CN106990154B - A kind of method and its application by adulterating camphorsulfonic acid radical ion synthesis of chiral conducting polymer - Google Patents
A kind of method and its application by adulterating camphorsulfonic acid radical ion synthesis of chiral conducting polymer Download PDFInfo
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- CN106990154B CN106990154B CN201710129976.2A CN201710129976A CN106990154B CN 106990154 B CN106990154 B CN 106990154B CN 201710129976 A CN201710129976 A CN 201710129976A CN 106990154 B CN106990154 B CN 106990154B
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- -1 camphorsulfonic acid radical ion Chemical class 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 23
- 229920001940 conductive polymer Polymers 0.000 title abstract description 11
- 239000002322 conducting polymer Substances 0.000 title abstract description 10
- 230000015572 biosynthetic process Effects 0.000 title abstract description 6
- 238000003786 synthesis reaction Methods 0.000 title abstract description 6
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
- 229920000128 polypyrrole Polymers 0.000 claims description 23
- 238000002474 experimental method Methods 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 229910052697 platinum Inorganic materials 0.000 claims description 13
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 12
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 11
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 238000002484 cyclic voltammetry Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000008055 phosphate buffer solution Substances 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 17
- 239000002131 composite material Substances 0.000 abstract description 13
- 239000012528 membrane Substances 0.000 abstract description 9
- 229920006254 polymer film Polymers 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 8
- 230000005611 electricity Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- 241000723346 Cinnamomum camphora Species 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000005557 chiral recognition Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000005518 electrochemistry Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003759 clinical diagnosis Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000840 electrochemical analysis Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
-
- 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
- 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
Abstract
The method and its application that the present invention relates to a kind of by adulterating camphorsulfonic acid radical ion synthesis of chiral conducting polymer, comprising the following steps: the polymer film, peroxidating composite membrane of polymer, electrochemical process that electropolymerization adulterates camphorsulfonic acid radical ion identify Tryptophan enantiomer.The beneficial effects of the present invention are: method is simple for preparation doping camphorsulfonic acid radical ion polymer, preparation process is environment friendly and pollution-free, and the peroxidating composite membrane of polymer modified electrode can efficiently identify Tryptophan enantiomer.
Description
Technical field
The method and its application that the present invention relates to a kind of by adulterating camphorsulfonic acid radical ion synthesis of chiral conducting polymer,
Belong to electrochemical analysis and field of biotechnology.
Background technique
Due to the emergence of chiral engineering, so developing the economy, being quick, sensitive and real-time chiral Recognition technology seems very
It is necessary.It is raw to can be applied to process detection, process control and clinical diagnosis etc. for the chiral sensor development trend important as one
It generates in living, causes the extensive concern of people.
Conducting polymer is also known as conducting polymer, refers to through means such as doping, can make conductivity in semiconductor and lead
Polymer within the scope of body.It is often referred to intrinsic conducting polymer, contains alternate singly-bound and double bond on this kind of main polymer chains,
So as to form big conjugated π system.A possibility that flowing of pi-electron produces conduction.The not conduction Jing Guo doping treatment
Polymer conductivity is very low, belongs to insulator.Conducting polymer materials not only have the items of metal and inorganic semiconductor special
Property, also there is electrochemical redox activity.Common conductive polymer electrodes material has: polyaniline, polypyrrole, polythiophene
Deng.
As the chiral conducting high polymers object for having started chiral macromolecular uncharted field, scientific researcher is produced
Great attraction.The advantages of chiral conducting high polymers object is: electric conductivity is good；In solution, it is good that it can be embodied
The ability that changes of receiving pH value；In solution, there is outstanding oxidation-reduction quality；Good chiral selectivity；It is excellent
Molecule distinguishability.These abilities make it in the future in electrochemical switch, chiral chromatogram, chiral chemistry sensor, film layer analysis
The fields such as technology and Surface Modified Electrodes obtain broad development.When chiral to having as chiral matrix or chiral electrode material
Electrically conductive organic polymer polymer carries out in use, there are the latter unique mechanics, electricity and electrochemical properties can use
It is represented in journey.Using the characteristic that can be adsorbed by polymer backbone functional group, the intracorporal film of particle, animals and plants and nanometer
Fiber etc. can make with them, using these functions, can open up on identification, the purification of specific molecular are carried out wider
Wealthy space.
