CN104860998A - Dual-core ionic iridium coordination compound and uses thereof - Google Patents
Dual-core ionic iridium coordination compound and uses thereof Download PDFInfo
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- CN104860998A CN104860998A CN201410058465.2A CN201410058465A CN104860998A CN 104860998 A CN104860998 A CN 104860998A CN 201410058465 A CN201410058465 A CN 201410058465A CN 104860998 A CN104860998 A CN 104860998A
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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
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
The present invention discloses a dual-core ionic iridium coordination compound, which is a novel organic light-emitting material concurrently having pressing discoloration and aggregation inducing, wherein the molecular formula is C54H34F20Ir2N12P2, the relative molecular mass is 1678.14 g/mol, and the coordination compound melting point is 315 DEG C. The preparation method comprises: adding 2-fluorophenyl pyrazole dichlorendic and a ligand bpba to a round bottom flask in a mixing manner according to a ratio of 1:(1.0-1.5), adding equal amounts of methanol and dichloromethane as a solvent to the flask, carrying out dark stirring reflux for 4 h under the protection of nitrogen gas at a temperature of 78 DEG C, cooling to a room temperature after completing the reaction, adding potassium hexafluorophosphate, stirring for 1 h, and filtering to obtain orange solid powder [(2Fppz)2Ir-(bpba)-Ir(2Fppz)2]2PF6. The dual-core ionic iridium coordination compound of the present invention can be used in organic gas sensors.
Description
Technical field
The present invention relates to a kind of double-core ionic type iridium complex, there is the character of aggregation-induced emission and compacting variable color simultaneously, belong to chemosynthesis technical field.
Background technology
Ionic type iridium complex, because possessing the advantages such as luminous efficiency is high, emission wavelength is adjustable, thus makes it to receive extensive concern in optical physics Chemical activator field.Such as, ionic type iridium complex is all widely used in solid luminescent electrochemical cell, sensor, Photocatalyzed Hydrogen Production and bioprobe.But we find that this kind of title complex luminous efficiency under the condition of high density is often on a declining curve in actual applications, namely create the gathering Quenching of fluorescence, this just seriously limits the development of this type of title complex in practical application area.In recent years along with deeply carrying out metal complexes aggregation-induced emission enhancement phenomenal research, the title complex problem that luminous efficiency declines in higher concentrations is progressively solved.
The organic small molecule material in recent years with compacting metachromatism gets most of the attention.This material can be applied in the Application Areass such as sensor, message memory and safety anti-fake cleverly.Because ionic type iridium complex has higher luminous efficiency compared with organic small molecule material, the ionic type iridium complex therefore finding aggregation-induced emission and the compacting variable color character simultaneously with high-luminous-efficiency becomes the study hotspot of current field of light emitting materials.
Once the monokaryon ionic type iridium complex with aggregation-induced emission character was reported in pertinent literature, their the highest fluorescence quantum efficiency is 16.2% (Dalton Trans. 2012,41,523 – 530), and our design and synthesis has gone out the higher double-core ionic type iridium complex with aggregation-induced emission character of a kind of fluorescence quantum efficiency (33%).
So far, the monokaryon ionic transition metal complex of iridium simultaneously with aggregation inducing phenomenon and compacting variable color character only has 2 examples (Dalton Trans. 2012,41,9590 – 9593; J.Mater.Chem. C, 2013,1,1440 – 1449), and have the double-core ionic transition metal complex of iridium of aggregation inducing phenomenon and compacting variable color character also there is not been reported simultaneously.
Summary of the invention
The present invention discloses a kind of double-core ionic type iridium complex, is a kind of novel organic luminescent material simultaneously with compacting variable color and aggregation inducing character.
Double-core ionic type iridium complex provided by the invention (is called for short: [(2Fppz)
2ir-(bpba)-Ir (2Fppz)
2] 2PF
6), its structural formula is as follows:
Wherein: molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C; Bpba represents N, and N '-(two-2-pyridyl)-Isosorbide-5-Nitrae-di-imidogen benzene, 2Fppz represents 2-fluorophenyl pyrazoles.
