CN101812171B - Conductive polymer for biosensor and preparation method thereof - Google Patents
Conductive polymer for biosensor and preparation method thereof Download PDFInfo
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- CN101812171B CN101812171B CN2010101460220A CN201010146022A CN101812171B CN 101812171 B CN101812171 B CN 101812171B CN 2010101460220 A CN2010101460220 A CN 2010101460220A CN 201010146022 A CN201010146022 A CN 201010146022A CN 101812171 B CN101812171 B CN 101812171B
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Abstract
The invention provides a conductive polymer for a biosensor and a preparation method thereof in order to solve the problem puzzling the academia for long time about how to combine a bioactive unit to a metal non-inactively and permanently and that bioactive molecules are connected to the conductive polymer in one step. The bioactive unit is first introduced into a conductive polymer monomer, and then the conductive polymer with bioactivity is directly formed in situ on the surface of an electrode in one step by adopting an in-situ electrochemical combinatorial synthesis method and an independent addressing microelectrode array technique so as to obtain a functional microelectrode array applied to the biosensor. The conductive polymer for the biosensor and the preparation method make the development of the biosensor towards the direction of intensification, microminiaturization and micro power consumption become possible, can promote the development of disease diagnosis, medicament screening, health care, judicial expertise, food detection, environmental monitoring, individualized medicament and the like and industrial chains thereof, and have far-reaching social meaning and broad market value.
Description
Technical field
The present invention relates to a kind of conductive polymers that is used for biosensor and preparation method thereof, specifically, relate to synthetic (combinatorial synthesis) method of a kind of employing electrochemical in-situ combination; Make have the biological activity unit (like DNA, RNA, peptide; Protein, enzyme, adaptive thing (aptamer); Tissue, cell etc.) conductive polymers one step is directly fixed on the electrode, obtains the functionalization microelectrode array to be applied to biosensor.
Background technology
Biosensor is a new and high technology that is interpenetrated and grown up by multiple subjects such as information biology, biological cybernetics, bionics, biocomputer, biology, chemistry, physics, medical science, electronic technology, is a kind of quick, parallel, little quantized analytical procedure of material being carried out molecular level.The test substance biosensor of flowing through, through molecular recognition, the signal that cross reaction between the biological activity unit is expressed is converted into through physics or chemical transverter can quantitative and accessible electrical signal, and carries out informationization and digitizing with computer.Biosensor technology is the new growth point between information and biotechnology; Along with the development of Internet of Things and the promotion of bio-science, information science and Materials science development; And The application of new technique such as photoconduction, optical fiber, superconduction, nanotechnology, intelligent material; The further collection of realization information and transmission, processing are integrated, intelligent; Particularly molecular biology combines with new subject such as microtronics, photoelectronics, Micrometer-Nanometer Processing Technology and nanotechnology, new technology, is just changing the looks of traditional medicine, health care, medical diagnosis on disease, food inspection, environmental monitoring.Biosensor is that the perfection of biotechnology and infotech is merged; It is the materialization of bioinformation; Be the strategic forward position of Internet of Things, grasped biosensor technology and, just equaled to have captured a strategic high ground of Internet of Things it digitizing, robotization, microminiaturization, intensification, intellectuality.Study on Biosensor is developed, and has become the new focus of development in science and technology of world, forms the important component part of 21 century rising high tech industry, has the important strategic meaning.
Conductive polymers has broad application prospects in fields such as optics, electromagnetism and chemistry because of its particular structural and excellent physical chemistry.In recent years, conductive polymers has been obtained certain achievement in research in the application of technical field of biological material.The application of conductive polymers in technical field of biological material is to see as biosensor more.Generally, biologically active substances such as different enzymes, coenzyme, antibody, DNA even cell and tissue are fixed in the conductive polymers, form various novel biosensors.This transmitter has characteristics such as response performance is strong, and making processes is simple, controlled.In making up conductive polymers biosensor process, electrochemical method simple to operate, that be easy to control is adopted in synthesizing of polymkeric substance usually.In polymerization process, biologically active substance both can be aggregated to electrode surface with polymer monomer simultaneously, also can be earlier and monomer whose be adsorbed on electrode surface, reoxidize polymerization and form the bio-identification solid state device.Therebetween; Through controlling polymers electropolymerization process effectively; Biologically active substance can be fixed to the privileged site of various types of electrodes or electrode, also can biologically active substances such as two or more enzymes is fixed in same layers of polymer film simultaneously or be individually fixed on the multilayer polymeric film.Conductive polymers is as molecular wire, and its 3-D solid structure can make electronics directly transmit at biomolecules (active site) and electrode surface, significantly improves the response characteristic of biosensor.Spatial distribution in film of thickness through the controlled polymerization film, biomolecules, the indexs such as voidage of polymeric membrane can be adjusted the response characteristic and the selectivity of biosensor.
