CN104892503B - A kind of preparation method of the ＇ dioctyl phthalate of 2,2 ＇ bipyridyls 4,4 - Google Patents
A kind of preparation method of the ＇ dioctyl phthalate of 2,2 ＇ bipyridyls 4,4 Download PDFInfo
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- CN104892503B CN104892503B CN201510291480.6A CN201510291480A CN104892503B CN 104892503 B CN104892503 B CN 104892503B CN 201510291480 A CN201510291480 A CN 201510291480A CN 104892503 B CN104892503 B CN 104892503B
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- bipyridyl
- potassium permanganate
- dioctyl phthalate
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- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
- C07D213/807—Processes of preparation by oxidation of pyridines or condensed pyridines
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- 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
- C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses 2,2' of one kind bipyridyls 4, the preparation method of 4' dioctyl phthalate belongs to the synthesis technical field of sensitization fuel and medicine intermediate.Technical scheme main points are：4,4' dimethyl 2,2' bipyridyls are dissolved in the mixed system of water and nitric acid and 2,2' bipyridyl 4,4' dioctyl phthalate is made by potassium permanganate oxidation.The present invention is easy to operate, and reaction condition is gentle, and the reaction time is relatively short, and products therefrom yield is higher, and the post-reaction treatment is simple, and product, which is easy to crystallize from system, to be separated out, and is easy to separate and obtain target compound, is adapted to large-scale production.
Description
Technical field
The invention belongs to be sensitized the synthesis technical field of fuel and medicine intermediate, and in particular to and 2,2'- of one kind bipyridyls-
The preparation method of 4,4'- dioctyl phthalate.
Background technology
Bipyridyliumses derivative is the important source material of complex functionality section bar material, can have conjugated electrons with various metals formation
The complex of system, these complexs have good photoelectric conversion effect.They are used as energy converting material-dye sensitization
Agent, plays an important role in DSSC.During wherein 2,2'- bipyridyls are Bipyridine compound
Important one kind, it can be widely used for inspection as important chemical industry synthesis intermediate with each metal ion species formation complex
Survey presence and its content of trace metal ion etc..It can also form important noble metal complexes ligand, for preparing
Photoelectron transfer Complexes, for preparing solar cell.2,2'- bipyridyl -4,4'- dioctyl phthalate has N heterocyclic ligands and O's
Carboxyl ligand, its complex with some metals DSSC and C-C keys couple play the role of it is important,
Therefore the green high-efficient synthetic method for studying such compound is of great significance and value.Publication No. CN
103183636A patent under palladium chtalyst, carries out reducing couple with 2- chloroisonicotinic acids in the reduction system of inorganic base and glycerine
The method that 2,2'- bipyridyl -4,4'- dioctyl phthalate is made in connection reaction, accessory substance is more, and reacts more complicated, reaction condition
It is harsher.A kind of simple preparation method of 2,2'- bipyridyl -4,4'- dioctyl phthalate is by aoxidizing 4,4'- dimethyl -2,2'-
What the methyl on bipyridyl was obtained, the effective method for oxidation studied and explore 4,4'- dimethyl -2,2'- bipyridyls is that have very much
It is necessary.Current method for oxidation uses potassium bichromate or chromium trioxide is reacted in sulfuric acid system, although these react
It is swift in response, it is simple to operate, but corrosivity and the larger concentrated sulfuric acid of harmfulness have been used, heavy metal chromium ion pair environmental hazard
Larger, reaction needs heating, with certain danger, is not suitable for large-scale industrial production.Publication No. CN
102321017A patent is that 4,4'- dimethyl -2,2'- bipyridyls are used into potassium permanganate in the mixed system of glacial acetic acid and water
The method of oxidation avoids the use of potassium bichromate and sulfuric acid, but target product is difficult to separate from reaction system, post processing
It is complex.
The content of the invention
Present invention solves the technical problem that there is provided a kind of 2,2'- connection simple to operate, safe and reliable and higher yield
The preparation method of pyridine -4,4'- dioctyl phthalate.