The synthetic method of double-core ionic type iridium complex provided by the invention, is characterized in that:
By 2-fluorophenyl pyrazoles dichloro bridge and part N; N '-(two-2-pyridyl)-1; 4-di-imidogen benzene is with 1:(1.0 ~ 1.5) ratio be mixed to join in 50ml round-bottomed flask; in flask, add equivalent more respectively methyl alcohol, methylene dichloride make solvent; 78 DEG C of lucifuge stirring and refluxing 4h under nitrogen protection; room temperature is cooled to after reaction terminates; add Potassium Hexafluorophosphate; stir 1 hour; filter afterwards; obtain orange solids powder, i.e. double-core ionic type iridium complex: [(2Fppz)
2ir-(bpba)-Ir (2Fppz)
2] 2PF
6.
The property representation of double-core ionic type iridium complex of the present invention is as follows:
1. single crystal structure:
The crystal of title complex of the present invention is that it obtains at the mixing solutions of acetonitrile (good solvent) and water (poor solvent) by slowly volatilizing, and determines complex structure with X-ray single crystal diffraction instrument.Title complex [(2Fppz)
2ir-(bpba)-Ir (2Fppz)
2] 2PF
6single crystal structure as shown in Figure 1, as can be seen from Figure 1 this title complex is obtained by four 2-fluorophenyl Pyrazole Ligands and one the 3rd part bpba and the two metal iridium Atomic coordinate containing schiff bases structure.Show that this title complex is under solids bulk state by crystal structure analysis, stronger π-π the * of intermolecular existence interacts, this stronger molecular interaction well limits the Space Rotating of the 3rd part, and title complex will be caused under solid states to produce stronger fluorescent emission.
2. photoluminescent property:
Fig. 2 is title complex of the present invention fluorescence emission spectrum of (curve 2) in (curve 1) and acetonitrile solution under pressed powder state, as can be seen from spectrum, this title complex has very strong fluorescent emission in the solid state, but almost do not launch under solution state, this phenomenon belongs to one of aggregation-induced emission nature and characteristic.Under pressed powder state, its maximum emission wavelength is 616nm, emissive porwer 2750, and fluorescence quantum efficiency is 33%, and title complex emissive porwer in the acetonitrile solution of deoxygenation is only 62, and fluorescence quantum efficiency is 0.004%.The solid luminescent intensity of this title complex is comparatively significantly improved under solution state, this may be because complex molecule in the solid state comparatively under solution state Intermolecular Forces strengthen, cause intramolecular 3rd part in the solid state to rotate to be restricted, this interaction makes its luminous intensity under solid states improve a lot.
3. aggregation inducing character:
Title complex of the present invention is dissolved in acetonitrile solvent by Fig. 3, by dripping the aqueous solution in solution, observe the change with the ratio change complex fluorescent intensity of water content in solution, wherein acetonitrile solvent is the good solvent of title complex, and the aqueous solution is the poor solvent of title complex.Title complex is luminous hardly in pure acetonitrile solvent as we can see from the figure, but along with the increase of water content ratio in solution, the emissive porwer of system improves, when water content reaches 60% time, fluorescent emission intensity has obvious enhancing, afterwards along with the fluorescent emission intensity of the continuation increase title complex of water content ratio strengthens gradually, this phenomenon demonstrates this title complex simultaneously and has aggregation inducing character.
4. suppress variable color character:
Fig. 4 be title complex of the present invention under ultra violet lamp, its fluorescence maximum emission wavelength with grinding before and after occur change, wherein 1B representative grinding before, 1G representative grinding after.As we can see from the figure, by grinding, obvious Red Shift Phenomena is had before title complex maximum emission wavelength after grinding comparatively grinds, red emission has been become from orange light emission, its maximum emission wavelength also by 616nm red shift to 634nm, therefore, ground by external force, obtain the title complex of the present invention with compacting variable color character very well.
positively effect of the present invention is:the synthetic route of part and title complex is short, and reaction yield is high, and reaction product is easily purified, and saves a large amount of organic solvent.Double-core ionic type iridium complex makes it to become the Multifunctional luminous material of latest model structure as luminescent material because having compacting variable color and aggregation-induced emission character simultaneously, can as organic gas sensor.
