CN116769181A - Zinc-based molecular crystal blue-green light material and preparation method thereof - Google Patents
Zinc-based molecular crystal blue-green light material and preparation method thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 67
- 239000013078 crystal Substances 0.000 title claims abstract description 61
- 239000011701 zinc Substances 0.000 title claims abstract description 61
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 52
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 pyridine-4-carbonyl Chemical group 0.000 claims abstract description 15
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 7
- 239000011259 mixed solution Substances 0.000 claims abstract description 6
- 238000001027 hydrothermal synthesis Methods 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 3
- FFGFSQOCKQVECP-UHFFFAOYSA-N 2,5-dipyridin-4-yl-1,3,4-oxadiazole Chemical compound C1=NC=CC(C=2OC(=NN=2)C=2C=CN=CC=2)=C1 FFGFSQOCKQVECP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 5
- 230000005284 excitation Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 abstract description 9
- 239000000243 solution Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000009210 therapy by ultrasound Methods 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000010586 diagram Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910052761 rare earth metal Inorganic materials 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
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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
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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
- 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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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
A zinc-based molecular crystal blue-green light material and a preparation method thereof, wherein the chemical formula of the zinc-based molecular crystal blue-green light material is { [ Zn (pcd)]} n Wherein: n is a natural number from 1 to plus infinity; pdc is obtained by deprotonating N' - (pyridine-4-carbonyl) hydrazide. The preparation method comprises the steps of mixing zinc nitrate N, N-dimethylacetamide solution with the concentration of 0.1mol/L and 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole N, N-dimethylacetamide solution with the concentration of 0.1mol/L, carrying out ultrasonic treatment for 10min, putting the mixed solution into a closed hydrothermal reaction kettle, carrying out constant temperature reaction at 130 ℃ for 72h, taking out the product, separating the solid, and washing with N, N-dimethylacetamide for 3 times to obtain the zinc-based molecular crystal blue-green light material. The zinc-based molecular crystal blue-green light material has good luminous brightness and luminous efficiency, and canAnd replacing noble metal blue-green light material.
Description
Technical Field
The invention relates to a zinc-based molecular crystal blue-green light material and a preparation method thereof, belonging to the technical field of luminescent materials.
Background
The metal luminescent molecular crystal material can fully utilize the energy of all singlet states and triplet states due to the heavy atomic effect and the strong spin orbit coupling effect, thereby improving the luminous efficiency. Currently, research on metal luminescent molecular crystal materials mainly focuses on transition metals of the 6 th period and rare earth metals of the 7 th period, and particularly on noble metal luminescent materials such as ruthenium, osmium, iridium and platinum of the 6 th period is most widely studied. However, the noble metals such as ruthenium, osmium, iridium, platinum and the like in the period 6 and the rare earth metals in the period 7 are rare in the crust, and mining is difficult, so that the use cost of the noble metal luminescent molecular crystal material is high, the noble metal belongs to non-renewable resources, and the problem of raw material shortage is brought after large-scale production. On the other hand, such noble metals are often highly toxic, and their large-scale application also brings about serious environmental pollution and life health problems. The defects of high use cost, unfriendly environment and the like lead the large-scale application of the series of metal luminescent molecular crystal materials to be greatly limited. Therefore, there is a need to find alternative metals for synthesizing metal luminescent molecular crystal materials.
Compared with the transition noble metal of the 6 th period and the rare earth metal of the 7 th period, the zinc metal of the 4 th period has the advantages of abundant resources, low cost, easy obtainment, low toxicity and environmental friendliness. In addition, the zinc metal has rich fluorescence emission properties, and has rich and colorful luminescence peak positions, rich resources, low price, low toxicity and environmental friendliness, so that the zinc metal luminescent molecular crystal material has good potential application prospect in the fields of luminescent devices, optical sensing, nonlinear optics and the like.
Currently, the reported luminescent molecular crystal materials mainly comprise zinc-based 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole molecular crystal materials, however, the application of 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole to generate N' - (pyridine-4-carbonyl) hydrazide for hydrolysis reaction to design and synthesize zinc-based molecular crystal blue-green light materials, which are not reported in open literature at present.
Disclosure of Invention
The invention aims to solve the defects of high use cost and unfriendly environment of the existing transition noble metal of the 6 th period and rare earth metal molecular crystal material of the 7 th period, find a molecular crystal blue-green light material which is rich in alternative resources, low in price, low in toxicity and friendly to environment, and provide a zinc-based molecular crystal blue-green light material and a preparation method thereof.
