CN102127424B - Iridium metal coordination compound organic fluorescent nanoparticles and preparation method thereof - Google Patents
Iridium metal coordination compound organic fluorescent nanoparticles and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the technical field of organic nanometer science and discloses iridium metal coordination compound organic fluorescent nanoparticles. The nanoparticles have the characteristics of rectangular or square shape, sizes between 400 nanometers and 3,000 nanometers, structures shown as a formula I, high optical property, capability of emitting red fluorescent light of about 635 nanometers and important potential value in the field of optical function organic nanomaterials. In the preparation method of the nanomaterial, a pyridine-containing cationic metal iridium coordination compound reacts with carboxylic acid under the action of super-molecular self-assembly. The invention has the advantages of simplicity in operation, mild condition, low equipment requirement, environmental friendliness and the like.
Description
Technical field
The present invention relates to the organic nano material field, be specifically related to a kind of complex of iridium organic fluorescence nano material based on the supramolecule self-assembly and preparation method thereof.
Background technology
Scientific circles generally believe, nanotechnology is a main engine of 21 century economic growth, and it will become " decisive technology " above network technology and gene engineering, and will become the most promising material.Nowadays the research of traditional inorganic nano material had a large amount of reports, organic nano material becomes the research direction of field of nanometer material technology gradually.Be subjected to the restriction of the mode of action between the molecule, lower and the easy distillation of the molten boiling point of organic small molecule material, the preparation method of most inorganic nano materials also is not suitable for organic nano material, and exploring the new preparation method of organic nano material has become the new study hotspot of field of nanometer material technology.
Non-covalent interaction between supramolecular chemistry is based on minute and form the chemistry of molecule aggregates is mainly studied two or more molecules generate molecule aggregates by the non covalent bond weak interactions such as hydrogen bond, Van der Waals force, pi-pi accumulation, charge effect, dipole/dipolar interaction, hydrophilic/hydrophobic interaction and the synergy between them structure and function.Self-assembly is the important means of supramolecular chemistry research, namely spontaneously forms molecule aggregates by the weak effect between dividing.
At title complexs such as iridium, platinum, rhenium, ruthenium and osmium of photochemistry field phosphorescence heavy metal complex, because remarkable optical physics and spectrochemical property receive increasing concern, it has had a lot of bibliographical informations at aspects such as Optochemical sensor, photocatalyst, photochemistry biomarkers.Yet as the phosphor material of superior performance, the research of phosphorescence heavy metal complex aspect the organic fluorescence nano material is relatively less.The present invention has not only synthesized new phosphorescence heavy metal iridium complex, also use the method for supramolecule self-assembly, prepare a kind of new iridium metal coordination compound organic fluorescent nanoparticles by the weak interaction between complex of iridium and pyridine groups and the carboxylic acid, expanded heavy metal complex continuing to use aspect the organic fluorescence nano material.
Summary of the invention
The object of the present invention is to provide a kind of iridium metal coordination compound organic fluorescent nanoparticles.
The present invention also provides the preparation method of this nanoparticle.
