CN106990154A - A kind of method and its application by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates - Google Patents
A kind of method and its application by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates Download PDFInfo
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- CN106990154A CN106990154A CN201710129976.2A CN201710129976A CN106990154A CN 106990154 A CN106990154 A CN 106990154A CN 201710129976 A CN201710129976 A CN 201710129976A CN 106990154 A CN106990154 A CN 106990154A
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- camphorsulfonic acid
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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 22
- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 15
- 239000002322 conducting polymer Substances 0.000 title claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 21
- 239000002131 composite material Substances 0.000 claims abstract description 18
- 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 16
- 239000012528 membrane Substances 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 229920006254 polymer film Polymers 0.000 claims abstract description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 16
- 238000002474 experimental method Methods 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 15
- 229910052697 platinum Inorganic materials 0.000 claims description 13
- 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
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000002484 cyclic voltammetry Methods 0.000 claims description 5
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 claims description 3
- 239000008055 phosphate buffer solution Substances 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 238000007654 immersion Methods 0.000 claims 1
- 239000007788 liquid Substances 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
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 229920000128 polypyrrole Polymers 0.000 description 15
- 230000000694 effects Effects 0.000 description 8
- 230000005611 electricity Effects 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 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
- 238000005516 engineering process Methods 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
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000005518 electrochemistry Effects 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
- 239000008363 phosphate buffer Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004065 semiconductor Substances 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 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta 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
- 150000001875 compounds Chemical class 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
- 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
- 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 present invention relates to a kind of method and its application by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates, comprise the following steps：Polymer film, peroxidating composite membrane of polymer, the electrochemical process identification Tryptophan enantiomer of electropolymerization doping camphorsulfonic acid radical ion.The beneficial effects of the invention are as follows：Preparing doping camphorsulfonic acid radical ion polymer, method is simple, and preparation process is environment friendly and pollution-free, and the peroxidating composite membrane of polymer modified electrode can efficiently recognize Tryptophan enantiomer.
Description
Technical field
The present invention relates to a kind of method and its application by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates,
Belong to electrochemical analysis and biological technical field.
Background technology
Due to the emergence of chiral engineering, so developing the economy, quick, sensitive and real-time chiral Recognition technology seems very
It is necessary.Chiral sensor can be applied to process detection, process control and clinical diagnosis etc. raw as an important development trend
Produce in living, cause the extensive concern of people.
Conducting polymer is also known as conducting polymer, refers to by means such as doping, can cause electrical conductivity in semiconductor and lead
Polymer in the range of body.Intrinsic conducting polymer is often referred to, alternate singly-bound and double bond are contained on this Type of Collective owner's chain,
So as to form big conjugated pi system.The flowing of pi-electron generates the possibility of conduction.The not no 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 with electrochemical redox activity.Conventional conductive polymer electrodes material has：Polyaniline, polypyrrole, polythiophene
Deng.
As the chiral conducting high polymers thing for having started chiral macromolecular uncharted field, scientific researcher is generated
Great attraction.The advantage of chiral conducting high polymers thing is：Electric conductivity is good；In solution, its can be embodied good
Bear the ability that pH value changes；In solution, with 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 field such as technology and Surface Modified Electrodes obtains broad development.When as chiral matrix or chiral electrode material to possessing chirality
Electrically conductive organic polymer polymer is carried 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, film and nanometer in particulate, animal and plant body
Fiber etc. can make with them, using these functions, can open up wider on identification, the purification of specific molecular are carried out
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
The operation such as China is obtained, and is d-isomer, synthetic product is raceme.10- camphorsulfonic acids are that camphor is obtained by sulfonating reaction
's.
The present invention is doped processing from monomer molecule as host material, and chiral anion is doped into monomer molecule
Polymerisation in.Experiment makes monomer molecule be polymerize in (+) -10- camphorsulfonic acid aqueous solution by electrochemical means, shape
The composite membrane of polymer material adulterated into camphorsulfonic acid radical ion, and applied to electrochemical recognition Tryptophan enantiomer.
The content of the invention
It is an object of the invention to which chiral anion is doped in the polymerisation of monomer molecule, synthesis of chiral conduction is poly-
Compound and the research for being applied to electrochemistry chiral Recognition.