The present invention is to solve above-mentioned technical problem to adopt the following technical scheme that, one kind 2,2'- bipyridyl -4,4'- dioctyl phthalate
Preparation method, it is characterised in that：4,4'- dimethyl -2,2'- bipyridyls are dissolved in the mixed system of water and nitric acid and passed through
2,2'- bipyridyl -4,4'- dioctyl phthalate is made in potassium permanganate oxidation, specifically includes following steps：（1）By 4,4'- dimethyl -2,
2'- bipyridyls are dissolved in the mixed system of water and nitric acid, be stirred and heated to 80 DEG C, potassium permanganate is added portionwise, a collection of before treating
The potassium permanganate of secondary addition is reacted to clarification, adds the potassium permanganate of next batch, maintains the temperature at 80 DEG C of reaction 6h；
（2）Reaction solution is cooled to room temperature, suction filtration is depressurized, insoluble matter is filtered off, then addition concentrated hydrochloric acid adjusts the pH of filtrate in filtrate
It is worth for 1, stands crystallization, after crystallization is complete, depressurize suction filtration, filter cake is washed with deionized, 2 is obtained after products therefrom drying,
2'- bipyridyl -4,4'- dioctyl phthalate.
Further limit, 1g 4 in preparation process, 4'- dimethyl -2,2'- bipyridyl correspondence mixed system reclaimed water 10-
100mL。
Further limit, the volume ratio of nitric acid and water is 1-30 in described mixed system:100.
Further limit, the mol ratio of 4,4'- dimethyl -2,2'- bipyridyl and potassium permanganate is 1 in preparation process:2-
8。
The invention has the advantages that：（1）Reaction system is simple, using only potassium permanganate, water（Solvent）And nitric acid
（Oxidant）, these reagents belong to general chemistry reagent, cheap and easy to get, prepare cost low；（2）This reaction meets Green Chemistry
Theory, it is to avoid chromium trioxide or potassium bichromate etc. have to environment the use of the oxidant of pollution；（3）It is easy to operate, react bar
Part is gentle, and the reaction time is relatively short, and products therefrom yield is higher, and the post-reaction treatment is simple, and product is easy to from system
Middle crystallization is separated out, and is easy to separate and obtain target compound, is adapted to large-scale production.
Compared with prior art, main innovation is in reaction system to add nitric acid the present invention, nitric acid
Addition 4,4'- dimethyl -2,2'- bipyridyls is dissolved in reaction system, reaction is carried out in homogeneous system, while nitric acid
The sour environment provided also enhances the oxidability of potassium permanganate.Potassium permanganate oxygen is used in the mixed system of water and nitric acid
Change 4,4'- dimethyl -2,2'- bipyridyls, reaction condition is relatively mild, and it is no using environmentally harmful oxidant, and
PH regulation causes target product 2,2'- bipyridyl -4,4'- dioctyl phthalate is easy to crystallize from system to separate out in post processing.This is anti-
It should can be all smoothed out at laboratory and industrialization large-scale production, with larger Practical significance.
Embodiment
The above to the present invention is described in further details by the following examples, but this should not be interpreted as to this
The scope for inventing above-mentioned theme is only limitted to following embodiment, and all technologies realized based on the above of the present invention belong to this hair
Bright scope.
Embodiment 1
The synthesis of 2,2'- bipyridyl -4,4'- dioctyl phthalate
In the four-hole bottle equipped with magneton, thermometer and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 40mL water and 4mL nitric acid, 80 DEG C are heated under stirring, and keep
This temperature adds potassium permanganate solid (common 6.3g, 0.04mol) in five times, and the potassium permanganate once added before treating is reacted to dissolved clarification
Afterwards, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution decompression is taken out
Filter, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.Treat
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried, obtained
To target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.2g, yield is 86%.
Embodiment 2
The synthesis of 2,2'- bipyridyl -4,4'- dioctyl phthalate
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 40mL water and 4mL nitric acid, 80 DEG C are heated under stirring, and keep
This temperature adds potassium permanganate solid (common 12.6g, 0.08mol) in five times, and the potassium permanganate once added before treating is reacted to molten
After clear, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution decompression is taken out
Filter, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.Treat
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried, obtained
To target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.35g, yield is 89%.
