CN102706929B - A kind of preparation of Photocrosslinkable modified hyaluronic acid molecular engram sensor - Google Patents
A kind of preparation of Photocrosslinkable modified hyaluronic acid molecular engram sensor Download PDFInfo
- Publication number
- CN102706929B CN102706929B CN201210142383.7A CN201210142383A CN102706929B CN 102706929 B CN102706929 B CN 102706929B CN 201210142383 A CN201210142383 A CN 201210142383A CN 102706929 B CN102706929 B CN 102706929B
- Authority
- CN
- China
- Prior art keywords
- hyaluronic acid
- preparation
- electrode
- modified
- photocrosslinkable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- RYZFIIBQTGKTFO-UHFFFAOYSA-N CN(C)Oc(cc1)cc(O2)c1C=CC2=O Chemical compound CN(C)Oc(cc1)cc(O2)c1C=CC2=O RYZFIIBQTGKTFO-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention discloses a kind of preparation method of the molecular engram sensor as made from Photocrosslinkable modified hyaluronic acid.This method belongs to the technical field that polymer material science is combined with chemical sensor.The present invention reacts the modified hyaluronic acid that Photocrosslinkable is made by natural macromolecular hyaluronic acid and photosensitive monomer, and it is molten altogether with template molecule (microsphere), obtains trace macromolecular colloid solution.Electrode is inserted in the solution, with constant potential electro-deposition method in the macromolecular film of electrode surface formation Photocrosslinkable, through photocrosslinking, template molecule elution, obtains the film modified electrode of imprinted polymer.The modified electrode is connected the molecular recognition sensor that may make up and be capable of single-minded recognition template molecule with sensing equipment and computer.Sensor produced by the present invention has specific selectivity, will be widely used in fields such as biological medicine, food security and environment monitorings.
Description
Technical field
The present invention relates to a kind of preparation method of Photocrosslinkable modified hyaluronic acid molecular engram sensor, set by molecule
Macromolecule of the meter synthesis with specific functionality.Molecular engram with Response to selection is obtained by molecular engram and electro-deposition
Sensor.Belong to the technical field that polymer material science and chemical sensor are combined.
Background technology
Hyaluronic acid (HA) is a kind of unique linear macromolecule acid mucopolysaccharide, by glucuronic acid and N2Acetylamino
The dissacharide units of glucose are alternately and repeatedly formed by connecting, with good biocompatibility and degradability.
Molecular imprinting technology (MIT) is also referred to as template imprinting technology, is to be prepared using manual method to specific molecular (i.e. trace
Molecule or template molecule) there is single-minded sexual reaction, and ask the molecularly imprinted polymer (MIP) in structure hole with specific sky
Technology.Because MIP has highly cross-linked structure, stability is good, can be in harshnesses such as high temperature, high pressure, organic solvent, acid, alkali
Used in environment, and it is cheap, so that the preferable sensitive material as sensor.MIPs is applied to sensor, can be made
Into MIPs sensors, its principle is to combine high selectivity specific to MIT with the high sensitivity of various sensing technologies, from
And realize the rapidly and efficiently selective enumeration method to target compound.
In recent years, molecular imprinting technology is obtained in space and knot from bionics angle using artificial synthesized method
Close and matched completely with a certain specific molecular (microsphere, template molecule) on site, the specific molecular can be specifically bound
High polymer material, so as to realize molecular recognition, is finally applied to molecular recognition sensor.Resulting molecularly imprinted polymer is again
It is referred to as " plastics antibody ", i.e., with the recognition performance and selectivity same with natural antibody, again has and macromolecule is same
High stability and weatherability, thus with more actual application value.
From molecularly imprinted polymer to molecular recognition sensor, the immobilization of imprinted polymer is committed step, and electricity is heavy
Homogeneous controllable, the base material adhesive force of area method film forming thickness is excellent, good weatherability.
Therefore, it is the good biocompatibility of natural macromolecular and degradability and identification that molecular imprinting technology is provided is steady
It is qualitative, it is combined in the way of electro-deposition, the sensor prepared will in fields such as biological medicine, food security and environment monitorings
It is widely used.
