CN109735104A - A kind of soluble conductive polypyrrole and preparation method thereof of poly ion liquid doping - Google Patents
A kind of soluble conductive polypyrrole and preparation method thereof of poly ion liquid doping Download PDFInfo
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- CN109735104A CN109735104A CN201910090904.0A CN201910090904A CN109735104A CN 109735104 A CN109735104 A CN 109735104A CN 201910090904 A CN201910090904 A CN 201910090904A CN 109735104 A CN109735104 A CN 109735104A
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Abstract
The present invention relates to a kind of soluble conductive polypyrroles and preparation method thereof of poly ion liquid doping; the soluble conductive polypyrrole of the poly ion liquid doping; it is characterized in that; preparation method includes: liquor ferri trichloridi to be added under nitrogen protection in the mixed solution of pyrrole monomer and poly ion liquid; it is reacted; it is used as dopant it is not necessary that acid is added, obtains the soluble conductive polypyrrole of poly ion liquid doping.The present invention introduces poly ion liquid in the polymerization process of polypyrrole, so that polypyrrole can dissolve in DMSO equal solvent, has expanded the application field of polypyrrole.
Description
Technical field
The present invention relates to a kind of soluble conductive polypyrroles of poly ion liquid doping, specifically, what is involved is one kind
It can be uniformly dispersed in multi-solvents such as the preparation method of water, DMSO, DMF, DMAC and conductive polypyrrole.
Background technique
Polypyrrole than more typical structural conductive high polymer, contains pi-electron cloud structure energy as a kind of in strand
It is enough so that its molecular structure i.e. degree of oxidation and protonation is changed by chemical doping during the preparation process, formed from
Domain, so that this common insulating polymer be made to become the high molecular material for capableing of conduction.And because it can be by continuous
Doping way or compound condition are improved, relatively good electric conductivity can be obtained；The molecular structure of itself causes it with non-
The physical property of Chang Youyi, and stable structure, it is more friendly to environment；Synthesis material easily obtains, and can pass through a variety of methods
Synthesis, numerous excellent properties such as easy to operate have attracted a large amount of concern.
But since there are conjugatedπbonds in the strand of polypyrrole, generating strong conjugation causes its rigidity and interchain
It interacts stronger, it is insoluble under normal circumstances not melt.Therefore, the synthesis better polypyrrole of processability is their ability to industrialization
The main points of production and investment actual use.
Poly ion liquid is a kind of material for having both ionic liquid and polymer property, has special performance, can apply
In various fields.With science and technology, the development of research, poly ion liquid similarly constantly innovation and development, in polymer chemistry, energy
Source and materials science field have attracted huge concern.Not only due to it combines the only of the ionic liquid with macromolecular structure
Characteristic energy, more because it creates new characteristic and function.In recent years, imidazole type poly ion liquid is synthesized for dispersing agent,
For example it can stablize the nanometer materials such as the carbon nanotube in water phase and in organic phase, such as multi wall, single-walled carbon nanotube
(MWCNTs, SWCNTs) and graphene sheet layer.
It must be added to acid in the polymerization of electric polypyrrole at present, such as hydrochloric acid, benzene sulfonic acid could obtain good as dopant
The polypyrrole of good electric conductivity, non-acid adding class dopant does not have electric conductivity；And it has not seen at present and poly ion liquid is substituted into acid
The report of conductive Soluble Polypyrrole is prepared as doped polypyrrole agent.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of soluble electric polypyrroles and its system of no acid doping
Preparation Method, for the present invention by the way that poly ion liquid is added in the course of the polymerization process as dopant, obtaining one kind can be in DMSO equal solvent
In there is preferable deliquescent polypyrrole；Production method process of the present invention is compared with the traditional method, and is obtained in the condition of no acid doping
To conductive and soluble polypyrrole, the polymerization and application field of polypyrrole have been expanded.