The key that makes up the conductive polymers biosensor is how biologically active substance to be fixed on the conductive polymerized film effectively, and keeps its biological activity to greatest extent, the bio-identification solid state device that formation can prolonged and repeated effect.The fixing means that biologically active substance is commonly used mainly contains entrapping method, covalent method, absorption method and crosslinking.Wherein see that so that entrapping method more this method depends on electrochemical polymerization and realizes, that is, in electrochemical polymerization, biologically active substance with the form fix of embedding in conductive polymerized film.At present, though the conductive polymers Study on Biosensor has obtained certain achievement, some problems have also been faced simultaneously.But as do not have a conductive polymers biosensor that conventional equipment can be made stable duplication of production, this to a great extent limit the widespread use of this type of transmitter at analysis field.
Summary of the invention
The present invention for solve puzzlement academia for a long time how with non-inactivation ground, biological activity unit and be permanently attached on the metal and can also settle at one go bioactive molecules is inserted the difficult problem of conductive polymers; A kind of conductive polymers that is used for biosensor and preparation method thereof is provided, has made intensification, microminiaturization and little power consumption of biosensor become reality.
For realizing the foregoing invention purpose, the concrete technical scheme that the present invention adopts is following:
The conductive polymers that is used for biosensor of the present invention has following general formula:
R=S in the general formula or NH;
R1 in the general formula can be 1,2 or 3 for
n wherein;
X represents the biological activity unit, can be DNA, RNA, peptide, protein, enzyme, coenzyme, antibody, tissue or cell, preferred coenzyme R-vitamin H (Biotin);
R2 in the general formula is a hydrogen.
The preparation method who is used for the conductive polymers of biosensor of the present invention comprises following concrete steps:
A) preparation has the unitary conductive polymers monomer of biological activity
To have the unitary glycol phosphoramidite of biological activity is dissolved in the anhydrous acetonitrile; Add the monomeric anhydrous acetonitrile of conductive polymers then, wherein: having unitary glycol phosphoramidite of biological activity and the monomeric mol ratio of conductive polymers is 10: 1～1: 10; Add an amount of 5-ethylmercapto group tetrazole (ETT) acvator (activator), the concentration that makes the acvator anhydrous acetonitrile of formation is 0.25mol/L; After at room temperature stirring 20～40 minutes, carry out underpressure distillation to Powdered; Add excessive oxidation solution (oxidation solution), said oxidizing solution is to be dissolved in THF by iodine: water: the mass ratio of triethylamine is to form in 8: 1: 1 the mixed solvent, and the mass percent concentration of solution is 4%; After stirring 5～15 minutes under the room temperature, be reduced to neutrality with Sulfothiorine, then the decompression steam THF, with chloroform extraction, organic layer behind anhydrous sodium sulfate drying, the evaporated under reduced pressure organic solvent; Add mass percent concentration at last and be 10% ammonium hydroxide aqueous solution deprotection, be neutralized to neutrality with 0.2M hydrochloric acid after decompression steams excessive ammonia, it is subsequent use to put into-4 ℃ of refrigerators;
B) microelectrode array is based upon on the logic circuit chip of independent addressing; Each electrode on this circuit is connected by the transistorized switch of complementary metal oxide semiconductor (CMOS), through sending the electronic address signal to the common junction circuit further to SRAM (SRAM) conducting this switch relevant with each electrode; Microelectrode array is placed in the fluid reactor, the reaction solution in the reactor drum be step a) prepare have the unitary conductive polymers monomer of biological activity and its molar weight 1～10 times without the conductive polymers monomer of modifying and mix as electrolytical Repone K in right amount; Open with 10 milliseconds; The pulse of 10 milliseconds of passes; At 0.5～1.5 volt; The control of the logical circuit of 30 second total time down, the conductive polymers of biologically active generates rapidly in the electrode surface original position immediately, after washed with de-ionized water, dries up with nitrogen and promptly gets the functionalization microelectrode array that is used for biosensor.
