WO1992014741A1 - Complexes mono, bis ou tris (2,2'-bipyridine substituee) d'un metal choisi parmi le fer, le ruthenium, l'osmium ou le vanadium et leurs procedes de preparation - Google Patents
Complexes mono, bis ou tris (2,2'-bipyridine substituee) d'un metal choisi parmi le fer, le ruthenium, l'osmium ou le vanadium et leurs procedes de preparation Download PDFInfo
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- WO1992014741A1 WO1992014741A1 PCT/CH1992/000033 CH9200033W WO9214741A1 WO 1992014741 A1 WO1992014741 A1 WO 1992014741A1 CH 9200033 W CH9200033 W CH 9200033W WO 9214741 A1 WO9214741 A1 WO 9214741A1
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- bipyridine
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- mono
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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 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
- 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
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/005—Compounds of elements of Group 5 of the Periodic System without metal-carbon linkages
-
- 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
-
- 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
Definitions
- the present invention relates to a new family of mono, bis or tris (2,2 '- substituted bipyridine) complexes of a metal chosen from iron, ruthenium, osmium or vanadium, the bipyridine being substituted by at least one electron donor group.
- the invention also relates to processes for the preparation of these complexes.
- mediators such as ferrocene are quite volatile or unstable especially when exposed to light and the sensors must be kept under fairly strict conditions of light and temperature.
- mediators including ferrocene decompose in water by hydrolysis which is annoying when the sensors are used in the blood.
- oxygen competes with some of these mediators and the results of glucose concentration measurements vary depending on the amount of oxygen present in the blood. This can be annoying depending on whether one works with venous blood or arterial blood.
- the new family of mono, bis or tris (2,2 '-bipyridine substituted) complexes of a metal M has the following general formula (I):
- M is chosen from iron, osmium, ruthenium or vanadium.
- L represents a bipyridine substituted by at least one electron donor group, giving the complex the redox properties desired for a mediator.
- This electron donor group is preferably chosen from an OH group, an alkoxy group, an aryloxy group or a primary, secondary or tertiary amino group.
- L 1 , L 2 , L 3 , L 4 are ligands forming a coordination complex with iron, osmium, ruthenium or vanadium.
- the ligand L preferably represents a bipyridine bisubstituted in position 4.4 'and more particularly 4,4'- dihydroxy - 2,2' - bipyridine, 4,4 '- dimethoxy - 2,2 '- bipyridine, or 4,4' - bis (N, N -ethylamino) - 2,2 '- bipyridine also known as 4,4'- bis (N, N - diethylamino) - 2 , 2 '- bipyridine, the complexes then having the following general formulas, referenced (II), (III) and (IV) respectively:
- the ligands L 1 , L 2 , L 3 and L 4 are mono, bi, tri or tetradentate ligands and can be combined in the following way:
- L 1 , L 2 , L 3 and L 4 each represent a monodentate ligand and are totally or partially identical to each other or different from each other,
- L 1 and L 2 together form a bidentate ligand and L 3 and L 4 are identical or different and each represent a monodentate ligand,
- L 1 and L 2 on the one hand and L 3 and L 4 on the other hand respectively form a bidentate ligand
- L 1 represents a monodentate ligand and L 2 , L 3 and L 4 together form a tridentate ligand
- L 1 , L 2 , L 3 to L 4 together form a tetradentate ligand.
- monodentate ligands that can be used, there may be mentioned: CN-, Cl-, Br-, I-, SCN-, H 2 O, NH 3 , triphenylphosphine, trialkylphosphines, primary, secondary or tertiary amines, pyridine or pyridines substituted with Cl, NH 2 , NO 2 or with an alkyl group.
- bidentate ligands which can be used, there may be mentioned: ethylene diamine, 1,2 - bis (2 - pyridyl) ethane, oxalic acid O - CO-CO-O-, Tacetylacetone CH 3 -CO- CH 2 -CO-CH 3 , glycine NH 2 -CH 2 -COO-, and preferably bipyridines and phenanthrolines bisubstituted by an R group, and an R 2 group, R 1 and R 2 may be identical or different and each representing hydrogen, NO 2 , Cl, an alkyl group, an aryl group, an OH group, an alkoxy group, an aryloxy group or a primary, secondary or tertiary amino group.
- the terpyridine of general formula (V) will preferably be used
- R 3 represents hydrogen or an alkyl group.
- ligand L a tris complex (ligand L) of a metal is obtained M chosen from iron, ruthenium, osmium or vanadium.
- the preferred tris (ligand L) complexes of the present invention are:
- L 1 and L 2 together form a first bidentate ligand and L 3 and L 4 together form a second bidentate ligand and moreover only the first bidentate ligand is identical to the ligand L, a bis complex (ligand L) of the metal M, M being as defined above.
