CN114539447A - Self-calibration ratio temperature probe based on europium metal polymer and preparation method thereof - Google Patents
Self-calibration ratio temperature probe based on europium metal polymer and preparation method thereof Download PDFInfo
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Abstract
The invention relates to a self-calibration ratio temperature probe based on europium metal polymer and a preparation method thereof, wherein the structural expression of the rare earth metal polymer is Poly [ (VTPY-Eu) -co-VTPE-co-MMA]The method synthesizes a block copolymer with vinyl tetraphenylethylene, methyl methacrylate and terpyridine derivatives through free radical polymerization, and obtains Eu-containing Eu through coordination reaction3+The test result of the rare earth metal polymer multicolor luminescent material shows that the rare earth metal polymer multicolor luminescent material has reversible stimulus responsiveness to temperature, has the characteristic of reversible change of light color within the range of 40-110 ℃, and can read out the temperature change in real time through the specific value of the 613nm and 483nm characteristic peak intensities in the rare earth polymer.In addition, the double luminescent centers I613nm/I483nmThe ratio of the luminous intensity to the temperature has good linear relation, self-calibration temperature detection can be realized, and the detection sensitivity can reach 3.8 percent DEG C‑1. Multiple tests prove that the system has excellent repeatability and reliability, and is expected to be practically applied in the field of temperature detection as a novel temperature sensing material.
Description
Technical Field
The invention belongs to the field of rare earth metal polymer luminescent materials, relates to a self-calibration ratiometric temperature probe based on europium metal polymer and a preparation method thereof, and particularly relates to a rare earth metal polymer with self-calibration ratiometric temperature detection performance and a preparation method thereof.
Background
Temperature is one of the basic physical parameters that people need to pay attention to in production, life and scientific research. Conventional contact thermometers have been reported as: expansion thermometer, thermal resistance thermometer and metal thermocouple thermometer, these traditional thermometers easily receive external environment influence, lead to measuring inaccurate, and sensitivity reduces, can't satisfy in the high and new technology field of present to the temperature detection of complex environment. The non-contact fluorescent temperature sensor has the advantages of high response speed, real-time detection, high sensitivity and the like, and people pay attention to the non-contact fluorescent temperature sensor, so that designing and synthesizing a temperature probe with high sensitivity, high precision and high response speed is a research hotspot and frontier in the field at present.
Among the numerous temperature-sensitive materials reported at present, rare earth metal polymers have long fluorescence lifetime and large Stokes shift, and also have good color rendering property, high color purity and thermal stability, and the materials often have stimulus responsiveness to temperature, thereby providing a basis for preparing rare earth luminescent materials with temperature response. For example, patent CN201310232750.7 discloses a dual rare earth metal organic framework material with temperature detection and a preparation method thereof, the prepared rare earth temperature sensitive material realizes detection in the range of 14-300K based on the fluorescence intensity ratio of characteristic emission peaks of europium and terbium, but the currently reported rare earth-metal organic framework material is mostly used for temperature detection in the low temperature range, the temperature measurement range is narrow, the MOFs fluorescence temperature probes in the higher temperature region with higher demand are fewer, the practical application value is lower, and secondly, although the emission peak intensity ratio based on two rare earth ions is readThe temperature-out method is a better detection method, but one more rare earth ion increases the complexity of the system, and the energy transfer between terbium ions and europium ions exists in the system besides the energy transfer of the organic ligand to the rare earth, so that the energy transfer process of the whole system becomes complicated; tetraphenyl ethylene is a high-performance aggregation-induced emission material reported in recent years, and is combined with rare earth metal ions, so that the tetraphenyl ethylene is expected to be applied to a ratiometric fluorescence temperature probe. In 2009, a temperature-sensitive polymer material obtained by radical copolymerization of functional monomer based on tetraphenyl ethylene and AIBN was reported in literature (L, Tang, et al. a fluorescent thermal analyzer operating in aggregation-induced polymerization mechanism: binding thermal transitions of PNIPAM in water. chem. comm., 2009, 33,4974-4976), and temperature reading was achieved by detecting the intensity change of the tetraphenyl ethylene emission peak of a single luminescence center, and temperature detection by fluorescence intensity change is a rapid and convenient method for detection, but only one luminescence center is greatly influenced by light source and material, and the accuracy of the detected result is not high; in recent years, there has also been literature on the preparation of stimuli-responsive materials by combining tetraphenylethylene with rare earth ions, such as (Z.H.Tang, et al, White-Light-Emitting AIE/Eu3+-fashion Ion Gel with multiple fluorescent-Responsive Properties, ACS application, mater, interfaces,2020,12,45420-45428) prepared multicolor luminescence stimuli-Responsive hydrogel materials with AIE Properties, doping of tetraphenyl ethylene-containing polymers with europium Ion metal polymers resulted in hydrogel systems with different light colors by changing the doping ratio, and the stimulus responsiveness under the conditions including acid and base and different solvents was studied.
