CN107556330A - A kind of core copper [I] complex blue light material of pyridine tetrazole four and preparation method thereof - Google Patents
A kind of core copper [I] complex blue light material of pyridine tetrazole four and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to a kind of core copper [I] complex blue light material of pyridine tetrazole four, core copper [I] the complex blue light material of pyridine tetrazole four is that perchlorate two [5 [2 pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane] closes four bronze medals [I] complex, and its molecular formula is C112H96Cl2Cu4N10O8P.The present invention also provides the preparation method of two kinds of pyridine tetrazole four core copper [I] complex blue light materials.Pyridine tetrazole four core copper [I] complex blue light material belongs to a kind of new blue light emitting material, has good development prospect.
Description
Technical field
The present invention relates to a kind of core copper [I] complex blue light material of pyridine tetrazole four and preparation method thereof, belong to luminous
New material synthesis technical field.
Background technology
Because of the influence of heavy atoms effect and strong Effect of Spin-orbit Coupling, metal emitting complexes are in theory using all
Singlet state and triplet energies, are substantially improved luminous efficiency.At present, the research of metal emitting complexes focus primarily upon the 5th,
Six cycles, especially group VIII transition metal, such as ruthenium, osmium, iridium and platinum.The transition metal in the five, the six cycles is (except first and second pair
Outside a few metal of race) content is rare in the earth's crust, and exploitation is difficult, therefore is made based on such noble metal emitting complexes
It is higher with cost, and can also bring raw material nervous after large-scale application.In addition, such precious metal chemical complex generally have it is larger
The compound such as toxicity, especially ruthenium, osmium, rhenium, thus, the luminescent material based on such precious metal chemical complex is after large-scale application
Environmental pollution can also be brought and bring injury to production and application person.The defects of high use cost and unfriendly environment, causes theirs
Large-scale application is extremely restricted, thus people be particularly desirable to look for outside the five, the six cycles it is other alternative
Metal.
The transition metal in the five, the six cycles is compared, the copper metal of period 4, not only aboundresources, cheap, and
Environmentally friendly and luminous uniqueness.In addition, univalent copper complex has the visible phosphorescent emissions of excellent room temperature, lighting can be ultraviolet
Change to near-infrared, cover whole visible region.It is aboundresources, cheap, luminous unique and environmentally friendly etc. many excellent
Point make it that monovalence copper emitting complexes are all in luminescent device, intellectual material, optical sensor, nonlinear optics, photovoltaic device etc.
It is multi-field to show good application prospect.
At present, the copper emitting complexes that document discloses report mainly have monovalence copper mononuclear complex and cluster compound.Monovalence copper
Cluster compound is because structure is novel, and geometric configuration enriches, and coordination mode is various, more next in recent years many advantages, such as luminosity uniqueness
More receive much attention.However, build multinuclear copper using the multiple tooth cheland of azacyclo- and organic double phosphine assistant ligands
The document report of [I] complex luminescent material is seldom, especially multinuclear copper [I] complex blue light emitting material.
Using the multiple tooth cheland 5- of pyridine tetrazole [2- pyridine radicals] tetrazoles and double double [diphenyl of phosphine assistant ligand
Phosphine] methane, design four core copper [I] complex blue light emitting materials of synthesis and preparation method thereof, there has been no document at present to disclose report
Road.
The content of the invention
It is an object of the invention to overcome the defect of prior art, there is provided a kind of core copper [I] of pyridine tetrazole four coordinates
Thing blue light material and preparation method thereof, it belongs to a kind of new blue light emitting material.
What the present invention was realized in：
The present invention provides a kind of core copper [I] complex blue light material of pyridine tetrazole four, the core copper of pyridine tetrazole four
[I] complex blue light material closes for perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane]
Four bronze medals [I] complex, its molecular formula are C112H96Cl2Cu4N10O8P8。
Further, perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane] closes four
Copper [I] complex crystal category monoclinic system, P21/ c space groups, cell parameter：A=15.4418 (13), b=23.077 (2), β=113.265 (2) °,Mr=2452.66, Z=2, Dc=1.424g
cm-3, μ=1.045mm-1, GOF=1.060.