The invention adopts the technical scheme that the zinc-based molecular crystal blue-green light material has a chemical formula of { [ Zn (pcd)]} n Wherein: n is a natural number from 1 to plus infinity; pdc is obtained by deprotonating N' - (pyridine-4-carbonyl) hydrazide.
The zinc-based molecular crystal blue-green light material is crystallized in a monoclinic system,P2 1 /cspace group, unit cell parameters are: a= 7.5127 (2) a, b= 14.3973 (4) a, c= 11.1624 (3) a, α=90°, β= 94.944 (2) °, γ=90°, and crystal volume 1202.86 (6) a 3 ，Z=4。
The N' - (pyridine-4-carbonyl) hydrazide is prepared by hydrolysis of 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole.
The zinc-based molecular crystal blue-green light material can emit blue-green light under 365nm ultraviolet excitation, has blue light CIE coordinate of (0.1742,0.2778), and can be applied to the field of blue-green light materials.
The invention discloses a preparation method of a zinc-based molecular crystal blue-green light material, which comprises the following steps:
(1) The organic compound 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole and Zn (NO) 3 ) 2 . 6H 2 O is dissolved in N, N-dimethylacetamide to obtain a mixed solution;
(2) And (3) placing the mixed solution into a hydrothermal reaction kettle, reacting for 1-96 hours at the constant temperature of 90-130 ℃, taking out the product, separating the solid, and washing the solid for multiple times by using N, N-dimethylacetamide to obtain the zinc-based molecular crystal blue-green light material.
The 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole, zn (NO) 3 ) 2 . 6H 2 O, N the molar ratio of N-dimethylacetamide is 1:1:322.
The beneficial effects of the invention are as follows: the zinc-based molecular crystal blue-green light material prepared by the invention has the advantages of simple and easy synthesis, high yield and high repeatability. The zinc-based molecular crystal blue-green light material has good luminous brightness and luminous efficiency, can replace noble metal blue-green light materials, and can be applied on a large scale. The zinc-based molecular crystal blue-green light material has good blue-green light characteristics, and blue light CIE coordinates of the material are (0.1742, 0.2778), so that the material can be applied to the field of blue-green light materials.
Drawings
FIG. 1 is a schematic diagram of the synthetic procedure of the zinc-based molecular crystal blue-green material of the present invention;
FIG. 2 is a diagram showing the crystal structure of the zinc-based molecular crystal blue-green material of the present invention;
FIG. 3 is a three-dimensional block diagram of a zinc-based molecular crystal blue-green material;
FIG. 4 is an x-ray powder diffraction pattern of a zinc-based molecular crystalline blue-green material;
FIG. 5 is a fluorescence spectrum of a zinc-based molecular crystal blue-green material;
FIG. 6 is a CIE chromaticity diagram of zinc-based molecular crystalline blue-green materials.
Detailed Description
The preparation method of the zinc-based molecular crystal blue-green light material comprises the following synthesis steps:
mixing zinc nitrate N, N-dimethylacetamide solution with the concentration of 0.1mol/L with 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole N, N-dimethylacetamide solution with the concentration of 0.1mol/L, and performing ultrasonic treatment for 10min, placing the mixed solution into a closed hydrothermal reaction kettle, performing constant temperature reaction at 130 ℃ for 72h, taking out the product, separating the solid, and washing with N, N-dimethylacetamide for 3 times to obtain the zinc-based molecular crystal blue-green light material.
The properties of the zinc-based molecular crystal blue-green light material prepared in the embodiment are characterized as follows:
(1) Structure determination of zinc-based molecular crystal blue-green light material in this example:
the crystal structure of this example was measured using a Supernova X-ray single crystal diffractometer, using Mo-kα rays (λ= 0.71073 a) monochromatized with graphite as the incident radiation source, collecting diffraction points in ω - Φ scan, obtaining unit cell parameters by least square correction, obtaining the crystal structure from the difference Fourier electron density map using the SHELXL-97 direct method, and correcting by Lorentz and polarization effects. All H atoms are synthesized by the difference Fourier and determined by the ideal position calculation. The detailed crystal measurement data are shown in Table 1.
