CN109020828A - A kind of schiff bases copper complex and its preparation method and application - Google Patents
A kind of schiff bases copper complex and its preparation method and application Download PDFInfo
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- CN109020828A CN109020828A CN201810828635.9A CN201810828635A CN109020828A CN 109020828 A CN109020828 A CN 109020828A CN 201810828635 A CN201810828635 A CN 201810828635A CN 109020828 A CN109020828 A CN 109020828A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The invention discloses a kind of schiff bases copper complex and its preparation method and application, preparation method includes the following steps: that 5- chloro-salicylic aldehyde is dissolved in ethyl alcohol by (1), obtains solution I；2,6- dimethylaniline is dissolved in ethyl alcohol, obtains solution II；Solution II is added into solution I, solution III is obtained；Acetic acid is added in solution III, obtains reaction solution；Reaction solution is heated to reflux 1h, is cooled to room temperature, stands and solid is precipitated, filtering, and with cold ethanol washing solid, finally obtain ligand；(2) ligand that step (1) synthesizes is dissolved in ethyl alcohol, obtains solution IV；Copper nitrate is dissolved in ethyl alcohol, obtains solution V；Solution V is added into solution IV, mixed liquor is obtained；By mixed liquor back flow reaction 1.5h, heat filtering is cooling by filtrate, and standing and black bulk crystals are precipitated is complex；The present invention explores schiff bases complex in the potential using value of field of light emitting materials.
Description
Technical field
The invention belongs to electroluminescent organic material and preparation method thereof technical fields, and in particular to a kind of schiff bases copper
Complex and its preparation method and application.
Background technique
The sustained and rapid development of information technology proposes the brightness of information display system, color, resolution ratio, energy consumption etc.
Higher requirement.Maturation applies in display technology for light emitting diode, thin film electroluminescence and thick dielectric electroluminescent,
And wherein Organic Light Emitting Diode (OLED) is market Primary Actor.In recent years, with market to high quality, high reliability,
The demand of large information capacity display device increasingly increases, and OLED technology has obtained significant progress, and there are many OLED products at present
It puts goods on the market.
Electroluminescent organic material refers to the macromolecule or Small molecule organic materials that light can be issued under electric field action, leads to
Often there should be very strong luminescence generated by light in the solid state, the electroluminescent efficiency of material is determined by its photoluminescence efficiency, only
Material with high photoluminescence efficiency is possible to the electroluminescent organic material become.Small molecule organic light emission material
Expect electroluminescent efficiency with higher and better carrier transmission performance, wherein the unique smooth object of metal organic complex
Rationality matter is got growing concern in field of light emitting materials, and metal ion is formed by the hair of complex with organic ligand
Light ability and the architectural characteristic of organic ligand and metal ion have very big relationship.Schiff bases is as a kind of representative
Organic ligand, imine group can be introduced in system by design, schiff bases has the ability of chelated mineral, can with it is each
Metalloid cation carries out self assembly and forms metal complex.
Schiff bases and its metal complex because its with special structure and due to unique electrochemistry and optical property
Numerous areas causes the extensive concern of scientific worker.Schiff base metal complex has very in field of organic electroluminescence
Considerable application prospect, especially bigcatkin willow aldehydes.After introducing the different substituents such as halogen on salicylide phenyl ring, since electronics is imitated
It answers, the influence of three-dimensional effect, has a significant impact to the application performance of the schiff bases and metal complex that synthesize thereafter.Currently,
5- chloro-salicylic aldehyde and 2, the synthesis of 6- dimethylaniline schiff bases and its copper complex and crystal structure have not been reported, the present invention
A kind of schiff bases copper complex has been synthesized, and has had studied its photoluminescence performance, has explored schiff bases complex in luminescent material
The potential using value in field.
Summary of the invention
The present invention provides a kind of schiff bases copper complex and its preparation method and application, by by 5- chloro-salicylic aldehyde and 2,
The condensation of 6- dimethylaniline, obtains schiff base ligand, then schiff base ligand is reacted with copper nitrate, copper ion is made to enter Schiff
In the cavity that aar ligand N, N, O, O are constituted, schiff bases copper complex is formed, and detects the schiff bases copper complex as hair
The performance of luminescent material.
The present invention is achieved by the following technical solution.
