CN106892867B - A kind of 8-hydroxyquinoline Zn complex crystal and preparation method thereof with ferroelectric property - Google Patents
A kind of 8-hydroxyquinoline Zn complex crystal and preparation method thereof with ferroelectric property Download PDFInfo
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- CN106892867B CN106892867B CN201710114508.8A CN201710114508A CN106892867B CN 106892867 B CN106892867 B CN 106892867B CN 201710114508 A CN201710114508 A CN 201710114508A CN 106892867 B CN106892867 B CN 106892867B
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- 0 *c1cccc2c1nc(C=C[C@@]1C(C(F)(F)F)=CC=CC1)cc2 Chemical compound *c1cccc2c1nc(C=C[C@@]1C(C(F)(F)F)=CC=CC1)cc2 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N Cc1nc(c(O)ccc2)c2cc1 Chemical compound Cc1nc(c(O)ccc2)c2cc1 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N O=Cc1c(C(F)(F)F)cccc1 Chemical compound O=Cc1c(C(F)(F)F)cccc1 ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 1
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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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- 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-hydroxyquinoline Zn complex crystal and preparation method thereof with ferroelectric property.Shown in the chemical constitution such as formula (I) of 8-hydroxyquinoline Zn complex crystal provided by the present invention, with unique ferroelectric property, and good thermal stability, longer fluorescence lifetime and high luminous intensity are shown, it can be used for preparing regulatable ferroelectricity luminescent device；In addition, Zn complex crystal provided by the present invention is free of rare earth element, low raw-material cost derives from a wealth of sources, and equipment is simple, and process optimization has wide Commercial Prospect, it can be achieved that large-scale production.
Description
Technical field
The invention belongs to metal complex fields, and in particular to a kind of 8-hydroxyquinoline Zn complex with ferroelectric property
Crystal and preparation method thereof.
Background technology
Ferroelectric crystal materials are a kind of crystalline materials with ferroelectric property.Such material has the object of ferroelectricity block materials
Rationality matter, such as ferroelectric properties, dielectric property, piezoelectric property, pyroelectricity characteristic are widely used in microelectronic component, miniature
The fields such as machinery, sensor.And ferroelectricity luminescent material, it is the ferroelectric material for being provided simultaneously with ferroelectric properties and photoluminescence property,
There is considerable application value in regulatable photoelectric material and devices field.
Luminescent material be the substance of lighting function is finally undertaken in device, therefore the luminous efficiency of luminescent material, shine the longevity
The properties such as life and luminescent chromaticity will all have a direct impact the performance of OLED.As the luminescent material in OLED should have as
Lower condition：1) there is efficient solid state fluorescence, without apparent concentration quenching phenomena；2) there is good chemical stability and heat
Stability does not react with electrode and carrier transmission material；3) it is easy to form fine and close noncrystalline membrane and is not easy to tie
It is brilliant；4) there is emission wavelength appropriate；5) there is good conductive characteristic and certain carrier transport ability.
8-hydroxyquinoline metal complex has good thermal stability, high fluorescence and its good electron-transport work(
Can, therefore become one of the material for being applied to most reliable electron-transport and transmitting in OLED.Probe into the 8- hydroxyls with ferroelectric property
Base quinoline develops novel ferroelectric luminescent material, can expand the application field of such material, meet under different condition
Application demand.The ferroelectricity luminescent material reported contains expensive thulium, such as rare earth doped bismuth titanate mostly
(BiLn)4Ti3O12, rare earth doping barium titanate (BaLn) TiO3, rear-earth-doped vanadic acid bismuth (BiLn)2VO5.5Etc. systems.Therefore it studies
The novel ferroelectric luminescent crystal material that exploitation is inexpensively easily prepared is of great significance to the commercialization of such material.
Invention content
In view of this, the present invention provides a kind of with the 8-hydroxyquinoline Zn complex crystal of ferroelectric property and its preparation
Method, 8-hydroxyquinoline Zn complex crystal provided by the present invention not only have ferroelectric property, also have both higher shine by force
The advantages that degree, good thermal stability and longer fluorescence lifetime.
The specific technical solution of the present invention is as follows：
The present invention provides a kind of 8-hydroxyquinoline Zn complex crystal with ferroelectric property has as shown in formula I
Structure：
The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline Zn complex crystal, including：
A) 2- methyl -8-hydroxyquinoline and 2- trifluoromethylated benzaldehydes are reacted in reaction dissolvent, is reacted
Intermediate；
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand；
C) the obtained ligands of step b) and zinc salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline zinc and matches
Close object.
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 10~12h.
