CN106928434A - A kind of method and its application by the tartrate ion synthesis of chiral conducting polymer that adulterates - Google Patents
A kind of method and its application by the tartrate ion synthesis of chiral conducting polymer that adulterates Download PDFInfo
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
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Abstract
The present invention relates to a kind of method by the tartrate ion synthesis of chiral conducting polymer that adulterates and its application, comprise the following steps：The polymer film of electropolymerization doping tartrate ion, peroxidating composite membrane of polymer, electrochemical process identification Tryptophan enantiomer.The beneficial effects of the invention are as follows：Method is simple to prepare doping tartrate ion polymer, 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 by the tartrate ion synthesis of chiral conducting polymer that adulterates and its application, category
In 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, also known as conducting polymer, refers to that, 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 is 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.Not by the conduction of 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 be analysed in electrochemical switch, chiral chromatogram, chiral chemistry sensor, film layer in the future
The field such as technology and Surface Modified Electrodes obtains broad development.When as chiral matrix or chiral electrode material to possessing chirality
When electrically conductive organic polymer polymer is used, mechanics, electricity and the electrochemical properties that the latter has uniqueness can used
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 the identification of specific molecular, purification are carried out
Wealthy space.
Tartaric acid is a kind of chiral organic acid, there is two identical asymmetric carbon atoms in molecule, there are three kinds of isomers,
Respectively L- (+)-tartaric acid, D- (-)-tartaric acid and meso-tartaric acid, wherein L- (+)-tartaric acid and D- (-)-tartaric acid
It is the stereoisomer of mapping, and meso-tartaric acid does not have optical activity then.Tartaric acid is the accessory substance of brewing industry, often
In for food industry, particularly plus in the beverage.It is extremely cheap due to tartaric acid in chiral Recognition, it is actual should
Can often abandon reclaiming in.
The present invention is doped treatment from monomer molecule as host material, and chiral anion is doped into monomer molecule
Polymerisation in.Experiment makes monomer molecule be polymerized in D- (-)-aqueous tartaric acid solution by electrochemical means, is formed
The composite membrane of polymer material of tartrate ion doping, and it is applied to electrochemical recognition Tryptophan enantiomer.
The content of the invention
It is an object of the invention to chiral anion is doped in the polymerisation of monomer molecule, synthesis of chiral is conductive poly-
Compound is simultaneously applied to the research of electrochemistry chiral Recognition.
A kind of method and its application by the tartrate ion synthesis of chiral conducting polymer that adulterates of the present invention, bag
Include following steps：
The polymer film of a, electropolymerization doping tartrate ion：Monomer molecule is dissolved in D- (-)-tartaric acid solution
Well mixed to be configured to monomer mixed solution, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, platinized platinum
Electrode is that, to electrode, saturated calomel electrode (SCE) is reference electrode, is dipped in mixed liquor, and applying phase induced current carries out perseverance
Electric current is polymerized, and obtains the polymer film modified electrode of doping tartrate ion.
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 PBS, 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 preparation respectively
L-/D- tryptophan solutions in, differential pulse scanning is carried out after standing.
Further, the concentration of D- (-)-tartaric 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 applying electric current is 0.3mA, and the electropolymerization time is 10~600s.
Further, the concentration of PBS 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：Method is simple to prepare doping tartrate ion polymer, preparation process
It 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 tartrate 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 D- (-)-tartaric acid modified electrode tryptophan enantiomer in comparative example two.
Specific embodiment
Presently in connection with specific embodiment, the invention will be further described, and following examples are intended to illustrate 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 tartrate ion includes following steps：
(1) the well mixed monomer that is configured to is mixed in 0.15M pyrrole monomers being dissolved in into 0.045M D- (-)-tartaric acid solution
Liquid is closed, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is to electrode, saturation calomel
Electrode (SCE) is reference electrode, is dipped in carrying out Galvanostatic polymerization in mixed liquor, and applying electric current is 0.3mA, electropolymerization time
It is 60s, obtains the polypyrrole film modified electrode of doping tartrate ion.
(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 PBSs, in 0~1.2V
(vs.SCE) in the range of electrochemical window, cyclic voltammetric 40 is swept with the speed of 0.1V/s and is 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, saturated calomel electrode (SCE) is reference electrode, it is immersed respectively in the 1.0mM L-/D- tryptophan solutions 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 pair L-Trp of overoxidised polypyrrole prepared by method has preferable recognition effect, IL/IDIt is 3.36.
Comparative example one：
The composite polypyrrole film modified electrode that cyclic voltammetry prepares doping tartrate ion includes following steps：
(1) the well mixed monomer that is configured to is mixed in 0.15M pyrrole monomers being dissolved in into 0.045M D- (-)-tartaric acid solution
Liquid is closed, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is to electrode, saturation calomel
Electrode (SCE) is reference electrode, is dipped in mixed liquor, in the range of the electrochemical window of -0.6~0.8V (vs.SCE),
Cyclic voltammetric 5 is swept with the speed of 0.1V/s to enclose, obtain the polypyrrole film modified electrode of doping tartrate ion.
