CN106892868A - A kind of 8 oxyquinoline Zn complexes with one-dimensional catenary structure and preparation method thereof - Google Patents
A kind of 8 oxyquinoline Zn complexes with one-dimensional catenary structure and preparation method thereof Download PDFInfo
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- CN106892868A CN106892868A CN201710114518.1A CN201710114518A CN106892868A CN 106892868 A CN106892868 A CN 106892868A CN 201710114518 A CN201710114518 A CN 201710114518A CN 106892868 A CN106892868 A CN 106892868A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/30—Metal salts; Chelates
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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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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
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Abstract
The application belongs to metal complex field, and in particular to a kind of 8 oxyquinoline Zn complexes with one-dimensional catenary structure and preparation method thereof.8 oxyquinoline Zn complex provided by the present invention, shown in its chemical constitution such as formula (I), with unique one-dimensional catenary structure, and good dissolubility, heat endurance and high luminous intensity are shown, can be used as wet processing and make associated light emitting device；Additionally, the preparation method of the 8 oxyquinoline Zn complexes with one-dimensional catenary structure of present invention offer is simple to operate, raw material sources extensively, are capable of achieving large-scale production, with wide Commercial Prospect.
Description
Technical field
The invention belongs to metal complex field, and in particular to a kind of 8-hydroxyquinoline zinc with one-dimensional catenary structure is matched somebody with somebody
Compound and preparation method thereof.
Background technology
Organic electroluminescence device (OLED) has that visual angle is wide, low in energy consumption, fast response time, process is simple, can realize entirely
The advantages of color shows, therefore had broad application prospects in FPD and solid light source field.From the U.S. in 1987
C.W.Tang has reported since making organic electroluminescence device using three (8-hydroxyquinoline) aluminium (Alq3) that numerous is new first
Electroluminescent organic material (OELM, Organic Electroluminescence Materials) is successfully synthesized to meet
Improve the requirement of OLED performance.
Luminescent material is the final material for undertaking lighting function in device, therefore the luminous efficiency of luminescent material, luminous longevity
The property such as life and luminescent chromaticity will all have a direct impact to the performance of OLED.As the luminescent material in OLED should possess as
Lower condition：1) with efficient solid state fluorescence, without obvious concentration quenching phenomena；2) with good chemical stability and heat
Stability, does not react with electrode and carrier transmission material；3) easily form fine and close noncrystalline membrane and be difficult knot
It is brilliant；4) with appropriate emission wavelength；5) with good conductive characteristic and certain carrier transport ability.
8-hydroxyquinoline metal complex has good heat endurance, high fluorescence and its good electric transmission work(
Can, therefore as being applied to one of most reliable electric transmission and the material of transmitting in OLED.However, the metal complexes is molten
Solution property and film forming are poor, prepare difficulty greatly, limit such complex and are prepared in luminescent device as a kind of luminescent material
Scale application in field.
The content of the invention
In view of this, the invention provides a kind of 8-hydroxyquinoline Zn complex with one-dimensional catenary structure and its preparation
Method, 8-hydroxyquinoline Zn complex provided by the present invention has luminous intensity higher, good heat endurance, Yi Jiliang
Good dissolubility.
Concrete technical scheme of the invention is as follows：
The invention provides a kind of 8-hydroxyquinoline Zn complex with one-dimensional catenary structure, with as shown in formula I
Structure：
Present invention also offers a kind of preparation method of the above-mentioned 8-hydroxyquinoline Zn complex with one-dimensional catenary structure,
Including：
A) by 2- methyl -8-hydroxyquinoline and 2,4- dichlorobenzaldehydes are reacted in reaction dissolvent, in being reacted
Mesosome；
B) reaction intermediate for obtaining step a) reacts with pyridine, water successively, obtains part；
C) part and zinc salt for obtaining step b) are reacted in reaction dissolvent, are obtained the 8-hydroxyquinoline zinc and are matched somebody with somebody
Compound.
Preferably, reaction dissolvent described in step a) is acetic anhydride.
Preferably, the condition of the step a) reactions is：It is heated to reflux under the protection of inert gas；
The inert gas includes nitrogen, argon gas or helium；
The temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h.
Preferably, step b) first heating stirrings after pyridine is added, then add water and are heated at reflux.
It is furthermore preferred that the temperature of the heating stirring is 132~135 DEG C, the time is 20~30min；
The temperature being heated at reflux is 132~135 DEG C, and the time is 3~5h.
