CN114874452A - Rare earth terbium-based molecular crystalline state green light material and preparation method thereof - Google Patents
Rare earth terbium-based molecular crystalline state green light material and preparation method thereof Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 66
- 229910052771 Terbium Inorganic materials 0.000 title claims abstract description 58
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract description 46
- 150000002910 rare earth metals Chemical class 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title abstract description 9
- -1 (p-carboxyphenyl) amino Chemical group 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000003446 ligand Substances 0.000 claims abstract description 13
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000001514 detection method Methods 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- 230000005284 excitation Effects 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- NGJJZCPADSICRI-UHFFFAOYSA-N 4-[[4,6-bis(4-carboxyanilino)-1,3,5-triazin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N=C(NC(=NC=1C=CC(=CC=1)C(O)=O)N1)NC1=NC1=CC=C(C(O)=O)C=C1 NGJJZCPADSICRI-UHFFFAOYSA-N 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 150000001217 Terbium Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- ULJUVCOAZNLCJZ-UHFFFAOYSA-K trichloroterbium;hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Tb+3] ULJUVCOAZNLCJZ-UHFFFAOYSA-K 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 238000004729 solvothermal method Methods 0.000 abstract 1
- 238000010586 diagram Methods 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000002050 diffraction method Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000005672 electromagnetic field Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 230000005678 Seebeck effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000006903 response to temperature Effects 0.000 description 1
- 239000011540 sensing material Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 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
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
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- G01—MEASURING; TESTING
- G01K—MEASURING TEMPERATURE; MEASURING QUANTITY OF HEAT; THERMALLY-SENSITIVE ELEMENTS NOT OTHERWISE PROVIDED FOR
- G01K11/00—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00
- G01K11/20—Measuring temperature based upon physical or chemical changes not covered by groups G01K3/00, G01K5/00, G01K7/00 or G01K9/00 using thermoluminescent materials
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Abstract
A rare earth terbium-based molecular crystalline state green light material and a preparation method thereof are disclosed, and the chemical formula is as follows: [ Tb ] 2 (TATAB) 2 ·solvents]} n Wherein TATAB is 2,4, 6-tris [ (p-carboxyphenyl) amino group]-1,3, 5-triazine anionic ligand, solvants being solvent molecules. The material is prepared by a solvothermal method, can emit 470-640 nm green light under the excitation of 337nm ultraviolet light, has green light CIE coordinates (0.2928, 0.6044) which are close to saturated green light CIE coordinates, can be used as a green light material, can realize temperature fluorescence sensing, has a wide temperature detection range (303K-373K), and is expected to be practically applied to the temperature sensing aspect.
Description
Technical Field
The invention relates to a rare earth terbium-based molecular crystalline state green light material and a preparation method thereof, belonging to the technical field of molecular crystal materials.
Background
Temperature is an important physical parameter in the fields of human life and natural science, and therefore its accurate measurement is of great significance in scientific and human development. Conventional contact thermometers such as glass thermometers, thermocouples based on the seebeck effect, and thermal resistance thermometers must be used for contact measurement, and the applications in many extreme environments such as strong electromagnetic field environments, the state of a measured object in rapid movement, microfluidic systems, and in living bodies (tissues and even cells) are greatly limited. Compared with conventional contact thermometers, luminescence-based thermometer technology has unique characteristics including non-invasiveness, accuracy, applicability under fast motion and strong electromagnetic fields. Therefore, there is a need to develop and develop luminescence-based thermometer technology.
As a novel luminescent thermometer, the terbium-based molecular crystalline state fluorescent sensing material has the characteristics of a molecular crystalline state material and rare earth terbium ions, has designability and abundant luminescent sites, and becomes an excellent choice for preparing the fluorescent thermometer. The material has the unique advantages of larger Stokes shift, high brightness, high color purity (green), longer fluorescence life, no external interference on luminescent color and the like. Due to the emission characteristic of rare earth terbium metal, the emission peak position hardly moves along with the temperature change, so that the temperature measurement parameter is limited to the fluorescence intensity.
Therefore, the temperature can be detected simply through the change of the fluorescence intensity along with the change of the temperature, and the method has the characteristics of high precision, high sensitivity, tiny size, short response time, good adaptability and the like.
Publication No. CN110846021A discloses a green light-emitting photochromic dye, which comprises a photochromic material, wherein the photochromic material is a green light-emitting material, and the green light-emitting material comprises any one or a combination of two or more of terbium, a compound A2 and a compound B2. The green material is used only for the color-changing dye. The prior art has not reported that a green material is used for fluorescence temperature sensing.
Disclosure of Invention
The invention aims to provide a rare earth terbium-based molecular crystalline state green light material for fluorescence temperature sensing and a preparation method thereof, in order to realize temperature sensing of the green light material.