The described unitary glycol phosphoramidite of biological activity that has is meant and has the unitary glycol phosphoramidite of DNA, RNA, peptide, protein, enzyme, coenzyme, antibody, tissue or cell; Describedly have a glycol phosphoramidite that the unitary glycol phosphoramidite of biological activity preferably has vitamin H-vitamin H.
Described conductive polymers monomer can be that general formula is: the pyrrole derivative of
, n wherein can be 1,2 or 3.
Described conductive polymers monomer can also be that general formula is: the thiophene derivant of
, n wherein can be 1,2 or 3.
Said electrode can be metal, metal alloy, carbon nanotube, vitreous carbon, graphite, doping oxide, indium tin oxide, silicon oxide, gallium arsenide semiconductor, metal-doped polymkeric substance or stupalith, preferable alloy.
Said metal can be selected from platinum, iridium, palladium, gold and silver, copper, mercury, nickel, zinc, titanium, tungsten or aluminium, preferred platinum.
Just because of each electrode all with its under independent addressing logic and amplifying circuit be connected; So all have intelligent sensing and signal enlarging function; When scanning each electrode with certain pulse wave, can produce a small dipole polarization electronic signal, this signal is slightly variant because of the variation of the residing coenocorrelation of electrode (having or not the molecular recognition reaction); Therefore; The utilization of CMOS provides unprecedented repeatability, and the ability of synthetic polymer microarray makes bio-sensing be able to become a reality in the micron of high flexible and the sub-micrometer range.
The inventor also discovers: along with the carrying out of reaction, the polymer molecule of biologically active and conduction constantly extends when forming current path, and from the nano particle to the nanofiber, last fiber and fiber connect into the sheet network structure successively.Through regulation and control monomer concentration, current density and reaction times isoreactivity radical polymerization condition, the polymer growth that can control biologically active and conduction becomes nanofiber.Because nanometer fibrous conductive polymers has the three-dimensional microcosmic structure of nanometer; Have unique chemical, physical properties; Therefore; Can significantly improve detection sensitivity, shorten the reaction times of detecting greatly, make biosensor develop into possibility to intensification, microminiaturization and little power consumption direction to biomolecules or cell.
Compared with prior art, breakthrough point of the present invention mainly contain following some:
1, through earlier the biological activity unit being introduced in the conductive polymers monomer; Adopt electrochemical in-situ combination compound method then; Can one the step directly form the conductive polymers of biologically active in position, solved puzzlement academia for a long time how with non-inactivation ground, biological activity unit and be permanently attached on the electrode and can also settle at one go bioactive molecules is inserted the difficult problem of conductive polymers.
2, through regulation and control monomer concentration, current density and reaction times isoreactivity radical polymerization condition; Can control conductive polymers grows into nanometer fibrous; Thereby significantly improve detection sensitivity to biomolecules or cell; Shorten the reaction times of detecting greatly, make biosensor develop into possibility to intensification, microminiaturization and little power consumption direction.
3, because biosensor of the present invention is as probe with conductive-nano-fibers; Have highly sensitive, sampling quantity is little, favorable reproducibility, speed fast, high-throughput, microminiaturization, little power consumption, digitisation, be easy to carry and advantage such as execute-in-place; With the interaction of Internet of Things under; Can realize the monitoring of public place epidemic infectious diseases, reach the purpose that prevents trouble before it happens.Therefore, the present invention can promote the development of medical diagnosis on disease, drug screening, health care, judicial expertise, food inspection, environmental monitoring, personalized medicine etc. and above industrial chain, has far-reaching social effect and vast market and is worth.
Description of drawings
Fig. 1 is the structural representation of the independent addressing logic chip among the present invention; Among the figure: 1 is meant the polyreaction driving circuit; 2 are meant the electrode that connects conducting through inner addressing; 3 are meant the electrode that connects through inner addressing but in experiment, have a mind to no power and keep inertia;
Fig. 2 is the photo of the prepared functionalization microelectrode array of embodiment 3 under the light of chamber (electrode of 16 micron diameters amplify through 100 times of optics obtain);
Fig. 3 is the photo of the prepared functionalization microelectrode array of embodiment 4 under the light of chamber (electrode of 16 micron diameters amplify through 50 times of optics obtain).
Embodiment
Below in conjunction with embodiment to the present invention do further in detail, intactly explanation; Used chemical reagent is all to the buying of U.S. Sigma-Aldrich company among the embodiment, and the acvator (activator) and the oxidizing solution (oxidation solution) of the usefulness that vitamin H glycol phosphoramidite and confession DNA are synthetic are to purchase from U.S. Glen Research company.