A kind of iridium metal coordination compound organic fluorescent nanoparticles has the pattern of rectangular parallelepiped or square, and particle diameter is at 400～3000nm, and the concrete structure formula is:
This iridium metal coordination compound organic fluorescent nanoparticles is a kind of the contain cationic metal iridium complex of pyridine and effect preparation that carboxylic acid passes through the supramolecule self-assembly, make complex of iridium and trimesic acid carry out the supramolecule self-assembly by reactive force between hydrogen bond, charge effect, pi-pi accumulation equimolecular and form, its step comprises:
(1) preparation 2-phenylpyridine iridium dichloro bridge title complex (is used [(ppy)
2IrCl
2Ir (ppy)
2] expression, wherein ppy is the 2-phenylpyridine): under the oxygen free condition, get iridium chloride and 2-phenylpyridine that mol ratio is 0.1～2.5:1, be dissolved in the mixed solution of cellosolvo and water, wherein cellosolvo and water volume ratio are 20～1:1; Above-mentioned mixing solutions is heated to 60～135 ℃, and stirring reaction was cooled to 5 ℃～35 ℃ after 1～45 hour, had yellow mercury oxide to generate; Get the washing of precipitate drying, obtain phenylpyridine iridium dichloro bridge title complex;
Can distinguish water and washing with alcohol precipitation and vacuum-drying, obtain yellow solid product 2-phenylpyridine iridium dichloro bridge title complex [(ppy)
2IrCl
2Ir (ppy)
2];
The mol ratio of iridium chloride and 2-phenylpyridine is preferably 0.4～1.5:1;
(2) preparation 3,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex: under oxygen free condition, getting mol ratio is the 2-phenylpyridine iridium dichloro bridge title complex and 3 of 0.1～3:1,8-dibromo-o phenanthroline, (volume ratio 0.1～10:1) is heated to 30～65 ℃ to add the mixed solution of methylene dichloride and methyl alcohol again; Behind the stirring reaction 1～40 hour, remove solvent, purifying gets red solid product 3,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex;
2-phenylpyridine iridium dichloro bridge title complex and 3,8-dibromo-o phenanthroline mol ratio are preferably 0.3～1:1;
The method of purifying is column chromatography, to remove the dissolution of solid that obtains behind the solvent in methylene dichloride, silica gel column chromatography, and be the methylene dichloride of 1:3～3:1 and the mixed solvent wash-out of methyl alcohol with volume ratio, the Fractional Collections elutriant, obtain red solid product 3,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex after merging drying.
(3) preparation 3,8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex: under oxygen free condition, taking by weighing respectively mol ratio is 3 of 0.1～3:1,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex and 4-ethynyl pyridine are in three-necked flask, add reactant total mole number 1～40% tetrakis triphenylphosphine palladium and 1～30% and cuprous iodide, adding volume ratio is the degassed tetrahydrofuran (THF) of 20～1:1 and the mixed solvent of triethylamine again, then be heated to 30～85 ℃, stirring reaction 1～45 hour; After question response finished, desolventizing with dichloromethane extraction, washing, drying, got red solid product 3 through column chromatography purification, 8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex.
The method of column chromatography purification is, with the dissolution of solid that obtains after dichloromethane extraction, washing and the drying in chloroform, silica gel column chromatography, and be the methylene dichloride of 1:3～3:1 and the mixed solvent wash-out of methyl alcohol with volume ratio, the Fractional Collections elutriant, obtain the red solid product, 8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex after merging drying.
The method that wherein prepares the 4-ethynyl pyridine is: under nitrogen protection; get mol ratio and be the 4-bromopyridine hydrochloride of 3～0.1:1 and trimethylsilyl acetylene in three-necked flask; the adding mole number is respectively 1～40% and 1～30% tetrakis triphenylphosphine palladium and cuprous iodide; adding volume ratio is the degassed tetrahydrofuran (THF) of 25～1:1 and the mixed solvent of triethylamine again; then control temperature at 5～35 ℃; stirred 1～30 hour; after question response finishes; add an amount of water after screwing out most of solvent; use again n-hexane extraction; the collected organic layer washing; anhydrous magnesium sulfate drying; after screwing out solvent residuum is dissolved in the methyl alcohol; the Potassium monofluoride that adds again 0.1～10 times of equivalent; the control temperature stirred 1～35 hour at 5～35 ℃, screwed out most of methyl alcohol; use extracted with diethyl ether; washing; anhydrous magnesium sulfate drying, the column chromatography white solid product 4-ethynyl pyridine of purifying to get.
(4) preparation complex of iridium organic fluorescence nanoparticle: be that the mixed solvent of the acetonitrile of 20～1:1 and methyl alcohol is respectively with 3 with volume ratio, 8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex and trimesic acid dissolving, then the ratio that is in molar ratio 10～0.1:1 mixes two settled solutions, and in the adjusting mixture solution concentration of complex of iridium at 0.1～100 μ mol/ml, the control temperature is at 5～50 ℃, stir 0.1h～7d, it is muddy that settled solution becomes, there is small precipitation to generate, gets precipitation and namely get complex of iridium organic fluorescence nanoparticle.
The concentration of complex of iridium is preferably 0.1～10 μ mol/ml in the mixture solution.
Because complex of iridium has abundant optical physics and spectrochemical property, the prepared iridium metal coordination compound organic fluorescent nanoparticles of the present invention has remarkable optical property, character with phosphorescent emissions, launching centre is about 635 nanometers, can send the red fluorescence about 635nm, have great potential using value in light function organic nano material field.