Camphorsulfonic acid is a kind of chiral organic acid, and natural camphor is to make raw material with camphor tree, through steam distillation, fractionation and liter
What the operations such as China obtained, be d-isomer, synthetic product is raceme.10- camphorsulfonic acid is that camphor is obtained by sulfonating reaction
's.
The present invention selects monomer molecule to be doped processing as host material, and chiral anion is doped to monomer molecule
Polymerization reaction in.Experiment polymerize monomer molecule in (+) -10- camphorsulfonic acid aqueous solution by electrochemical means, shape
At the composite membrane of polymer material that camphorsulfonic acid radical ion adulterates, and it is applied to electrochemical recognition Tryptophan enantiomer.
Summary of the invention
It is an object of the invention to which chiral anion to be doped in the polymerization reaction of monomer molecule, synthesis of chiral conduction is poly-
It closes object and is applied to the research of electrochemistry chiral Recognition.
A kind of method and its application by adulterating camphorsulfonic acid radical ion synthesis of chiral conducting polymer of the present invention,
The following steps are included:
A, monomer molecule the polymer film of electropolymerization doping camphorsulfonic acid radical ion: is dissolved in (+) -10- camphorsulfonic acid
It is uniformly mixed in solution and is configured to monomer mixed solution, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is work electricity
Pole, platinum plate electrode are to electrode, and saturated calomel electrode (SCE) is reference electrode, is dipped in mixed liquor, applies corresponding electric current
Galvanostatic polymerization is carried out, the polymer film modified electrode of doping camphorsulfonic acid radical ion is obtained.
B, peroxidating composite membrane of polymer: experiment uses three-electrode system, and composite membrane of polymer modified electrode is work electricity
Pole, platinum plate electrode are to electrode, and saturated calomel electrode (SCE) is reference electrode, is dipped in phosphate buffer solution, is carried out
Cyclic voltammetry scan obtains the composite membrane of polymer modified electrode of peroxidating.
C, electrochemical process identifies Tryptophan enantiomer: experiment uses three-electrode system, the modification of peroxidating composite membrane of polymer
Electrode is working electrode, and platinum plate electrode is to electrode, and saturated calomel electrode (SCE) is reference electrode, it is immersed to preparation respectively
L-/D- tryptophan solution in, after standing carry out differential pulse scanning.
Further, the concentration of (+) -10- camphorsulfonic acid is 0.01~0.5M in mixed liquor in step a, and the concentration of monomer is
0.05~2.0M carries out Galvanostatic polymerization, and application electric current is 0.3mA, and the electropolymerization time is 10~600s.
Further, the concentration of phosphate buffer solution is 0.1M in step b, and pH is 7.0~8.0.
Further, the concentration of L-/D- tryptophan solution is 0.1~10mM in step c, and time of repose is 2~180s.
The beneficial effects of the present invention are: method is simple for preparation doping camphorsulfonic acid radical ion polymer, prepared
Journey is environment friendly and pollution-free, and the peroxidating composite membrane of polymer modified electrode can efficiently identify Tryptophan enantiomer.
Detailed description of the invention
This experiment is further illustrated with reference to the accompanying drawing.
Fig. 1 is the scanning electron microscope (SEM) photograph of the doping camphorsulfonic acid radical ion polypyrrole film of galvanostatic method polymerization in embodiment one.
Fig. 2 is the complex film modified electrode tryptophan enantiomer of overoxidised polypyrrole of galvanostatic method polymerization in embodiment one
Recognition effect figure.
Fig. 3 is the complex film modified electrode tryptophan mapping of overoxidised polypyrrole of cyclic voltammetry polymerization in comparative example one
The recognition effect figure of body.
Fig. 4 is the recognition effect figure of (+) -10- camphorsulfonic acid modified electrode tryptophan enantiomer in comparative example two.
Specific embodiment
Presently in connection with specific embodiment, the invention will be further described, following embodiment be intended to illustrate invention rather than
Limitation of the invention further.