Embodiment 3
The synthesis of 2,2'- bipyridyl -4,4'- dioctyl phthalate
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 40mL water and 4mL nitric acid, 80 DEG C are heated under stirring, and keep
This temperature adds potassium permanganate solid (common 25.28g, 0.16mol) in five times, and the potassium permanganate once added before treating is reacted to molten
After clear, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution decompression is taken out
Filter, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.Treat
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried, obtained
To target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.44g, yield is 91%.
Embodiment 4
The synthesis of 2,2'- bipyridyl -4,4'- dioctyl phthalate
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 40mL water and 8mL nitric acid, 80 DEG C are heated under stirring, and keep
This temperature adds potassium permanganate solid (common 12.6g, 0.08mol) in five times, and the potassium permanganate once added before treating is reacted to molten
After clear, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution decompression is taken out
Filter, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.Treat
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried, obtained
To target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.59g, yield is 94%.
Embodiment 5
The synthesis of 2,2'- bipyridyl -4,4'- dioctyl phthalate
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 40mL water and 12mL nitric acid, 80 DEG C are heated under stirring, and protect
Hold this temperature and add potassium permanganate solid (common 12.6g, 0.08mol) in five times, before treating the potassium permanganate that once adds react to
After dissolved clarification, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution is depressurized
Suction filtration, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried,
Obtain target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.49g, yield is 92%.
Embodiment 6
The synthesis of 2,2'- bipyridyl -4,4'- dioctyl phthalate
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 40mL water and 2mL nitric acid, 80 DEG C are heated under stirring, and keep
This temperature adds potassium permanganate solid (common 12.6g, 0.08mol) in five times, and the potassium permanganate once added before treating is reacted to molten
After clear, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution decompression is taken out
Filter, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.Treat
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried, obtained
To target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.59g, yield is 94%.
Embodiment 7
2,2 '-bipyridyl -4,4 '-dioctyl phthalate synthesis
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 40mL water and 0.4mL nitric acid, 80 DEG C are heated under stirring, and protect
Hold this temperature and add potassium permanganate solid (common 12.6g, 0.08mol) in five times, before treating the potassium permanganate that once adds react to
After dissolved clarification, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution is depressurized
Suction filtration, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried,
Obtain target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.69g, yield is 96%.
Embodiment 8
2,2 '-bipyridyl -4,4 '-dioctyl phthalate synthesis
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 80mL water and 8mL nitric acid, 80 DEG C are heated under stirring, and keep
This temperature adds potassium permanganate solid (common 12.6g, 0.08mol) in five times, and the potassium permanganate once added before treating is reacted to molten
After clear, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution decompression is taken out
Filter, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.Treat
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried, obtained
To target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.10g, yield is 84%.
Embodiment 9
2,2 '-bipyridyl -4,4 '-dioctyl phthalate synthesis
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 200mL water and 20mL nitric acid, 80 DEG C are heated under stirring, and protect
Hold this temperature and add potassium permanganate solid (common 12.6g, 0.08mol) in five times, before treating the potassium permanganate that once adds react to
After dissolved clarification, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution is depressurized
Suction filtration, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried,
Obtain target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.00g, yield is 82%.
Embodiment 10
2,2 '-bipyridyl -4,4 '-dioctyl phthalate synthesis
In the four-hole bottle equipped with thermometer, magneton and reflux condensing tube, 3.7g (0.02mol) analytically pure 4 is added,
In 4 '-dimethyl -2,2 '-bipyridyl, the mixed system for being dissolved in 400mL water and 40mL nitric acid, 80 DEG C are heated under stirring, and protect
Hold this temperature and add potassium permanganate solid (common 12.6g, 0.08mol) in five times, before treating the potassium permanganate that once adds react to
After dissolved clarification, the potassium permanganate of next batch is added, reaction stops heating after 6 hours.It is cooled to after room temperature, reaction solution is depressurized
Suction filtration, after insoluble matter is filtered off, adds concentrated hydrochloric acid, regulation pH value is 1 in filtrate.Crystallization is stood, there is white crystal precipitation.