Disclosure of Invention
Technical problem to be solved
In order to avoid the defects of the prior art, the invention providesA self-calibration ratio temperature probe based on europium metal polymer and a preparation method thereof are provided, the self-calibration ratio temperature probe has a self-calibration temperature detection performance, the preparation method is based on tetraphenylethylene and rare earth europium metal polymer and the temperature detection application thereof, the prepared rare earth metal polymer has reversible stimulus responsiveness to temperature, the intensity ratio of an emission peak (483nm) of tetraphenylethylene part and an emission peak (613nm) of europium ion has a good linear relation with the temperature, the temperature can be read in real time according to the luminous intensity ratio, and the detection sensitivity can reach 3.8 percent DEG C-1And is expected to be used as a novel temperature sensing material to be practically applied in the field of temperature detection.
Technical scheme
The self-calibration ratiometric temperature probe based on the europium metal polymer is characterized in that the probe is a block copolymer, and the structural expression is Poly [ (VTPY-Eu) -co-VTPE-co-MMA ], wherein VTPE is vinyl tetraphenylethylene, VTPY is 4 '- ((4-vinylbenzyl) oxygen) -2, 2': 6 ', 2' -terpyridine, and MMA is methyl methacrylate.
A method for preparing the self-calibration ratiometric temperature probe based on the europium metal polymer is characterized by comprising the following steps of:
step 1: dissolving vinyl tetraphenylethylene, 4 '- ((4-vinylbenzyl) oxy) -2, 2': 6 ', 2' -terpyridine and methyl methacrylate in DMF (dimethyl formamide) through a free radical polymerization reaction, introducing nitrogen for 10min, adding an initiator AIBN, stirring, heating, refluxing and reacting for 20-24 h at 80-90 ℃, cooling to room temperature after the reaction is finished, precipitating, washing, filtering and drying to obtain a block polymer skeleton Poly [ VTPY-co-VTPE-co-MMA ];
the molar ratio of the 4 '- ((4-vinylbenzyl) oxy) -2, 2': 6 ', 2' -terpyridine to the vinyl tetraphenylethylene to the methyl methacrylate is 1:2: 50;
step 2: mixing the polymer skeleton with rare earth complex Eu (TTA)3·2H2Dissolving O in THF, stirring and heating at 60-70 ℃ for reflux reaction for 4-6 h, cooling to room temperature after the reaction is finished, precipitating, filtering and washing to obtain rare earth europium metal polymer Poly [ (VTPY-Eu) -co-VTPE-co-MMA]；
The mass ratio of the reactants is that the polymer skeleton: eu (TTA)3·2H2O＝[270～350mg]:[3～5mg]。
The precipitant in the step 1 is water.
The detergent used for washing in the step 1 is acetone.
And the drying time in the step 1 and the step 2 is 1-2 h.
The precipitating agent in the step 2 is diethyl ether and n-hexane which are 1: 1.
The application of the self-calibration ratiometric temperature probe based on the europium metal polymer is characterized in that: the temperature detection device is used for temperature detection.
Advantageous effects
The invention provides a self-calibration ratio temperature probe based on a europium metal polymer and a preparation method thereof, wherein the structural expression of the rare earth metal polymer is Poly [ (VTPY-Eu) -co-VTPE-co-MMA]The method synthesizes a block copolymer with vinyl tetraphenylethylene, methyl methacrylate and terpyridine derivatives through free radical polymerization, and obtains Eu-containing Eu through coordination reaction3+The test result of the rare earth metal polymer multicolor luminescent material shows that the rare earth metal polymer multicolor luminescent material has reversible stimulus responsiveness to temperature, has the characteristic of reversible change of light color within the range of 40-110 ℃, and can read out the temperature change in real time through the specific value of the 613nm and 483nm characteristic peak intensities in the rare earth polymer. In addition, the double luminescent centers I613nm/I483nmThe ratio of the luminous intensity to the temperature has good linear relation, self-calibration temperature detection can be realized, and the detection sensitivity can reach 3.8 percent DEG C-1. Multiple tests prove that the system has excellent repeatability and reliability, and is expected to be practically applied in the field of temperature detection as a novel temperature sensing material.