The object of the invention provides a kind of schiff bases copper complex, the preparation method of the schiff bases copper complex include with
Lower step:
(1) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands: 5- chloro-salicylic aldehyde is dissolved in ethyl alcohol, obtains
To solution I；2,6- dimethylanilines are dissolved in ethyl alcohol, obtained solution II；Solution II is added into solution I, solution is obtained
Ⅲ；Glacial acetic acid is added in solution III, obtains reaction solution；Reaction solution is heated to 76 DEG C~78 DEG C back flow reaction 1h, is cooled to
Room temperature stands and solid is precipitated, filtering, and with cold ethanol washing solid, finally obtaining Orange red solid is the chloro- 2- (2,6- of 4-
Dimethylaniline ylmethyl) phenol ligands；
The 5- chloro-salicylic aldehyde: 2,6- dimethylaniline molar ratios are 1:1, and the III solute total mass concentration of solution is
0.05g/mL~0.09g/mL, the addition volume of the glacial acetic acid are the 0.1%~0.2% of III volume of solution；
(2) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex: the 4- that step (1) is synthesized
Chloro- 2- (2,6- dimethylaniline ylmethyl) phenol ligands are dissolved in ethyl alcohol, obtain solution IV；Gerhardite is dissolved in second
Alcohol obtains solution V；Solution V is added into solution IV, mixed liquor is obtained；Mixed liquor is heated to 76 DEG C~78 DEG C reflux
1.5h is reacted, heat filtering is cooling by filtrate, and standing and black bulk crystals are precipitated is 4- chloro- 2- (2,6- accelerine bases
Methyl) phenol copper complex；
4- chloro-salicylic aldehyde contracting 2, the 6- dimethyl benzene amine ligand: Gerhardite molar ratio is 2:1, the mixing
Liquid solute total mass concentration is 0.01g/mL~0.02g/mL.
Compared with prior art, the present invention has the following advantages: preparation method principle of the invention is simple, condition temperature
With, it is easily operated, 5- chloro-salicylic aldehyde and 2,6- dimethylaniline are condensed, obtain schiff base ligand, then by schiff base ligand with
Copper nitrate reaction, forms schiff bases copper complex, realizes inorganic ions and the cooperation containing photosensitive group organic matter, and open
A kind of advanced luminescent material is had issued, schiff bases is explored in the potential using value of field of organic electroluminescence, is ground for after
Study carefully and lays the foundation.
Detailed description of the invention
Fig. 1 is the preparation flow figure of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex in the present invention；
Fig. 2 is the crystal knot of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) the phenol copper complex prepared in the present invention
Composition；
Fig. 3 is the infrared spectrogram of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands and its copper complex；
Fig. 4 is the UV absorption figure of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands and its copper complex；
Fig. 5 is the fluorescence spectra of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex；
Fig. 6 is HOMO, LUMO and energy of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands and its complex
Band calculates figure；
Fig. 7 is the chloro- 2- of cyclic voltammetry 4- (2,6- dimethylaniline ylmethyl) phenol ligands and its copper complex
Electrochemistry figure.
Specific embodiment
In order to enable those skilled in the art to more fully understand, technical solution of the present invention is practiced, below with reference to tool
The invention will be further described for body embodiment and data, but illustrated embodiment is not as a limitation of the invention.
Experimental method and detection method described in following each embodiments are unless otherwise specified conventional method；It is described
Reagent and material can be commercially available on the market unless otherwise specified.
Embodiment 1
Preparation flow as shown in Figure 1 prepares the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex, specifically
Steps are as follows:
(1) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands: 1.56g 5- chloro-salicylic aldehyde is weighed
Into 100mL round-bottomed flask, 30mL ethyl alcohol stirring and dissolving is added, 1.21g 2 is then added, the ethyl alcohol of 6- dimethylaniline is molten
Liquid 20mL is added 0.05mL glacial acetic acid, obtains reaction solution；Reaction solution is heated to 76 DEG C of back flow reaction 1h, is cooled to room temperature,
It stands and solid is precipitated, filtering, and with cold ethanol washing solid, finally obtaining Orange red solid is 4- chloro- 2- (2,6- diformazans
Base aminopropyltriethoxysilane) phenol ligands；
(2) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex: step (1) synthesis is weighed
It is molten that the stirring of 30mL ethyl alcohol is added to 100mL round-bottomed flask in the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands 0.52g
Solution, adds the ethanol solution 20mL of 0.24g Gerhardite, obtains mixed liquor；It is anti-that mixed liquor is heated to 76 DEG C of reflux
1.5h is answered, heat filtering is cooling by filtrate, and standing and black bulk crystals are precipitated is the chloro- 2- of 4- (2,6- accelerine base first
Base) phenol copper complex.