After crystallization is complete, decompression suction filtration is carried out, and the white crystal of gained is washed with deionized.Finally product vacuum is dried,
Obtain target product 2,2 '-bipyridyl -4,4 '-dioctyl phthalate 4.00g, yield is 82%.
Spectral data：
Target product 2,2 '-bipyridyl -4,4 ' structure of-dioctyl phthalate is：
FT-IR(cm-1)KBr：ν3440（By force）, 2446（By force）, 1730（By force）, 1605（By force）, 1463（By force）, 1365（By force）,
1290（By force）, 1269（By force）.
Elementary analysis：
2,2 '-bipyridyl -4,4 '-dioctyl phthalate（Molecular formula C12H8N2O4）Calculated value：C 59.02, H 3.30, N 11.50, O
26.18；Assay value：C 59.09, H 3.55, N 11.53.
Embodiment above describes general principle, principal character and the advantage of the present invention, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, the original for simply illustrating the present invention described in above-described embodiment and specification
Reason, under the scope for not departing from the principle of the invention, various changes and modifications of the present invention are possible, and these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (1)
1. one kind 2, the preparation method of 2'- bipyridyl -4,4'- dioctyl phthalate, it is characterised in that：By 4,4'- dimethyl -2,2'- connection
Pyridine is dissolved in the mixed system of water and nitric acid and 2,2'- bipyridyl -4,4'- dioctyl phthalate, tool is made by potassium permanganate oxidation
Body step is：Added in the four-hole bottle equipped with thermometer, magneton and reflux condensing tube 3.7g analytically pure 4,4 '-dimethyl-
2,2 '-bipyridyl in the mixed system for being dissolved in 40mL water and 0.4mL nitric acid, is heated to 80 DEG C, and keep this temperature point under stirring
After five addition 12.6g potassium permanganate solids, potassium permanganate solid reaction to the dissolved clarification once added before, next group is added
Stop heating after secondary potassium permanganate solid, reaction 6h, be cooled to after room temperature, reaction solution is depressurized into suction filtration, insoluble matter to be filtered off
After matter, concentrated hydrochloric acid is added in filtrate, regulation pH value is 1, stands crystallization, there is white crystal precipitation, after crystallization is complete, is carried out
Depressurize suction filtration, and be washed with deionized gained white crystal, finally product vacuum is dried, obtain target product 2,2 '-
Bipyridyl -4,4 '-dioctyl phthalate.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5585279A (en) * | 1986-01-23 | 1996-12-17 | Davidson; Robert S. | Time-resolved luminescence binding assays using a fluorescent transition metal label other than ruthenium |
| CN102321017A (en) * | 2011-07-08 | 2012-01-18 | 天津工业大学 | Method for preparing 2, 2'-bipyridyl-4, 4'-dioctyl phthalate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005082511A (en) * | 2003-09-05 | 2005-03-31 | Ube Ind Ltd | Method for producing carboxy compound |
| JP2006193444A (en) * | 2005-01-12 | 2006-07-27 | Koei Chem Co Ltd | Method for producing 4,4'-dicarboxy-2,2'-bipyridine |
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- 2015-06-01 CN CN201510291480.6A patent/CN104892503B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5585279A (en) * | 1986-01-23 | 1996-12-17 | Davidson; Robert S. | Time-resolved luminescence binding assays using a fluorescent transition metal label other than ruthenium |
| CN102321017A (en) * | 2011-07-08 | 2012-01-18 | 天津工业大学 | Method for preparing 2, 2'-bipyridyl-4, 4'-dioctyl phthalate |
Non-Patent Citations (1)
| Title |
|---|
| Preparation and Photochemical Reactivity of Surfactant Ruthenium( 11) Complexes in Monolayer Assemblies and at Water-Solid Interfaces;Gerhard Sprintschnik，等;《Journal of the American Chemical Society》;19770720;第99卷(第15期);4947-4954 * |
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