However, yet there are no in the range of applicant reads up the literature is used for prepared by molecular engram sensor by hyaluronic acid
Document and patent are disclosed.Southern Yangtze University's (application number in its application for a patent for invention is disclosed：201010109960) one kind is proposed
The electro-deposition preparation method of molecular recognition sensor.Applicant obtains cladding mould with the ionic photosensitive copolymers self assembly of synthesis
The trace micella of plate molecule, by constant potential electro-deposition, photocrosslinking, and template molecule elution obtain trace micella
Film modified electrode, itself and sensing equipment and computer is connected and composed the molecular recognition sensing for being capable of single-minded recognition template molecule
Device and the analysis detection for being used for template molecule.But the photosensitive copolymers described in the patent are limited only to some synthetic macromolecules.This
Invention breaks through this limitation, and by hyaluronic acid, this natural macromolecular introduces molecular engram sensor, is realized in the way of electro-deposition
The combination of the identification stability of natural macromolecular good biocompatibility and degradability and molecular engram, so as to further open up
The wide application field of natural macromolecular.
The content of the invention
(1) hyaluronic acid (HA) is modified：It is 1~10% hyaluronic acid by the hyaluronic acid mass fraction soluble in water that is made into
The aqueous solution, sequentially adds triethylamine, tetra-n-butyl ammonium bromide and photosensitive monomer, is raised at room temperature after 12~24h of uniform stirring
Temperature is reacted after 5~10h to 50 DEG C~70 DEG C, is cooled to room temperature on this condition.Unreacted monomer, freezing are removed in dialysis
Dry, or supercritical drying had both obtained the modified hyaluronic acid of Photocrosslinkable.
(2) preparation of photosensitive molecular trace electrodeposited film modified electrode：By the modified hyaluronic acid of obtained Photocrosslinkable
It is codissolved in water, then adds template molecule in the solution with light trigger ring azo amidine class VA-044, template molecule is added
Measure as the 2%~30% of photosensitive polymerization amount of substance, be stirred overnight, trace macromolecular colloid solution is made.Electrode insertion colloid is molten
Apply a constant potential after liquid to it, make charged trace colloidal particle to electrode surface swimming and electro-deposition film forming.By ultraviolet
Light irradiation obtains molecularly imprinted polymer (MIP) electrode film.Finally, elution removes template molecule, obtains molecularly imprinted polymer
Modified electrode.
(3) preparation of molecular engram sensor：Will be as the molecularly imprinted polymer electrode and sensing equipment obtained by (2) step
Molecular recognition sensor can be obtained after connection.
It is used for the preparation of electrochemical sensor using natural macromolecular hyaluronic acid, the structure of hyaluronic acid is as shown in Figure 1：
The structure of Photocrosslinkable modified hyaluronic acid is as shown in Figure 2：
Wherein R is：
Described hyaluronic acid modified photosensitive monomer is selected：Methyl propenoic acid glycidyl ether, allyl glycidyl
Glycerin ether, 7- glycidoxy -4- methylcoumarins.
The preparation method of described Photocrosslinkable modified hyaluronic acid molecular engram sensor, it is characterised in that by initial
MOLECULE DESIGN impart modified hyaluronic acid photaesthesia response, pH sensitiveness and electro-deposition film forming.
Described template molecule is selected：Acamol, glucose, trimerization piperazine amine.
Described electrode is the electrode of sensing equipment, and electrode surface material is conductive material, can be gold, glass
Carbon.
Described Electrodeposition Conditions are：Constant potential value is 0.1V~60V, electrodeposition time 5s~10min.
The ultraviolet photograph spoke time of described photosensitive molecular imprinted polymer film is that (uviol lamp is high-pressure mercury to 5min~15min
Lamp, power：1000~2000W, irradiation distance：1~5cm)
The application of molecular engram sensor：The sensor can be with selective enumeration method template molecule (microsphere), with special
One selectivity.In use, by this molecular recognition sensor and computer link, its electrode contact test fluid, according to either with or without letter
The power of number detection and signal judges whether the size containing template molecule and concentration.
Beneficial effects of the present invention：From hyaluronic acid, this natural macromolecular is modified, by itself characteristic with
The fusion of molecular imprinting technology and electro-deposition techniques, has prepared the molecular engram sensor with specific selectivity.The present invention
Application for natural macromolecular in electrochemical sensor field opens a feasible road really.This method can be with simultaneously
The different template molecule by choosing, and corresponding Molecular Design is carried out to starting monomer, it is final to determine sensor institute energy
The molecule of identification, therefore the composite can be widely applied to the association areas such as chemical industry, biological medicine, food, environmental protection tests.