Preferably, in step b) after pyridine is added first heating stirring, water is then added and is heated at reflux.
Preferably, the temperature of the heating stirring is 142~145 DEG C, and the time is 20~30min；
The temperature being heated at reflux is 142~145 DEG C, and the time is 3~5h.
Preferably, zinc salt described in step c) includes：One kind in zinc iodide, zinc perchlorate, zinc nitrate or zinc chloride or
It is a variety of；
The molar ratio of the ligand and zinc salt is (1~3):(4~7).
Preferably, the step c) reaction dissolvents are the mixed solution of n,N-Dimethylformamide and methanol；
The ratio of the ligand and N,N-dimethylformamide is 1mmol:(45~55) mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is (4~6):(2~4).
Preferably, the temperature reacted described in step c) is 60~80 DEG C, and the time is for 24 hours.
The present invention provides a kind of 8-hydroxyquinoline Zn complex crystal, shown in chemical constitution such as formula (I), have uniqueness
Ferroelectric property, and show good thermal stability, longer fluorescence lifetime and high luminous intensity, can be used for preparing controllable
Ferroelectricity luminescent device；In addition, Zn complex crystal provided by the present invention is free of rare earth element, low raw-material cost, source
Extensively, equipment is simple, and process optimization has wide Commercial Prospect, it can be achieved that large-scale production.
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
The embodiment of invention for those of ordinary skill in the art without creative efforts, can also basis
The attached drawing of offer obtains other attached drawings.
Fig. 1 is the nuclear magnetic resonance spectroscopy of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 2 is the crystal structure figure of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 3 is the layer structure figure of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 4 is the PXRD figures of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 5 is the ultraviolet spectra for titration figure of ligand and zinc complexation process in embodiment 1；
Fig. 6 is the Solid fluorescene spectrum figure of 8-hydroxyquinoline Zn complex and ligand in embodiment 1；
Fig. 7 is the fluorescence lifetime curve graph of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 8 is the thermogravimetric analysis figure (TGA) of the 8-hydroxyquinoline Zn complex obtained in embodiment 1；
Fig. 9 is the ferroelectric hysteresis loop of a small amount of 8-hydroxyquinoline Zn complex solid sample plates under room temperature in embodiment 1.
Specific implementation mode
The present invention provides a kind of 8-hydroxyquinoline Zn complex crystal with ferroelectric property has as shown in formula (I)
Structure：
The present invention also provides a kind of preparation methods of above-mentioned 8-hydroxyquinoline Zn complex crystal, including：
A) 2- methyl -8-hydroxyquinoline and 2- trifluoromethylated benzaldehydes are reacted in reaction dissolvent, is reacted
The chemical name of intermediate, the reaction intermediate is (E) -2- [2- trifluoromethyl-phenyls vinyl] -8- acetoxyl group quinoline；
Wherein, the reaction equation involved in step a) is as follows：
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand, the chemical name of the ligand
For (E) -2- [2- trifluoromethyl-phenyls vinyl] -8-hydroxyquinoline；
Wherein, the reaction equation involved in step b) is as follows：
C) the obtained ligands of step b) and zinc salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline zinc and matches
Close object；
Wherein, the reaction equation involved 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 preferably 10~12h, more preferably
11h；
The inert gas is preferably nitrogen, argon gas or helium, more preferably nitrogen；
The molar ratio of 2- methyl -8-hydroxyquinoline and 2- trifluoromethylated benzaldehydes 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 142~145 DEG C, and the time is 20~30min；
The temperature being heated at reflux is 142~145 DEG C, and the time is 3~5h.
In the present invention, zinc salt described in step c) is preferably one in zinc iodide, zinc perchlorate, zinc nitrate or zinc chloride
Kind is a variety of, more preferably zinc iodide；The reaction dissolvent is the mixed solution of N,N-dimethylformamide and methanol.
Further, the molar ratio of the ligand and zinc salt is preferably (1~3):(4~7), more preferably 1:4；
The ratio of the ligand and N,N-dimethylformamide is preferably 1mmol:(45~55) mL, more preferably 1mmol:
50mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is preferably (4~6):(2~4), more preferably 5:
3；
The temperature of the reaction is 60~80 DEG C, and the time is for 24 hours.
Technical scheme of the present invention is clearly and completely described below in conjunction with description of the invention attached drawing, it is clear that
Described embodiment is a part of the embodiment of the present invention, instead of all the embodiments.Those skilled in the art should manage
Solution, modifies to specific embodiments of the present invention or is replaced on an equal basis to some technical characteristics, without departing from the present invention
The spirit of technical solution should all cover in the scope of protection of the invention.
