CN106046371A - Polypyrrole derivative covalent functionalized graphene nano-grade hybrid nonlinear optical material and preparation method thereof - Google Patents
Polypyrrole derivative covalent functionalized graphene nano-grade hybrid nonlinear optical material and preparation method thereof Download PDFInfo
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- CN106046371A CN106046371A CN201610357139.0A CN201610357139A CN106046371A CN 106046371 A CN106046371 A CN 106046371A CN 201610357139 A CN201610357139 A CN 201610357139A CN 106046371 A CN106046371 A CN 106046371A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0611—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polypyrroles
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- G—PHYSICS
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/3523—Non-linear absorption changing by light, e.g. bleaching
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Abstract
The invention relates to the technical field of nano-grade hybrid nonlinear optical functional material, and specifically relates to a type of polypyrrole derivative functionalized graphene nano-grade hybrid nonlinear optical functional material with good nonlinear optical absorption performance, and a preparation method thereof. According to the invention, polypyrrole derivative is covalently bonded on the surface of graphene through esterification and thermal reduction reactions. Through the synergistic effect between the two, the solubility and dispersion stability of graphene in a polar organic solvent are improved, and the nonlinear optical absorption performance of graphene is enhanced. The preparation method is easy to realize. The nonlinear optical performance of the prepared nano-grade hybrid material is substantially improved. The method has important scientific research value and potential application prospect.
Description
Technical field
Present invention relates particularly to a class and there is the Polypyrrole derivatives covalent functionalization graphite of preferable non-linear absorption performance
Nanometer heterocomplex nonlinear optics functional material of alkene and preparation method thereof, belongs to military project laser protection Material Field.
Background technology
Along with the fast development of laser technology and being continuously increased of laser application, laser is except in civilian science skill
Outside the application of art, in military field, (laser weapon) also has a lot of application.In order to prevent the high intensity energy due to laser
The harm that amount and laser weapon are brought, in recent years for the research also continuous weight by national governments of laser protective material
Depending on.In terms of lasing safety, preferable optical Limiting (non-linear) material has the unrivaled advantage of traditional defense material, because
Optical limiting materials can present linear transmittance when light intensity is the highest, and transmitance diminishes when light intensity height such that it is able to
Reach preferable lasing safety effect.
After Geim first passage micromechanics stripping method in 2004 obtains single-layer graphene from graphite, people are just caused
Explosion type interest to Graphene.Graphene is because of the two-dimensional structure of its uniqueness and excellent electricity, optics, calorifics and mechanicalness
Paying close attention to of energy, extremely scientific research personnel, rapidly becomes the study hotspot of material, chemistry, physics and engineering field, but due to it
Dissolubility is poor, and its actual application is somewhat limited.Therefore, design, prepare solubility based on Graphene and have
Machine/macromolecular material becomes the graphene-based photoelectric functional material of development and the key of optics.Polypyrrole is a kind of point
The internal conducting high polymers thing with conjugated pi electron system of son, has broad application prospects in field of photoelectric material,
Can be used for energy storage material, electrochemical sensor, biomedicine, electronics and optical material etc..The linear conjugate structure of polypyrrole makes
Intramolecular has bigger conjugated pi electron system, the pi-electron in molecule can move freely, therefore in conjugated system
Polypyrrole has preferable electric conductivity and optical nonlinearity.Graphene can be grafted to by suitably design synthetic method
Surface, thus reach improve Graphene solubility property and strengthen the purpose of its nonlinear optical absorptive property.To this end, association area
Research worker carried out substantial amounts of research and probe, with attempt design, preparation there is preferable solubility property and excellent non-thread simultaneously
The graphene nano heterocomplex nonlinear optics functional material of the Polypyrrole derivatives covalent functionalization of property optical absorptive character.
Summary of the invention
It is an object of the invention to for obtain a class novel, there is preferable nonlinear optical absorption and solubility property simultaneously
The graphene nano heterocomplex nonlinear optics functional material of Polypyrrole derivatives covalent functionalization.