Preparation method of the present invention is simple to operate, and reaction conditions is gentle, and environment is not polluted.
Description of drawings
Fig. 1 is the FE-SEM electromicroscopic photograph of the complex of iridium organic fluorescence nanoparticle among the embodiment 1.
Fig. 2 is the EDS energy spectrum analysis of the complex of iridium organic fluorescence nanoparticle among the embodiment 1.
Fig. 3 is the FE-SEM electromicroscopic photograph of the complex of iridium organic fluorescence nanoparticle among the embodiment 2.
Fig. 4 is the fluorescence spectrum figure of the complex of iridium organic fluorescence nanoparticle among the embodiment 2.
Embodiment
Just the present invention will be further described for embodiment, is not used for limiting the present invention.
Embodiment 1
(1) preparation 2-phenylpyridine iridium dichloro bridge title complex, [(ppy)
2IrCl
2Ir (ppy)
2], wherein ppy is the 2-phenylpyridine: under nitrogen protection, take by weighing respectively IrCl
33H
2O(5.2mmol) and 2-phenylpyridine (11.3mmol) in three-necked flask, then adding volume ratio is the cellosolvo of 7:3 and the mixed solvent of water, and above-mentioned mixing solutions is heated to 115 ℃, stirs after 18 hours, be cooled to room temperature, have yellow mercury oxide to generate.With respectively water and washing with alcohol, the vacuum-drying of above-mentioned precipitation, obtain yellow solid product 2-phenylpyridine iridium dichloro bridge title complex [(ppy)
2IrCl
2Ir (ppy)
2].
(2) preparation 3; 8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex: under nitrogen protection; take by weighing respectively 2-phenylpyridine iridium dichloro bridge title complex (0.25mmol) and 3; 8-dibromo-o phenanthroline (0.60mmol) joins in the three-necked flask; adding volume ratio is the methylene dichloride of 3:2 and the mixed solvent of methyl alcohol again; then be heated to 60 ℃; behind the stirring reaction 15 hours; reaction solution revolved to boil off desolventize drying; with dissolution of solid in a small amount of methylene dichloride; silica gel column chromatography and the wash-out (mixed solvent of methylene dichloride and methyl alcohol; volume ratio is that 1:3～3:1), the Fractional Collections elutriant merges; get red solid product 3,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex after the drying.
1H?NMR:(400MHz,CDCl
3),δ(ppm):9.19(d,2H,J=2.0Hz),8.67(s,2H),8.16(d,2H,J=2.0Hz),7.96(d,2H,J=8.0Hz),7.79(t,2H,J=7.8Hz),7.73(d,2H,J=7.2Hz),7.35(d,2H,J=5.6Hz),7.09(t,2H,J=7.2Hz),6.99(q,4H,J=6.4Hz),6.34(d,2H,J=7.2Hz)。
(3) preparation 4-ethynyl pyridine: under nitrogen protection; take by weighing respectively 4-bromopyridine hydrochloride (2.67mmol) and trimethylsilyl acetylene (0.80ml) in three-necked flask; add tetrakis triphenylphosphine palladium (0.20mmol) and cuprous iodide (0.34mmol); adding volume ratio is the degassed tetrahydrofuran (THF) of 6:1 and the mixed solvent 50ml of triethylamine again; then control temperature at 20 ℃; stirred 15 hours; after question response finishes; add an amount of water after screwing out most of solvent; use again n-hexane extraction, the collected organic layer washing; anhydrous magnesium sulfate drying is dissolved in residuum in the methyl alcohol behind the back-out solvent; add again dihydrate of potassium fluoride (5.80mmol); the control temperature stirred 13 hours at 20 ℃, screwed out most of methyl alcohol; use extracted with diethyl ether; washing; anhydrous magnesium sulfate drying; with dissolution of solid in a small amount of ether, silica gel column chromatography and wash-out (methylene dichloride), Fractional Collections elutriant; merge the dry white solid product 4-ethynyl pyridine that gets.