The present invention provides a kind of preparation method of core copper [I] the complex blue light material of pyridine tetrazole four, including following step
Suddenly：
Step 1：Under an argon atmosphere, mol ratio 2:2:1 [Cu [MeCN]4][ClO4], double [diphenylphosphine] methane,
5- [2- pyridine radicals] tetrazole stirring at normal temperature in dichloromethane reacts 2-4 hours, obtains the first reaction mixture；
Step 2：The hydrogen-oxygen with 5- [2- pyridine radicals] tetrazole part equimolar amounts is added into first reaction mixture
Change sodium, and continue stirring at normal temperature reaction 1-2 hours, obtain the second reaction mixture；
Step 3：The solvent of second reaction mixture is evaporated, tied again using dichloromethane-n-hexane mixed solvent
Crystalline substance, filtration and recrystallization obtain colourless crystalline products, are washed 3-4 times using ether, colorless solid product are obtained after vacuum drying, i.e.,
Four bronze medals [I] complex is closed for perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane].
Further, in step 3, the solvent of the second reaction mixture is evaporated using Rotary Evaporators, dichloromethane
The volume ratio of alkane-n-hexane in the mixed solvent dichloromethane and n-hexane is 1:10.
The present invention also provides a kind of preparation method of core copper [I] the complex blue light material of pyridine tetrazole four, including following
Step：
Step 1：Under an argon atmosphere, mol ratio 1:(5-10):2:1 perchlorate hexahydrate's copper, excessive copper powder, double [two
Phenylphosphine] methane, 5- [2- pyridine radicals] tetrazoles acetonitrile-dichloromethane in the mixed solvent stirring at normal temperature react 2-4 hours, obtain
To the first reaction mixture；
Step 2：The hydrogen-oxygen with 5- [2- pyridine radicals] tetrazole part equimolar amounts is added into first reaction mixture
Change sodium, and continue stirring at normal temperature reaction 1-2 hours, obtain the second reaction mixture；
Step 3：After second reaction mixture is filtered, solvent evaporated, carried out with dichloromethane-n-hexane mixed solvent
Recrystallization, the colourless crystalline products that filtration and recrystallization obtains, is washed 3-4 times with ether, and colorless solid production is obtained after vacuum drying
Thing, as perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane] close four bronze medals [I] and coordinated
Thing.
Further, in step 1, the volume ratio of acetonitrile-dichloromethane in the mixed solvent acetonitrile and dichloromethane is 1:
2。
Further, in step 3, the solvent of the second reaction mixture is evaporated using Rotary Evaporators, dichloromethane
The volume ratio of alkane-n-hexane in the mixed solvent dichloromethane and n-hexane is 1:10.
The invention has the advantages that：
The invention provides a kind of core copper [I] complex blue light material of pyridine tetrazole four and preparation method thereof, it belongs to
A kind of new blue light emitting material.5- [2- are selected in pyridine tetrazole four core copper [I] complex blue light emitting material of the present invention
Pyridine radicals] tetrazole and double [diphenylphosphine] methane main purpose and meaning：It is more by application 5- [2- pyridine radicals] tetrazole
Tooth cheland and double [diphenylphosphine] methane bridge ligands, it is close to adjust the space multistory effect of copper [I] complex and electronics
Degree distribution, realizes the solid state blue emission characteristic of copper [I] complex, at normal temperatures, its solid luminescent wavelength maximum is
467nm, solid luminescent life-span are 30 μ s, and solid luminescent quantum efficiency is 67%.
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
There is the required accompanying drawing used in technology description to be briefly described, it should be apparent that, drawings in the following description are only this
Some embodiments of invention, for those of ordinary skill in the art, on the premise of not paying creative work, can be with
Other accompanying drawings are obtained according to these accompanying drawings.
Fig. 1 is perchlorate two provided in an embodiment of the present invention [5- [2- pyridine radicals] tetrazole base] four [double [hexichol
Base phosphine] methane] close four bronze medals [I] complex crystal structure chart.