The graphene nano heterocomplex nonlinear optics functional material of Polypyrrole derivatives covalent functionalization, described nanometer is miscellaneous
Compound functional material is made up of redox graphene and hydroxylating Polypyrrole derivatives, described hydroxylating Polypyrrole derivatives with
Covalent bond is modified on redox graphene surface；The structure of described nanometer heterocomplex functional material is RGO-PPy:
The preparation method of described Polypyrrole derivatives covalent functionalization graphene nanometer heterocomplex nonlinear optical material, bag
Include following steps:
(1) chloride graphene oxide GOC (O) Cl is prepared:
Under nitrogen protection, thionyl chloride and N, the mixed solvent of N '-dimethyl Methanamide DMF add graphite oxide
Alkene, carries out reaction kinetic, and after reaction terminates, product is cooled, filter, wash, and obtains black powder product, is
Chloride graphene oxide GOC (O) Cl；
(2) preparation Polypyrrole derivatives PPy-OH containing hydroxyl:
Add pyrroles and hydroxy benzaldehyde, rear ultrasonic addition oxidant Ammonium persulfate. in deionized water, carry out
Polyreaction, product, through filtering, washing, obtains black powder product, is hydroxylating Polypyrrole derivatives PPy-OH；
(3) the stannic oxide/graphene nano hybrid material GO-PPy of Polypyrrole derivatives functionalization is prepared:
Under ultrasonic, in proportion by step (1) products therefrom GOC (O) Cl and step (2) product PPy-OH be suspended in
In machine polar solvent and acid binding agent, under nitrogen protection, carrying out esterification, product is cooled, filter, wash, and is gathered
The stannic oxide/graphene nano heterocomplex nonlinear optics functional material GO-PPy of azole derivatives covalent functionalization；
(4) the graphene nano hybrid material RGO-PPy of Polypyrrole derivatives functionalization is prepared
Under ultrasonic, step (3) products therefrom GO-PPy is suspended in organic polar solvent, under nitrogen protection, carries out heat
Reduction reaction, product is cooled, filter, wash, be dried, and obtains the graphene nano of Polypyrrole derivatives covalent functionalization
Heterocomplex nonlinear optics functional material RGO-PPy.
In step (1), the temperature of described reaction kinetic is 80 DEG C, and the response time is 36 hours.
In step (1), in described mixed solvent, thionyl chloride and N, the volume ratio of N '-dimethyl Methanamide is 25:1；
In step (1), described in be filtered into: by reactant mixture by 0.45 μm nylon membrane filter；Described washing is for using
Oxolane removes thionyl chloride and other impurity of excess.
In step (2), the mass ratio of described pyrroles, hydroxy benzaldehyde and oxidant Ammonium persulfate. is 4:3:4.
In step (2), described in be filtered into: by reactant mixture by 0.45 μm nylon membrane filter；Described washing is for using
Deionized water and ethanol wash away unreacted pyrroles, oxidant and other impurity.
In step (3), the mass ratio of described GOC (O) Cl and PPy-OH is 3:4.
In step (3), described organic polar solvent is DMF, and described acid binding agent is triethylamine.
In step (3), the temperature of described esterification is 80 DEG C, and the response time is 6 days.
In step (3), described in be filtered into by reactant mixture by 0.45 μm nylon membrane filter；Described washing is for make respectively
Excess PPy-OH and other impurity is removed with deionized water, dichloromethane and ethanol.
In step (4), described organic polar solvent is DMF；The temperature of described thermal reduction reaction is 150 DEG C, the response time
It it is 2 days.
In step (4), described in be filtered into by reactant mixture by 0.45 μm nylon membrane filter；Described washing is for make respectively
Wash with deionized water and ethanol；Described being dried is 50 DEG C of vacuum drying, and the time is 2 days.
Polypyrrole derivatives covalent functionalization graphene nanometer heterocomplex nonlinear optical material of the present invention, it is special
Levying and be, under 532nm, 4ns pulse laser irradiation, described RGO-PPy has preferable nonlinear optical absorptive property, it is possible to
For optical sensitive device or eye protection from laser.
The invention have the benefit that
(1) preparation method that the present invention provides is simple, with Graphene covalent bond, Polypyrrole derivatives can be formed two
Unit's nano hybridization nonlinear optics functional material.
(2) preparation method of the present invention, effectively improves Graphene dissolubility in organic polar solvent and dispersion
Stability.
(3) the Polypyrrole derivatives covalent functionalization graphene nanometer heterocomplex nonlinear optics function prepared by the present invention
Material has than single oxidation of precursor Graphene, Polypyrrole derivatives and the graphite oxide of Polypyrrole derivatives covalent functionalization
The more preferable nonlinear optical absorptive property of alkene, has extraordinary anti-laser ability.