Preferably, zinc salt includes described in step c)：One or more in zinc perchlorate, zinc nitrate and zinc chloride；
The mol ratio of the part and zinc salt is (3~5):(8~12).
Preferably, the step c) reaction dissolvents are the mixed solution of DMF and methyl alcohol；
The ratio of the part and N,N-dimethylformamide is 1mmol:(100~150) mL；
The mixed volume ratio of the N,N-dimethylformamide and methyl alcohol is (1~4):(0.5~2).
Preferably, the temperature reacted described in step c) is 60~80 DEG C, and the time is 24h.
The invention provides a kind of 8-hydroxyquinoline Zn complex with one-dimensional catenary structure, its chemical constitution such as formula
(I) shown in, with unique one-dimensional catenary structure, and good heat endurance, dissolubility and high luminous intensity are shown, can be made
For a kind of performance is good, cost is relatively low, the clear and definite novel soluble small light-emitting molecules of space structure；The present invention is by 8- hydroxyl quinolines
Chlorine atom is introduced in quinoline group, the dissolubility and film forming of complex is improve, associated light device can be made using wet processing
Part, it is to avoid using complicated preparation technology and making apparatus, preparation cost is cheap, and raw material sources extensively, are capable of achieving large-scale
Production, with wide Commercial Prospect.
Brief description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
The accompanying drawing to be used needed for having technology description is briefly described, it should be apparent that, drawings in the following description are only this
Inventive embodiment, for those of ordinary skill in the art, on the premise of not paying creative work, can also basis
The accompanying drawing of offer obtains other accompanying drawings.
Fig. 1 is the proton nmr spectra of 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 2 is the crystal structure figure of 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 3 is the one-dimensional catenary structure figure of 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 4 schemes for the PXRD of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 5 is part and the ultraviolet spectra for titration figure of zinc salt coordination in embodiment 1；
Fig. 6 is the fluorescence titration spectrogram of Zn complex and part in embodiment 1；
Fig. 7 is the 8-hydroxyquinoline Zn complex obtained in embodiment 1 and the fluorescence spectra of part；
Fig. 8 is the fluorescence lifetime curve of Zn complex and matched curve figure obtained in embodiment 1；
Fig. 9 is the thermogravimetric analysis figure (TGA) of 8-hydroxyquinoline Zn complex obtained in embodiment 1.
Specific embodiment
The invention provides a kind of 8-hydroxyquinoline Zn complex with one-dimensional catenary structure, with as shown in formula I
Structure：
In the present invention, the 8-hydroxyquinoline Zn complex crystal belongs to centrosymmetric monoclinic system, its space group
It is C2/c, is one-dimensional space paradigmatic structure, its construction unit includes two parts of Zn (II) atomic nucleus of hexa-coordinate.
Present invention also offers a kind of preparation method of above-mentioned 8-hydroxyquinoline Zn complex, including：
A) by 2- methyl -8-hydroxyquinoline and 2,4- dichlorobenzaldehydes are reacted in reaction dissolvent, in being reacted
Mesosome, the chemical name of the reaction intermediate is (E) -2- [2,4- Dichloro-phenyl vinyl] -8- acetoxyl group quinoline；
Wherein, the reaction equation being related in step a) is as follows：
B) reaction intermediate for obtaining step a) reacts with pyridine, water successively, obtains part, the chemical name of the part
It is (E) -2- [2,4- Dichloro-phenyls vinyl] -8-hydroxyquinoline；
Wherein, the reaction equation being related in step b) is as follows：
C) part and zinc salt for obtaining step b) are reacted in reaction dissolvent, are obtained the 8-hydroxyquinoline zinc and are matched somebody with somebody
Compound, its molecular formula is Zn (C17H11Cl2NO)2；
Wherein, the reaction equation being related in step c) is as follows：
In the present invention, the reaction dissolvent employed in step a) is preferably acetic anhydride；
The condition of the reaction is：It is heated to reflux under the protection of inert gas.
Further, the temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h；
The inert gas is preferably nitrogen, argon gas or helium, more preferably nitrogen；
The mol ratio of 2- methyl -8-hydroxyquinoline and 2,4 dichloro benzene formaldehyde is preferably (1~1.5):1.
In the present invention, in step b) after pyridine is added first heating stirring, then add water and be heated at reflux.