Embodiment 1
(1) preparation of reaction intermediate
A, 2- methyl -8-hydroxyquinoline 0.68g and 2- trifluoromethylated benzaldehyde 0.72g is weighed in the round-bottomed flask of 100mL
In, the acetic anhydride dissolving of 20mL is added, obtains mixed liquor；
B, by the mixed liquor that step A is obtained carried out under the protection of nitrogen magnetic agitation, 143 DEG C be heated to reflux 11h, with
The progress of reaction, the color of reaction solution are gradually deepened, and switch to brown by the beginning light yellow, reaction solution is in opaque muddy
Turbid state is also precipitated with a small amount of solid in reaction process；Solid is filtered with 100mL water, and is cleaned repeatedly three times, vacuum drying
After obtain 1.1g white solid state reaction intermediates, yield 88%.
(2) preparation of ligand
The reaction intermediate of 0.71g is dissolved in the 100mL round-bottomed flasks equipped with 10mL pyridines, 143 DEG C of heating stirrings
5mL water is added after 30min, while water is added, solution quickly becomes dark cloudy state；Continue heating reflux reaction 4 hours
Afterwards, stop reaction, appropriate distilled water is added, place cooling precipitation solid；Solid is filtered with 100mL water, and is cleaned repeatedly three times,
0.57g light yellow solid ligands, yield 90% are obtained after vacuum drying.
(3) preparation of 8-hydroxyquinoline Zn complex
The above-mentioned ligands of 3.1mg (0.01mmol) are dissolved in DMF (0.5mL) and MeOH (0.3mL), ZnI is then added2
The DMF solution of (0.04mmol), is sealed in the vial of 10mL, and for 24 hours, cooling collect obtains pale red crystal for 80 DEG C of heating,
It is washed several times with MeOH, dries to obtain the 8-hydroxyquinoline Zn complex at room temperature.Wherein, the volume ratio of DMF and MeOH
It is 5:3.
(4) Structural Identification of 8-hydroxyquinoline Zn complex
Using MRI scan complex hydrogen signal and its hydrogen signal is pointed out, the results are shown in Figure 1；
The ir data of product, characteristic waves (cm are measured using Fourier Transform Infrared Spectrometer-1) it is 3050,2930,
2830,1620,1550,1500,1030,1280.
The crystal structure of the complex product, measuring temperature are measured using Bruker Smart 1000CCD single crystal diffractometers
For 123K, carries out data convert with SAINT programs and integrate to obtain crystal structure figure, as a result as shown in figures 2-3, single crystal X-ray
Diffraction data shows that complex crystal of the present invention belongs to non-centrosymmetrical rhombic system, and space group is Pna2 (1).It is centered around Zn
Zn-N around atom is Zn-O isThree Zn atoms pass through four
O atom bridging (ZnZn=3.229,3.312 Hes on different phenolic hydroxyl groups)。
The complex is measured using PXRD, as shown in figure 4, the PXRD p-wires and simulation curve energy of complex
It is preferable to coincide, illustrate that 8-hydroxyquinoline class Zn complex is single pure phase.
Fig. 5 is the ultraviolet spectra for titration figure of ligand and zinc salt coordination, simulates the process of ligand (L) and metallic zinc coordination,
It is gradually carried out with the instillation reaction of zinc solution, significant change occurs in absorption peak.Two major absorbance peaks of ligand are concentrated
Ultraviolet absorption peak at 280~320nm, 280nm is the signal peak of quinoline ring, and the UV absorption of 310nm or so is due to electricity
Caused by lotus shifts.In Figure 5, with the continuous instillation of zinc ion, the molar ratio moment of zinc ion and ligand changes, and rubs
You are than being more than 1:When 2, absorption curve changes no longer, illustrates that the reaction was complete between ligand and zinc ion.
The photoluminescent property of complex solid at ambient temperature is as shown in fig. 6, Zn complex has very at 640nm emission peaks
Strong luminescence generated by light, excitation wavelength are 325nm, emit stronger red light.This is derived from metal and turns to the charge between ligand
It moves (MLCT).
Fig. 7 is the fluorescence lifetime curve and matched curve figure of complex, is fitted to test data, by calculating to obtain this
The fluorescence lifetime of the 8-hydroxyquinoline Zn complex crystal of embodiment is 9.97ns.
Thermogravimetric analysis further is carried out to 8-hydroxyquinoline class Zn complex monokaryon crystal.Determination condition is：Heating rate
For 10 DEG C/min, ranging from 30~1000 DEG C of measuring temperature, as shown in figure 8,8-hydroxyquinoline Zn complex crystal is in the first rank
For the weightless temperature range of section at 345 DEG C~440 DEG C, mass fraction reduces 55.3%.Illustrate that the complex can be higher
At a temperature of relatively stablize, provide necessary condition for vacuum evaporation process making devices.