Embodiment 1: preparation has the unitary pyrrole derivative monomer of biological activity
Vitamin H glycol phosphoramidite is dissolved in the anhydrous acetonitrile, adds the anhydrous acetonitrile of 1-FMOC-3-pyrroles's methyl alcohol then, wherein: the mol ratio of vitamin H glycol phosphoramidite and 1-FMOC-3-pyrroles's methyl alcohol is 10: 1～1: 10; Add an amount of 5-ethylmercapto group tetrazole (ETT) acvator, the concentration that makes the acvator anhydrous acetonitrile of formation is 0.25mol/L; After at room temperature stirring 30 minutes, carry out underpressure distillation to Powdered; Add excessive oxidation solution, said oxidizing solution is to be dissolved in THF by iodine: water: the mass ratio of triethylamine is to form in 8: 1: 1 the mixed solvent, and the mass percent concentration of solution is 4%; Stir under the room temperature after 10 minutes, be reduced to neutrality with Sulfothiorine, decompression steams THF then, with chloroform extraction, organic layer behind anhydrous sodium sulfate drying, the evaporated under reduced pressure organic solvent; Add mass percent concentration at last and be 10% ammonium hydroxide aqueous solution deprotection, be neutralized to neutrality with 0.2M hydrochloric acid after decompression steams excessive ammonia, put into-4 ℃ refrigerator is subsequent use and get final product, the reaction formula of present embodiment is following:
Similarly compound method also is applicable to have saturated or unsaturated hydro carbons substituting group on 4; Aromatic series (comprising heterocycle) type substituting group; Hydro carbons and/or aromatic series (comprising heterocycle) ether or thioether class substituting group; The halogen substituting group; One-level or secondary alcohols substituting group through protected silane; Amine substituting group through FMOC or BOC protection; Symmetrical or asymmetric substituted tertiary amine; Acid amides or sulfonamides substituting group; The substituent 1-FMOC-3-pyrroles's methyl alcohol of the substituted carboxylic acid esters of saturated or unsaturated hydrocarbons; The 1-FMOC-3-epolamine; 1-FMOC-3-pyrroles's propyl alcohol; 1-BOC-3-pyrroles's methyl alcohol; 1-BOC-3-epolamine or 1-BOC-3-pyrroles's propyl alcohol.
Embodiment 2: preparation has the unitary thiophene derivant monomer of biological activity
Vitamin H glycol phosphoramidite is dissolved in the anhydrous acetonitrile, adds the anhydrous acetonitrile of 3-thiophen(e)alcohol then, wherein: the mol ratio of vitamin H glycol phosphoramidite and 3-thiophen(e)alcohol is 10: 1～1: 10; Add an amount of 5-ethylmercapto group tetrazole (ETT) acvator, the concentration that makes the acvator anhydrous acetonitrile of formation is 0.25mol/L; After at room temperature stirring 30 minutes, carry out underpressure distillation to Powdered; Add excessive oxidation solution, said oxidizing solution is to be dissolved in THF by iodine: water: the mass ratio of triethylamine is to form in 8: 1: 1 the mixed solvent, and the mass percent concentration of solution is 4%; Stir under the room temperature after 10 minutes, be reduced to neutrality with Sulfothiorine, decompression steams THF then, with chloroform extraction, organic layer behind anhydrous sodium sulfate drying, the evaporated under reduced pressure organic solvent; Add mass percent concentration at last and be 10% ammonium hydroxide aqueous solution deprotection, be neutralized to neutrality with 0.2M hydrochloric acid after decompression steams excessive ammonia, put into-4 ℃ refrigerator is subsequent use and get final product, the reaction formula of present embodiment is following:
Similarly compound method also is applicable to have saturated or unsaturated hydro carbons substituting group on 4; Aromatic series (comprising heterocycle) type substituting group; Hydro carbons and/or aromatic series (comprising heterocycle) ether or thioether class substituting group; The halogen substituting group; One-level or secondary alcohols substituting group through protected silane; Amine substituting group through FMOC or BOC protection; Symmetrical or asymmetric substituted tertiary amine; Acid amides or sulfonamides substituting group; The substituent 3-thiophen(e)alcohol of the substituted carboxylic acid esters of saturated or unsaturated hydrocarbons; 3-thiophene ethanol or 3-thiophene propyl alcohol.
