CN109721621A - A kind of preparation method of the conductive polymer material of specific recognition tumour cell - Google Patents
A kind of preparation method of the conductive polymer material of specific recognition tumour cell Download PDFInfo
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- 210000004881 tumor cell Anatomy 0.000 title claims abstract description 21
- 229920001940 conductive polymer Polymers 0.000 title claims abstract description 20
- 239000002861 polymer material Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000001704 evaporation Methods 0.000 claims abstract description 8
- 238000004440 column chromatography Methods 0.000 claims abstract description 7
- 230000008020 evaporation Effects 0.000 claims abstract description 7
- ZUDCKLVMBAXBIF-UHFFFAOYSA-N 3,4-dimethoxythiophene Chemical compound COC1=CSC=C1OC ZUDCKLVMBAXBIF-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 235000002597 Solanum melongena Nutrition 0.000 claims description 6
- 244000061458 Solanum melongena Species 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- 238000001226 reprecipitation Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- 238000004458 analytical method Methods 0.000 claims 1
- 239000002024 ethyl acetate extract Substances 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 238000010025 steaming Methods 0.000 claims 1
- 201000011510 cancer Diseases 0.000 abstract description 5
- 206010028980 Neoplasm Diseases 0.000 abstract description 4
- 230000009545 invasion Effects 0.000 abstract description 3
- 238000013399 early diagnosis Methods 0.000 abstract description 2
- XFGDAPQOKJYPQP-UHFFFAOYSA-N 1-chloropropane-1,2-diol Chemical compound CC(O)C(O)Cl XFGDAPQOKJYPQP-UHFFFAOYSA-N 0.000 abstract 1
- 238000012216 screening Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 239000002322 conducting polymer Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- ZXPSRPAUXQIYID-UHFFFAOYSA-N [N].[Na] Chemical compound [N].[Na] ZXPSRPAUXQIYID-UHFFFAOYSA-N 0.000 description 2
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000835 electrochemical detection Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- -1 2- (azidom ethyl) -2,3- dihydro thiophene Chemical compound 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 238000004082 amperometric method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000010041 electrostatic spinning Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- ZMCNEDHZYNUOKW-UHFFFAOYSA-N phenoxyboronic acid pyridine Chemical compound C1(=CC=CC=C1)OB(O)O.N1=CC=CC=C1 ZMCNEDHZYNUOKW-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a kind of preparation methods of the conductive polymer material of specific recognition tumour cell, it is characterized in that, the following steps are included: (1), in a nitrogen atmosphere, by the toluene of 28ml, 1.36g, 3,4- dimethoxy-thiophene, the 2.60g of 10.4mmol, the 3- of 23.1mmol chloro- 1,2- propylene glycol and 0.16g, 0.92mmol p-methyl benzenesulfonic acid monohydrate are added in double-neck flask, mix and react for 24 hours under conditions of 90 DEG C；(2), it will purify to obtain EDOT-Cl by column chromatography after the mixture evaporation in step (1).The present invention has the advantage that the present invention has been synthetically prepared flexible, tumor cell specific identification conductive polymer material, the non-mark to tumour cell is realized, non-invasion specific recognition will be malignant tumour screening, early diagnosis of cancer, care diagnostic provide effective means.
Description
Technical field
The present invention relates to technical field of polymer materials, in particular to a kind of conductive polymers of specific recognition tumour cell
The preparation method of sub- material.
Background technique
Sialic acid (SialicAcid, SA) is distributed across the molecule that sugar-chain end is concentrated in cell membrane surface sugar chain, mirror
Arrangement and unique anionic polar in its outermost layer (chain end), SA plays important in the pathological processes of body
Effect.Some special cases are removed, the overexpression of cell surface SA is usually the performance of cancer progression.Therefore, the measurement of SA with
The diagnosis of cancerous condition has substantial connection.Now, it is circulating in the market there are many SA quantification kit, and these remove multistage enzyme
Promote reaction and is accompanied by the operation of the marks such as fluorescence, it is not only expensive, and determine to usually require one day or so.Further, since
These methods need to be discharged SA etc. in sugar chain with SA enzyme or strong acid treatment and pre-process, therefore these methods are completely broken to cell
The instant detection for being unsuitable for cell of bad property.