FIG. 1 is a synthetic procedure for zinc-based molecular crystal blue-green material. As can be seen from the figures: 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole undergoes hydrolysis to form N' - (pyridine-4-carbonyl) hydrazide.
Fig. 2 is a crystal structure of a zinc-based molecular crystal blue-green material. As can be seen from the figures: 1 Zn in the minimum asymmetric structural unit 2+ Ion, 1N' - (pyridine-4-carbonyl) hydrazide, wherein Zn 2+ The ion adopts a coordination mode of five coordination triangle bipyramids, and is respectively coordinated with 2 oxygen atoms from 2N '- (pyridine-4-carbonyl) hydrazides and 3 nitrogen atoms from 3N' - (pyridine-4-carbonyl) hydrazides.
Fig. 3 is a structural diagram of a zinc-based molecular crystal blue-green material, from which it can be seen that: the zinc-based molecular crystal blue-green light material is connected into a three-dimensional structure diagram through N' - (pyridine-4-carbonyl) hydrazide.
(2) Phase purity test for zinc-based molecular crystalline blue-green materials:
the x-ray powder diffraction pattern of the zinc-based molecular crystalline blue-green material was tested in a room temperature environment, as shown in fig. 4.
As can be seen from FIG. 4, the measured powder diffraction pattern is comparable to its simulated pattern, except that some peaks have slightly different intensities, and the positions and types of the peaks are well matched, which indicates that the zinc-based molecular crystal blue-green material has higher phase purity.
(3) Characterization of fluorescence properties of zinc-based molecular crystal blue-green light materials:
the method for measuring fluorescence data of zinc-based molecular crystal blue-green light material in this embodiment is as follows: and (3) measuring the solid fluorescence performance of the zinc-based molecular crystal blue-green light material under the condition of 365nm excitation wavelength by using an Edinburgh FLS920 under the condition of room temperature.
As can be seen from fig. 5, the zinc-based hybrid material for blue light emission exhibits 1 fluorescence spectrum characteristic peak at 474nm, which is pi→pi and/or pi→n transition from the ligand, which is ligand to Zn, under 365nm ultraviolet excitation at room temperature 2+ Effective energy transfer of ions.
As can be seen from fig. 6, the CIE coordinates corresponding to the fluorescence spectrum of the zinc-based molecular crystal blue-green light material are (0.1742, 0.2778), and the CIE coordinates are in the blue-green light region, and can be applied to the field of blue-green light materials.
Claims (5)
1. A zinc-based molecular crystal blue-green light material is characterized in that the chemical formula of the zinc-based molecular crystal blue-green light material is { [ Zn (pcd)]} n Wherein: n is a natural number from 1 to plus infinity; pdc is obtained by deprotonating N' - (pyridine-4-carbonyl) hydrazide; the zinc-based molecular crystal blue-green light material is crystallized in a monoclinic system,P2 1 /cspace group, unit cell parameters are: a= 7.5127 (2) a, b= 14.3973 (4) a, c= 11.1624 (3) a, α=90°, β= 94.944 (2) °, γ=90°, and crystal volume 1202.86 (6) a 3 ，Z=4。
2. The preparation method of the zinc-based molecular crystal blue-green light material is characterized by comprising the following steps:
(1) The organic compound 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole and Zn (NO) 3 ) 2 . 6H 2 O is dissolved in N, N-dimethylacetamide to obtain a mixed solution;
(2) And (3) placing the mixed solution into a hydrothermal reaction kettle, reacting for 1-96 hours at the constant temperature of 90-130 ℃, taking out the product, separating the solid, and washing the solid for multiple times by using N, N-dimethylacetamide to obtain the zinc-based molecular crystal blue-green light material.
3. The zinc-based molecular crystal blue-green light material according to claim 1, wherein the N' - (pyridine-4-carbonyl) hydrazide is prepared by hydrolysis of 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole.
4. The zinc-based molecular crystal blue-green light material according to claim 1, wherein the zinc-based molecular crystal blue-green light material is capable of emitting blue-green light under excitation of 365nm ultraviolet light, and has a blue light CIE coordinate of (0.1742,0.2778).
5. The method for preparing zinc-based molecular crystal blue-green light material according to claim 2, wherein the 2, 5-bis (4-pyridyl) -1,3, 4-oxadiazole and Zn (NO 3 ) 2 . 6H 2 O, N the molar ratio of N-dimethylacetamide is 1:1:322.
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