Brief description of the drawings：
Fig. 1 is the K obtained by embodiment 13[Fe(CN)6] bare electrode, deposited MIP membrane electrodes circulation volt
Pacify spectrogram.Fig. 2 be with paracetamol (acamol) be the preparation-obtained MIP sensors of template molecule in 0.2mM
DPVs curves in acamol solution.
Embodiment
Technical solution of the present invention is not limited to following lifted embodiment, in addition to appointing between each embodiment
Meaning combination.
Embodiment 1
(1) modified synthesis of Photocrosslinkable modified hyaluronic acid：
Weighing 1.02g hyaluronic acids, (molecular weight is 2 × 105Da) it is dissolved in 100mL deionized waters, after dissolving completely, point
Jia Ru not 5.62g methyl propenoic acid glycidyl ethers, 2.2mL triethylamines, 2.2g TBABs, at room temperature uniform stirring
24h, rise temperature is reacted after 5h to 60 DEG C, is cooled to room temperature on this condition.Unreacted monomer is removed in dialysis, and freezing is dry
It is dry both to obtain Photocrosslinkable modified hyaluronic acid.
(2) preparation of trace colloidal solution：
Photocrosslinkable modified hyaluronic acid made from step (1) is codissolved in light trigger ring azo amidine class VA-044
Water, mass fraction is respectively 5% and 3 ‰, then adds in the solution template molecule acamol, is stirred overnight.
Acamol and Photocrosslinkable modified hyaluronic acid mass ratio are 1: 3.
(3) preparation of electrochemistry molecular recognition sensor：
Glass-carbon electrode is successively with 1.0 μm and 0.3 μm of Al2O3Slurry is polished to minute surface on chamois leather, then moves into super in ultra-pure water
Sound cleans 2~3min, then successively with 1: 1 ethanol, 1: 1HNO3, ultra-pure water and absolute ethyl alcohol be cleaned by ultrasonic, dry.It will locate in advance
The glass-carbon electrode insertion trace colloidal solution managed, applies+2V voltage, makes the electric trace colloidal particle of bear to electrode
Surface swimming simultaneously deposits film forming, and electrode surface is placed under uviol lamp with after a large amount of ultrapure waters and irradiates 5min, made electrode surface
Photo-crosslinking occurs for colloidal particle.Electrode is soaked in the acetic acid, methanol solution that volume ratio is 2: 8 again, 10h, elution pair is stirred
Acetaminophenol, obtains trace film modified electrode.The electrode is connected with electrochemical workstation Ji Wei molecular recognition sensor, its
There is single-minded selectivity to acamol.
Embodiment 2
(1) synthesis of Photocrosslinkable modified hyaluronic acid：
Weighing 1.02g hyaluronic acids, (molecular weight is 2 × 105Da) it is dissolved in 100mL deionized waters, after dissolving completely, point
Jia Ru not 7.49g methyl propenoic acid glycidyl ethers, 3.3mL triethylamines, 3.3g TBABs, at room temperature uniform stirring
Temperature is raised after 24h to 60 DEG C, reacts on this condition after 5h, is cooled to room temperature.Unreacted monomer is removed in dialysis, and freezing is dry
It is dry both to obtain Photocrosslinkable modified hyaluronic acid.
(2) trace colloidal solution prepare it is same as Example 1.
(3) electrochemistry molecular recognition sensor prepare it is same as Example 1.
Embodiment 3
(1) synthesis of Photocrosslinkable modified hyaluronic acid：
Weighing 1.02g hyaluronic acids, (molecular weight is 3 × 105Da) it is dissolved in 100mL deionized waters, after dissolving completely, point
Jia Ru not 7.49g methyl propenoic acid glycidyl ethers, 3.3mL triethylamines, 3.3g TBABs, at room temperature uniform stirring
Temperature is raised after 24h to 60 DEG C, reacts on this condition after 5h, is cooled to room temperature.Unreacted monomer is removed in dialysis, and freezing is dry
It is dry both to obtain Photocrosslinkable modified hyaluronic acid.
(2) molecular imprinting electrochemical sensor prepare it is same as Example 1.