A kind of soluble conductive polypyrrole of poly ion liquid doping of the invention, which is characterized in that preparation method packet
It includes: liquor ferri trichloridi being added under nitrogen protection in the mixed solution of pyrrole monomer and poly ion liquid, reacted, obtained
The soluble conductive polypyrrole adulterated to poly ion liquid.
Preferably, the reaction is added without acid or acid solution as dopant.
Preferably, the mass ratio of the pyrroles and poly ion liquid is 1:1-4:1.
Preferably, the poly ion liquid is PIL-Cl, structural formula are as follows:
Wherein n is 10-50.
The present invention also provides the preparation method of the soluble conductive polypyrrole of above-mentioned poly ion liquid doping, features
It is, comprising:
Step a: water removal deoxygenation processing is carried out to reaction vessel；
Step b: pyrrole monomer and water are added into reaction vessel, stirs to get pyrrole monomer solution；
Step c: being added Iron(III) chloride hexahydrate in water, and stirring obtains liquor ferri trichloridi；
Step d: make poly ion liquid be dissolved in water then be added step b reaction vessel in, obtain pyrrole monomer and
The mixed solution of poly ion liquid；
Step e: under nitrogen protection by the resulting liquor ferri trichloridi of step c be added the resulting pyrrole monomer of step b and
In the mixed solution of poly ion liquid, reacted；
Step f: by reaction product adding into acetone obtained in step e, stirring, separation of solid and liquid is precipitated, and is sunk
It is dried in vacuo behind shallow lake, obtains the soluble conductive polypyrrole of poly ion liquid doping.
Preferably, the concentration of chromium solution is 5-10 grams per liter in the step b.
Preferably, the concentration of liquor ferri trichloridi is 1-5 mol/L in the step c.
Preferably, the poly ion liquid in the step d and the mass ratio of pyrroles in step b are 1-1.4:1.
Preferably, the concentration of the poly ion liquid of mixed liquor is 20-150 grams per liter in the step d.
Preferably, the reaction in the step e carries out under stiring, and temperature is 0-10 DEG C, reaction time 3-5
Hour.
Preferably, the volume ratio of the acetone in the step f and reaction product obtained in step e is 3-5:1.
The principle of the present invention is to make pyrroles that polymerization reaction occur by oxidant of ferric trichloride, is added in the course of the polymerization process poly-
Soluble electric polypyrrole is prepared in ionic liquid PIL-Cl.The structure composition of gained polypyrrole, compound ratio, machinability
Energy, resistivity can pass through nuclear magnetic resoance spectrum, fourier transform infrared spectroscopy, thermogravimetic analysis (TGA), dissolubility test, transmitted electron
The tests such as microscope, four probe method are characterized.
Soluble conductive polypyrrole prepared in accordance with the present invention, low in raw material price is convieniently synthesized, reacts controllability
It is good.It, can uniform dissolution by the addition poly ion liquid in the polymerization process of pyrroles to improve its processing performance
In DMSO, DMF, DMAC equal solvent, this develops the application value of polypyrrole to application field, bigizationner for widening polypyrrole
Etc. be of great significance.
Detailed description of the invention
Fig. 1 is the nuclear magnetic spectrogram of soluble conductive polypyrrole prepared by the present invention；
Wherein: figure a, b, c respectively correspond the one-dimensional of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Nucleus magnetic hydrogen spectrum map.
Fig. 2 is the infrared spectrogram of soluble conductive polypyrrole prepared by the present invention；
Wherein: figure a, b, c respectively correspond the infrared of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Spectrogram.
Fig. 3 is the thermogravimetric curve of soluble conductive polypyrrole prepared by the present invention；
Wherein: a, b, c respectively correspond the thermal weight loss of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Curve.
Fig. 4 is the photo that soluble conductive polypyrrole prepared by the present invention dissolves in DMSO, DMF, DMAC；
Wherein: the soluble conductive polypyrrole that a, b, c respectively correspond comparative example 1 and embodiment 1, prepared by example 2 DMSO,
Dissolution situation in DMF, DMAC equal solvent.