Fig. 9 be at room temperature electric field strength be set as 50kV and 60kV a small amount of Zn complex solid sample plates ferroelectric hysteresis loop.
The sample shows as weak ferroelectric property at ambient temperature, and under conditions of 50kV, polarizability is 0.065 μ c/cm2；?
Under the field strength of 60kV, polarizability is 0.095 μ c/cm2。
In conclusion while the 8-hydroxyquinoline class Zn complex crystal has ferroelectric property, have both preferable heat
Stability, luminous intensity and fluorescence lifetime.It is extensive to prepare raw material sources, it is cheap, and synthesis condition is mild, operation letter
It is single, it is suitable for preparing regulatable ferroelectricity luminescent device.
Obviously, the above embodiment of the present invention be only to clearly illustrate example of the present invention, and not be pair
The restriction of embodiments of the present invention.For those of ordinary skill in the art, may be used also on the basis of the above description
To make other variations or changes in different ways.There is no necessity and possibility to exhaust all the enbodiments.It is all this
All any modification, equivalent and improvement etc., should be included in the claims in the present invention made by within the spirit and principle of invention
Protection domain within.
Claims (9)
1. a kind of 8-hydroxyquinoline Zn complex crystal with ferroelectric property has structure shown in formula I：
2. a kind of preparation method of 8-hydroxyquinoline Zn complex crystal described in claim 1, including：
A) 2- methyl -8-hydroxyquinoline and 2- trifluoromethylated benzaldehydes are reacted in reaction dissolvent, it is intermediate obtains reaction
Body；
B) reaction intermediate that step a) is obtained is reacted with pyridine, water successively, obtains ligand；
C) the obtained ligands of step b) and zinc salt are reacted in reaction dissolvent, obtains the 8-hydroxyquinoline zinc cooperation
Object.
3. preparation method according to claim 2, which is characterized in that reaction dissolvent described in step a) is acetic anhydride.
4. preparation method according to claim 2, which is characterized 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 is nitrogen, argon gas or helium；
The temperature being heated to reflux is 140~145 DEG C, and the time is 10~12h.
5. preparation method according to claim 2, which is characterized 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, which is characterized in that the temperature of the heating stirring is 142~145 DEG C,
Time is 20~30min；
The temperature being heated at reflux is 142~145 DEG C, and the time is 3~5h.
7. preparation method according to claim 2, which is characterized in that zinc salt is described in step c)：Zinc iodide, perchloric acid
It is one or more in zinc, zinc nitrate or zinc chloride；
The molar ratio of the ligand and zinc salt is (1~3):(4~7).
8. preparation method according to claim 2, which is characterized in that reaction dissolvent described in step c) is N, N- dimethyl
The mixed solution of formamide and methanol；
The ratio of the ligand and N,N-dimethylformamide is 1mmol:(45~55) mL；
The mixed volume ratio of the N,N-dimethylformamide and methanol is (4~6):(2~4).
9. preparation method according to claim 2, which is characterized in that the temperature reacted described in step c) is 60~80
DEG C, the time is for 24 hours.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104744499A (en) * | 2015-02-27 | 2015-07-01 | 广东工业大学 | Trifluoromethyl quinoline-containing cadmium complex tetramer as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104744499A (en) * | 2015-02-27 | 2015-07-01 | 广东工业大学 | Trifluoromethyl quinoline-containing cadmium complex tetramer as well as preparation method and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| A novel trimeric Zn (II) complex based on 8-hydroxyquinoline with trifluoromethylbenzene group: Synthesis, crystal structure, photophysical properties and DNA binding;Yanping Huo等;《Journal of Molecular Structure》;20150612(第1098期);311-317 * |
| Self-Assembly of Five 8-Hydroxyquinolinate-Based Complexes: Tunable Core,;Guozan Yuan等;《Chemistry – An Asian Journal》;20141231;第9卷(第7期);1913-1921 * |
| Synthesis and luminescent properties of Zn complex based on 8-hydroxyquinoline group containing 3,5-bis(trifluoromethyl) benzene unit with unique crystal structure;Yanping Huo等;《Tetrahedron》;20100917;第66卷(第45期);8635-8640 * |
| 新型含三氟甲基八羟基喹啉锌配合物的合成及紫外、荧光性质研究;聂晓李 等;《无机化学学报》;20130930;第29卷(第9期);1805-1812 * |
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