Summary of the invention
In order to solve the above technical problems, being conceived to the flexibility of appropriate means, minimize, the conducting polymer material of low cost
The new type heterocycle boric acid of specificity capture SA is imported into conducting polymer as ligand molecular with the methods of Bioconjugation by material
On backbone, synthesized SA induction novel conducting polymer, using electrochemical method without mark, non-invasion detect mailgnant form tumour into
Exhibition.
Technical solution provided by the invention is a kind of preparation side of the conductive polymer material of specific recognition tumour cell
Method, which comprises the following steps:
(1), in a nitrogen atmosphere, by the toluene of 28ml, 1.36g, 3,4- dimethoxy-thiophene, the 2.60g of 10.4mmol,
The 3- chlorine-1,2-propylene glycol and 0.16g of 23.1mmol, 0.92mmol p-methyl benzenesulfonic acid monohydrate are added in double-neck flask, mix
Merging is reacted for 24 hours under conditions of 90 DEG C；
(2), it will purify to obtain EDOT-Cl by column chromatography after the mixture evaporation in step (1)；
(3), by the N of 30ml, dinethylformamide, 1.18g, the EDOT-Cl and 0.48g of 6.18mmol, 7.4mmol is folded
Nitrogen sodium is added in flask, mixes and mixture flows back 1.5h under conditions of 120 DEG C；
(4), the mixture in step (3) is cooled to room temperature, and the MiliQ water of 15ml is added in mixed solution,
And it is extracted with ethyl acetate three times；
(5), the organic phase of step (4) mixture is further rinsed with water after extracting and is done afterwards with anhydrous magnesium sulfate three times
Dry, distillation is collected into EDOT-N3；
(6), by the tetrahydrofuran of 10ml, the EDOT-N of 0.99g, 5.1mmol3, 1.6g, the triphenylphosphine of 6.1mmol and
The 2M sodium hydrate aqueous solution of 10ml is blended in eggplant type flask, and reacts 3h under conditions of 50 DEG C；
(7), mixture in step (6) is cooled to room temperature, adjusts mixture ph, makes pH < 2, then to use methylene chloride
Washing is three times；
(8), the water phase of the mixture in collection step (7) is adjusting its pH value, makes its pH > 12, then extracted with methylene chloride
It takes three times；
(9), with the organic phase of the mixture in anhydrous magnesium sulfate drying steps (7), evaporation is filtered, EDOT-NH is obtained2；
(10), by 0.65g, the EDOT-NH of 3.8mmol2, 0.63g, the 5- boron picolinic acid of 3.8mmol, the water of 7ml and
The methanol of 13ml is added in eggplant type reaction flask and 10min is stirred at room temperature；
(11), then 12h will be reacted in mixture that 1.6g, the DMT-MM of 5.7mmol are added in step (10)；
(12), after reaction, MeOH and water are removed in distillation, then by goo CH2Cl2/ MeOH (20/1) eluent
Solvent is removed in column chromatography for separation, distillation, and 1mol L is then added-1Solvent is removed in distillation after HCl, in CH2Cl2In in reprecipitation,
Filtering obtains product EDOT-BPA.
Preferably, the dosage of the ethyl acetate is 15ml.
Preferably, the methylene chloride in the step (7) and (8) is 15ml.
Preferably, the earning rate of the EDOT-Cl is 56%.
Preferably, the EDOT-N3Earning rate be 81%.
Preferably, the EDOT-NH2Earning rate be 75%.
Preferably, the EDOT-BPA earning rate is 75%.
The invention has the following advantages over the prior art: the present invention has been synthetically prepared flexible, tumor cell specific
It identifies conductive polymer material, realizes the non-mark to tumour cell, non-invasion specific recognition will sieve for malignant tumour
It looks into, early diagnosis of cancer, care diagnostic provides effective means.
Detailed description of the invention
Fig. 1 is a kind of synthetic route schematic diagram of the conductive polymer material of specific recognition tumour cell of the present invention.
Fig. 2 is a kind of Electrochemical Detection tumour cell of the conductive polymer material of specific recognition tumour cell of the present invention
Route schematic diagram figure.
Specific embodiment
Present invention will be described in further detail below with reference to the accompanying drawings.
