CA2110828A1 - Transition metal complexes having 2,2'-bipyridine ligands substituted by at least one ammonium alkyl radical, their method of manufacture and use thereof as a redox mediator - Google Patents

Transition metal complexes having 2,2'-bipyridine ligands substituted by at least one ammonium alkyl radical, their method of manufacture and use thereof as a redox mediator

Info

Publication number
CA2110828A1
CA2110828A1 CA002110828A CA2110828A CA2110828A1 CA 2110828 A1 CA2110828 A1 CA 2110828A1 CA 002110828 A CA002110828 A CA 002110828A CA 2110828 A CA2110828 A CA 2110828A CA 2110828 A1 CA2110828 A1 CA 2110828A1
Authority
CA
Canada
Prior art keywords
transition metal
alkyl radical
manufacture
metal complexes
alk
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.)
Granted
Application number
CA002110828A
Other languages
French (fr)
Other versions
CA2110828C (en
Inventor
David Fraser
Shaik Mohammed Zakeeruddin
Michael Graetzel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Asulab AG
Original Assignee
David Fraser
Shaik Mohammed Zakeeruddin
Michael Graetzel
Asulab S.A.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by David Fraser, Shaik Mohammed Zakeeruddin, Michael Graetzel, Asulab S.A. filed Critical David Fraser
Publication of CA2110828A1 publication Critical patent/CA2110828A1/en
Application granted granted Critical
Publication of CA2110828C publication Critical patent/CA2110828C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/002—Osmium compounds
    • C07F15/0026—Osmium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium compounds without a metal-carbon linkage
    • 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 System
    • C07F15/02—Iron compounds
    • C07F15/025—Iron compounds without a metal-carbon linkage
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium

Abstract

Complexes of the general formula I

(see formula I) wherein R1, R2 and R3, which may be the same or different, each represent a straight or branched alkyl radical having 1 to 5 carbon atoms or together with the adjacent nitrogen atom a heterocyclic radical having 5 to 7 carbon atoms;
"alk" represents a straight or branched alkylene radical having 1 to 5 carbon atoms; R4 to R8, which may be the same or different, represent hydrogen, or a hydroxy, alkoxy, aryloxy or primary secondary or tertiary amino group, or the group -alk-N+(R1R2R3) wherein "alk", R1, R2 and R3 have the meanings given above; M represents a transition metal such as Fe, Ru or Os; X represents an anion and n is an integer corresponding to the number of positive charges of tree complex.
CA002110828A 1992-12-15 1993-12-07 Transition metal complexes having 2,2'-bipyridine ligands substituted by at least one ammonium alkyl radical, their method of manufacture and use thereof as a redox mediator Expired - Lifetime CA2110828C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9215214 1992-12-15
FR9215214A FR2699170B1 (en) 1992-12-15 1992-12-15 Complexes of a transition metal with 2,2'-bipyridine ligands substituted by at least one alkyl ammonium radical, their manufacturing process and their use as redox mediator.

Publications (2)

Publication Number Publication Date
CA2110828A1 true CA2110828A1 (en) 1994-06-16
CA2110828C CA2110828C (en) 2005-02-15

Family

ID=9436701

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002110828A Expired - Lifetime CA2110828C (en) 1992-12-15 1993-12-07 Transition metal complexes having 2,2'-bipyridine ligands substituted by at least one ammonium alkyl radical, their method of manufacture and use thereof as a redox mediator

Country Status (9)

Country Link
US (1) US5410059A (en)
EP (1) EP0602488B1 (en)
JP (1) JP3751032B2 (en)
KR (1) KR940014424A (en)
AT (1) ATE178333T1 (en)
AU (1) AU665327B2 (en)
CA (1) CA2110828C (en)
DE (1) DE69324217T2 (en)
FR (1) FR2699170B1 (en)

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Also Published As

Publication number Publication date
DE69324217T2 (en) 1999-11-04
ATE178333T1 (en) 1999-04-15
FR2699170A1 (en) 1994-06-17
AU5240493A (en) 1994-08-04
DE69324217D1 (en) 1999-05-06
KR940014424A (en) 1994-07-18
AU665327B2 (en) 1995-12-21
EP0602488B1 (en) 1999-03-31
CA2110828C (en) 2005-02-15
EP0602488A1 (en) 1994-06-22
FR2699170B1 (en) 1995-07-28
JP3751032B2 (en) 2006-03-01
US5410059A (en) 1995-04-25
JPH06263781A (en) 1994-09-20

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