1H?NMR:(400MHz,CDCl
3),δ(ppm):8.59(q,2H,J=2.0Hz),7.35(q,2H,J=2.0Hz),3.30(s,1H)。
(4) preparation 3,8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex: under nitrogen protection, take by weighing respectively 3,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex (1.5mmol) and 4-ethynyl pyridine (0.82g, 7.8mmol) in three-necked flask, add tetrakis triphenylphosphine palladium (150mg, 0.13mmol) and cuprous iodide (68mg, 0.36mmol);
Adding volume ratio is the degassed tetrahydrofuran (THF) of 5:1 and the mixing solutions of triethylamine again, then is heated to 65 ℃, and stirring reaction is 21 hours under the nitrogen protection; After question response finishes, revolve to boil off and remove most of solvent, with dichloromethane extraction, washing, anhydrous magnesium sulfate drying;
In a small amount of chloroform, (mixed solvent of methylene dichloride and methyl alcohol, volume ratio are 1:3～3:1) for silica gel column chromatography and wash-out with dissolution of solid, the Fractional Collections elutriant, merge, get red solid product 3,8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex after the drying.
1H?NMR:(400MHz,DMSO),δ(ppm):9.23(d,2H,J=1.6Hz),8.69(s,4H),8.43(s,2H),8.27(d,2H,J=8.4Hz),8.15(d,2H,J=2.0Hz),7.96(d,2H,J=7.6Hz),7.90(t,2H,J=7.4Hz),7.67(d,2H,J=5.6Hz),7.54(d,4H,J=4.0Hz),7.07(t,2H,J=7.4Hz),6.98(m,4H),6.27(d,2H,J=7.2Hz)。
(5) preparation complex of iridium organic fluorescence nanoparticle: be that the mixed solvent of the acetonitrile of 3:1 and methyl alcohol is respectively with 3 with volume ratio, 8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex and trimesic acid dissolving, then two settled solutions are mixed for the ratio of 4:3 in molar ratio, and in the adjusting mixture solution concentration of complex of iridium at 3 μ mol/ml, the control temperature is at 30 ℃, stirred 8 hours, it is muddy that settled solution becomes, there is small precipitation to generate, gets precipitation and namely get complex of iridium organic fluorescence nanoparticle.
The result of the present embodiment is shown in the FE-SEM Electronic Speculum of Fig. 1, and major part is the pattern of rectangular parallelepiped, and it is the pattern of square that small portion is also arranged.Fig. 2 is the EDS energy spectrum analysis of this nanoparticle, and as can be seen from the figure this nanoparticle is that complex of iridium and trimesic acid form by supramolecule self-assembly effect really.
Embodiment 2
Step (1)～(4) are with embodiment 1.
(5) synthesized 3,8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex and trimesic acid are respectively the mixed solvent dissolving of acetonitrile and the methyl alcohol of 20:1 with volume ratio, then two settled solutions are mixed for the ratio of 3:2 in molar ratio, and in the adjusting mixture solution concentration of complex of iridium at 5 μ mol/ml, the control temperature is at 30 ℃, stirred 120 hours, it is muddy that settled solution becomes, there is small precipitation to generate, gets precipitation and namely get complex of iridium organic fluorescence nanoparticle.
The FE-SEM Electronic Speculum figure of the present embodiment products obtained therefrom as shown in Figure 3, major part is the pattern of rectangular parallelepiped, it is the pattern of square that small portion is also arranged.
Resulting metal iridium complex organic fluorescence nanoparticle carries out emmission spectrum test, experimental result as shown in Figure 4, under the exciting light of 365 nanometers, the launching centre of this nanoparticle is the very high red fluorescences of purity of color in 635 nanometers.
Embodiment 3
IrCl in the step (1)
33H
2The consumption of O is 11mmol, and the consumption of 2-phenylpyridine is 11.3mmol, and all the other steps are with embodiment 1.The result is with embodiment 1.
Embodiment 4
In the step (4) 3, the consumption of 8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex is 15mmol, and the consumption of 4-ethynyl pyridine is 7.8mmol, and the consumption of tetrakis triphenylphosphine palladium is 0.25mmol, the consumption of cuprous iodide is 0.4mmol, and all the other steps are with embodiment 1.The result is with embodiment 1.
Embodiment 5
The consumption of 2-phenylpyridine iridium dichloro bridge title complex is 0.5mmol in the step (2), and the consumption of 3,8-dibromo-o phenanthroline is 0.5mmol, and all the other steps are with embodiment 1.The result is with embodiment 1.