Embodiment 3: preparation is used for the electric polypyrrole of biosensor
Microelectrode array is based upon on the logic circuit chip (seeing shown in Figure 1) of independent addressing; Each electrode on this circuit is connected by the transistorized switch of complementary metal oxide semiconductor (CMOS), through sending the electronic address signal to the common junction circuit further to SRAM (SRAM) conducting this switch relevant with each electrode; Microelectrode array is placed in the fluid reactor, and the reaction solution in the reactor drum is 1～10 times the pyrroles who has the substituent pyrrole monomer of vitamin H and its molar weight who prepares and mixes as electrolytical Repone K in right amount; Open with 10 milliseconds, the pulse of 10 milliseconds of passes is at 1.5 volts; The logical circuit control of 30 second total time down; The electric polypyrrole of biologically active generates rapidly in the electrode surface original position immediately, after washed with de-ionized water, dries up with nitrogen and promptly gets the functionalization microelectrode array that is used for biosensor, and Fig. 2 is the photo of chamber light lower electrode, and (electrode of 16 micron diameters amplifies through 100 times of optics and obtains; Wherein circle is an electrode, is isolator around the electrode).
Embodiment 4: preparation is used for the conductive polythiophene of biosensor
Microelectrode array is based upon on the logic circuit chip (seeing shown in Figure 1) of independent addressing; Each electrode on this circuit is connected by the transistorized switch of complementary metal oxide semiconductor (CMOS), through sending the electronic address signal to the common junction circuit further to SRAM (SRAM) conducting this switch relevant with each electrode; Microelectrode array is placed in the fluid reactor, and the reaction solution in the reactor drum is 1～10 times the thiophene that has the substituent thiophene monomer of vitamin H and its molar weight for preparing and mixes as electrolytical Repone K in right amount; Open with 10 milliseconds, the pulse of 10 milliseconds of passes is at 2.0 volts; The logical circuit control of 30 second total time down; The conductive polythiophene of biologically active generates rapidly in the electrode surface original position immediately, after washed with de-ionized water, dries up with nitrogen and promptly gets the functionalization microelectrode array that is used for biosensor, and Fig. 3 is the photo of chamber light lower electrode, and (electrode of 16 micron diameters amplifies through 50 times of optics and obtains; Wherein circle is an electrode, is isolator around the electrode).
The electrode that uses among the embodiment is platinum, can be substituted by iridium or other metals (for example: palladium, gold and silver, copper, mercury, nickel, zinc, titanium, tungsten, aluminium) or metal alloy, carbon nanotube, vitreous carbon, graphite, doping oxide, indium tin oxide, silicon oxide, gallium arsenide semiconductor, metal-doped polymkeric substance or stupalith.
Claims (10)
1. a conductive polymers that is used for biosensor is characterized in that, has following general formula:
R=S in the general formula or NH;
R1 in the general formula is 1,2 or 3 for
n wherein;
X represents the biological activity unit;
R2 in the general formula is a hydrogen.
2. the conductive polymers that is used for biosensor according to claim 1 is characterized in that, said biological activity unit is DNA, RNA, peptide, protein, enzyme, coenzyme, antibody, tissue or cell.
3. the conductive polymers that is used for biosensor according to claim 2 is characterized in that, said biological activity unit is vitamin H-vitamin H.