- the preferred bis (ligand L) complexes of the present invention are: - the bis (4,4 '- dihydroxy - 2,2' - bipyridine) mono (2,2 '- bipyridine) complexes of the metal M,
- L 1 and L 2 together form a first bidentate ligand and L 3 and L 4 together form a second bidentate ligand and that moreover this first and this second ligand are different from the ligand L
- a mono complex is obtained (ligand L) of a metal M chosen from iron, ruthenium, osmium or vanadium.
- the preferred mono complexes (ligand L) of the present invention are the following:
- the preferred mono complexes are the following:
- the present invention also provides methods of preparing the complexes described above.
- the invention relates in particular to a process for the preparation of a tris complex (ligand L) of a metal M chosen from iron, ruthenium, osmium or vanadium.
- the ligand L is a bidentate ligand chosen from 4.4 '- dimethoxy - 2.2' - bipyridine, 4.4 '- dihydroxy - 2.2' - bipyridine or 4.4 '- bis (N, N - ethylamino) - 2,2 '- bipyridine.
- this process consists in:
- Ligand A is in most cases identical to or close enough to ligand L to transform into this ligand L during the reaction.
- Ligand A can, for example, be of the same nature as ligand L, but be substituted differently. This is the case in Example 1, where one starts from a bipyridine bisubstituted by two methoxy groups to result in a bipyridine bisubstituted by two hydroxy groups.
- Example 1 as well as in Examples 5 and 11 described below, 4.4 '- dimethoxy -2.2' - bipyridine is used to produce complexes with 4.4 '- dihydroxy- 2, 2 '- bipyridine, because the latter is not commercially available, given the difficulties and manufacturing costs.
- the nature of the soluble salt of the metal M varies as a function of the latter. Depending on whether the metal M is iron, ruthenium, osmium or vanadium, the soluble salts are respectively FeCl 2 , K 2 OsCl 6 , RuCl 3 or VCl 3 .
- the invention relates firstly to a process for the preparation of a tris (4,4 '- dihydroxy - 2,2' - bipyridine) complex of a metal M chosen from iron, ruthenium, osmium or vanadium.
- this process consists in:
- the soluble salts of the metal M are identical to those which have been described previously.
- the OH groups can then form to lead to a tris (4,4 '- dihydroxy - 2,2' - bipyridine) complex of the metal M.
- the complex obtained is filtered, washed with a mixture (1:10 vol / vol) of acetone and diethyl ether and then dried under high vacuum.
- PBS phosphate buffer solution: 100 mM NaCl, NaH 2 PO 4 10 mM, first adjusted to pH 7.4, then to pH 1 and to pH 13
- a carbon electrode we obtain:
- the process for preparing the tris complex (ligand L) of metal M will consist of:
- solvents used methanol, DMF and / or water
- these solvents make it possible to reduce the metal M from an oxidation state + 3 to a state + 2 for ruthenium, from a state + 4 to a state + 2 for osmium and from a state + 3 in a state + 2 for vanadium.
- Iron does not change oxidation state, it is already in oxidation state + 2.
- vanadium it is necessary to use additional reagents to reach the state of oxidation 0 desired.
- the sample dissolved in CD 2 Cl 2 has an OCH 3 peak at 4.1 ppm and aromatic proton peaks between 6.8 ppm and 8.0 ppm, compared to a tetramethylsilane standard.
- This process consists of:
- the soluble metal salt M is identical to those described above.
- the complex obtained is filtered, washed with a mixture (1:10 vol / vol) of acetone and diethyl ether and dried under high vacuum.
- the present invention also relates to the preparation of a bis (ligand L) mono (ligand B) complex of a metal M chosen from iron, osmium, ruthenium or vanadium, the ligand L being chosen from 4.4 ' - dimethoxy - 2,2 '- bipyridine, 4,4' - dihydroxy -2,2 '- bipyridine or 4,4' - bis (N, N - ethylamino) - 2,2 '-bipyridine) and the ligand B being a bidentate ligand such as those cited at the beginning of the description.
- a metal M chosen from iron, osmium, ruthenium or vanadium
- the ligand L being chosen from 4.4 ' - dimethoxy - 2,2 '- bipyridine, 4,4' - dihydroxy -2,2 '- bipyridine or 4,4' - bis (N, N - ethylamino) - 2,2 '
- a soluble salt of the metal M (M being as defined above), with a substantially stoichiometric amount of 4.4 '- dimethoxy - 2.2' - bipyridine in the presence of a mixture of suitable solvents, in particular for example, water and methanol in the case of the first ligand L and ethylene glycol in the second case, then to, - reflux this solution under a nitrogen atmosphere, at atmospheric pressure and for example, at a temperature between 70 and 80 ° C if you use water and methanol or at a temperature between 190 and 200 ° C if your uses ethylene glycol.