(3) electrochemistry molecular recognition sensor prepare it is same as Example 1
Embodiment 4
(1) modified synthesis of Photocrosslinkable modified hyaluronic acid is same as Example 1.
(2) preparation of trace colloidal solution：
Photocrosslinkable modified hyaluronic acid made from step (1) is codissolved in light trigger ring azo amidine class VA-044
Water, mass fraction is respectively 5% and 3 ‰, then adds in the solution template molecule glucose, is stirred overnight.Glucose and
Photocrosslinkable modified hyaluronic acid mass ratio is 1: 3.
(3) preparation of electrochemistry molecular recognition sensor：
Glass-carbon electrode is successively with 1.0 μm and 0.3 μm of Al2O3Slurry is polished to minute surface on chamois leather, then moves into super in ultra-pure water
Sound cleans 2~3min, then successively with 1: 1 ethanol, 1: 1HNO3, ultra-pure water and absolute ethyl alcohol be cleaned by ultrasonic, drying to pre-process
Good glass-carbon electrode insertion trace colloidal solution, applies+2V voltage, makes the electric trace colloidal particle of bear to electrode table
Face swimming simultaneously deposits film forming, and electrode surface is placed under uviol lamp with after a large amount of ultrapure waters and irradiates 5min, made electrode surface glue
Photo-crosslinking occurs for body particle.Electrode is soaked in ethyl acetate solution again, 10h is stirred, glucose is eluted, obtains blotting membrane and repair
Adorn electrode.The electrode is connected with electrochemical workstation Ji Wei molecular recognition sensor, and it has single-minded selectivity to glucose.
Embodiment 5
(1) synthesis of Photocrosslinkable modified hyaluronic acid is same as Example 3
(2) preparation of molecular imprinting electrochemical sensor：By Photocrosslinkable modified hyaluronic acid and light made from step (1)
Initiator ring azo amidine class VA-044 is codissolved in water, and mass fraction is respectively 5% and 3 ‰, then by template molecule trimerization piperazine amine
Add in the solution, be stirred overnight.Trimerization piperazine amine and Photocrosslinkable modified hyaluronic acid mass ratio are 1: 3.
(3) preparation of electrochemistry molecular recognition sensor：
Glass-carbon electrode is successively with 1.0 μm and 0.3 μm of Al2O3Slurry is polished to minute surface on chamois leather, then moves into super in ultra-pure water
Sound cleans 2~3min, then successively with 1: 1 ethanol, 1: 1HNO3, ultra-pure water and absolute ethyl alcohol ultrasound, dry.It will pre-process
Glass-carbon electrode insertion trace colloidal solution, apply+2V a voltages, make bear electricity trace colloidal particle swum to electrode surface
Move and deposit film forming, electrode surface is placed under uviol lamp with after a large amount of ultrapure waters and is irradiated 5min, make electrode surface colloid grain
Photo-crosslinking occurs for son.Electrode is soaked in the acetic acid, methanol solution that volume ratio is 2: 8 again, 8h is stirred, elutes trimerization piperazine amine,
Obtain trace film modified electrode.The electrode is connected with electrochemical workstation Ji Wei molecular recognition sensor, and it has to trimerization piperazine amine
There is single-minded selectivity.
Claims (8)
1. a kind of preparation method of Photocrosslinkable modified hyaluronic acid molecular engram sensor, it is characterised in that including following step
Suddenly：
(1) it is hyaluronic acid modified：It is 1~10% hyaluronic acid aqueous solution by the hyaluronic acid mass fraction soluble in water that is made into,
Sequentially add triethylamine, tetran-butylphosphonium bromide by and photosensitive monomer, temperature is raised after 12~24h of uniform stirring at room temperature to 50
DEG C~70 DEG C, react on this condition after 5~10h, be cooled to room temperature, unreacted monomer, freeze-drying are removed in dialysis, or super
Critical drying had both obtained the modified hyaluronic acid of Photocrosslinkable；
(2) preparation of molecularly imprinted polymer modified electrode：By the modified hyaluronic acid and light trigger of obtained Photocrosslinkable
Ring azo amidine class VA-044 is codissolved in water, is then added template molecule in the aqueous solution, and template molecule addition is can light
The 2~30% of the modified hyaluronic acid quality of crosslinking, are stirred overnight, and trace macromolecular colloid solution, electrode insertion colloid is made
Apply a constant potential after solution to it, make charged trace colloidal particle to electrode surface swimming and electro-deposition film forming, by purple
Outer light irradiation obtains photosensitive molecular imprinted polymer film, and finally, elution removes template molecule, obtains molecularly imprinted polymer modification
Electrode；
(3) preparation of molecular engram sensor：Will be as the molecularly imprinted polymer modified electrode and sensing equipment obtained by step (2)
Molecular engram sensor can be obtained after connection.