Further, the temperature of the heating stirring is 132~135 DEG C, and the time is 20~30min；
The temperature being heated at reflux is 132~135 DEG C, and the time is 3~5h.
In the present invention, zinc salt described in step c) is preferably the one kind or many in zinc perchlorate, zinc nitrate and zinc chloride
Plant, more preferably zinc perchlorate；The reaction dissolvent is preferably the mixed solution of N,N-dimethylformamide and methyl alcohol.
Further, the mol ratio of the part and zinc salt is preferably (3~5):(8~12), more preferably 4:10；
The ratio of the part and N,N-dimethylformamide is preferably 1mmol:(100~150) mL, more preferably
1mmol:125mL；
The mixed volume of the N,N-dimethylformamide and methyl alcohol is than being preferably (1~4):(0.5~2), more preferably
2:1；
The temperature of the reaction is 60~80 DEG C, and the time is 24h.
Technical scheme is clearly and completely described below in conjunction with the specific embodiment of the invention, it is clear that
Described embodiment is a part of embodiment of the invention, rather than whole embodiments.Those skilled in the art should manage
Solution, modifies to specific embodiment of the invention or some technical characteristics is replaced on an equal basis, without deviating from the present invention
The spirit of technical scheme, all should cover in the scope of protection of the invention.
Embodiment 1
(1) preparation of intermediate
A, weigh 2- methyl -8-hydroxyquinoline 1.75g and 2,4- dichlorobenzaldehyde 1.74g in the round-bottomed flask of 100mL,
The acetic anhydride dissolving of 10mL is added, mixed liquor is obtained；
B, the mixed liquor for obtaining step A carried out under the protection of nitrogen magnetic agitation, 145 DEG C be heated to reflux 20h, with
The carrying out of reaction, the color of reaction solution gradually deepens, and brown is switched to by the beginning light yellow, and reaction solution is in opaque muddy
Turbid state, also separates out in course of reaction with a small amount of solid；
C, reaction solution are poured into reaction solution in the frozen water of 100mL after being cooled to room temperature, separate out yellow solid, filtrate
Extracted three times with dichloromethane, merge the organic phase obtained by three extractions；The acetic acid in organic phase, Ran Houyong are washed away with distilled water
Anhydrous sodium sulfate drying, then organic phase concentrated under reduced pressure obtains crude product；
D, carry out silica gel column layer as eluant, eluent with petrol ether/ethyl acetate and be separated by decantation to 3.46g intermediates, yield is
88%.
(2) preparation of part
The intermediate of 1g is dissolved in the 100mL round-bottomed flasks equipped with 10mL pyridines, is added after 133 DEG C of heating stirring 30min
Enter 5mL water, while adding water, solution quickly becomes dark cloudy state；Continue heating reflux reaction after 4 hours, obtain oil
The dope of shape, stops reaction.Substantial amounts of crude product solid is separated out after cooling, with petrol ether/ethyl acetate as eluant, eluent point
From obtaining yellow powder part, yield 93.6%.
(3) preparation of 8-hydroxyquinoline Zn complex
Above-mentioned part (0.004mmol) is dissolved in DMF (0.5mL), MeOH (0.25mL) is added, Zn is eventually adding
(ClO4)2The DMF solution of (0.01mmol), is sealed in the vial of 10mL, and 80 DEG C of heating 24h, cooling collection obtains red bar
Shape crystal, is washed with MeOH, is dried at 30 DEG C, obtains product, yield 86%.Wherein, the volume ratio of DMF and MeOH is 2:1.
(4) Structural Identification of 8-hydroxyquinoline Zn complex
The hydrogen signal of complex and its hydrogen signal pointed out using NMRS, as a result as shown in Figure 1；
The ir data of product, its characteristic waves (cm are determined using FTIS-1) it is 3050,2930,
2830,1620,1550,1500,1030,1280.