Embodiment 2
Preparation flow as shown in Figure 1 prepares the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex, specifically
Steps are as follows:
(1) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands: 1.56g 5- chloro-salicylic aldehyde is weighed
Into 100mL round-bottomed flask, 30mL ethyl alcohol stirring and dissolving is added, 1.21g 2 is then added, the ethyl alcohol of 6- dimethylaniline is molten
Liquid 20mL is added 0.1mL glacial acetic acid, obtains reaction solution；Reaction solution is heated to 78 DEG C of back flow reaction 1h, is cooled to room temperature, it is quiet
Precipitation solid is set, is filtered, and with cold ethanol washing solid, finally obtaining Orange red solid is 4- chloro- 2- (2,6- dimethyl
Aminopropyltriethoxysilane) phenol ligands；
(2) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex: step (1) synthesis is weighed
It is molten that the stirring of 30mL ethyl alcohol is added to 100mL round-bottomed flask in the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands 0.52g
Solution, adds the ethanol solution 20mL of 0.24g Gerhardite, obtains mixed liquor；It is anti-that mixed liquor is heated to 78 DEG C of reflux
1.5h is answered, heat filtering is cooling by filtrate, and standing and black bulk crystals are precipitated is the chloro- 2- of 4- (2,6- accelerine base first
Base) phenol copper complex.
By taking embodiment 1 as an example, the chloro- 2- of 4- (2, the 6- dimethylaniline ylmethyl) phenol ligands and its copper of synthesis are detected
The structure and luminescent properties of complex are as a result as follows:
The crystal structure of copper complex is made of two ligands and a Cu (II) as seen from Figure 2, center Cu
(II) ion has four-coordination geometry, respectively in two bidentate ligands two N atoms and two O atoms be coordinated, shape
It is configured at planar；Cu (II) and ligand are formed by Cu-N and are good for long value in 0.19772 (16) nm~0.20004 (15) nm
Between, with the bond angle centered on Cu (II) between 87.72 (16) °~180.0 °, Cu-O bond distance's value is in 0.18788 (15) nm
Between~0.1884 (14) nm.In order to reduce steric hindrance, dihedral angle is between two phenyl ring in ligand in copper complex
89.3°；Cu (II) ion and ligand by two five yuan of chelate rings of coordination formation (chelate ring A and chelate ring B have C1, C6,
C7, N1, O1, Cu1 and Cu1, O1A, C1A, C6A, C7A, N1A are formed, and the dihedral angle between two chelate rings is 0 °).By Fig. 3
As can be seen that occurring 1620cm in ligand-1Locate the stretching vibration absworption peak of imido grpup C=N, C=N stretches in copper complex
Contracting vibration absorption peak appears in 1608cm-1Between, compared to red shift has occurred；The stretching vibration of Ar-O appears in ligand
1281cm-1At wave number, and 1322cm is appeared in copper complex-1Place；In 753-770cm-1The new peak of appearance can be attributed to
The absorption peak of Cu-N shows that imines (C=N) takes part in coordination；Meanwhile in 605-625cm-1The new peak of appearance can be attributed to
The absorption peak of Cu-O shows that the oxygen of phenolic hydroxyl group takes part in coordination.
It can be obtained by the UV absorption figure of Fig. 4 ligand and copper complex, there are two relatively strong at 262nm and 337nm for ligand
Absorption peak, and copper complex at 260nm, 300nm and 381nm there are three absorption peak, these are by between metal and ligand
Electric charge transfer and with caused by internal electric charge transfer；The UV absorption sideband that ligand is calculated according to map is 3.22eV, and copper is matched
The UV absorption sideband for closing object is 2.85eV, this illustrates that the latter is easier to carry out electron transition than the former.By Fig. 5 fluorescence spectrum
Tu Ke get measures optimum excitation wave a length of 450nm, the maximum emission wavelength 508nm of copper complex in DMSO solvent, hair
Blue green light.Fig. 6 shows that the energy band of ligand is 4.07eV, and the energy band of copper complex is 3.29eV, and the latter is greater than the former, says
Bright copper complex is easier to carry out electron transition than ligand, this is consistent with the electron transition trend result of optical computing.