Accompanying drawing explanation
Fig. 1 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The syntheti c route figure of functional material；
Fig. 2 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
Functional material and the infrared spectrogram of precursor thereof；
Fig. 3 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The thermogravimetric spectrogram of functional material and precursor thereof；
Fig. 4 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The Raman spectrogram of functional material and precursor graphene oxide thereof；
Fig. 5 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
Functional material and the transmission electron microscope picture of precursor graphene oxide thereof.a-GO,b-PPy,c-GO-PPy,d-RGO-PPy；
Fig. 6 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The x-ray photoelectron energy spectrogram of functional material and precursor graphene oxide thereof；
Fig. 7 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The uv-visible absorption spectra figure of functional material and precursor thereof；
Fig. 8 is the presoma related in the claims in the present invention 1 and prepared organic-inorganic materials
Nonlinear optical absorption figure.
Detailed description of the invention
Below by way of specific embodiment, present invention is described or is described further, and gives detailed embodiment
With concrete operating process, its object is to be more fully understood that the technical connotation of the present invention, but protection scope of the present invention does not limits
In following embodiment.
Embodiment 1
Step 1:
Under nitrogen protection, thionyl chloride (25mL) and N, the mixed solvent of N '-dimethyl Methanamide (1mL) add oxygen
Functionalized graphene (0.3g), under the conditions of 80 DEG C, reacts 36 hours.After reaction terminates, question response liquid is cooled to room temperature, by reactant liquor
Filter with the nylon membrane of 0.45 μm, then remove residual thionyl chloride therein with anhydrous tetrahydro furan cyclic washing, be dried
Obtain black powder product, be chloride graphene oxide GOC (O) Cl.
Step 2:
In 20mL deionized water, add pyrroles (0.2g) and hydroxy benzaldehyde (0.15g), ultrasonic uniform after add oxygen
Agent Ammonium persulfate. (0.2g), carries out polyreaction, and after reaction terminates, question response liquid is cooled to room temperature.Reactant liquor is used 0.45 μ
The nylon membrane of m filters, then removes unreacted pyrroles, oxidant with deionized water and ethanol cyclic washing and other is miscellaneous
Matter, obtains black powder product, is hydroxylating Polypyrrole derivatives PPy-OH.
Step 3:
Under nitrogen protection, in GOC (O) Cl (60mg) suspension of 50mL dry DMF, add Polypyrrole derivatives
(80mg) with 6mL triethylamine.Then react 6 days at 80 DEG C.After reaction terminates, stirring is cooled to room temperature naturally.By reactant liquor
Pour in 150mL deionized water, filter with the nylon membrane of 0.45 μm, more respectively with deionized water, dichloromethane and ethanol
Washing, to remove reaction raw materials Polypyrrole derivatives and other impurity of excess, dried in vacuum overnight, i.e. obtains polypyrrole and derives
The stannic oxide/graphene nano heterocomplex nonlinear optics functional material GO-PPy of thing covalent functionalization.
Step 4:
Under ultrasonic, embodiment 3 products therefrom GO-PPy (40mg) is suspended in DMF (50mL), under nitrogen protection,
150 DEG C carry out thermal reduction reaction 2 days, after reactant is cooled to room temperature, are poured into by reactant liquor in 150mL deionized water, use
The nylon membrane of 0.45 μm filters, more respectively by deionized water and washing with alcohol, is vacuum dried 2 days, is i.e. gathered at 50 DEG C
The graphene nano heterocomplex nonlinear optics functional material RGO-PPy of azole derivatives covalent functionalization.
The graphene nano heterocomplex nonlinear optics merit of the Polypyrrole derivatives covalent functionalization prepared by Fig. 1 present invention
The syntheti c route figure of energy material；
Fig. 2 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
Functional material and the infrared spectrogram of precursor thereof；This infrared spectrogram shows that Polypyrrole derivatives covalent modification is at Graphene table
Face.
Fig. 3 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The thermogravimetric spectrogram of functional material and precursor thereof；This thermogravimetric spectrogram shows that Polypyrrole derivatives covalent modification is at graphene oxide table
Face.
Fig. 4 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The Raman spectrogram of functional material and precursor graphene oxide thereof；This Raman spectrum figure shows that Polypyrrole derivatives covalent modification is at oxygen
Functionalized graphene surface.