Accompanying drawing explanation
Fig. 1 is title complex of the present invention [(2Fppz)
2ir-(bpba)-Ir (2Fppz)
2] 2PF
6single crystal structure figure;
Fig. 2 is the title complex of the present invention fluorescent emission spectrogram of (2) under (1) and acetonitrile solution state in the solid state;
Fig. 3 is title complex of the present invention in the mixed solvent of acetonitrile and water with its fluorescent emission spectrogram of change of water content ratio;
Fig. 4 be title complex of the present invention under ultra violet lamp, grinding before and after fluorescent emission spectrogram;
Fig. 5 be title complex of the present invention under ultra violet lamp, it is as the effect figure of methylene dichloride gas sensor.
Embodiment
To be illustrated further description the present invention by following examples, and do not limit the present invention in any way, under the prerequisite not deviating from technical solution of the present invention, any change that those of ordinary skill in the art made for the present invention easily realize or change all will fall within right of the present invention.
embodiment 1
By 2-fluorophenyl pyrazoles dichloro bridge 0.1043g(0.1mmol) and part N; N '-(two-2-pyridyl)-1; 4-di-imidogen benzene 0.0284g(0.1mmol) be mixed in 50ml round-bottomed flask; the methyl alcohol 15ml, the methylene dichloride 15ml that add equivalent respectively make solvent; 78 DEG C of lucifuge stirring and refluxing 4h under nitrogen protection; room temperature is cooled to after reaction terminates; add Potassium Hexafluorophosphate 0.0368g(0.2mmol); stir 1 hour; filter afterwards, obtain orange solids powder 0.1340g(79.8%).Molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C.Single crystal structure figure as shown in Figure 1.
embodiment 2
By 2-fluorophenyl pyrazoles dichloro bridge 0.1043g(0.1mmol) and part N, N '-(two-2-pyridyl)-1,4-di-imidogen benzene 0.0341g(0.12mmol) be mixed in 50ml round-bottomed flask, the methyl alcohol 15ml, the methylene dichloride 15ml that add equivalent respectively make solvent, 78 DEG C of lucifuge stirring and refluxing 4h under nitrogen protection, room temperature is cooled to after reaction terminates, add Potassium Hexafluorophosphate 0.0368g(0.2mmol), stir 1 hour, filter afterwards, obtain orange solids powder 0.1450g(86.4%); Molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C.Single crystal structure figure as shown in Figure 1.
embodiment 3
By 2-fluorophenyl pyrazoles dichloro bridge 0.2086g(0.2mmol) and part N, N '-(two-2-pyridyl)-1,4-di-imidogen benzene 0.0625g(0.22mmol) be mixed in 50ml round-bottomed flask, the methyl alcohol 15ml, the methylene dichloride 15ml that add equivalent respectively make solvent, 78 DEG C of lucifuge stirring and refluxing 4h under nitrogen protection, room temperature is cooled to after reaction terminates, add Potassium Hexafluorophosphate 0.0736g(0.4mmol), stir 1 hour, filter afterwards, obtain orange solids powder 0.2688g(80.1%); Molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C.Single crystal structure figure as shown in Figure 1.
embodiment 4
By 2-fluorophenyl pyrazoles dichloro bridge 0.2086g(0.2mmol) and part N, N '-(two-2-pyridyl)-1,4-di-imidogen benzene 0.0738g(0.26mmol) be mixed in 50ml round-bottomed flask, the methyl alcohol 15ml, the methylene dichloride ml that add equivalent respectively make solvent, 78 DEG C of lucifuge stirring and refluxing 4h under nitrogen protection, room temperature is cooled to after reaction terminates, add Potassium Hexafluorophosphate 0.0736g(0.4mmol), stir 1 hour, filter afterwards, obtain orange solids powder 0.2840g(84.6%); Molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C.Single crystal structure figure as shown in Figure 1.
embodiment 5
By 2-fluorophenyl pyrazoles dichloro bridge 0.2086g(0.2mmol) and part N, N '-(two-2-pyridyl)-1,4-di-imidogen benzene 0.0795g(0.28mmol) be mixed in 50ml round-bottomed flask, the methyl alcohol 15ml, the methylene dichloride 15ml that add equivalent respectively make solvent, 78 DEG C of lucifuge stirring and refluxing 4h under nitrogen protection, room temperature is cooled to after reaction terminates, add Potassium Hexafluorophosphate 0.0736g(0.4mmol), stir 1 hour, filter afterwards, obtain orange solids powder 0.2910g(86.7%); Molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C.Single crystal structure figure as shown in Figure 1.