Using ferrocene as internal standard, tetra-n-butyl ammonium perchlorate is supporting electrolyte, and cyclic voltammetry ligand and copper are matched
Object electrochemistry figure is closed, by Fig. 7 it can be concluded that the initial oxidation potential of ligand is 1.06eV, the initial oxidation potential of copper complex
For 1.15eV, according to HOMO=- [(Eonset-Eferrocene)+4.80] (eV) and LUMO=Egopt+ HOMO calculate reason ligand and
The HOMO and lumo energy of copper complex are respectively as follows: ligand, HOMO=-5.33eV and LUMO=-2.62eV, and energy band is
3.40V；Copper complex, HOMO=-5.42eV and LUMO=-2.57eV, energy band 2.85.
Above-mentioned map is detailed in attached drawing.
Obviously, various changes and modifications can be made to the invention without departing from of the invention by those skilled in the art
Spirit and scope.In this way, if these modifications and changes of the present invention belongs to the model of the claims in the present invention and its equivalent technologies
It is also intended to include these modifications and variations within enclosing.
Claims (3)
1. a kind of preparation method of schiff bases copper complex, which comprises the following steps:
(1) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol ligands: 5- chloro-salicylic aldehyde is dissolved in ethyl alcohol, obtains molten
Liquid I；2,6- dimethylanilines are dissolved in ethyl alcohol, obtained solution II；Solution II is added into solution I, solution III is obtained；Molten
Glacial acetic acid is added in liquid III, obtains reaction solution；Reaction solution is heated to 76 DEG C~78 DEG C back flow reaction 1h, is cooled to room temperature, it is quiet
Precipitation solid is set, is filtered, and with cold ethanol washing solid, finally obtaining Orange red solid is 4- chloro- 2- (2,6- dimethyl benzenes
Aminomethyl) phenol ligands；
The 5- chloro-salicylic aldehyde: 2,6- dimethylaniline molar ratios are 1:1, and the III solute total mass concentration of solution is 0.05g/
ML~0.09g/mL, the addition volume of the glacial acetic acid are the 0.1%~0.2% of III volume of solution；
(2) synthesis of the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl) phenol copper complex: the chloro- 2- of 4- that step (1) is synthesized
(2,6- dimethylaniline ylmethyl) phenol ligands are dissolved in ethyl alcohol, obtain solution IV；Gerhardite is dissolved in ethyl alcohol, is obtained
Solution V；Solution V is added into solution IV, mixed liquor is obtained；Mixed liquor is heated to 76 DEG C~78 DEG C back flow reactions
1.5h, heat filtering is cooling by filtrate, and standing and black bulk crystals are precipitated is the chloro- 2- of 4- (2,6- dimethylaniline ylmethyl)
Phenol copper complex；
4- chloro-salicylic aldehyde contracting 2, the 6- dimethyl benzene amine ligand: Gerhardite molar ratio is 2:1, the mixed liquor solute
Total mass concentration is 0.01g/mL~0.02g/mL.
2. schiff bases copper complex made of preparation method according to claim 1.
3. application of the schiff bases copper complex according to claim 2 in field of light emitting materials.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229176A (en) * | 2019-07-17 | 2019-09-13 | 山西农业大学 | A kind of fragrance plane schiff bases copper complex and its preparation method and application |
| CN111018893A (en) * | 2019-11-25 | 2020-04-17 | 桂林医学院 | Sulfur-containing amino alcohol Schiff base copper complex and preparation and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103896800A (en) * | 2014-04-23 | 2014-07-02 | 桂林理工大学 | Iodine-containing sandwich copper compound and application thereof |
| CN107840807A (en) * | 2017-10-01 | 2018-03-27 | 桂林理工大学 | A kind of schiff bases copper complex and preparation method thereof |
-
2018
- 2018-07-25 CN CN201810828635.9A patent/CN109020828B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103896800A (en) * | 2014-04-23 | 2014-07-02 | 桂林理工大学 | Iodine-containing sandwich copper compound and application thereof |
| CN107840807A (en) * | 2017-10-01 | 2018-03-27 | 桂林理工大学 | A kind of schiff bases copper complex and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| LOPAMUDRA CHAKRABORTY，等: "Synthesis, mesomorphic and photo-physical properties of few d- and f- block metals coordinated to polar Schiff"s bases", 《LIQUID CRYSTALS》 * |
| 于静，等: "Schiff碱金属配合物的研究进展", 《化学研究》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229176A (en) * | 2019-07-17 | 2019-09-13 | 山西农业大学 | A kind of fragrance plane schiff bases copper complex and its preparation method and application |
| CN111018893A (en) * | 2019-11-25 | 2020-04-17 | 桂林医学院 | Sulfur-containing amino alcohol Schiff base copper complex and preparation and application thereof |
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