Fig. 5 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
Functional material and the transmission electron microscope picture of precursor graphene oxide thereof.a-GO,b-PPy,c-GO-PPy,d-RGO-PPy.
Fig. 6 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The x-ray photoelectron energy spectrogram of functional material and precursor graphene oxide thereof.This bright polypyrrole of x-ray photoelectron power spectrum graphs
Derivant covalent modification is in surface of graphene oxide.
Fig. 7 is the graphene nano heterocomplex nonlinear optics of the Polypyrrole derivatives covalent functionalization prepared by the present invention
The uv-visible absorption spectra figure of functional material and precursor thereof；This ultraviolet visible absorption spectra figure shows: Polypyrrole derivatives
Covalent modification is at graphenic surface and there is therebetween π-π interaction.
Fig. 8 is the presoma related in the claims in the present invention 1 and prepared organic-inorganic materials
Nonlinear optical absorption figure.This spectrogram shows prepared Polypyrrole derivatives covalent functionalization graphene nanometer heterocomplex non-thread
Property optical functional materials has than single oxidation of precursor Graphene, Polypyrrole derivatives and Polypyrrole derivatives covalent functionalization
The more preferable nonlinear optical absorptive property of graphene oxide, there is extraordinary anti-laser ability.
Claims (10)
1. the nonlinear optical material of Polypyrrole derivatives covalent functionalization graphene, it is characterised in that by reduction-oxidation graphite
Alkene and hydroxylating Polypyrrole derivatives, described hydroxylating Polypyrrole derivatives is modified at redox graphene table with covalent bond
Face, structural formula is:
The preparation side of the nonlinear optical material of Polypyrrole derivatives covalent functionalization graphene the most according to claim 1
Method, it is characterised in that comprise the steps:
(1) chloride graphene oxide GOC (O) Cl is prepared:
Under nitrogen protection, thionyl chloride and N, the mixed solvent of N '-dimethyl Methanamide DMF add graphene oxide, enters
Row reaction kinetic, after reaction terminates, product is cooled, filter, wash, and obtains black powder product, is acyl chlorides
Change graphene oxide GOC (O) Cl；
(2) preparation Polypyrrole derivatives PPy-OH containing hydroxyl:
Add pyrroles and hydroxy benzaldehyde, rear ultrasonic addition oxidant Ammonium persulfate. in deionized water, be polymerized
Reaction, product, through filtering, washing, obtains black powder product, is hydroxylating Polypyrrole derivatives PPy-OH；
(3) the stannic oxide/graphene nano hybrid material GO-PPy of Polypyrrole derivatives functionalization is prepared:
Under ultrasonic, in proportion by step (1) products therefrom GOC (O) Cl and step (2) product PPy-OH be suspended in organic pole
Property solvent and acid binding agent in, under nitrogen protection, carry out esterification, product is cooled, filter, wash, and obtains polypyrrole
The stannic oxide/graphene nano heterocomplex nonlinear optics functional material GO-PPy of derivant covalent functionalization；
(4) the graphene nano hybrid material RGO-PPy of Polypyrrole derivatives functionalization is prepared:
Under ultrasonic, step (3) products therefrom GO-PPy is suspended in organic polar solvent, under nitrogen protection, carries out thermal reduction
Reaction, product is cooled, filter, wash, be dried, and obtains the graphene nano heterozygosis of Polypyrrole derivatives covalent functionalization
Thing nonlinear optics functional material RGO-PPy.
Preparation method the most according to claim 2, it is characterised in that in step (1), the temperature of described reaction kinetic is
80 DEG C, the response time is 36 hours.
Preparation method the most according to claim 2, it is characterised in that in step (1), in described mixed solvent, protochloride
Sulfone and N, the volume ratio of N '-dimethyl Methanamide is 25:1；Described it is filtered into: by reactant mixture by 0.45 μm nylon membrane mistake
Filter；Described washing is thionyl chloride and other impurity using oxolane to remove excess.
Preparation method the most according to claim 2, it is characterised in that in step (2), described pyrroles, hydroxy benzaldehyde
It is 4:3:4 with the mass ratio of oxidant Ammonium persulfate..
Preparation method the most according to claim 2, it is characterised in that in step (2), described in be filtered into: by reaction mix
Thing is filtered by 0.45 μm nylon membrane；Described washing for use deionized water and ethanol wash away unreacted pyrroles, oxidant and
Other impurity.