A kind of method and its application by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates of the present invention,
Comprise the following steps：
A, electropolymerization doping camphorsulfonic acid radical ion polymer film：Monomer molecule is dissolved in (+) -10- camphorsulfonic acids
It is well mixed in solution and is configured to monomer mixed solution, experiment uses three-electrode system, glass-carbon electrode (diameter 3mm) is work electricity
Pole, platinum plate electrode is that, to electrode, saturated calomel electrode (SCE) is reference electrode, is dipped in mixed liquor, applies phase induced 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 is that, to electrode, 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 identification Tryptophan enantiomer：Experiment uses three-electrode system, the modification of peroxidating composite membrane of polymer
Electrode is working electrode, and platinum plate electrode is that, to electrode, saturated calomel electrode (SCE) is reference electrode, and it is immersed to preparation respectively
L-/D- tryptophan solutions in, after standing carry out differential pulse scanning.
Further, the concentration of (+) -10- camphorsulfonic acids 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 solutions is 0.1~10mM in step c, and time of repose is 2~180s.
The beneficial effects of the invention are as follows：Preparing doping camphorsulfonic acid radical ion polymer, method is simple, prepared
Journey is environment friendly and pollution-free, and the peroxidating composite membrane of polymer modified electrode can efficiently recognize Tryptophan enantiomer.
Brief description of the drawings
This experiment is further illustrated below in conjunction with the accompanying drawings.
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 pair 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 enantiomers in comparative example two.
Embodiment
Presently in connection with specific embodiment, the invention will be further described, following examples 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/DTryptophan enantiomer peak current ratio is represented, Δ E represents Tryptophan enantiomer peak voltage difference, ILWith
IDL-Trp and D-trp peak point current, E are represented respectivelyLAnd EDL-Trp and D-trp peak magnitude of voltage are represented respectively.
Embodiment one：
The composite polypyrrole film modified electrode that galvanostatic method prepares doping camphorsulfonic acid radical ion includes following steps：
(1) 0.15M pyrrole monomers are dissolved in be well mixed in 0.045M (+) -10- camphorsulfonic acid solution and are configured to monomer
Mixed liquor, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is that saturation is sweet to electrode
Mercury electrode (SCE) is reference electrode, is dipped in mixed liquor and carries out Galvanostatic polymerization, and application electric current is 0.3mA, during electropolymerization
Between be 60s, obtain adulterate 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) is reference electrode, is dipped in 0.1M pH=7.0 phosphate buffer solutions, in 0~1.2V
(vs.SCE) in the range of electrochemical window, cyclic voltammetric 40 is swept with 0.1V/s speed and enclosed, the polypyrrole for obtaining peroxidating is answered
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, during saturated calomel electrode (SCE) is reference electrode, the 1.0mM L-/D- tryptophan solutions that it is immersed to preparation respectively,
Stand and differential pulse scanning is carried out after 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 pair L-Trp of overoxidised polypyrrole prepared by method has preferable recognition effect, IL/IDFor 9.37.
Comparative example one：
The composite polypyrrole film modified electrode that cyclic voltammetry prepares doping camphorsulfonic acid radical ion includes following step
Suddenly：
(1) 0.15M pyrrole monomers are dissolved in be well mixed in 0.045M (+) -10- camphorsulfonic acid solution and are configured to monomer
Mixed liquor, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is that saturation is sweet to electrode
Mercury electrode (SCE) is reference electrode, is dipped in mixed liquor, in -0.6~0.8V (vs.SCE) electrochemical window scope
It is interior, cyclic voltammetric 5 is swept with 0.1V/s speed and 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) is reference electrode, is dipped in 0.1M pH=7.0 phosphate buffer solutions, in 0~1.2V
(vs.SCE) in the range of electrochemical window, cyclic voltammetric 40 is swept with 0.1V/s speed and enclosed, the polypyrrole for obtaining peroxidating is answered
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, during saturated calomel electrode (SCE) is reference electrode, the 1.0mM L-/D- tryptophan solutions that it is immersed to preparation respectively,
Stand and differential pulse scanning is carried out after 90s, the recognition effect figure of Tryptophan enantiomer is shown in Fig. 3, IL/IDFor 5.05.
Comparative example two：
Potentiostatic method, which prepares (+) -10- camphorsulfonic acids modified electrode, includes following steps：
(1) experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is, to electrode, to satisfy
It is reference electrode with calomel electrode (SCE), is dipped in 0.045M (+) -10- camphorsulfonic acid solution of preparation, using permanent electricity
Position method, application+1.0V potential deposition 600s prepares (+) -10- camphorsulfonic acid modified electrodes.
