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NZ773861B2 - Poly(allyl glycidyl ether)-based redox polymer and electrochemical biosensor using same - Google Patents
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NZ773861B2 - Poly(allyl glycidyl ether)-based redox polymer and electrochemical biosensor using same - Google Patents

Poly(allyl glycidyl ether)-based redox polymer and electrochemical biosensor using same Download PDF

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NZ773861B2
NZ773861B2 NZ773861A NZ77386119A NZ773861B2 NZ 773861 B2 NZ773861 B2 NZ 773861B2 NZ 773861 A NZ773861 A NZ 773861A NZ 77386119 A NZ77386119 A NZ 77386119A NZ 773861 B2 NZ773861 B2 NZ 773861B2
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group
carbon atoms
unsubstituted
chemical formula
ghmatters
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NZ773861A
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NZ773861A (en
Inventor
In Seok Jeong
Young Jea Kang
Hyunseo Shin
Bona Yang
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I Sens Inc
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Priority claimed from KR1020190114354A external-priority patent/KR102244655B1/en
Application filed by I Sens Inc filed Critical I Sens Inc
Priority claimed from PCT/KR2019/012084 external-priority patent/WO2020060194A1/en
Publication of NZ773861A publication Critical patent/NZ773861A/en
Publication of NZ773861B2 publication Critical patent/NZ773861B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/002—Osmium compounds
    • C07F15/0026—Osmium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/338—Polymers modified by chemical after-treatment with inorganic and organic compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/001—Enzyme electrodes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/001—Enzyme electrodes
    • C12Q1/004—Enzyme electrodes mediator-assisted
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/001—Enzyme electrodes
    • C12Q1/005—Enzyme electrodes involving specific analytes or enzymes
    • C12Q1/006—Enzyme electrodes involving specific analytes or enzymes for glucose
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • C12Q1/32—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving dehydrogenase
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
    • G01N27/28—Electrolytic cell components
    • G01N27/30—Electrodes, e.g. test electrodes; Half-cells
    • G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
    • G01N27/3271—Amperometric enzyme electrodes for analytes in body fluids, e.g. glucose in blood
    • G01N27/3272—Test elements therefor, i.e. disposable laminated substrates with electrodes, reagent and channels
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
    • G01N27/28—Electrolytic cell components
    • G01N27/30—Electrodes, e.g. test electrodes; Half-cells
    • G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
    • G01N27/3275—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction
    • G01N27/3277—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction being a redox reaction, e.g. detection by cyclic voltammetry
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables

Abstract

The present invention relates to a redox polymer which can be used in an electrochemical sensor, and particularly, in a polymer backbone of an electron transfer mediator of the electrochemical sensor. More specifically, the present invention relates to: a redox polymer which can be used in a poly(allyl glycidyl ether)-based electrochemical sensor comprising a repeating unit derived from allyl glycidyl ether; and an electron transfer mediator and an electrochemical sensor comprising same, wherein the redox polymer is advantageous in confirming the completion of reaction during manufacture, has high transition metal complex immobilization efficiency, has low possibility of having problems of toxicity and side effects, and can add various functions.

Claims (1)