Preparation method the most according to claim 2, it is characterised in that in step (3), described GOC (O) Cl's and PPy-OH
Mass ratio is 3:4；Described organic polar solvent is DMF, and described acid binding agent is triethylamine.
Preparation method the most according to claim 2, it is characterised in that in step (3), the temperature of described esterification is 80
DEG C, the response time is 6 days；Reactant mixture is filtered by described being filtered into by 0.45 μm nylon membrane；Described washing is for make respectively
Excess PPy-OH and other impurity is removed with deionized water, dichloromethane and ethanol.
Preparation method the most according to claim 2, it is characterised in that in step (4), described organic polar solvent is DMF；
The temperature of described thermal reduction reaction is 150 DEG C, and the response time is 2 days；Reactant mixture is passed through 0.45 μm Buddhist nun by described being filtered into
Dragon membrane filtration；Described washing is washed for using deionized water and ethanol respectively；Described being dried is 50 DEG C of vacuum drying, the time
It it is 2 days.
Polypyrrole derivatives covalent functionalization graphene nanometer heterocomplex nonlinear optics material the most according to claim 1
Material, it is characterised in that under 532nm, 4ns pulse laser irradiation, described RGO-PPy has preferable nonlinear optical absorption
Can, it is possible to for optical sensitive device or eye protection from laser.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107056822A (en) * | 2017-05-23 | 2017-08-18 | 江苏大学 | Porphyrin N doping redox graphene nonlinear optical material and preparation method thereof |
| CN108047406A (en) * | 2017-12-15 | 2018-05-18 | 福州大学 | A kind of preparation method of graphene/polypyrrole methylene third-order nonlinear optical composite material |
| CN113077919A (en) * | 2021-03-25 | 2021-07-06 | 徐州医科大学 | Metal Pd-loaded graphene/polypyrrole composite material and preparation method and application thereof |
| CN115348995A (en) * | 2020-03-31 | 2022-11-15 | 多佛欧洲公司 | Ink composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140133000A1 (en) * | 2012-11-12 | 2014-05-15 | Samsung Electronics Co., Ltd. | Photorefractive polymer composite, and photorefractive device and hologram display device including the same |
| CN105218556A (en) * | 2015-09-25 | 2016-01-06 | 江苏大学 | Porphyrin-redox graphene nonlinear optical material and preparation method thereof |
| CN105254640A (en) * | 2015-09-25 | 2016-01-20 | 江苏大学 | Stannum porphyrin axial covalent functionalized reduced graphene oxide nonlinear optical materials, and preparation method thereof |
-
2016
- 2016-05-26 CN CN201610357139.0A patent/CN106046371A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140133000A1 (en) * | 2012-11-12 | 2014-05-15 | Samsung Electronics Co., Ltd. | Photorefractive polymer composite, and photorefractive device and hologram display device including the same |
| CN105218556A (en) * | 2015-09-25 | 2016-01-06 | 江苏大学 | Porphyrin-redox graphene nonlinear optical material and preparation method thereof |
| CN105254640A (en) * | 2015-09-25 | 2016-01-20 | 江苏大学 | Stannum porphyrin axial covalent functionalized reduced graphene oxide nonlinear optical materials, and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 虞王: ""基于石墨烯的光限幅功能材料的设计和制备"", 《万方数据》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107056822A (en) * | 2017-05-23 | 2017-08-18 | 江苏大学 | Porphyrin N doping redox graphene nonlinear optical material and preparation method thereof |
| CN107056822B (en) * | 2017-05-23 | 2019-05-31 | 江苏大学 | Porphyrin-N doping redox graphene nonlinear optical material and preparation method thereof |
| CN108047406A (en) * | 2017-12-15 | 2018-05-18 | 福州大学 | A kind of preparation method of graphene/polypyrrole methylene third-order nonlinear optical composite material |
| CN108047406B (en) * | 2017-12-15 | 2019-06-07 | 福州大学 | A kind of preparation method of graphene/polypyrrole methylene third-order nonlinear optical composite material |
| CN115348995A (en) * | 2020-03-31 | 2022-11-15 | 多佛欧洲公司 | Ink composition |
| CN113077919A (en) * | 2021-03-25 | 2021-07-06 | 徐州医科大学 | Metal Pd-loaded graphene/polypyrrole composite material and preparation method and application thereof |
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Application publication date: 20161026 |