2. preparation method according to claim 1, it is characterised in that the molecular weight of hyaluronic acid used is 2 × 104~3
×105。
3. preparation method according to claim 1, it is characterised in that modified photosensitive monomer can select following one kind
Or several GMAs, allyl glycidyl ether, 7- glycidoxy -4- methylcoumarins, and it is transparent
The mol ratio of matter acid and photosensitive monomer is 1: 5~1: 30.
4. preparation method according to claim 1, it is characterised in that modification is imparted by initial MOLECULE DESIGN transparent
Matter acid photaesthesia response, pH sensitiveness and electro-deposition film forming.
5. preparation method according to claim 1, it is characterised in that the template molecule used from acamol,
Glucose, melamine.
6. preparation method according to claim 1, it is characterized in that electrode surface material is conductive material.
7. preparation method according to claim 1, it is characterised in that the process conditions of electro-deposition are：Constant potential value is 0.1V
~60V, electrodeposition time 5s~10min.
8. preparation method according to claim 1, it is characterised in that the time of the ultraviolet light irradiation be 5min~
15min, the power of uviol lamp used is 1000~2000W, and irradiation distance is 1~5cm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210142383.7A CN102706929B (en) | 2012-05-10 | 2012-05-10 | A kind of preparation of Photocrosslinkable modified hyaluronic acid molecular engram sensor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210142383.7A CN102706929B (en) | 2012-05-10 | 2012-05-10 | A kind of preparation of Photocrosslinkable modified hyaluronic acid molecular engram sensor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102706929A CN102706929A (en) | 2012-10-03 |
| CN102706929B true CN102706929B (en) | 2017-09-01 |
Family
ID=46899868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210142383.7A Expired - Fee Related CN102706929B (en) | 2012-05-10 | 2012-05-10 | A kind of preparation of Photocrosslinkable modified hyaluronic acid molecular engram sensor |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102706929B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103757683B (en) * | 2014-01-07 | 2016-05-25 | 江南大学 | A kind of electro-deposition preparation method of photo-crosslinking type bio-based coating |
| CN105113054A (en) * | 2015-09-05 | 2015-12-02 | 常州大学 | Method for preparing hyaluronic acid derivative crosslinking fiber |
| CN105353010A (en) * | 2015-10-28 | 2016-02-24 | 江南大学 | Making method of molecularly imprinted electrochemical sensing electrode for detecting propylene chorohydrin |
| CN105353022A (en) * | 2015-10-28 | 2016-02-24 | 江南大学 | Flexible electrode-based molecularly imprinted electrochemical sensor making method |
| CN106908495A (en) * | 2017-01-05 | 2017-06-30 | 江南大学 | A kind of method that flexible molecule trace sensor is prepared based on carbon nanotube loaded polymer micelle |
| CN107976472B (en) * | 2017-11-22 | 2020-01-10 | 江南大学 | Preparation method of biological pollution-resistant coating on surface of sensor electrode |
| CN108562629B (en) * | 2018-04-24 | 2020-02-18 | 中南民族大学 | Ion selective electrode for detecting melamine and detection method |
| CN109481729A (en) * | 2018-11-23 | 2019-03-19 | 南京华开生物科技有限公司 | A kind of low molecular weight sodium hyaluronate isotonic liquid dressing and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101776635A (en) * | 2010-02-02 | 2010-07-14 | 江南大学 | Preparation method of molecular recognition sensor by electro-deposition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10042023C2 (en) * | 2000-08-08 | 2003-04-10 | Biognostic Ag | Capsules that encapsulate solid particles of signal-generating substances and their use in bioassays for the detection of target molecules in a sample |
-
2012
- 2012-05-10 CN CN201210142383.7A patent/CN102706929B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101776635A (en) * | 2010-02-02 | 2010-07-14 | 江南大学 | Preparation method of molecular recognition sensor by electro-deposition |
Non-Patent Citations (5)