embodiment 6
By 2-fluorophenyl pyrazoles dichloro bridge 0.2086g(0.2mmol) and part N, N '-(two-2-pyridyl)-1,4-di-imidogen benzene 0.0852g(0.30mmol) be mixed in 50ml round-bottomed flask, the methyl alcohol 15ml, the methylene dichloride 15ml that add equivalent respectively make solvent, 78 DEG C of lucifuge stirring and refluxing 4h under nitrogen protection, room temperature is cooled to after reaction terminates, add Potassium Hexafluorophosphate 0.0736g(0.4mmol), stir 1 hour, filter afterwards, obtain orange solids powder 0.2900g(86.4%); Molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C.Single crystal structure figure as shown in Figure 1.
the application of the present invention in organic gas sensor is as follows:
practical example 1
1, Preparatory work of experiment
The title complex 0.01678g embodiment of the present invention prepared is dissolved in 4ml acetonitrile solvent, the silica-gel plate that preparation two pieces is clean afterwards, get two capillaries more respectively and draw the acetonitrile solution being dissolved with title complex, and will the acetonitrile solution point of title complex be dissolved with on silica-gel plate.
Prepare two clean transparent drug bottles, add 5ml dichloromethane solvent in a drug bottle wherein, another drug bottle does not then add dichloromethane solvent, does blank with this empty bottle.
Put into two drug bottles by unsettled respectively for the two blocks of silica-gel plates having adsorbed title complex, silica-gel plate can not be stained with dichloromethane solution, builds bottle cap afterwards.
2, sensor properties research
In darkroom, with ultra violet lamp previously prepd two, the drug bottle speckling with title complex silica-gel plate is housed, find in the drug bottle not having dichloromethane solution, title complex has very strong orange light emission, and containing in the drug bottle of dichloromethane solution, along with dichloromethane solution volatilization in the vial, the fluorescence bright spot of title complex can increasing along with methylene dichloride organic gas in bottle, gradually Fluorescence-quenching occurs, until after two minutes, fluorescence bright spot disappears (see Fig. 5) substantially.Prove that this title complex can as good organic gas sensor.
Claims (3)
1. a double-core ionic type iridium complex, structural formula is as follows:
Wherein: molecular formula is C
54h
34f
20ir
2n
12p
2, relative molecular mass is 1678.14g/mol, and the fusing point of title complex is 385 DEG C.
2. the synthetic method of double-core ionic type iridium complex according to claim 1, is characterized in that:
By 2-fluorophenyl pyrazoles dichloro bridge and part N; N '-(two-2-pyridyl)-1; 4-di-imidogen benzene is with 1:(1.0 ~ 1.5) ratio mixing; the methyl alcohol, the methylene dichloride that add equivalent respectively make solvent, under nitrogen protection 78 DEG C of lucifuge stirring and refluxing 4h, are cooled to room temperature after reaction terminates; add Potassium Hexafluorophosphate; stir 1 hour, filter afterwards, obtain orange solids powder.
3. the application of double-core ionic type iridium complex in organic gas sensor described in claim 1.
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|---|---|---|---|---|
| CN112574256A (en) * | 2020-12-11 | 2021-03-30 | 江苏大学 | Cationic type binuclear iridium-bipyridine phenylenediamine crystal material and preparation method thereof |
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Non-Patent Citations (3)
| Title |
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| 单国刚: "新型阳离子铱金属配合物的设计合成及其性质的研究", 《中国博士学位论文全文数据库工程科技I辑》 * |
| 晁凯: "唑啉、噻唑啉铱锌配合物及新型双核西佛碱铱配合物的合成与光电性能研究", 《中国优秀硕士学位论文全文数据库工程科技I辑》 * |
| 林桂霞: "系列新型离子型铱配合物的合成与光电性能研究", 《中国优秀硕士学位论文全文数据库工程科技I辑》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112574256A (en) * | 2020-12-11 | 2021-03-30 | 江苏大学 | Cationic type binuclear iridium-bipyridine phenylenediamine crystal material and preparation method thereof |
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