Fig. 2 is perchlorate two provided in an embodiment of the present invention [5- [2- pyridine radicals] tetrazole base] four [double [hexichol
Base phosphine] methane] close four bronze medals [I] complex solid state fluorescence emission spectrum.
Embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, the technical scheme in the embodiment of the present invention is carried out clear, complete
Site preparation describes, it is clear that described embodiment is only part of the embodiment of the present invention, rather than whole embodiments.It is based on
Embodiment in the present invention, those of ordinary skill in the art obtained on the premise of creative work is not made it is all its
Its embodiment, belongs to the scope of protection of the invention.
Such as Fig. 1 and Fig. 2, the embodiment of the present invention provides a kind of core copper [I] complex blue light material of pyridine tetrazole four, described
Core copper [I] the complex blue light material of pyridine tetrazole four is that [5- [2- pyridine radicals] the tetrazole base] four of perchlorate two is [double
[diphenylphosphine] methane] four bronze medals [I] complex is closed, its molecular formula is C112H96Cl2Cu4N10O8P8.Molecular weight is 2282.9.
Its English name：[Cu4[5-(2-pyridyl)tetrazolate]2[bis(diphenylphosphino)
methane]4][ClO4]2, it is abbreviated as：[Cu4[pytz]2[dppm]4][ClO4]2。
Its molecular structure is：
The present invention provides a kind of preparation method of core copper [I] the complex blue light material of pyridine tetrazole four, and (this is the first
Preparation method), comprise the following steps：
Step 1：Under an argon atmosphere, mol ratio 2:2:1 [Cu [MeCN]4][ClO4], double [diphenylphosphine] methane,
5- [2- pyridine radicals] tetrazole [abbreviation pytzH] stirring at normal temperature in dichloromethane reacts 2-4 hours, obtains the first reaction mixing
Liquid.
Step 2：The hydrogen-oxygen with 5- [2- pyridine radicals] tetrazole part equimolar amounts is added into first reaction mixture
Change sodium, and continue stirring at normal temperature reaction 1-2 hours, obtain the second reaction mixture.
Step 3：The solvent of second reaction mixture is evaporated, tied again using dichloromethane-n-hexane mixed solvent
Crystalline substance, filtration and recrystallization obtain colourless crystalline products, are washed 3-4 times using ether, colorless solid product are obtained after vacuum drying, i.e.,
Four bronze medals [I] complex is closed for perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane].Its
In, the solvent of the second reaction mixture is evaporated using Rotary Evaporators, dichloromethane-n-hexane in the mixed solvent dichloromethane
Volume ratio with n-hexane is 1:10.
The reaction mechanism of this preparation method is：
The present invention also provides a kind of preparation method of core copper [I] the complex blue light material of pyridine tetrazole four, and (this is second
Kind preparation method), comprise the following steps：
Step 1：Under an argon atmosphere, mol ratio 1:(5-10):2:1 perchlorate hexahydrate's copper [Cu [ClO4]2·
6H2O], excessive copper powder, double [diphenylphosphine] methane [abbreviation dppm], 5- [2- pyridine radicals] tetrazole [abbreviation pytzH] is in second
Nitrile-dichloromethane in the mixed solvent stirring at normal temperature reaction 2-4 hours, obtains the first reaction mixture.Wherein, acetonitrile-dichloromethane
The volume ratio of alkane in the mixed solvent acetonitrile and dichloromethane is 1:2.
Step 2：The hydrogen-oxygen with 5- [2- pyridine radicals] tetrazole part equimolar amounts is added into first reaction mixture
Change sodium, and continue stirring at normal temperature reaction 1-2 hours, obtain the second reaction mixture；
Step 3：After second reaction mixture is filtered, solvent evaporated, carried out with dichloromethane-n-hexane mixed solvent
Recrystallization, the colourless crystalline products that filtration and recrystallization obtains, is washed 3-4 times with ether, and colorless solid production is obtained after vacuum drying
Thing, as perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane] close four bronze medals [I] and coordinated
Thing.Wherein, the solvent of the second reaction mixture is evaporated using Rotary Evaporators, dichloromethane-n-hexane in the mixed solvent two
The volume ratio of chloromethanes and n-hexane is 1:10.