The crystal structure of the complex product is determined using German Brooker X single crystal diffractometers, temperature of the measurement is 298K, is adopted
With the Mo-K alpha rays through graphite monochromator monochromatizationIrradiation, diffraction data is collected using scan mode, is used
SAINT programs carry out data convert integration and obtain crystal structure figure, as a result as shown in figures 2-3, Advances in crystal X-ray diffraction tables of data
Bright complex crystal of the present invention belongs to monoclinic system, and space group is C2/c, is one-dimensional space paradigmatic structure, and its construction unit is included
One Zn of hexa-coordinate (II) and two parts.Zn (II) atom at center receives from two N and O of different ligands, while
Adjacent center metal Zn is linked into by the space structure that one dimensional infinite extends by the phenol oxygen atom of other parts.Wherein,
ZnZn distances areThe Zn-N being centered around around Zn atoms isZn-O isWithThere is weaker C-HO hydrogen bond actions (hydroxyl O atom in the intramolecular of complex 3
C-H groups on vinyl),∠ C-HO=128.9 °, Zn of these hydrogen bonds in polymer
Important function has been played in construction unit.
The complex is measured using PXRD, as shown in figure 4, the PXRD p-wires and simulation curve energy of complex
Preferably it coincide, illustrates that 8-hydroxyquinoline class Zn complex is single pure phase.
Fig. 5 is the ultraviolet spectra for titration figure of part and zinc salt coordination, simulates the process of part (L) and metallic zinc coordination,
As the instillation reaction of zinc solution is progressively carried out, absworption peak occurs in that significant change.Two major absorbance peaks of part are concentrated
Ultraviolet absorption peak at 300~400nm, 298nm is the signal peak of quinoline ring, and the UV absorption of 347nm or so is due to electricity
Lotus transfer causes.In Figure 5, with the increase for adding zinc ion ratio of zinc salt, acromion of the part at 347nm is with zinc
The addition of salt is gradually reduced, and occurs in that maximum absorption wavelength occurs obvious Red Shift Phenomena, absworption peak of the part at 304nm
There is new complex absworption peak to 319nm at 448nm in red shift.Possible cause from absworption peak red shift is：Match somebody with somebody in complex
The transfer of electric charge between body or between part inside so that the LUMO interorbitals on HOMO tracks on benzene oxygen ring and pyridine ring
Generation π → π * electron transitions.As shown in Figure 5, with the continuous instillation of zinc ion, zinc ion occurs with the mol ratio moment of part
Change, mol ratio is more than 1:When 2, no longer absorption curve change illustrates reacted complete between part and zinc ion.
In order to further detect the characteristics of luminescence of part and complex, we have followed the trail of part and zinc salt in methanol solution
(10-4Mol/L the fluorescence titration process in).As shown in fig. 6, part is under the excitation of 340nm, the transmitting of its fluorescent liquid
Crest is 464nm (blueness)；Under the excitation of 340nm (orange-yellow), its fluorescent liquid transmitting crest is complex
608nm.After part and zinc are coordinated as can see from Figure 6, the wavelength of fluorescence of compound there occurs obvious red shift, and we recognize
For reason has two：First, the π track reverse coupleds after metal-complexing between metal and part increased the flowing of main orbit electronics
Property, ionic bond is formed between metal ion and part；Second, metallic element increases the bond distance of hexatomic ring in being added to ring after coordination
Plus, form a non-radiative track to reduce maximum system energy by suppressing the flowing of phenyl ring electronics and increasing rigidity, and finally
Cause the reduction of π~π * orbital energies.
Ligands and complexes photoluminescent property at ambient temperature is as shown in fig. 7, Zn complex has at 626nm emission peaks
Very strong luminescence generated by light, excitation wavelength is 360nm, launches stronger red light.(the λ em=compared with free ligand L1-L3
457nm), it most there occurs red shift with big launch wavelength.This is derived from turning with the electric charge between internal or part for complex
Move.
Fig. 8 is the fluorescence lifetime curve and matched curve figure of complex, and test data is fitted, by calculating this
The fluorescence lifetime of the 8-hydroxyquinoline Zn complex monokaryon crystal of embodiment is 2.90ns.
Thermogravimetric analysis further is carried out to 8-hydroxyquinoline class Zn complex monokaryon crystal.Condition determination is：Heating rate
It is 10 DEG C/min, measurement temperature scope is 20~1000 DEG C, as shown in figure 9,8-hydroxyquinoline Zn complex monokaryon crystal is the
At 364 DEG C~422 DEG C, its mass fraction reduces 14.97% to the weightless temperature scope in one stage.Illustrate the complex can compared with
Stablize relatively at temperature high, for vacuum evaporation process making devices provides necessary condition.