Peroxidating composite membrane of polymer modified electrode tryptophan enantiomer of the present invention is identified as follows:
RL/D=IL/ID
Δ E=ED-EL
In formula, RL/DIndicate that Tryptophan enantiomer peak current ratio, Δ E indicate Tryptophan enantiomer peak voltage difference, ILWith
IDRespectively indicate L-Trp and D-trp peak point current, ELAnd EDRespectively indicate L-Trp and D-trp peak voltage value.
Embodiment one:
The composite polypyrrole film modified electrode of galvanostatic method preparation doping camphorsulfonic acid radical ion including the following steps:
(1) 0.15M pyrrole monomer is dissolved in be uniformly mixed in 0.045M (+) -10- camphorsulfonic acid solution and is configured to monomer
Mixed liquor, experiment use three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is to be saturated sweet to electrode
Mercury electrode (SCE) is reference electrode, is dipped in mixed liquor and carries out Galvanostatic polymerization, and applications electric current is 0.3mA, when electropolymerization
Between be 60s, obtain doping camphorsulfonic acid radical ion polypyrrole film modified electrode.
(2) experiment uses three-electrode system, and composite polypyrrole film modified electrode is working electrode, and platinum plate electrode is to electricity
Pole, saturated calomel electrode (SCE) are reference electrode, are dipped in 0.1M pH=7.0 phosphate buffer solution, in 0~1.2V
(vs.SCE) within the scope of electrochemical window, cyclic voltammetric 40 is swept with the speed of 0.1V/s and is enclosed, the polypyrrole for obtaining peroxidating is multiple
Close film modified electrode.
(3) experiment uses three-electrode system, and the complex film modified electrode of overoxidised polypyrrole is working electrode, and platinum plate electrode is
To electrode, saturated calomel electrode (SCE) is reference electrode, it is immersed respectively in the 1.0mM L-/D- tryptophan solution of preparation,
Differential pulse scanning is carried out after standing 90s, the recognition effect figure of Tryptophan enantiomer is shown in Fig. 2.As can be seen from the figure constant current
The complex film modified electrode of overoxidised polypyrrole of method preparation has preferable recognition effect, I to L-TrpL/IDIt is 9.37.
Comparative example one:
The composite polypyrrole film modified electrode of cyclic voltammetry preparation doping camphorsulfonic acid radical ion includes following step
It is rapid:
(1) 0.15M pyrrole monomer is dissolved in be uniformly mixed in 0.045M (+) -10- camphorsulfonic acid solution and is configured to monomer
Mixed liquor, experiment use three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is to be saturated sweet to electrode
Mercury electrode (SCE) is reference electrode, is dipped in mixed liquor, in the electrochemical window range of -0.6~0.8V (vs.SCE)
It is interior, cyclic voltammetric 5 is swept with the speed of 0.1V/s and is enclosed, the polypyrrole film modified electrode of doping camphorsulfonic acid radical ion is obtained.
(2) experiment uses three-electrode system, and composite polypyrrole film modified electrode is working electrode, and platinum plate electrode is to electricity
Pole, saturated calomel electrode (SCE) are reference electrode, are dipped in 0.1M pH=7.0 phosphate buffer solution, in 0~1.2V
(vs.SCE) within the scope of electrochemical window, cyclic voltammetric 40 is swept with the speed of 0.1V/s and is enclosed, the polypyrrole for obtaining peroxidating is multiple
Close film modified electrode.
(3) experiment uses three-electrode system, and the complex film modified electrode of overoxidised polypyrrole is working electrode, and platinum plate electrode is
To electrode, saturated calomel electrode (SCE) is reference electrode, it is immersed respectively in the 1.0mM L-/D- tryptophan solution of preparation,
Differential pulse scanning is carried out after standing 90s, the recognition effect figure of Tryptophan enantiomer is shown in Fig. 3, IL/IDIt is 5.05.
Comparative example two:
Potentiostatic method prepares (+) -10- camphorsulfonic acid modified electrode including the following steps:
(1) experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is to satisfy to electrode
It is reference electrode with calomel electrode (SCE), is dipped in 0.045M (+) -10- camphorsulfonic acid solution of preparation, using permanent electricity
(+) -10- camphorsulfonic acid modified electrode is prepared in position method, the potential deposition 600s of application+1.0V.