The technical scheme for realizing the invention is as follows, the rare earth terbium-based molecular crystalline state green light material has the chemical formula: [ Tb ] 2 (TATAB) 2 ·solvents]} n ,
Wherein TATAB is 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine anion ligand, solvants is solvent molecule, and n is a natural number from 1 to positive infinity.
The structural formula of TATAB is as follows:
the rare earth terbium-based molecular crystalline state green light material belongs to a monoclinic system, and the space group isP2 1 /cThe unit cell parameters are: a =28.9143(8) A, b = 22.3632(5) A, c = 15.0887(4) A,α= 90°,ß= 103.553 °,γ= 90 °。
the infrared absorption peak of the rare earth terbium-based molecular crystalline state green light material is as follows: 3391m, 3263m, 1660s, 1545s, 1465m, 1387m, 1235s, 1168s, 781 s.
The rare earth terbium-based molecular crystalline green light material comprises basic units, wherein 2 kinds of terbium ions with different coordination exist in the basic units of the rare earth terbium-based molecular crystalline green light material, 2 kinds of 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine anion ligands, the terbium ions are coordinated with oxygen atoms in the 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine anion ligands to form one-dimensional terbium chains in space, and the terbium chains further form three-dimensional structures in space through the 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine.
The preparation method of the rare earth terbium-based molecular crystalline state green light material comprises the following steps:
terbium salt and 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine ligand in a mass ratio of 1: 1-1: 5 are fully mixed in a solvent, and then the mixture is cured for 24-72 hours at the temperature of 60-150 ℃ to obtain colorless blocky crystals, namely the rare earth terbium-based molecular crystalline state green-light material.
The terbium salt comprises terbium chloride hexahydrate; the solvent comprises a mixed solvent of water and N, N-dimethylformamide.
The dosage ratio of the terbium salt to the 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine ligand mixture to the solvent is 100mg: 500 mg-100 mg: 2500 mg.
The invention has the beneficial effects that the rare earth terbium-based molecular crystalline state green light material can be used for fluorescence temperature sensing; the breadth of rare earth materials and molecular crystalline materials is expanded; the rare earth terbium-based molecular crystalline green-light material provided by the invention has the advantages of simple preparation process, mild reaction conditions and easiness in large-scale preparation; the rare earth terbium-based molecular crystalline state green light material provided by the invention can emit green light of 470-640 nm, can realize temperature fluorescence sensing, and has a wider temperature detection range (303K-373K)
Drawings
FIG. 1 is a three-dimensional structure diagram of a rare earth terbium-based molecular crystalline green light material of the present invention;
FIG. 2 is a fluorescence spectrum of a rare earth terbium-based molecular crystalline green light material according to the present invention;
FIG. 3 is a CIE coordinate diagram of a rare earth terbium-based molecular crystalline green light material of the present invention;
FIG. 4 is a fluorescence spectrum of the crystalline green material of the rare earth terbium-based molecule of the present invention in response to temperature.
Detailed Description
The present embodiment is a rare earth terbium-based molecular crystalline green light material, and its chemical formula is: [ Tb ] 2 (TATAB) 2 ·solvents]} n ,
Wherein TATAB is 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine anion ligand, solvants is solvent molecule, and n is a natural number from 1 to positive infinity;
the structural formula of TATAB is as follows:
the preparation method of the rare earth terbium-based molecular crystalline green light material comprises the following steps:
100mg of terbium chloride hexahydrate and 150mg of 2,4, 6-tris [ (p-carboxyphenyl) amino ] -1,3, 5-triazine ligand are dissolved in 1500mg of N, N-dimethylformamide, and then are cured for 48 hours at the temperature of 120 ℃ to obtain colorless bulk crystals, namely the rare earth terbium-based molecular crystalline state green-light material.
The terbium-based molecular crystalline green-light rare earth material prepared in this example was characterized as follows:
(1) the structure of the rare earth terbium-based molecular crystalline green material of the embodiment is determined as follows:
the crystal structure is measured by using a Supernova type X-ray single crystal diffractometer, using Mo-Kalpha rays (lambda = 0.71073A) subjected to graphite monochromatization as an incident radiation source, collecting diffraction points in an omega-phi scanning mode, correcting by a least square method to obtain unit cell parameters, solving a difference Fourier electron density diagram by using a SHELXL-97 direct method to obtain a crystal structure, and correcting by Lorentz and a polarization effect. All H atoms were synthesized by difference Fourier and determined by ideal position calculation, and detailed crystallography (removal of solvent molecules) data are shown in table 1.