The rare earth metal polymer provided by the invention has good thermal stability and cyclicity, can be used as a self-calibration fluorescent temperature probe within a temperature range of 40-110 ℃, and particularly has potential application value in a white light LED device.
Firstly, the invention introduces vinyl tetraphenylethylene with AIE property as a luminescent reference group, endows polymer chain segment with AIE performance, and simultaneously makes up the defect that terbium metal is used in the traditional rare earth ratio fluorescent temperature-sensitive material to increase the complexity of the system. And in the polymer chain segment, the terpyridine derivative, 2-thenoyl trifluoroacetone and europium are coordinated, so that the red light luminous intensity of the rare earth ions is greatly improved. By changing the mass ratio of the polymer skeleton to the rare earth complex, rare earth metal polymers with different light colors can be obtained, and the light-emitting wavelength covers the whole visible light region.
More importantly, the rare earth metal polymer synthesized by the invention has reversible stimulus responsiveness to temperature, can obviously see reversible change of light color in the temperature changing process, and has the intensity ratio I of two luminescence centers483nm/I613nmHas good linear relation with temperature, and the detection sensitivity can reach 3.8 percent DEG C-1. The results of the embodiments show that the rare earth metal polymer provided by the invention is expected to be used as a novel temperature sensing material to be practically applied in the field of temperature detection.
Drawings
FIG. 1: structural schematic of europium metal polymer
FIG. 2: the rare earth metal polymer of example 1 showed a change in luminescence property in a temperature range of 40 to 110 deg.C
FIG. 2 a: variable temperature fluorescence spectrogram of rare earth metal polymer in the temperature range of 40-110 DEG C
FIG. 2 b: CIE coordinate diagram of rare earth metal polymer in 40-110 deg.C range
FIG. 2 c: the rare earth metal polymer has 483nm and 613nm emission peak intensity changes in the temperature range of 40-110 DEG C
FIG. 2 d: repeated experiment of rare earth metal polymer under repeated 40-110 ℃ circulation with light emitting condition changing with temperature
FIG. 3: (a) at different temperatures, in rare-earth polymers483nm/I613nmA fitted curve of the value of (b) as a function of temperature, (b) a sensitivity curve of the rare earth metal polymer at different temperatures
Detailed Description
The invention will now be further described with reference to the following examples and drawings:
example 1
(1) Synthesis of Polymer backbones
Weighing 88mg of 4 '- ((4-vinylbenzyl) oxy) -2, 2': 6 ', 2' -terpyridine and 200mg of vinyl tetraphenylethylene
mg, 2g of methyl methacrylate, dissolving in 4ml of DMF solvent, introducing nitrogen for 10min, adding AIBN 30mg, heating to 85 ℃, refluxing for 24h, cooling to room temperature after the reaction is finished, adding water for precipitation to form white powder, washing and filtering by using acetone and water in a ratio of 1:1, and drying in a vacuum drying oven for 2h to obtain the polymer skeleton Poly [ VTPY-co-VTPE-co-MMA ].
(2) Synthesis of rare earth metal polymers
200mg of polymer skeleton, 3mg Eu (TTA)3·2H2And O, adding the mixture into 2ml of THF solvent, heating and refluxing for 4h at the reaction temperature of 60 ℃, precipitating with diethyl ether and n-hexane in a ratio of 1:1, filtering, and drying for 2h to obtain the rare earth metal polymer.
The rare earth polymer in example 1 emits white light under 365nm ultraviolet lamp irradiation, and then undergoes a temperature-variable spectrum test to test the fluorescence spectrum at 40-110 ℃, as shown in fig. 2-3, which shows the CIE coordinates of the rare earth metal polymer at different temperatures. The fluorescence intensity changes at 483nm and 613nm at 40-110 deg.C were analyzed at the same time (FIG. 2c), and the results show that I483nm/I613nmThe polymer has good linear relation with temperature, and has higher sensitivity to temperature detection (figure 3), and the multiple temperature-changing fluorescence cycle test result of the rare earth metal polymer shows that the polymer has good cyclicity to light emission at different temperatures (figure 2 d).