| Title |
|---|
| Electrodeposition of hyaluronic acid and composite films;F. Sun,et al.;《Surface Engineering》;20091231;第25卷(第8期);621-627 * |
| Paracetamol Sensor Based on Molecular Imprinting by Photosensitive Polymers;Xiaohong Wang,et al.;《Electroanalysis》;20130628;第25卷(第8期);1907-1916 * |
| Photocrosslinked Hyaluronic Acid Hydrogels: Natural, Biodegradable Tissue Engineering Scaffolds;Jennie Baier Leach,et al.;《BIOTECHNOLOGY AND BIOENGINEERING》;20030605;第82卷(第5期);578-589 * |
| 双亲性大分子自组装及其胶束传感器;王晓红;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20140215;全文 * |
| 辐照交联改性透明质酸的研究;陈森军 等;《北京化工大学学报(自然科学版)》;20090520;第36卷(第3期);46-49 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102706929A (en) | 2012-10-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102706929B (en) | A kind of preparation of Photocrosslinkable modified hyaluronic acid molecular engram sensor | |
| Wei et al. | Near-infrared light-responsive electrochemical protein imprinting biosensor based on a shape memory conducting hydrogel | |
| Huang et al. | Modification of hydrophobic hydrogels into a strongly adhesive and tough hydrogel by electrostatic interaction | |
| Yang et al. | Tunable interpenetrating polymer network hydrogels based on dynamic covalent bonds and metal–ligand bonds | |
| CN101776635B (en) | Preparation method of molecular recognition sensor by electro-deposition | |
| CN108676178B (en) | Preparation method of modified polysaccharide hydrogel and prepared modified polysaccharide hydrogel | |
| Chen et al. | Construction of a flexible electrochemiluminescence platform for sweat detection | |
| Zhu et al. | Ion-responsive chitosan hydrogel actuator inspired by carrotwood seed pod | |
| CN107732003B (en) | A kind of preparation method of the PAH/PAMAM self-assembled multilayer film based on piezoelectric membrane | |
| Wei et al. | Preparation of gas-responsive imprinting hydrogel and their gas-driven switchable affinity for target protein recognition | |
| Xiong-Hui et al. | A review on bio-macromolecular imprinted sensors and their applications | |
| Ye et al. | Tailoring the glucose-responsive volume phase transition behaviour of Ag@ poly (phenylboronic acid) hybrid microgels: from monotonous swelling to monotonous shrinking upon adding glucose at physiological pH | |
| Wang et al. | Facile preparation of PHEMA hydrogel induced via Tannic Acid-Ferric ions for wearable strain sensing | |
| CN105623174A (en) | Polyaniline/liquid crystal elastomer composite membrane material and preparation method thereof | |
| Perez-Madrigal et al. | Polypyrrole-supported membrane proteins for bio-inspired ion channels | |
| CN110128594B (en) | temperature/pH dual-sensitive high-strength nano composite hydrogel and preparation method thereof | |
| Wu et al. | Stretchable and highly sensitive polyelectrolyte microgels-enhanced polyacrylamide hydrogel composite for strain sensing | |
| Barbero | Functional materials made by combining hydrogels (cross-linked polyacrylamides) and conducting polymers (polyanilines)—A critical review | |
| Liu et al. | Highly stretchable, self-adhesive, ambient-stable, and wide-temperature adaptable hydrophobic ionogels for wearable strain sensors | |
| CN107300582A (en) | Antibiotic detection means and its manufacture method, detection method based on microsensor | |
| He et al. | Antifouling electrochemical biosensor based on conductive hydrogel of DNA Scaffold for ultrasensitive detection of ATP | |
| Wu et al. | Dynamic cross-linking network construction of carboxymethyl starch enabling temperature and strain bimodal film sensors | |
| Kishi | Energy conversion | |
| CN109298038A (en) | A kind of MnCo2O4The preparation method and application of/Polyaniline-modified Glassy Carbon Electrode | |
| Zhu et al. | Synthesis of molecularly imprinted polymer via visible light activated RAFT polymerization in aqueous media at room temperature for highly selective electrochemical assay of glucose |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20170901 Termination date: 20210510 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |