CN117887463A - Preparation method of temperature response type red phosphorescent material, obtained product and application - Google Patents
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Abstract
The invention belongs to the technical field of composite material preparation, and particularly relates to a preparation method of a temperature response type red phosphorescent material, an obtained product and application. According to the invention, a microwave-assisted heating method is adopted, pyrene is used as a carbon source, citric acid and biuret are used as control materials, two CDs are synthesized, and the CDs are embedded into a PMMA matrix, so that a red phosphorescent material which has obvious color contrast and is responsive to temperature is obtained. The invention determines that the large conjugated structure and the high graphitization degree effectively regulate the triplet state, so that the singlet-triplet state energy gap of the material is reduced. On the other hand, PMMA generates a large amount of hydroxyl groups in the pyrolysis process, and the amino groups and carboxyl groups on the surfaces of two CDs are recombined or broken to form hydrogen bonds. Eventually, temperature responsive phosphorescence is produced. In addition, the rigid PMMA matrix blocks the non-radiative transition process, resulting in the phosphorescent material emitting blue fluorescence upon ultraviolet irradiation and red phosphorescence upon cessation of irradiation.
Description
Technical Field
The invention belongs to the technical field of composite material preparation, and particularly relates to a preparation method of a temperature response type red phosphorescent material, an obtained product and application.
Background
With the continuous improvement of information security standards, the application of information security in different environments is widely focused. Meanwhile, the phosphorescent material has the advantages of long luminous time and good visual contrast, and has great application potential in the field of information security. In this context, various stimuli-responsive phosphorescent materials, such as humidity-responsive, ultraviolet-responsive, temperature-responsive, mechanical stress-responsive, and multi-stimulus-responsive phosphorescent materials have been explored. However, the host materials of stimulus-responsive phosphorescence have problems of strict selection, complex synthesis process, poor phosphorescence performance, and the like, which seriously hamper the development of stimulus-responsive phosphorescence. Thus, finding a phosphorescent material that produces a high performance stimulus response from a single emission source has become a key development challenge.
The carbon-based nano luminescent material (carbon dots) is a novel luminescent material developed in recent years, and has the advantages of simple preparation and purification process, stable photophysical and chemical properties, adjustable emission characteristics, easy functional modification, good water solubility and biocompatibility and the like, and has great application prospects in various fields of chemical/biological sensing, biological imaging, medical diagnosis and treatment, photocatalysis, photoelectric devices and the like. However, scientific researchers have focused on the fluorescent property regulation and preparation, the luminous mechanism and the exploration of potential application of the materials in recent years, and have limited research on the long-life luminous performance of the materials.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a preparation method of a temperature response type red phosphorescent material.
The invention also provides a temperature-responsive red phosphorescent material prepared by the preparation method.
It is another object of the present invention to provide the use of the above temperature responsive red phosphorescent material.
The technical scheme adopted by the invention for achieving the purpose is as follows:
the invention provides a preparation method of a temperature response type red phosphorescent material, which comprises the following steps:
(1) Uniformly grinding pyrene, a control material and AlCl 3-6H2 O after being mixed to obtain a solid mixture, then carrying out microwave treatment on the solid mixture until the reaction is complete, cooling to room temperature to obtain control material@CDs powder, and washing and purifying with deionized water for later use;
(2) Dissolving PMMA in DMF solution, and standing to obtain PMMA solution;
(3) Adding control material @ CDs into PMMA solution, performing ultrasonic treatment until the control material @ CDs is completely dissolved, dripping the mixed solution, cooling and solidifying to obtain a sample film, and drying the sample film to obtain a product.
Further, in the step (1), the mass ratio of the pyrene to the control material to the AlCl 3-6H2 O is 1.36:18-34:5.7.
Further, in step (1), the control material is biuret (Bi) or Citric Acid (CA).
Further, in the step (1), the microwave treatment is that the microwave treatment is firstly performed for 30min under the power of 280-290W, and then performed for 20-30min under the power of 350-360W.
Further, in the step (2), the concentration of the PMMA solution is 0.2g/mL.
Further, in step (3), the ratio of the control material @ CDs to PMMA was 1 mg/1 g.
Further, the drying treatment is a treatment at 70 ℃ for 60min.
The invention also provides a temperature-responsive red phosphorescent material prepared by the preparation method.
The invention also provides application of the temperature response type red phosphorescent material in the field of information encryption anti-counterfeiting.
The invention provides a simple strategy, and prepares the high-performance temperature excitation response red phosphorescent material by utilizing the hydrogen bond behaviors of CDs with large conjugated structures and polymethyl methacrylate (PMMA) under different temperature conditions. In this combination, the combination of rigid structures effectively limits the non-radiative transitions of the material, reduces energy loss, and achieves a distinct phosphorescent color contrast (blue to red).