1. CLAIMS ? ?Claim 1? A poly(allyl glycidyl ether)-based polymer for the preparation of an oxidation-reduction polymer material, 5 wherein a functional group selected from the group consisting of primary and secondary amine groups, an ammonium group, a halogen group, an epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, an isocyanate, an alcohol group and a silane group is introduced into the polymer, 10 the polymer has a structure of the following Chemical Formulas 1 or 2: [Chemical Formula 1] 20699871_1 (GHMatters) P114832.NZ [Chemical Formula 2] in the Chemical Formula 1 or 2, R and R may be each independently selected from the group 5 consisting of an unsubstituted alkylene group having 1 to 20 carbon atoms, an unsubstituted cycloalkylene group having 1 to 20 carbon atoms, an unsubstituted ethylene glycol group having 3 to 30 carbon atoms, an unsubstituted arylene group having 6 to 30 carbon atoms, an unsubstituted heteroarylene group having 3 to 30 carbon atoms, an unsubstituted alkenyl 10 group having 2 to 40 carbon atoms, and an unsubstituted alkynyl group having 2 to 40 carbon atoms; L to L are each independently selected from the group consisting of an unsubstituted alkylene group having 1 to 20 carbon atoms, an unsubstituted cycloalkylene group having 1 to 20 carbon atoms, an 15 unsubstituted ethylene glycol group having 3 to 30 carbon atoms, an unsubstituted arylene group having 6 to 30 carbon atoms, and an unsubstituted heteroarylene group having 3 to 30 carbon atoms; A to A are selected from the group consisting of primary and D1 D2 secondary amine groups, an ammonium group, a halogen group, an epoxy 20699871_1 (GHMatters) P114832.NZ group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, thiol group, an isocyanate, an alcohol group and a silane group; o is an integer of 10 to 300; p is an integer of 0 to 300; and 5 q is an integer of 10 to 300. ?Claim 2? The polymer for the preparation of oxidation-reduction polymer material according to claim 1, wherein the R and R are each independently selected from the group of polystyrene (PS), polyethylene glycol (PEG), 10 polyethylene oxide (PEO), polymethyl methacrylate (PMMA), polyvinylimidazole (PVI), polyvinylpyridine (PVP) and polysiloxane (PDMS), each having a molecular weight of 1,000 g/mol to 50,000 g/mol. ?Claim 3? The polymer for the preparation of oxidation-reduction polymer 15 material according to claim 1, wherein the functional group is introduced using a thiol-based compound having a functional group selected from the group consisting of primary and secondary amine groups, an ammonium group, a halogen group, an epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, thiol group, an isocyanate, an alcohol 20 group and a silane group by a click reaction. ?Claim 4? The polymer for the preparation of oxidation-reduction polymer material according to claim 3, wherein the thiol-based compound is a compound of the following Chemical Formula 3: 20699871_1 (GHMatters) P114832.NZ [Chemical Formula 3] HS-L -A wherein, the L is independently selected from the group consisting an 5 unsubstituted alkylene group having 1 to 20 carbon atoms, an unsubstituted cycloalkylene group having 1 to 20 carbon atoms, an unsubstituted ethylene glycol group having 3 to 30 carbon atoms, an unsubstituted arylene group having 6 to 30 carbon atoms, and an unsubstituted heteroarylene group having 3 to 30 carbon atoms, and 10 the A is selected from the group consisting of primary and secondary amine groups, an ammonium group, a halogen group, an epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, an isocyanate, an alcohol group and a silane group. ?Claim 5? 15 The polymer for the preparation of oxidation-reduction polymer material according to claim 1, wherein the polymer has a molecular weight of 1,000 g/mol to 50,000 g/mol. ?Claim 6? An oxidation-reduction polymer material for electrochemical sensor 20 comprising the polymer as set forth in any one of claims 1 to 5. ?Claim 7? The oxidation-reduction polymer material according to claim 6, wherein a functional group selected from the group consisting of primary and secondary amine groups, an ammonium group, a halogen group, an 20699871_1 (GHMatters) P114832.NZ epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, an isocyanate, an alcohol group and a silane group, and a transition metal complex are bound to the polymer. ?Claim 8? 5 The oxidation-reduction polymer material according to claim 7, wherein the transition metal complex has a structure represented by the following Chemical Formula 4: [Chemical Formula 4] 10 wherein, M is a transition metal selected from the group consisting of Os, Rh, Ru, Ir, Fe and Co; L and L are combined with each other to form a bidentate ligand G1 G2 selected from the following Chemical Formulas 5 to 7; 15 L and L are combined with each other to form a bidentate ligand G3 G4 selected from the following Chemical Formulas 5 to 7; L and L are each combined with each other to form a bidentate G5 G6 ligand selected from the following Chemical Formulas 5 to 7; 20699871_1 (GHMatters) P114832.NZ [Chemical Formula 5] [Chemical Formula 6] 5 [Chemical Formula 7] the R , R and R' are each independently selected from the group 1 2 1 consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted ethylene glycol group having 2 to 20 carbon atoms, an 10 unsubstituted alcohol group having 1 to 20 carbon atoms, an unsubstituted alkylhalogen group having 1 to 20 carbon atoms, an unsubstituted thiol group having 1 to 20 carbon atoms, an unsubstituted alkyl azide group having 3 to 20 carbon atoms, an unsubstituted aryl azide group having 7 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 40 carbon atoms, 20699871_1 (GHMatters) P114832.NZ an unsubstituted alkynyl group having 2 to 40 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen, the R to R are each independently selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an 5 unsubstituted cycloalkyl group having 3 to 40 carbon atoms, an unsubstituted aryl group having 6 to 50 carbon atoms, an unsubstituted heteroaryl group having 3 to 50 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted alcohol group having 1 to 20 carbon atoms, an unsubstituted alkylhalogen group having 1 to 20 carbon 10 atoms, an unsubstituted thiol group having 1 to 20 carbon atoms, an unsubstituted alkyl azide group having 3 to 20 carbon atoms, an unsubstituted aryl azide group having 7 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 20 carbon atoms, an unsubstituted arylamino group having 15 6 to 30 carbon atoms, an unsubstituted alkylsilyl group having 1 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 30 carbon atoms, an unsubstituted arylalkylamino group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 40 carbon atoms, an unsubstituted alkynyl group having 2 to 40 carbon atoms, a cyano group, a halogen group, 20 deuterium and hydrogen; the L is independently selected from the group consisting of an unsubstituted alkylene group having 1 to 20 carbon atoms, an unsubstituted cycloalkylene group having 1 to 20 carbon atoms, an unsubstituted ethylene glycol group having 2 to 30 carbon atoms, an unsubstituted arylene group 20699871_1 (GHMatters) P114832.NZ having 6 to 30 carbon atoms, and an unsubstituted heteroarylene group having 3 to 30 carbon atoms, and the A is selected from the group consisting of an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, isocyanate, 5 an alcohol group and a silane group. ?Claim 9? The oxidation-reduction polymer material according to claim 8, wherein the transition metal complex is functionalized with a functional group selected from the group consisting of an amine group, an ammonium 10 group, a halogen group, an epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, an isocyanate, an alcohol group, and a silane group. ?Claim 10? The oxidation-reduction polymer material according to claim 9, 15 wherein the functionalized transition metal complex has a structure of the following Chemical Formula 8a, 8b or 8c: [Chemical Formula 8a] 20699871_1 (GHMatters) P114832.NZ [Chemical Formula 8b] [Chemical Formula 8c] 5 ?Claim 11? The oxidation-reduction polymer material according to claim 8, having a structure of the following Chemical Formula 9 or 10: 20699871_1 (GHMatters) P114832.NZ [Chemical Formula 9] [Chemical Formula 10] 5 in the Chemical Formula 9 or 10, R and R are each independently selected from the group consisting of an unsubstituted alkylene group having 3 to 20 carbon atoms, an unsubstituted cycloalkylene group having 6 to 20 carbon atoms, an unsubstituted ethylene glycol group having 2 to 30 carbon atoms, an 10 unsubstituted arylene group having 6 to 30 carbon atoms, an unsubstituted 20699871_1 (GHMatters) P114832.NZ heteroarylene group having 3 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 40 carbon atoms and an unsubstituted alkynyl group having 2 to 40 carbon atoms, L to L are each independently selected from the group consisting of 5 an unsubstituted alkylene group having 1 to 20 carbon atoms, an unsubstituted cycloalkylene group having 1 to 20 carbon atoms, an unsubstituted ethylene glycol group having 3 to 30 carbon atoms, an unsubstituted arylene group having 6 to 30 carbon atoms, and an unsubstituted heteroarylene group having 3 to 30 carbon atoms; 10 A is selected from the group consisting of primary and secondary amine groups, an ammonium group, a halogen group, an epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, isocyanate, an alcohol group and a silane group; o is an integer of 0 to 300; 15 p is an integer of 0 to 300; q is an integer of 10 to 300; M is a transition metal selected from the group consisting of Os, Rh, Ru, Ir, Fe, and Co; L and L are combined with each other to form a bidentate ligand G1 G2 20 selected from Chemical Formulas 5 to 7; L and L are each combined with each other to form a bidentate G3 G4 ligand selected from Chemical Formulas 5 to 7; and L and L are each combined with each other to form a bidentate G5 G6 ligand selected from Chemical Formulas 5 to 7: 20699871_1 (GHMatters) P114832.NZ [Chemical Formula 5] [Chemical Formula 6] 5 [Chemical Formula 7] the R , R and R' are each independently selected from the group 1 2 1 consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted ethylene glycol group having 2 to 20 carbon atoms, an 10 unsubstituted alcohol group having 1 to 20 carbon atoms, an unsubstituted alkylhalogen group having 1 to 20 carbon atoms, an unsubstituted thiol group having 1 to 20 carbon atoms, an unsubstituted alkyl azide group having 3 to 20 carbon