Embodiment 6
Step (1)～(4) are with embodiment 2.
(5) synthesized 3,8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex and trimesic acid are respectively the mixed solvent dissolving of acetonitrile and the methyl alcohol of 2:1 with volume ratio, then two settled solutions are mixed for the ratio of 1:2 in molar ratio, and in the adjusting mixture solution concentration of complex of iridium at 10 μ mol/ml, the control temperature is at 30 ℃, stirred 1 hour, it is muddy that settled solution becomes, there is small precipitation to generate, gets precipitation and namely get complex of iridium organic fluorescence nanoparticle.
Claims (7)
1. an iridium metal coordination compound organic fluorescent particle is characterized in that, structural formula is suc as formula shown in the I:
And having the pattern of rectangular parallelepiped or square, particle diameter is at 400～3000nm.
2. the preparation method of the described iridium metal coordination compound organic fluorescent particle of claim 1 is characterized in that, may further comprise the steps:
(1) under oxygen free condition, get iridium chloride and 2-phenylpyridine that mol ratio is 0.1～2.5:1, be dissolved in the mixed solution of cellosolvo and water; Above-mentioned mixing solutions is heated to 60～135 ℃, and stirring reaction was cooled to 5 ℃～35 ℃ after 1～45 hour, had yellow mercury oxide to generate; Get the washing of precipitate drying, obtain phenylpyridine iridium dichloro bridge title complex;
(2) under oxygen free condition, getting mol ratio is 2-phenylpyridine iridium dichloro bridge title complex and 3, the 8-dibromo-o phenanthroline of 0.1～3:1, adds the mixed solution of methylene dichloride and methyl alcohol again, is heated to 30～65 ℃; Behind the stirring reaction 1～40 hour, remove solvent, purifying obtains 3,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex;
(3) under oxygen free condition, taking by weighing respectively mol ratio is 3 of 0.1～3:1,8-dibromo-o phenanthroline iridium 2-phenylpyridine title complex and 4-ethynyl pyridine are in three-necked flask, add the tetrakis triphenylphosphine palladium of reactant total mole number 1～40% and 1～30% cuprous iodide, adding volume ratio is the degassed tetrahydrofuran (THF) of 20～1:1 and the mixed solvent of triethylamine again, then be heated to 30～85 ℃, stirring reaction 1～45 hour; After question response finishes, desolventizing, extraction, washing, drying get red solid product 3 through column chromatography, 8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex;
(4) be that the mixed solvent of the acetonitrile of 1～20:1 and methyl alcohol is respectively with 3 with volume ratio, 8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex and trimesic acid dissolving, then by two settled solutions are mixed, 3,8-two (4-pyridine ethynyl) phenanthroline iridium 2-phenylpyridine title complex and trimesic acid mol ratio are 4:3～3:2, and in the adjusting mixture solution concentration of complex of iridium at 0.1～10 μ mol/ml, the control temperature is at 5～50 ℃, stir 0.1h～7d, it is muddy that settled solution becomes, there is small precipitation to generate, gets precipitation and namely get complex of iridium organic fluorescence particle.
3. the preparation method of the described iridium metal coordination compound organic fluorescent particle of claim 2 is characterized in that, cellosolvo and water volume ratio are 20～1:1 in the step (1).
4. the preparation method of the described iridium metal coordination compound organic fluorescent particle of claim 2 is characterized in that, the mol ratio of iridium chloride and 2-phenylpyridine is 0.1～2.5:1 in the step (1).
5. the preparation method of the described iridium metal coordination compound organic fluorescent particle of claim 2 is characterized in that, the volume ratio 0.1～10:1 of step (2) methylene dichloride and methyl alcohol; Described purifying is column chromatography.
6. the preparation method of the described iridium metal coordination compound organic fluorescent particle of claim 2 is characterized in that, step (2) 2-phenylpyridine iridium dichloro bridge title complex and 3,8-dibromo-o phenanthroline mol ratio are 0.1～3:1.
7. the preparation method of the described iridium metal coordination compound organic fluorescent particle of claim 2 is characterized in that, uses dichloromethane extraction, column chromatography purification in the step (3).
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