(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 PBSs, in 0~1.2V
(vs.SCE) in the range of electrochemical window, cyclic voltammetric 40 is swept with the speed of 0.1V/s and is 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, saturated calomel electrode (SCE) is reference electrode, it is immersed respectively in the 1.0mM L-/D- tryptophan solutions 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 2.14.
Comparative example two：
Potentiostatic method prepares D- (-)-tartaric acid 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 D- (-)-tartaric acid solution prepared, using constant potential
Method, applies the potential deposition 600s of+1.0V, prepares D- (-)-tartaric acid modified electrode.
(2) D- (-)-tartaric acid modified electrode for preparing is used for the identification of Tryptophan enantiomer, by modified electrode difference
Immerse in the 1.0mM L-/D- tryptophan solutions prepared, as shown in figure 4, IL/IDIt is 1.43.
Be doped to chiral anion in the polymerisation of monomer molecule by electrochemical means by the present invention, has synthesized chirality
Conducting polymer is simultaneously applied to the research of electrochemistry chiral Recognition.Result shows that peroxidating prepared by galvanostatic method is polymerized
The complex film modified electrode pair L-Trp of thing has recognition efficiency high, and the modified electrode or single wine prepared than cyclic voltammetry
Stone acid modified electrode possesses more excellent recognition effect.
Claims (4)
1. a kind of method and its application by the tartrate ion synthesis of chiral conducting polymer that adulterates, it is characterised in that：Step
It is rapid as follows：
The polymer film of a, electropolymerization doping tartrate ion：Monomer molecule is dissolved in D- (-)-tartaric acid solution and is mixed
Uniform to be configured to monomer mixed solution, experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, platinum plate electrode
It is that, to electrode, saturated calomel electrode (SCE) is reference electrode, is dipped in mixed liquor, applying phase induced current carries out constant current
Polymerization, obtains the polymer film modified electrode of doping tartrate 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 PBS, 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
Be 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. a kind of method by the tartrate ion synthesis of chiral conducting polymer that adulterates and its should according to claim 1
With, it is characterized in that：The concentration of D- (-)-tartaric acid is 0.01~0.5M in mixed liquor in the step a, and the concentration of monomer is
0.05~2.0M, carries out Galvanostatic polymerization, and applying electric current is 0.3mA, and the electropolymerization time is 10~600s.
3. a kind of method by the tartrate ion synthesis of chiral conducting polymer that adulterates and its should according to claim 1
With, it is characterized in that：Adulterate the polymer film modified electrode immersion PBS of tartrate ion in the step b
Concentration is 0.1M, and pH is 7.0~8.0, is circulated voltammetric scan.
4. a kind of method by the tartrate ion synthesis of chiral conducting polymer that adulterates and its should according to claim 1
With, it is characterized in that：Peroxidating composite membrane of polymer modified electrode immerses the dense of L-/D- tryptophan solutions respectively in the step c
It is 0.1~10mM to spend, and time of repose is 2~180s.
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| CN105037718A (en) * | 2015-08-27 | 2015-11-11 | 桂林理工大学 | Method for preparing conductive polyaniline nano tube by taking D-tartaric acid as template |
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| CN105424786A (en) * | 2015-10-29 | 2016-03-23 | 常州大学 | Method for preparation of peroxide polyaniline/beta-cyclodextrin composite film modified electrode and electrochemical recognition of tryptophan enantiomers |
| CN105753727A (en) * | 2016-02-24 | 2016-07-13 | 常州大学怀德学院 | Method for selectively separating amino acid optical isomers through molecular imprinting polypyrrole electrode mast |
| CN106018517A (en) * | 2016-05-16 | 2016-10-12 | 常州大学 | Preparation of tartaric acid-graphene quantum dot composite film modified electrode and application in tryptophan enantiomer recognition |
| CN106432720A (en) * | 2016-09-19 | 2017-02-22 | 上海应用技术大学 | Method for preparing polypyrrole doped molybdate |
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2017
- 2017-03-07 CN CN201710129979.6A patent/CN106928434B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101492536A (en) * | 2008-08-04 | 2009-07-29 | 南京理工大学 | Nano-polyaniline material with morphology inheritance and electrochemical preparation method |
| CN102876037A (en) * | 2012-09-25 | 2013-01-16 | 中南大学 | Method for preparing metal/polyaniline/plastic composite film through electrochemical in-situ polymerization |
| CN105037718A (en) * | 2015-08-27 | 2015-11-11 | 桂林理工大学 | Method for preparing conductive polyaniline nano tube by taking D-tartaric acid as template |
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| CN105753727A (en) * | 2016-02-24 | 2016-07-13 | 常州大学怀德学院 | Method for selectively separating amino acid optical isomers through molecular imprinting polypyrrole electrode mast |
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| CN106432720A (en) * | 2016-09-19 | 2017-02-22 | 上海应用技术大学 | Method for preparing polypyrrole doped molybdate |
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