Fig. 5 is the transmission electron microscope photo of soluble conductive polypyrrole prepared by the present invention；
Wherein: a, b respectively correspond embodiment 1, the transmission electron microscope of soluble conductive polypyrrole prepared by example 2 shines
Piece.
Fig. 6 is the conductivity of soluble conductive polypyrrole prepared by the present invention；
Wherein: a, b, c respectively correspond the conductivity of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1.
Fig. 7 is the nuclear magnetic spectrogram of poly ion liquid PIL-Cl.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Commercial product can be used shown in structural formula such as formula (I) in poly ion liquid PIL-Cl involved in embodiment,
Can also synthesize according to known methods, such as according to Publication No. CN105199090B, it is entitled " suitable for nonpolar solvent gather from
Sub- liquid-type acid indicator and its preparation " Chinese patent in record method synthesis.
Embodiment 1
A kind of soluble conductive polypyrrole of poly ion liquid doping, pyrroles and poly ion liquid PIL-Cl in raw material
Mass ratio is 1:1.
Above-mentioned poly ion liquid PIL-Cl, shown in structural formula such as formula (I), wherein n 22.According to Publication No.
CN105199090B, the China of entitled " suitable for the poly ion liquid type acid indicator of nonpolar solvent and its preparation " is specially
The method recorded in sharp embodiment 1 synthesizes, and gained precipitating is poly ion liquid PIL-Cl in step f.
The soluble conductive polypyrrole of above-mentioned poly ion liquid doping the preparation method comprises the following steps:
Step a: water removal deoxygenation processing, the water removal deoxygenation processing are as follows: by cleaning are carried out to 250 milliliters of three-necked flasks
250 milliliters of three-necked flasks are sufficiently dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b: under nitrogen protection, 1.01 grams of pyrroles and the stirring of 130 ml deionized waters are added into three-necked flask
Form uniform chromium solution；
Step c: be added in 10 milliliters of water 9.46 grams of Iron(III) chloride hexahydrates be uniformly mixed to obtain ferric trichloride it is molten
Liquid pours into constant pressure funnel；
Step d: 1.01 grams of poly ion liquid PIL-Cl stirrings are added in 50 milliliters of water dissolves it sufficiently, is then added
In the reaction vessel of step b, the mixed solution of pyrrole monomer and poly ion liquid is obtained；
Step e: under nitrogen protection by the resulting liquor ferri trichloridi of step c using constant pressure funnel in whipping process by
It is added dropwise in the mixed solution of the resulting pyrrole monomer of step b and poly ion liquid, is reacted under being stirred at 3 DEG C with 300rpm
4 hours；
Step f: by reaction product adding into acetone (volume ratio 1:4) obtained in step e, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains the soluble conductive polypyrrole of poly ion liquid doping.
Step g: product will be obtained in step f and is added in DMSO, DMF, DMAC to test its dissolubility.
Step h: the electric conductivity of product is obtained in four probe method testing procedure f.
Embodiment 2
A kind of soluble conductive polypyrrole of poly ion liquid doping, pyrroles and poly ion liquid PIL-Cl in raw material
Mass ratio is 1:3.
Above-mentioned poly ion liquid PIL-Cl, shown in structural formula such as formula (I), wherein n 17.According to Publication No.
CN105199090B, the China of entitled " suitable for the poly ion liquid type acid indicator of nonpolar solvent and its preparation " is specially
The method recorded in sharp embodiment 2 synthesizes, and gained precipitating is poly ion liquid PIL-Cl in step f.