(2) (+) -10- camphorsulfonic acid modified electrode prepared is used for the identification of Tryptophan enantiomer, by the modified electrode point
It does not immerse in the 1.0mM L-/D- tryptophan solution of preparation, as shown in figure 4, IL/IDIt is 1.86.
Chiral anion is doped in the polymerization reaction of monomer molecule by the present invention by electrochemical means, has synthesized chirality
Conducting polymer and the research for being applied to electrochemistry chiral Recognition.The result shows that the peroxidating polymerization of galvanostatic method preparation
The complex film modified electrode of object has high recognition efficiency to L-Trp, and modified electrode or single camphor tree than cyclic voltammetry preparation
Brain sulfonic Acid Modified Electrode possesses more excellent recognition effect.
Claims (4)
1. a kind of method of electrochemical recognition tryptophan enantiomter, it is characterised in that: steps are as follows:
A, the polypyrrole film of electropolymerization doping camphorsulfonic acid radical ion: by pyrrole monomer molecular melting in (+) -10- camphorsulfonic acid
It being uniformly mixed in solution and is configured to mixed liquor, experiment uses three-electrode system, and the glass-carbon electrode that diameter is 3mm is working electrode,
Platinum plate electrode is to electrode, and saturated calomel electrode (SCE) is reference electrode, is dipped in mixed liquor, apply corresponding electric current into
Row Galvanostatic polymerization obtains the polypyrrole film modified electrode of doping camphorsulfonic acid radical ion；
B, overoxidized polypyrrole film: experiment uses three-electrode system, adulterates the polypyrrole film modified electrode of camphorsulfonic acid radical ion
For working electrode, platinum plate electrode is to electrode, and saturated calomel electrode (SCE) is reference electrode, and it is molten to be dipped in phosphate-buffered
In liquid, cyclic voltammetry scan is carried out, obtains the polypyrrole film modified electrode of the doping camphorsulfonic acid radical ion of peroxidating；
C, electrochemical process identifies Tryptophan enantiomer: experiment uses three-electrode system, the doping camphorsulfonic acid radical ion of peroxidating
Polypyrrole film modified electrode be working electrode, platinum plate electrode is to electrode, and saturated calomel electrode (SCE) is reference electrode, will
It is immersed respectively in the L-/D- tryptophan solution of preparation, and differential pulse scanning is carried out after standing.
2. a kind of method of electrochemical recognition tryptophan enantiomter according to claim 1, it is characterized in that: the step
The concentration of (+) -10- camphorsulfonic acid is 0.01~0.5M in mixed liquor in a, and the concentration of pyrrole monomer is 0.05~2.0M, is carried out
Galvanostatic polymerization, application electric current are 0.3mA, and the electropolymerization time is 10~600s.
3. a kind of method of electrochemical recognition tryptophan enantiomter according to claim 1, it is characterized in that: the step
It is 0.1M, pH 7.0 that the polypyrrole film modified electrode that camphorsulfonic acid radical ion is adulterated in b, which immerses the concentration of phosphate buffer solution,
~8.0, carry out cyclic voltammetry scan.
4. a kind of method of electrochemical recognition tryptophan enantiomter according to claim 1, it is characterized in that: the step
The polypyrrole film modified electrode of the doping camphorsulfonic acid radical ion of peroxidating in c immerses the concentration of L-/D- tryptophan solution respectively
For 0.1~10mM, time of repose is 2~180s.
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Effective date of registration: 20240116 Address after: 710000 Factory Building 5, South Zone 1, Hongshengxing Aviation Technology Industrial Park, Dunhua Road, Airport New City, Xixian New District, Xi'an City, Shaanxi Province Patentee after: Xi'an Meinan Biotechnology Co.,Ltd. Address before: 230000 floor 1, building 2, phase I, e-commerce Park, Jinggang Road, Shushan Economic Development Zone, Hefei City, Anhui Province Patentee before: Dragon totem Technology (Hefei) Co.,Ltd. Effective date of registration: 20240116 Address after: 230000 floor 1, building 2, phase I, e-commerce Park, Jinggang Road, Shushan Economic Development Zone, Hefei City, Anhui Province Patentee after: Dragon totem Technology (Hefei) Co.,Ltd. Address before: Gehu Lake Road Wujin District 213164 Jiangsu city of Changzhou province No. 1 Patentee before: CHANGZHOU University |
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