The reaction mechanism of this preparation method is：
Illustrated below by way of two specific embodiments：
Embodiment 1：
Under an argon atmosphere, [Cu [MeCN]4][ClO4] (19.6mg, 0.060mmol), double [diphenylphosphine] methane
(23.1mg, 0.060mmol) and 5- [2- pyridine radicals] tetrazole (4.4mg, 0.030mmol) normal temperature in 10mL dichloromethane stir
Mix reaction 3 hours, rear toward sodium hydroxide (1.2mg, 0.030mmol) is added in the reaction solution, continuation stirring reaction 1 is small under normal temperature
When, after solvent is evaporated with Rotary Evaporators, with dichloromethane (1mL)-n-hexane (10mL) mixed solvent [volume ratio 1:
10] recrystallized.The colourless crystalline products that filtration and recrystallization obtains, are washed 3-4 times with 10mL ether, are obtained after vacuum drying
Colorless solid product (29.7mg, 0.013mmol), yield 87%.
Elementary analysis calculated value (C112H96Cl2Cu4N10O8P8) it is (%)：C 58.92,H 4.24,N 6.14；Measured value：C
58.95,H 4.21,N 6.12。
X-ray single crystal diffraction：Crystal category monoclinic system, P21/ c space groups, cell parameter：A=15.4418 (13), b=
23.077 (2),β=113.265 (2) °,Mr=2452.66, Z=2, Dc
=1.424g cm-3, μ=1.045mm-1, GOF=1.060, crystal structure figure is as shown in Figure 1.
Photoluminescence performance test result shows, solid-state is shown under pyridine tetrazole four core copper [I] the complex normal temperature
Blue emission property, its solid luminescent wavelength maximum are 467nm, and the solid luminescent life-span is 30 μ s, solid luminescent quantum efficiency
For 67%, its solid state fluorescence emission spectrum is as shown in Figure 2.
Embodiment 2：
Under an argon atmosphere, perchlorate hexahydrate's copper [Cu [ClO4]2·6H2O] (11.9mg, 0.032mmol) and excessive copper powder
(12.2mg, 0.192mmol) stirring at normal temperature in 5mL acetonitriles is reacted 30 minutes, rear to add double [diphenylphosphine] methane
The 10mL dichloromethane solutions of (24.6mg, 0.064mmol), continue stirring reaction and 5- [2- pyridine radicals] four nitrogen are added after 1 hour
Azoles part (4.7mg, 0.032mmol), continues stirring reaction under normal temperature 2 hours, rear toward adding sodium hydroxide in the reaction solution
(1.28mg, 0.032mmol), and continue stirring at normal temperature and react 1 hour, solvent is evaporated with Rotary Evaporators after filtering, with two
Chloromethanes (1mL)-n-hexane (10mL) mixed solvent [volume ratio 1:10] recrystallized.Filtration and recrystallization obtains colourless
Crystalline products, are washed 3-4 times with 10mL ether, and colorless solid product (29.7mg, 0.013mmol) is obtained after vacuum drying, production
Rate is 81%.Analysis and characterization experimental data is the same as embodiment 1.
The invention provides a kind of core copper [I] complex blue light material of pyridine tetrazole four and preparation method thereof, it belongs to
A kind of new blue light emitting material.5- [2- are selected in pyridine tetrazole four core copper [I] complex blue light emitting material of the present invention
Pyridine radicals] tetrazole and double [diphenylphosphine] methane main purpose and meaning：It is more by application 5- [2- pyridine radicals] tetrazole
Tooth cheland and double [diphenylphosphine] methane bridge ligands, it is close to adjust the space multistory effect of copper [I] complex and electronics
Degree distribution, realizes the solid state blue emission characteristic of copper [I] complex, at normal temperatures, its solid luminescent wavelength maximum is
467nm, solid luminescent life-span are 30 μ s, and solid luminescent quantum efficiency is 67%.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
God any modification, equivalent substitution and improvements made etc., should be included in the scope of the protection with principle.