In conjunction with attached drawing, as shown in Figure 1, a kind of preparation method of the conductive polymer material of specific recognition tumour cell,
Characterized by comprising the following steps:
(1), in a nitrogen atmosphere, by the toluene of 28ml, 1.36g, 3,4- dimethoxy-thiophene, the 2.60g of 10.4mmol,
The 3- chlorine-1,2-propylene glycol and 0.16g of 23.1mmol, 0.92mmol p-methyl benzenesulfonic acid monohydrate are added in double-neck flask, mix
Merging is reacted for 24 hours under conditions of 90 DEG C；
(2), it will purify to obtain EDOT-Cl by column chromatography after the mixture evaporation in step (1), that is, it is mixed after evaporating
It closes object and 2- (chloromethyl) 2,3- is obtained by column chromatography purifying (silica gel, hexanes/ch=8/2v/v)
Dihydrothieno [3,4-b] [1,4] dioxine (EDOT-Cl) 1 flaxen oily product；
(3), by the N of 30ml, dinethylformamide, 1.18g, the EDOT-Cl and 0.48g of 6.18mmol, 7.4mmol is folded
Nitrogen sodium is added in flask, mixes and mixture flows back 1.5h under conditions of 120 DEG C；
(4), the mixture in step (3) is cooled to room temperature, and the MiliQ water of 15ml is added in mixed solution,
And it is extracted with ethyl acetate three times；
(5), the organic phase of step (4) mixture is further rinsed with water after extracting and is done afterwards with anhydrous magnesium sulfate three times
Dry, distillation is collected into EDOT-N3；EDOT-N3For 2- (azidom ethyl) -2,3- dihydro thiophene promise [3,4-b] [Isosorbide-5-Nitrae] dioxin, palm fibre
Color oily product；
(6), by the tetrahydrofuran of 10ml, the EDOT-N of 0.99g, 5.1mmol3, 1.6g, the triphenylphosphine of 6.1mmol and
The 2M sodium hydrate aqueous solution of 10ml is blended in eggplant type flask, and reacts 3h under conditions of 50 DEG C；
(7), mixture in step (6) is cooled to room temperature, adjusts mixture ph, makes pH < 2, then to use methylene chloride
Washing is three times；
(8), the water phase of the mixture in collection step (7) is adjusting its pH value, makes its pH > 12, then extracted with methylene chloride
It takes three times；
(9), with the organic phase of the mixture in anhydrous magnesium sulfate drying steps (7), evaporation is filtered, EDOT-NH is obtained2；
EDOT-NH2For (2,3- dihydro-thiophene [3,4-b] [1,4] dioxin -2- acyl group) carbinolamine；
(10), by 0.65g, the EDOT-NH of 3.8mmol2, 0.63g, the 5- boron picolinic acid of 3.8mmol, the water of 7ml and
The methanol of 13ml is added in eggplant type reaction flask and 10min is stirred at room temperature；
(11), then 12h will be reacted in mixture that 1.6g, the DMT-MM of 5.7mmol are added in step (10)；
(12), after reaction, MeOH and water are removed in distillation, then by goo CH2Cl2/ MeOH (20/1) eluent
Solvent is removed in column chromatography for separation, distillation, and 1mol L is then added-1Solvent is removed in distillation after HCl, in CH2Cl2In in reprecipitation,
Filtering obtains product EDOT-BPA.
The dosage of the ethyl acetate is 15ml.
Methylene chloride in the step (7) and (8) is 15ml.
The earning rate of the EDOT-Cl is 56%.
The EDOT-N3Earning rate be 81%.
The EDOT-NH2Earning rate be 75%.
The EDOT-BPA earning rate is 75%.
As shown in Fig. 2, with pyridine phenyl boric acid modified conducting high molecular material (poly (3,4-
Ethylenedioxythiophene): PEDOT) Electrochemical Detection tumour cell, with electropolymerization, with electrostatic spinning, inkjet printing
The methods of preparation PEDOT derivative film electrode；And under condition of different pH, confirmation electrode to the selectivity of cell surface SA,
With amperometry, voltammetry, impedance method, field effect transistor (FieldEffect Transistor:FET) device etc. will point
Son identification reaction conversions are at electric signal.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, made any to repair
Change, equivalent replacement, improvement etc., is all included in the scope of protection of the present invention.
