the poly 3, 4-ethylenedioxythiophene nanoparticles is greater than or equal to 220S/cm;
preferably, the particle size of the poly 3, 4-ethylenedioxythiophene nano-particles is 40-60nm, preferably 50 nm.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016029586A1 (en) * 2014-08-29 2016-03-03 华南理工大学 Method for manufacturing flexible transparent conducting composite film

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016029586A1 (en) * 2014-08-29 2016-03-03 华南理工大学 Method for manufacturing flexible transparent conducting composite film

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* Cited by examiner, † Cited by third party
Title
GE CAO 等: "Highly Conductive and Highly Dispersed Polythiophene Nanoparticles for Fabricating High-Performance Conductive Adhesives", 《ACS APPLIED ELECTRONIC MATERIALS》 *
李淑香: "新型非汞膜电极的制备及用于重金属离子检测", 《中国优秀博硕士学位论文全文数据库（硕士） 工程科技Ⅰ辑》 *

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