In sum, the soluble 8-hydroxyquinoline Zn complex crystal with one-dimensional catenary structure in DMSO have compared with
Good stability and solubility, can have can wet processing property；And with of a relatively high luminous intensity and heat endurance, fit
Share in preparing corresponding luminescent device.
Obviously, the above embodiment of the present invention is only intended to clearly illustrate example of the present invention, and is not right
The restriction of embodiments of the present invention.For those of ordinary skill in the field, may be used also on the basis of the above description
To make other changes in different forms.There is no need and unable to be exhaustive to all of implementation method.It is all this
Any modification, equivalent and improvement made within the spirit and principle of invention etc., should be included in the claims in the present invention
Protection domain within.
Claims (9)
1. a kind of 8-hydroxyquinoline Zn complex with one-dimensional catenary structure, with the structure as shown in formula I：
2. the preparation method of the 8-hydroxyquinoline Zn complex described in a kind of claim 1, including：
A) by 2- methyl -8-hydroxyquinoline and 2,4- dichlorobenzaldehydes are reacted in reaction dissolvent, obtain reaction intermediate；
B) reaction intermediate for obtaining step a) reacts with pyridine, water successively, obtains part；
C) part and zinc salt for obtaining step b) are reacted in reaction dissolvent, are obtained the 8-hydroxyquinoline zinc and are coordinated
Thing.
3. preparation method according to claim 2, it is characterised in that reaction dissolvent described in step a) is acetic anhydride.
4. preparation method according to claim 2, it is characterised in that the condition reacted described in step a) is：In inertia
It is heated to reflux under the protection of gas；
The inert gas includes nitrogen, argon gas or helium；
The temperature being heated to reflux is 140~145 DEG C, and the time is 18~20h.
5. preparation method according to claim 2, it is characterised in that in step b) after pyridine is added first heating stirring,
Then water is added to be heated at reflux.
6. preparation method according to claim 5, it is characterised in that the temperature of the heating stirring is 132~135 DEG C,
Time is 20~30min；
The temperature being heated at reflux is 132~135 DEG C, and the time is 3~5h.
7. preparation method according to claim 2, it is characterised in that zinc salt includes described in step c)：Zinc perchlorate, nitre
One or more in sour zinc and zinc chloride；
The mol ratio of the part and zinc salt is (3~5):(8~12).
8. preparation method according to claim 2, it is characterised in that reaction dissolvent described in step c) is N, N- dimethyl
The mixed solution of formamide and methyl alcohol；
The ratio of the part and N,N-dimethylformamide is 1mmol:(100~150) mL；
The mixed volume ratio of the N,N-dimethylformamide and methyl alcohol is (1~4):(0.5~2).
9. preparation method according to claim 2, it is characterised in that the temperature reacted described in step c) is 60~80
DEG C, the time is 24h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109206405A (en) * | 2018-10-16 | 2019-01-15 | 阜阳师范学院 | Triazolyl quinoline copper complex with AIE property and preparation method thereof |
| CN112940275A (en) * | 2021-02-08 | 2021-06-11 | 北京石油化工学院 | Preparation method of metal organic framework compound material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1594327A (en) * | 2004-06-18 | 2005-03-16 | 中国科学院广州化学研究所 | Olefin monomer of multi-functional group 8-hydroxyquinoline metal complex and its preparation process and application |
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2017
- 2017-02-28 CN CN201710114518.1A patent/CN106892868B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1594327A (en) * | 2004-06-18 | 2005-03-16 | 中国科学院广州化学研究所 | Olefin monomer of multi-functional group 8-hydroxyquinoline metal complex and its preparation process and application |
Non-Patent Citations (1)
| Title |
|---|
| YANPING HUO等: "《Comparative studies on OLED performances of chloro and fluoro substituted Zn(II) 8-hydroxyquinolinates》", 《NEW J.CHEM.》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109206405A (en) * | 2018-10-16 | 2019-01-15 | 阜阳师范学院 | Triazolyl quinoline copper complex with AIE property and preparation method thereof |
| CN109206405B (en) * | 2018-10-16 | 2020-10-27 | 阜阳师范学院 | Triazolyl quinoline copper complex with AIE property and preparation method thereof |
| CN112940275A (en) * | 2021-02-08 | 2021-06-11 | 北京石油化工学院 | Preparation method of metal organic framework compound material |
| CN112940275B (en) * | 2021-02-08 | 2022-05-20 | 北京石油化工学院 | Preparation method of metal organic framework compound material |
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