Claims (7)
1. a kind of preparation method of the conductive polymer material of specific recognition tumour cell, which is characterized in that including following step
It is rapid:
(1), in a nitrogen atmosphere, by the toluene of 28ml, 1.36g, 3,4- dimethoxy-thiophene, the 2.60g of 10.4mmol,
The 3- chlorine-1,2-propylene glycol and 0.16g of 23.1mmol, 0.92mmol p-methyl benzenesulfonic acid monohydrate are added in double-neck flask, mix
Merging is reacted for 24 hours under conditions of 90 DEG C；
(2), it will purify to obtain EDOT-Cl by column chromatography after the mixture evaporation in step (1)；
(3), by the N of 30ml, dinethylformamide, 1.18g, the EDOT-Cl and 0.48g of 6.18mmol, 7.4mmol Sodium azide
It is added in flask, mixes and mixture flows back 1.5h under conditions of 120 DEG C；
(4), the mixture in step (3) is cooled to room temperature, and the MiliQ water of 15ml is added in mixed solution, be used in combination
Ethyl acetate extracts three times；
(5), the organic phase of step (4) mixture is further rinsed with water to dry with anhydrous magnesium sulfate afterwards three times, steaming after extracting
It evaporates and is collected into EDOT-N3；
(6), by the tetrahydrofuran of 10ml, the EDOT-N of 0.99g, 5.1mmol3, 1.6g, the triphenylphosphine of 6.1mmol and 10ml's
2M sodium hydrate aqueous solution is blended in eggplant type flask, and reacts 3h under conditions of 50 DEG C；
(7), mixture in step (6) is cooled to room temperature, adjusts mixture ph, makes pH < 2, then to be washed with methylene chloride
Three times；
(8), the water phase of the mixture in collection step (7) is adjusting its pH value, makes its pH > 12, then be extracted with dichloromethane three
It is secondary；
(9), with the organic phase of the mixture in anhydrous magnesium sulfate drying steps (7), evaporation is filtered, EDOT-NH is obtained2；
(10), by 0.65g, the EDOT-NH of 3.8mmol2, 0.63g, the 5- boron picolinic acid of 3.8mmol, the water of 7ml and 13ml
Methanol is added in eggplant type reaction flask and 10min is stirred at room temperature；
(11), then 12h will be reacted in mixture that 1.6g, the DMT-MM of 5.7mmol are added in step (10)；
(12), after reaction, MeOH and water are removed in distillation, then by goo CH2Cl2/ MeOH (20/1) elutes fluid column layer
Solvent is removed in analysis separation, distillation, and 1mol L is then added-1Solvent is removed in distillation after HCl, in CH2Cl2In in reprecipitation, filtering
Obtain product EDOT-BPA.
2. a kind of conductive polymer material of specific recognition tumour cell according to claim 1, it is characterised in that: institute
The dosage for stating ethyl acetate is 15ml.
3. a kind of conductive polymer material of specific recognition tumour cell according to claim 1, it is characterised in that: institute
The methylene chloride stated in step (7) and (8) is 15ml.
4. a kind of conductive polymer material of specific recognition tumour cell according to claim 1, it is characterised in that: institute
The earning rate for stating EDOT-Cl is 56%.
5. a kind of conductive polymer material of specific recognition tumour cell according to claim 1, it is characterised in that: institute
State EDOT-N3Earning rate be 81%.
6. a kind of conductive polymer material of specific recognition tumour cell according to claim 1, it is characterised in that: institute
State EDOT-NH2Earning rate be 75%.
7. a kind of conductive polymer material of specific recognition tumour cell according to claim 1, it is characterised in that: institute
The EDOT-BPA earning rate stated is 75%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111849006A (en) * | 2020-06-15 | 2020-10-30 | 上海大学 | Bionic functionalized PEDOT (PEDOT-PSS) film and preparation method thereof |
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|---|
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111849006A (en) * | 2020-06-15 | 2020-10-30 | 上海大学 | Bionic functionalized PEDOT (PEDOT-PSS) film and preparation method thereof |
| CN111849006B (en) * | 2020-06-15 | 2022-12-06 | 上海大学 | Bionic functionalized PEDOT (PEDOT-PSS) film and preparation method thereof |
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