The soluble conductive polypyrrole of above-mentioned poly ion liquid doping the preparation method comprises the following steps:
Step a: water removal deoxygenation processing, the water removal deoxygenation processing are as follows: by cleaning are carried out to 250 milliliters of three-necked flasks
250 milliliters of three-necked flasks are sufficiently dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b: under nitrogen protection, 1.01 grams of pyrroles and the stirring of 130 ml deionized waters are added into three-necked flask
Form uniform chromium solution；
Step c: be added in 10 milliliters of water 9.46 grams of Iron(III) chloride hexahydrates be uniformly mixed to obtain ferric trichloride it is molten
Liquid pours into constant pressure funnel；
Step d: 3.03 grams of poly ion liquid PIL-Cl stirrings are added in 50 milliliters of water dissolves it sufficiently, is then added
In the reaction vessel of step b, the mixed solution of pyrrole monomer and poly ion liquid is obtained；
Step e: under nitrogen protection by the resulting liquor ferri trichloridi of step c using constant pressure funnel in whipping process by
It is added dropwise in the mixed solution of the resulting pyrrole monomer of step b and poly ion liquid, is reacted under being stirred at 3 DEG C with 300rpm
4 hours；
Step f: by reaction product adding into acetone (volume ratio 1:4) obtained in step e, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains the soluble conductive polypyrrole of poly ion liquid doping.
Step g: product will be obtained in step f and is added in DMSO, DMF, DMAC to test its dissolubility.
Step h: the electric conductivity of product is obtained in four probe method testing procedure f.
Comparative example 1
A kind of traditional chemical oxidization method prepares electric polypyrrole.
Above-mentioned electric polypyrrole the preparation method comprises the following steps:
Step a: water removal deoxygenation processing, the water removal deoxygenation processing are as follows: by cleaning are carried out to 250 milliliters of three-necked flasks
250 milliliters of three-necked flasks are sufficiently dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b: under nitrogen protection, 1.01 grams of pyrroles and the stirring of 130 ml deionized waters are added into three-necked flask
Form uniform chromium solution；
Step c: be added in 10 milliliters of water 9.46 grams of Iron(III) chloride hexahydrates be uniformly mixed to obtain ferric trichloride it is molten
Liquid pours into constant pressure funnel；
Step d: under nitrogen protection by the resulting liquor ferri trichloridi of step c in whipping process using constant pressure funnel by
It is added dropwise in the resulting pyrrole monomer solution of step b, 4 hours of reaction is carried out under stirring at 3 DEG C with 300rpm；
Step f: by reaction product adding into acetone (volume ratio 1:4) obtained in step e, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains undoped polypyrrole.
Step g: product will be obtained in step f and is added in DMSO, DMF, DMAC to test its dissolubility.
Embodiment result is shown in attached drawing:
Fig. 1 a, 1b, 1c respectively correspond the one-dimensional core of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Magnetic hydrogen spectrogram spectrum, wherein the peak at 4.29-4.89ppm is the chemical shift for the secondary carbon proton being connected with ester group；5.74ppm place
Peak is the chemical shift for the tertiary carbon proton that ester group is connected；Multiplet at 7ppm-8ppm is the change of proton on phenyl ring and imidazole ring
Displacement study；Peak within the scope of 9.18-9.70ppm is the chemical shift for the secondary carbon proton being respectively connected on imidazole ring with two nitrogen.
Fig. 2 a, 2b, 2c respectively correspond the Fourier of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Transform infrared spectroscopy, wherein 3423cm-1Place is the characteristic peak of N-H stretching vibration；1554cm-1Place is that pyrroles's ring skeleton C=C stretches
Contracting vibration absorption peak；1313cm-1Place is antisymmetric stretching vibration absorption peak；1174cm-1Place is symmetrical stretching vibration absorption peak；
1043cm-1Place is C-N vibration absorption peak.
Fig. 3 a, 3b, 3c respectively correspond the thermal weight loss of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Curve.
The soluble conductive polypyrrole that a, b, c respectively correspond comparative example 1 and embodiment 1 in Fig. 4, prepared by example 2 DMSO,
Dissolubility in DMF, DMAC tests photo.This it appears that poly ion liquid improvement result deliquescent for polypyrrole.
Fig. 5 a, 5b respectively correspond the transmission electron microscope photo of the soluble conductive polypyrrole of embodiment 12 preparation, can see
The chondritic stacked form formed out is more close, and chondritic diameter is in 50nm or so.
Fig. 6 a, 6b, 6c corresponding embodiment 1, the conductivity of soluble conductive polyphenyl prepared by example 2 and comparative example 1, illustrate
After poly ion liquid is doped polypyrrole, sample becomes conductive from non-conductive.