(2) (+) -10- camphorsulfonic acids modified electrode prepared is used for the identification of Tryptophan enantiomer, by the modified electrode point
In the 1.0mM L-/D- tryptophan solutions for not immersing preparation, as shown in figure 4, IL/IDFor 1.86.
Chiral anion is doped in the polymerisation 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.As a result show, peroxidating polymerization prepared by galvanostatic method
The complex film modified electrode pair L-Trp of thing has high recognition efficiency, and the modified electrode prepared than cyclic voltammetry or single camphor tree
Brain sulfonic Acid Modified Electrode possesses more excellent recognition effect.
Claims (4)
1. a kind of method and its application by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates, it is characterised in that：
Step is as follows：
A, electropolymerization doping camphorsulfonic acid radical ion polymer film：Monomer molecule is dissolved in (+) -10- camphorsulfonic acid solution
In be well mixed and be configured to monomer mixed solution, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, platinum
Plate electrode is that, to electrode, saturated calomel electrode (SCE) is reference electrode, is dipped in mixed liquor, applies phase induced current and carries out
Galvanostatic polymerization, obtains the polymer film modified electrode of doping camphorsulfonic acid radical ion.
B, peroxidating composite membrane of polymer：Experiment uses three-electrode system, and composite membrane of polymer modified electrode is working electrode, platinum
Plate electrode is that, to electrode, saturated calomel electrode (SCE) is reference electrode, is dipped in phosphate buffer solution, is circulated
Voltammetric scan, obtains the composite membrane of polymer modified electrode of peroxidating.
C, electrochemical process identification Tryptophan enantiomer：Experiment uses three-electrode system, peroxidating composite membrane of polymer modified electrode
For working electrode, platinum plate electrode is that, to electrode, saturated calomel electrode (SCE) is reference electrode, it is immersed respectively the L- of preparation/
In D-trp solution, differential pulse scanning is carried out after standing.
2. according to claim 1 a kind of method by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates and its
Using, it is characterized in that：The concentration of (+) -10- camphorsulfonic acids is 0.01~0.5M, the concentration of monomer in mixed liquor in the step a
For 0.05~2.0M, Galvanostatic polymerization is carried out, application electric current is 0.3mA, and the electropolymerization time is 10~600s.
3. according to claim 1 a kind of method by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates and its
Using, it is characterized in that：The polymer film modified electrode immersion phosphate-buffered of doping camphorsulfonic acid radical ion is molten in the step b
The concentration of liquid is 0.1M, and pH is 7.0~8.0, carries out cyclic voltammetry scan.
4. according to claim 1 a kind of method by the camphorsulfonic acid radical ion synthesis of chiral conducting polymer that adulterates and its
Using, it is characterized in that：Peroxidating composite membrane of polymer modified electrode immerses L-/D- tryptophan solutions respectively in the step c
Concentration is 0.1~10mM, and time of repose is 2~180s.
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| CN113559318A (en) * | 2021-07-05 | 2021-10-29 | 四川大学 | Chiral conductive repair scaffold for promoting nerve function recovery and preparation method thereof |
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| CN1793884A (en) * | 2005-12-08 | 2006-06-28 | 复旦大学 | Chiral identification senser and its preparation method |
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| WO2013133688A1 (en) * | 2012-03-09 | 2013-09-12 | Mimos Berhad | Nanocomposite casting composition |
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2017
- 2017-03-07 CN CN201710129976.2A patent/CN106990154B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1793884A (en) * | 2005-12-08 | 2006-06-28 | 复旦大学 | Chiral identification senser and its preparation method |
| CN101077929A (en) * | 2006-05-26 | 2007-11-28 | 国家纳米科学中心 | Conducting polymer laminar nano composite material and its preparation method and use |
| WO2013133688A1 (en) * | 2012-03-09 | 2013-09-12 | Mimos Berhad | Nanocomposite casting composition |
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| Title |
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| 韩高义等: "手性环境下的手性N-取代吡咯电化学聚合及其微结构", 《高分子学报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113559318A (en) * | 2021-07-05 | 2021-10-29 | 四川大学 | Chiral conductive repair scaffold for promoting nerve function recovery and preparation method thereof |
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