- suitable solvents in particular for example, water and methanol in the case of the first ligand L and ethylene glycol in the second case
- the osmium bis (4,4 '- dihydroxy - 2,2' - bipyridine) Cl 2 complex thus obtained is in the form of blue crystals.
- the yield is 80 to 90%.
- the solution is allowed to reflux for at least 4 hours under a nitrogen atmosphere, at atmospheric pressure and at a temperature between 150 and 155 ° C.
- the solution is allowed to cool to room temperature and the solvent is completely eliminated by rotary evaporation.
- 10 ml of cold water are added thereto and the bis (4.4 '- bis (N, N - ethylamino) - 2.2' - bipyridine) Cl 2 osmium complex (which is hardly soluble) is isolated by filtration. Then this complex is washed with cold water and then with a mixture (1: 6 vol / vol) of acetone and diethyl ether to remove the traces of unreacted ligand, then it is dried under high vacuum.
- This process consists of:
- the chlorine complex will preferably be reacted with 4,4 '- dimethoxy - 2,2' - bipyridine, since it is more readily available on the market.
- the product is then dissolved in a minimum of ethanol and precipitated in the form of trifluoromethansulfonate by addition of trifluoromethansulfonic acid. Finally, the precipitate is filtered, washed with a mixture of acetone and diethyl ether (1: 6 vol / vol) and then dried under high vacuum.
- This complex has the following physicochemical properties: - Elemental analysis
- the product obtained is precipitated in the form of trifluoromethansulfonate by adding trifluoromethansulfonic acid diluted to the ethylene glycol solution.
- the bis (4,4 '- dihydroxy - 2,2' - bipyridine) mono (4,4 '- dimethyl - 2,2' - bipyridine) complex of osmium obtained is filtered, washed with a mixture of acetone and diethyl ether (1:10 vol / vol) and dried under high vacuum.
- the product obtained is precipitated in the form of trifluoromethansulfonate by addition of trifluoromethansulfonic acid.
- the precipitate is filtered, washed with a mixture (1: 6 vol / vol) of acetone and diethyl ether and then dried under high vacuum.
- the preparation processes which have just been described in Examples 7, 8 and 9 for osmium can be generalized to iron, ruthenium and vanadium.
- the invention relates to a process for the preparation of a mono (ligand L) bis (ligand B) complex of a metal M chosen from iron, osmium, ruthenium or vanadium.
- the ligand L is chosen as above from 4,4 '- dimethoxy - 2,2' - bipyridine, 4,4 '- dihydroxy - 2,2' - bipyridine or 4,4 '- bis (N, N - ethylamino) - 2,2 '- bipyridine and ligand B is one of the bidentate ligands mentioned at the beginning of the description.
- this process consists in:
- ligand A is generally identical to ligand L or is of the same nature as the latter with different substitutions.
- Example 11 illustrates the latter case, for example.
- the product is dissolved in a minimum of ethanol, then precipitated in the form of trifluoromethansulfonate by addition of trifluoromethansulfonic acid.
- the complex obtained in the form of a precipitate is filtered with a mixture of acetone and diethyl ether (1: 6 vol / vol), then dried under high vacuum.
- This complex has the following physico-chemical properties: - Redox potential E ° (normal potential)
- Ton dissolves the complex in an organic solvent such as Tacetonitrile in the presence of a 0.2 M LiClO 4 salt and Ton performs a potentiodynamic measurement with a glassy carbon electrode, we obtain E ° ⁇ + 500 mV (electrode of reference to calomel SCE).
- the product is precipitated in the form of trifluoromethansulfonate by addition of dilute trifluoromethansulfonic acid.
- the precipitate obtained is filtered, washed with a mixture (1: 6 vol / vol) of acetone and diethyl ether, then dried under high vacuum.
- L represents a 2,2′-bipyridine substituted by at least one electron donor group and L 1 , L 2 , L 3 , L 4 are ligands forming a coordination complex with the metal M.