4. the described preparation method who is used for the conductive polymers of biosensor of claim 1 is characterized in that, comprises following concrete steps:
A) preparation has the unitary conductive polymers monomer of biological activity
To have the unitary glycol phosphoramidite of biological activity is dissolved in the anhydrous acetonitrile; Add the monomeric anhydrous acetonitrile of conductive polymers then, wherein: having unitary glycol phosphoramidite of biological activity and the monomeric mol ratio of conductive polymers is 10: 1～1: 10; Add an amount of 5-ethylmercapto group tetrazole (ETT) acvator, the concentration that makes the acvator anhydrous acetonitrile of formation is 0.25mol/L; After at room temperature stirring 20～40 minutes, carry out underpressure distillation to Powdered; Add excessive oxidation solution, said oxidizing solution is to be dissolved in THF by iodine: water: form in the mixed solvent of triethylamine=8: 1: 1, the mass percent concentration of solution is 4%; After stirring 5～15 minutes under the room temperature, be reduced to neutrality with Sulfothiorine, then the decompression steam THF, with chloroform extraction, organic layer behind anhydrous sodium sulfate drying, the evaporated under reduced pressure organic solvent; Add 10% volatile caustic deprotection at last, be neutralized to neutrality with 0.2M hydrochloric acid after decompression steams excessive ammonia, it is subsequent use to put into-4 ℃ of refrigerators;
B) microelectrode array is based upon on the logic circuit chip of independent addressing; Each electrode on this circuit is connected by the transistorized switch of complementary metal oxide semiconductor (CMOS), through sending the electronic address signal to the common junction circuit further to SRAM (SRAM) conducting this switch relevant with each electrode; Microelectrode array is placed in the fluid reactor, the reaction solution in the reactor drum be step a) prepare have the unitary conductive polymers monomer of biological activity and its molar weight 1～10 times without the conductive polymers monomer of modifying and mix as electrolytical Repone K in right amount; Under logical circuit control; Open with 10 milliseconds; The pulse of 10 milliseconds of passes is at 0.5～1.5 volt, in 30 second total time; The conductive polymers of biologically active promptly is engraved in the electrode surface original position and generates, and after washed with de-ionized water, dries up with nitrogen and promptly gets the functionalization microelectrode array that is used for biosensor.
5. the preparation method who is used for the conductive polymers of biosensor according to claim 4; It is characterized in that the described unitary glycol phosphoramidite of biological activity that has is meant and has the unitary glycol phosphoramidite of DNA, RNA, peptide, protein, enzyme, coenzyme, antibody, tissue or cell.
6. the preparation method who is used for the conductive polymers of biosensor according to claim 5 is characterized in that, the described unitary glycol phosphoramidite of biological activity that has is meant the glycol phosphoramidite that has vitamin H-vitamin H.
7. the preparation method who is used for the conductive polymers of biosensor according to claim 4; It is characterized in that; Described conductive polymers monomer is that general formula is: the pyrrole derivative of
, n wherein is 1,2 or 3.
8. the preparation method who is used for the conductive polymers of biosensor according to claim 4; It is characterized in that; Described conductive polymers monomer is that general formula is: the thiophene derivant of
, n wherein is 1,2 or 3.
9. the preparation method who is used for the conductive polymers of biosensor according to claim 4; It is characterized in that said electrode is metal, metal alloy, carbon nanotube, vitreous carbon, graphite, doping oxide, indium tin oxide, silicon oxide, gallium arsenide semiconductor, metal-doped polymkeric substance or stupalith.
10. the preparation method who is used for the conductive polymers of biosensor according to claim 9 is characterized in that said electrode is a platinum.
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| CN102445472A (en) * | 2010-10-14 | 2012-05-09 | 北京华凯瑞微流控芯片科技有限责任公司 | Microfluidic chip-based sensor and preparation method thereof |
| CN102680550A (en) * | 2012-05-10 | 2012-09-19 | 合肥工业大学 | Conducting polymer one-dimensional nano array-based enzyme electrode for biological sensor and preparation method of conducting polymer one-dimensional nano array-based enzyme electrode |
| CN104458842B (en) * | 2014-12-03 | 2017-02-22 | 深圳鼎新融合科技有限公司 | Ultrasensitive DNA electrochemical detection method, reagent and system |
| CN104939403A (en) * | 2015-06-15 | 2015-09-30 | 苏州威尔德工贸有限公司 | Flexible wearable electronic fabric based on conductive nanofiber |
| EP3551784A4 (en) * | 2016-12-09 | 2020-12-16 | Manufacturing Systems Limited | Apparatus and methods for controlled electrochemical surface modification |
| CN110632126A (en) * | 2019-09-04 | 2019-12-31 | 东华大学 | Organophosphorus compound sensor and preparation method thereof |
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| CN1338521A (en) * | 2000-08-21 | 2002-03-06 | 浙江江南生物科技有限公司 | Electrochemical in-situ location method of biologic molecule on electrically conductive substrate |
| KR100481665B1 (en) * | 2001-07-09 | 2005-04-08 | 주식회사 큐시스 | Electrical conductive poly(thiophene) non-aqueous dispersion, method for preparing thereof, and its use |
| CN102212251B (en) * | 2003-04-22 | 2013-06-19 | E.I.内穆尔杜邦公司 | Water dispersible polythiophenes made with polymeric acid colloids |
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| CN101813701B (en) * | 2010-04-13 | 2012-12-26 | 无锡中美亿芯生物科技有限公司 | Method for preparing protein chip by in-situ synthesis |
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