Claims (7)
- A kind of 1. core copper [I] complex blue light material of pyridine tetrazole four, it is characterised in that the core copper of pyridine tetrazole four [I] complex blue light material closes for perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane] Four bronze medals [I] complex, its molecular formula are C112H96Cl2Cu4N10O8P8。
- A kind of 2. core copper [I] complex blue light material of pyridine tetrazole four as claimed in claim 1, it is characterised in that：High chlorine Acid group two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane] closes four bronze medals [I] complex crystal category monocline Crystallographic system, P 21/ c space groups, cell parameter：A=15.4418 (13), b=23.077 (2),β= 113.265 (2) °,Mr=2452.66, Z=2, Dc=1.424g cm-3, μ=1.045mm-1, GOF= 1.060。
- 3. a kind of preparation method of core copper [I] complex blue light material of pyridine tetrazole four as claimed in claim 1, its feature It is, comprises the following steps：Step 1：Under an argon atmosphere, mol ratio 2:2:1 [Cu [MeCN]4][ClO4], double [diphenylphosphine] methane, 5- [2- pyridine radicals] tetrazole stirring at normal temperature in dichloromethane reacts 2-4 hours, obtains the first reaction mixture；Step 2：The hydroxide with 5- [2- pyridine radicals] tetrazole part equimolar amounts is added into first reaction mixture Sodium, and continue stirring at normal temperature reaction 1-2 hours, obtain the second reaction mixture；Step 3：The solvent of second reaction mixture is evaporated, recrystallized using dichloromethane-n-hexane mixed solvent, Filtration and recrystallization obtains colourless crystalline products, is washed 3-4 times using ether, colorless solid product is obtained after vacuum drying, is Perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane] closes four bronze medals [I] complex.
- 4. the preparation method of core copper [I] complex blue light material of pyridine tetrazole four as claimed in claim 3, its feature exist In：In step 3, the solvent of the second reaction mixture is evaporated using Rotary Evaporators, dichloromethane-n-hexane mixing is molten The volume ratio of dichloromethane and n-hexane is 1 in agent:10.
- 5. a kind of preparation method of core copper [I] complex blue light material of pyridine tetrazole four as claimed in claim 1, its feature It is, comprises the following steps：Step 1：Under an argon atmosphere, mol ratio 1:(5-10):2:1 perchlorate hexahydrate's copper, excessive copper powder, double [diphenyl Phosphine] methane, 5- [2- pyridine radicals] tetrazoles react 2-4 hours in acetonitrile-dichloromethane in the mixed solvent stirring at normal temperature, obtain the One reaction mixture；Step 2：The hydroxide with 5- [2- pyridine radicals] tetrazole part equimolar amounts is added into first reaction mixture Sodium, and continue stirring at normal temperature reaction 1-2 hours, obtain the second reaction mixture；Step 3：After second reaction mixture is filtered, solvent evaporated, tied again with dichloromethane-n-hexane mixed solvent Crystalline substance, the colourless crystalline products that filtration and recrystallization obtains, is washed 3-4 times with ether, colorless solid product is obtained after vacuum drying, i.e., Four bronze medals [I] complex is closed for perchlorate two [5- [2- pyridine radicals] tetrazole base] four [double [diphenylphosphine] methane].
- 6. the preparation method of core copper [I] complex blue light material of pyridine tetrazole four as claimed in claim 5, its feature exist In：In step 1, the volume ratio of acetonitrile-dichloromethane in the mixed solvent acetonitrile and dichloromethane is 1:2.
- 7. the preparation method of core copper [I] complex blue light material of pyridine tetrazole four as claimed in claim 5, its feature exist In：In step 3, the solvent of the second reaction mixture is evaporated using Rotary Evaporators, dichloromethane-n-hexane mixing is molten The volume ratio of dichloromethane and n-hexane is 1 in agent:10.
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