atoms, an unsubstituted aryl azide group having 7 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 40 carbon atoms, 20699871_1 (GHMatters) P114832.NZ an unsubstituted alkynyl group having 2 to 40 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen, the R to R are each independently selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an 5 unsubstituted cycloalkyl group having 3 to 40 carbon atoms, an unsubstituted aryl group having 6 to 50 carbon atoms, an unsubstituted heteroaryl group having 3 to 50 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted alcohol group having 1 to 20 carbon atoms, an unsubstituted alkylhalogen group having 1 to 20 carbon 10 atoms, an unsubstituted thiol group having 1 to 20 carbon atoms, an unsubstituted alkyl azide group having 3 to 20 carbon atoms, an unsubstituted aryl azide group having 7 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 20 carbon atoms, an unsubstituted arylamino group having 15 6 to 30 carbon atoms, an unsubstituted alkylsilyl group having 1 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 30 carbon atoms, an unsubstituted arylalkylamino group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 40 carbon atoms, an unsubstituted alkynyl group having 2 to 40 carbon atoms, a cyano group, a halogen group, 20 deuterium and hydrogen; the L is independently selected from the group consisting of an unsubstituted alkylene group having 1 to 20 carbon atoms, an unsubstituted cycloalkylene group having 1 to 20 carbon atoms, an unsubstituted ethylene glycol group having 2 to 30 carbon atoms, an unsubstituted arylene group 20699871_1 (GHMatters) P114832.NZ having 6 to 30 carbon atoms, and an unsubstituted heteroarylene group having 3 to 30 carbon atoms, and X is a functional group selected from the group consisting of a triazole group, ether, thiol ether, an amide group, an urea group, an urethane 5 group and a silane group. ?Claim 12? A method for producing the oxidation-reduction polymer material as set forth in claim 6 comprising the steps of: (a) polymerizing allyl glycidyl ether in the presence of an initiator to 10 prepare a polyallyl-glycidyl ether-based polymer precursor; and (b) introducing a functional group selected from the group consisting of an amine group, an ammonium group, a halogen group, an epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, isocyanate, an alcohol group, and a silane group, and a transition 15 metal complex into the polymer precursor prepared in step (a). ?Claim 13? A method for manufacturing an electron transport medium comprising the steps of: coating the oxidation-reduction polymer material as set forth in claim 6 onto an electrode and then curing the coated electrode. 20 ?Claim 14? An electron transport medium which is manufactured by the method as set forth in claim 13. 20699871_1 (GHMatters) P114832.NZ ?Claim 15? An electrochemical biosensor comprising the electron transport medium which is manufactured by the method as set forth in claim 13. ?Claim 16? 5 A sensing layer for an electrochemical biosensor comprising an enzyme capable of subjecting a liquid biological sample to an oxidation- reduction reaction ; and the electron transport medium which is manufactured by the method as set forth in claim 13. 10 ?Claim 17? The sensing layer for an electrochemical biosensor according to claim 16, wherein the enzyme includes, one or more oxidoreductases selected from the group consisting of dehydrogenase, oxidase, and esterase; or 15 one or more oxidoreductases selected from the group consisting of dehydrogenase, oxidase and esterase, and one or more cofactors selected from the group consisting of flavin adenine dinucleotide (FAD), nicotinamide adenine dinucleotide (NAD), and pyrroloquinoline quinone (PQQ). 20 ?Claim 18? The sensing layer for an electrochemical biosensor according to claim 17, wherein the oxidoreductase is a glucose dehydrogenase capable of maintaining an activity of 70% or more for 1 week in a buffer solution at 37°C. 20699871_1 (GHMatters) P114832.NZ ?Claim 19? The sensing layer for an electrochemical biosensor according to claim 16, further comprising a carbon nanotube. ?Claim 20? 5 An electrochemical biosensor comprising the sensing layer for an electrochemical biosensor as set forth in claim 16. ?Claim 21? The electrochemical biosensor according to claim 20, wherein the electrochemical biosensor is a continuous blood glucose monitoring sensor. 10 ?Claim 22? The polymer for the preparation of oxidation-reduction polymer material according to claim 1, substantially as herein described with reference to any one of the Examples or
NZ773861A 2019-09-18 Poly(allyl glycidyl ether)-based redox polymer and electrochemical biosensor using same NZ773861B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR20180111633 2018-09-18
KR1020190114354A KR102244655B1 (en) 2018-09-18 2019-09-17 Poly allyl glycidyl ether-based redox polymer and Electrochemical biosensor using thereof
PCT/KR2019/012084 WO2020060194A1 (en) 2018-09-18 2019-09-18 Poly(allyl glycidyl ether)-based redox polymer and electrochemical biosensor using same

Publications (2)

Publication Number Publication Date
NZ773861A NZ773861A (en) 2024-09-27
NZ773861B2 true NZ773861B2 (en) 2025-01-07

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