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP92903806A EP0526603B1 (fr) | 1991-02-21 | 1992-02-19 | Utilisation de complexes mono, bis ou tris (2,2'-bipyridine substituée) d'un métal de transition comme capteurs ampérométriques |
US07/949,485 US5393903A (en) | 1991-02-21 | 1992-02-19 | Mono, bis or tris(substituted 2,2'-bipyridine) iron, ruthenium, osmium or vanadium complexes and their methods of preparation |
CA002080834A CA2080834C (fr) | 1991-02-21 | 1992-02-19 | Complexes mono, bis ou tris(2,2'-substituant-bipyridine) d'un metal choisi parmi le fer, le ruthenium, l'osmium ou le vanadium et leurs methodes de preparation |
DE69215596T DE69215596T2 (de) | 1991-02-21 | 1992-02-19 | Verwendung von Mono-, Bis- oder Tris-(Substituierte 2,2'-Bipyridin) Übergangsmetallkomplexen als Übermittler für ein amperiometrisches Signaleingabeglied |
AU12441/92A AU657307B2 (en) | 1991-02-21 | 1992-02-19 | Mono, bis or tris (2,2'-substituted bipyridine) complexes of a metal selected amongst iron, ruthenium, osmium or vanadium and preparation methods thereof |
NO92924019A NO924019L (no) | 1991-02-21 | 1992-10-16 | Mono-, bis- og tris-(substituert 2,2'-bipyridin) komplekser av jern, rutenium, osmium og vanadium og fremgangsmaate ved deres fremstilling |
CS923166A CZ316692A3 (en) | 1991-02-21 | 1992-10-19 | Mono-, bis- or tris(substituted 2,2'-bipyridine) complexes of iron, ruthenium, osmium or vanadium and process for preparing thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9102199A FR2673183B1 (fr) | 1991-02-21 | 1991-02-21 | Complexes mono, bis ou tris (2,2'-bipyridine substituee) d'un metal choisi parmi le fer, le ruthenium, l'osmium ou le vanadium et leurs procedes de preparation . |
FR91/02199 | 1991-02-21 |
Publications (1)
Publication Number | Publication Date |
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WO1992014741A1 true WO1992014741A1 (fr) | 1992-09-03 |
Family
ID=9410038
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CH1992/000033 WO1992014741A1 (fr) | 1991-02-21 | 1992-02-19 | Complexes mono, bis ou tris (2,2'-bipyridine substituee) d'un metal choisi parmi le fer, le ruthenium, l'osmium ou le vanadium et leurs procedes de preparation |
Country Status (9)
Country | Link |
---|---|
US (1) | US5393903A (fr) |
EP (1) | EP0526603B1 (fr) |
JP (1) | JP2855481B2 (fr) |
AT (1) | ATE145913T1 (fr) |
AU (1) | AU657307B2 (fr) |
CA (1) | CA2080834C (fr) |
DE (1) | DE69215596T2 (fr) |
FR (1) | FR2673183B1 (fr) |
WO (1) | WO1992014741A1 (fr) |
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WO2012079673A1 (fr) | 2010-12-15 | 2012-06-21 | Merck Patent Gmbh | Dispositif électroluminescent organique |
DE102010054525A1 (de) | 2010-12-15 | 2012-04-26 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
WO2012084115A1 (fr) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Dispositif électroluminescent organique |
DE102010055902A1 (de) | 2010-12-23 | 2012-06-28 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
WO2012126566A1 (fr) | 2011-03-24 | 2012-09-27 | Merck Patent Gmbh | Matériaux fonctionnels ioniques organiques |
WO2012152366A1 (fr) | 2011-05-12 | 2012-11-15 | Merck Patent Gmbh | Composés ioniques organiques, compositions et dispositifs électroniques |
DE102012016192A1 (de) | 2011-08-19 | 2013-02-21 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
WO2014079532A1 (fr) | 2012-11-20 | 2014-05-30 | Merck Patent Gmbh | Formulation dans un solvant de haute pureté pour la fabrication de dispositifs électroniques |
WO2016071465A1 (fr) * | 2014-11-05 | 2016-05-12 | Tap Biosystems (Phc) Limited | Complexes de ruthénium (ii) luminescents et leur utilisation dans des capteurs de ph |
Also Published As
Publication number | Publication date |
---|---|
US5393903A (en) | 1995-02-28 |
JPH05508420A (ja) | 1993-11-25 |
FR2673183B1 (fr) | 1996-09-27 |
CA2080834A1 (fr) | 1992-08-22 |
CA2080834C (fr) | 1999-12-21 |
EP0526603A1 (fr) | 1993-02-10 |
EP0526603B1 (fr) | 1996-12-04 |
DE69215596D1 (de) | 1997-01-16 |
JP2855481B2 (ja) | 1999-02-10 |
FR2673183A1 (fr) | 1992-08-28 |
AU1244192A (en) | 1992-09-15 |
ATE145913T1 (de) | 1996-12-15 |
DE69215596T2 (de) | 1997-06-19 |
AU657307B2 (en) | 1995-03-09 |
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