Example 2
Otherwise, as in example 1, only the three-step polymer skeleton and Eu (TTA)3·2H2The mass ratio of O is changed to 270mg and 6mg respectively, so that the polymer temperature probe material emitting pink light under a 365nm ultraviolet lamp can be obtained, and the change of the light color from pink light to white light is shown within the temperature range of 40-110 ℃.
EXAMPLE 3
Otherwise the same conditions as in example 1, except that only the three polymer skeleton and Eu (TTA)3·2H2The mass ratio of O is changed to 240mg and 3.6mg respectively, so that the polymer temperature probe material emitting white light under a 365nm ultraviolet lamp can be obtained, and the light color of the polymer temperature probe material changes from white light to blue light within the temperature range of 40-110 ℃.
The above description is provided for further details of the present invention with reference to specific embodiments, which should not be construed as limiting the present invention, but are foreseen and determined by those skilled in the art without disclosure of the present invention.
Claims (7)
1. The self-calibration ratiometric temperature probe based on the europium metal polymer is characterized by being a block copolymer, and the structural expression of the probe is Poly [ (VTPY-Eu) -co-VTPE-co-MMA ], wherein VTPE is vinyl tetraphenylethylene, VTPY is 4 '- ((4-vinylbenzyl) oxygen) -2, 2': 6 ', 2' -terpyridine, and MMA is methyl methacrylate.
2. A method of making the self-calibrating ratiometric temperature probe of claim 1, characterized by the steps of:
step 1: dissolving vinyl tetraphenylethylene, 4 '- ((4-vinylbenzyl) oxy) -2, 2': 6 ', 2' -terpyridine and methyl methacrylate in DMF (dimethyl formamide) through a free radical polymerization reaction, introducing nitrogen for 10min, adding an initiator AIBN, stirring, heating, refluxing and reacting for 20-24 h at 80-90 ℃, cooling to room temperature after the reaction is finished, precipitating, washing, filtering and drying to obtain a block polymer skeleton Poly [ VTPY-co-VTPE-co-MMA ];
the molar ratio of the 4 '- ((4-vinylbenzyl) oxy) -2, 2': 6 ', 2' -terpyridine to the vinyl tetraphenylethylene to the methyl methacrylate is 1:2: 50;
step 2: mixing the polymer skeleton with rare earth complex Eu (TTA)3·2H2Dissolving O in THF, stirring and heating at 60-70 ℃ for reflux reaction for 4-6 h, cooling to room temperature after the reaction is finished, precipitating, filtering and washing to obtain the rare earth europium metal polyCompound Poly [ (VTPY-Eu) -co-VTPE-co-MMA]；
The mass ratio of the reactants is that the polymer skeleton: eu (TTA)3·2H2O＝[270～350mg]:[3～5mg]。
3. The method of claim 2, wherein: the precipitant in the step 1 is water.
4. The method of claim 2, wherein: the detergent used for washing in the step 1 is acetone.
5. The method of claim 2, wherein: and the drying time in the step 1 and the step 2 is 1-2 h.
6. The method of claim 2, wherein: the precipitating agent in the step 2 is diethyl ether and n-hexane which are 1: 1.
7. Use of the europium metal polymer-based self-calibrating ratiometric temperature probe of claim 1, wherein: the temperature detection device is used for temperature detection.
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| US20210115328A1 (en) * | 2018-06-22 | 2021-04-22 | Bundesrepublik Deutschland, Vertreten Durch Den Bundesminister Für Wirtschaft Und Energie | Fluorescent particles with molecularly imprinted fluorescent polymer shells for cell staining applications in cytometry and microscopy |
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| CN106432348A (en) * | 2016-09-05 | 2017-02-22 | 南京邮电大学 | Visible light excitable ratio fluorescence thermosensitive probe based on europium complex and preparation method and application of probe |
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| US20210115328A1 (en) * | 2018-06-22 | 2021-04-22 | Bundesrepublik Deutschland, Vertreten Durch Den Bundesminister Für Wirtschaft Und Energie | Fluorescent particles with molecularly imprinted fluorescent polymer shells for cell staining applications in cytometry and microscopy |
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