TABLE 1 crystallography data for terbium rare earth based molecular crystalline state green materials
Fig. 1 is a three-dimensional structural diagram of the rare earth terbium-based molecular crystalline green light material of the present embodiment, wherein n is a natural number from 1 to positive infinity in the chemical formula of the rare earth terbium-based molecular crystalline green light material, which indicates that the material is a polymer.
(2) The fluorescent property of the rare earth terbium-based molecular crystalline green light material is characterized in that:
FIG. 2 is the solid fluorescence spectrum of the crystalline state green light material of rare earth terbium-based molecule in the present embodiment,
the figure shows that: the rare earth terbium-based molecular crystalline state green light material has 4 emission peaks at 489, 543, 590 and 620 nm, which are respectively originated from 5 D 4 → 7 F J (J = 6, 5, 4, 3)。
FIG. 3 is the CIE coordinates of the crystalline green material of the rare earth terbium-based molecule of the present embodiment,
as can be seen from the figure, the material has CIE coordinates (0.2928, 0.6044) and is located in a green light region, close to the CIE coordinates of saturated green light.
FIG. 4 shows fluorescence spectra of rare earth terbium-based molecular crystalline green materials at different temperatures.
As can be seen from the figure: under different temperature conditions, the fluorescence intensity of the rare earth terbium-based molecular crystalline state green light material is changed along with the fluorescent intensity. The fluorescence intensity of the rare earth terbium-based molecular crystalline state green-light material shows a descending trend along with the temperature rise, and the change is obvious, and finally fluorescence quenching occurs, which shows that the rare earth terbium-based molecular crystalline state green-light material has good fluorescence response to the temperature and can be used as a temperature fluorescent probe.
Claims (7)
1. The rare earth terbium-based molecular crystalline state green light material is characterized by having a chemical formula as follows: [ Tb ] 2 (TATAB) 2 ·solvents]} n ,
Wherein TATAB is 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine anion ligand, solvants is solvent molecule, and n is a natural number from 1 to positive infinity;
the structural formula of TATAB is as follows:
the rare earth terbium-based molecular crystalline state green light material belongs to a monoclinic system, and the space group isP2 1 /cThe unit cell parameters are: a =28.9143(8) A, b = 22.3632(5) A, c = 15.0887(4) A,α= 90°,ß= 103.553 °,γ= 90 °;
the infrared absorption peak of the rare earth terbium-based molecular crystalline state green light material is as follows: 3391m, 3263m, 1660s, 1545s, 1465m, 1387m, 1235s, 1168s, 781 s.
2. The terbium-based molecular crystalline green material according to claim 1, wherein 2 different coordination terbium ions and 2,4, 6-tris [ (p-carboxyphenyl) amino ] -1,3, 5-triazine anion ligands exist in the terbium-based molecular crystalline green material basic unit, and the terbium ions coordinate with oxygen atoms in the 2,4, 6-tris [ (p-carboxyphenyl) amino ] -1,3, 5-triazine anion ligands to form one-dimensional terbium chains in space, and the terbium chains further form a three-dimensional structure in space through the 2,4, 6-tris [ (p-carboxyphenyl) amino ] -1,3, 5-triazine.
3. The terbium-based molecular crystalline green material according to claim 1, wherein the terbium-based molecular crystalline green material is capable of emitting 470-640 nm green light under the excitation of 337nm ultraviolet light, and has green CIE coordinates (0.2928, 0.6044) close to saturated green CIE coordinates, which are green materials.
4. The terbium-based molecular crystalline green-light material according to claim 1, wherein the terbium-based molecular crystalline green-light material is prepared by a method comprising:
terbium salt and 2,4, 6-tri [ (p-carboxyphenyl) amino ] -1,3, 5-triazine ligand in a mass ratio of 1: 1-1: 5 are fully mixed in a solvent, and then the mixture is cured for 24-72 hours at the temperature of 60-150 ℃ to obtain colorless blocky crystals, namely the rare earth terbium-based molecular crystalline state green-light material.
5. The method of preparing a rare earth terbium-based molecular crystalline green material according to claim 3, wherein the terbium salt comprises terbium chloride hexahydrate; the solvent comprises a mixed solvent of water and N, N-dimethylformamide.
6. The method for preparing a terbium-based molecular crystalline green light material according to claim 3, wherein the dosage ratio of the terbium salt to the 2,4, 6-tris [ (p-carboxyphenyl) amino ] -1,3, 5-triazine ligand mixture to the solvent is 100mg: 500 mg-100 mg: 2500 mg.
7. The terbium rare earth-based molecular crystalline green light material according to claim 1, wherein the terbium rare earth-based molecular crystalline green light material can detect temperature through the change of a fluorescence signal, the temperature detection range is 303-373K, and the terbium rare earth-based molecular crystalline green light material can be applied to the field of temperature fluorescence sensing.
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