The one-dimensional nucleus magnetic hydrogen spectrum map of 1 poly ion liquid PIL-Cl of Fig. 7 corresponding embodiment, wherein the peak of 2.5ppm is deuterated
The chemical shift of DMSO；3.83ppm is the chemical shift of hydrogen on the carbon being connected on imidazole group with nitrogen；4.40ppm-4.75ppm
Multiplet in range is the chemical shift of hydrogen in the secondary carbon being connected with ester group；The unimodal uncle being connected for ester group at 5.73ppm
The chemical shift of hydrogen on carbon；Multiplet within the scope of 7ppm-8ppm is the chemical shift of hydrogen on carbon on phenyl ring and imidazole ring；
Peak within the scope of 9.0ppm-9.6ppm is the chemical shift of hydrogen in the secondary carbon being respectively connected on imidazole ring with two nitrogen.
Claims (10)
1. a kind of soluble conductive polypyrrole of poly ion liquid doping, which is characterized in that preparation method includes: to protect in nitrogen
Liquor ferri trichloridi is added in the mixed solution of pyrrole monomer and poly ion liquid under shield, is reacted, obtain polyion liquid
The soluble conductive polypyrrole of body doping.
2. the soluble conductive polypyrrole of poly ion liquid doping as described in claim 1, which is characterized in that the reaction
Acid or acid solution are added without as dopant.
3. the soluble conductive polypyrrole of poly ion liquid doping as described in claim 1, which is characterized in that the pyrroles
Mass ratio with poly ion liquid is 1:1-4:1.
4. the soluble conductive polypyrrole of poly ion liquid as described in claim 1 doping, which is characterized in that it is described gather from
Sub- liquid is PIL-Cl, structural formula are as follows:
Wherein n is 10-50.
5. the preparation method of the soluble conductive polypyrrole of poly ion liquid doping of any of claims 1-3,
It is characterized in that, comprising:
Step a: water removal deoxygenation processing is carried out to reaction vessel；
Step b: pyrrole monomer and water are added into reaction vessel, stirs to get pyrrole monomer solution；
Step c: being added Iron(III) chloride hexahydrate in water, and stirring obtains liquor ferri trichloridi；
Step d: make poly ion liquid be dissolved in water then be added step b reaction vessel in, obtain pyrrole monomer and gather from
The mixed solution of sub- liquid；
Step e: under nitrogen protection by the resulting liquor ferri trichloridi of step c be added the resulting pyrrole monomer of step b and gather from
In the mixed solution of sub- liquid, reacted；
Step f: by reaction product adding into acetone obtained in step e, stirring, separation of solid and liquid is precipitated, after obtaining precipitating
Vacuum drying obtains the soluble conductive polypyrrole of poly ion liquid doping.
6. the preparation method of the soluble conductive polypyrrole of poly ion liquid doping as claimed in claim 5, which is characterized in that
The concentration of chromium solution is 5-10 grams per liter in the step b.
7. the preparation method of the soluble conductive polypyrrole of poly ion liquid doping as claimed in claim 5, which is characterized in that
The concentration of liquor ferri trichloridi is 1-5 mol/L in the step c.
8. the preparation method of the soluble conductive polypyrrole of poly ion liquid doping as claimed in claim 5, which is characterized in that
The mass ratio of pyrroles is 1-1.4:1 in poly ion liquid and step b in the step d；Mixed liquor in the step d
The concentration of poly ion liquid is 20-150 grams per liter.
9. the preparation method of the soluble conductive polypyrrole of poly ion liquid doping as claimed in claim 5, which is characterized in that
Reaction in the step e carries out under stiring, and temperature is 0-10 DEG C, and the reaction time is 3-5 hours.
10. the preparation method of the soluble conductive polypyrrole of poly ion liquid doping as claimed in claim 5, feature exist
In the volume ratio of reaction product obtained in the acetone and step e in the step f is 3-5:1.
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