According to the invention, a microwave-assisted heating method is adopted, pyrene is used as a carbon source, citric acid and biuret are used as control materials, two CDs are synthesized in one step, and are embedded into a PMMA matrix, so that a red phosphorescent material which has obvious color contrast (from blue fluorescence to red phosphorescence) and is responsive to temperature is obtained. Through various testing and characterization methods, the invention determines that the large conjugated structure and high graphitization degree effectively regulate the triplet state, so that the singlet-triplet state energy gap (delta E ST) of the material is reduced. On the other hand, PMMA generates a large number of hydroxyl groups during the pyrolysis. This in turn leads to the action of recombination or cleavage of hydrogen bonds by amino and carboxyl groups located on the surface of both CDs. Eventually, temperature responsive phosphorescence is produced. In addition, the rigid PMMA matrix blocks the non-radiative transition process, resulting in the phosphorescent material emitting blue fluorescence upon ultraviolet irradiation and red phosphorescence upon cessation of irradiation.
The beneficial effects of the invention are as follows:
(1) The red phosphorescent material prepared by the invention has high color saturation and contrast, so that the red phosphorescent material becomes an ideal choice for information security application, and has wide application potential and market prospect;
(2) The preparation method provided by the invention is simple and quick, raw materials are easy to obtain, the cost is low, and the phosphorescent material with obvious response behavior under temperature stimulation is prepared.
Drawings
FIG. 1 is an ultraviolet-visible absorption spectrum of different control materials @ CDs, wherein (a) is Bi @ CDs and (b) is CA @ CDs;
FIG. 2 shows Raman spectra of different control materials @ CDs, wherein (a) is Bi @ CDs and (b) is CA @ CDs;
FIG. 3 is an XRD pattern for different control materials @ CDs, where (a) is Bi @ CDs and (b) is CA @ CDs;
FIG. 4 is a Fourier transform infrared spectrum of different control materials @ CDs, where (a) is Bi @ CDs and (b) is CA @ CDs;
FIG. 5 shows XPS spectra of (a, b) Bi@CDs and CA@CDs. (C-e) high resolution XPS fitting results of C1s and O1s and N1s spectra of Bi@CDs. (f, g) high resolution XPS fitting of C1s and O1s spectra of CA@CDs;
FIG. 6 is the solid Fluorescence (FL) and RTP emission spectra of (a, b) Bi@CDs-C-PMMA and CA@CDs-H-PMMA.
Detailed Description
The technical scheme of the invention is further explained and illustrated by specific examples.
Unless otherwise specified, the raw materials used in the preparation process of the present invention are all commercially available.
Example 1
(1) Synthesis of Bi@CDs
1.36 Mg of pyrene, 18 mg of biuret (Bi) and 5.7 mg of aluminum chloride hexahydrate (AlCl 3-6H2 O) were put into an agate mortar and uniformly ground. Then pouring the solid mixture into a beaker, treating for 30 minutes in a microwave oven under 288W power, heating for 20 minutes under 360W power until the reaction is complete, cooling to room temperature to obtain Bi@CDs powder, and finally washing and purifying with deionized water;
(2) Preparation of PMMA matrix
Dissolving 2 g PMMA in 10 ml DMF solution, and standing for one night to obtain PMMA solution;
(3) Preparation and heating treatment of Bi@CDs-PMMA composite material
2 Mg of Bi@CDs was added to a PMMA solution, sonicated until completely dissolved, the mixed solution was drop-coated on a glass slide, cooled and coagulated to obtain a sample film of Bi@CDs-PMMA, and then the sample film was subjected to a drying treatment (70 ℃ C., 60 minutes). The products obtained by heating and cooling to room temperature are called Bi@CDs-H-PMMA and Bi@CDs-C-PMMA respectively (H-heated to 70 ℃ C., C-cooled to room temperature).
Example 2
(1) Synthesis of CA@CDs
1.36 Mg of pyrene, 34 mg of Citric Acid (CA) and 5.7 mg of aluminum chloride hexahydrate (AlCl 3-6H2 O) were put into an agate mortar and uniformly ground. Then pouring the solid mixture into a beaker, treating for 30 minutes in a microwave oven under 288W power, heating for 20 minutes under 360W power until the reaction is complete, cooling to room temperature to obtain CA@CDs powder, and finally washing and purifying with deionized water;
(2) Preparation of PMMA matrix
Dissolving 2 g PMMA in 10 ml DMF solution, and standing for one night to obtain PMMA solution;
(3) Preparation and heating treatment of CA@CDs-PMMA composite material
2 Mg of CA@CDs was added to PMMA solution, sonicated until completely dissolved, the mixed solution was drop-coated on a glass slide, cooled and coagulated to obtain a sample film of CA@CDs-PMMA, and the sample film was then subjected to a drying treatment (70 ℃ C., 60 minutes). The products obtained by heating and cooling to room temperature are called CA@CDs-H-PMMA and CA@CDs-C-PMMA respectively (H-heated to 70 ℃ C., C-cooled to room temperature).
Effect examples
The materials prepared in examples 1-2 were characterized for properties, specifically:
1. from the ultraviolet-visible (UV-vis) absorption spectra fig. 1a, it can be determined that bi@cds have peaks at 270 nm, 306 nm and 324 nm, representing pi-pi and N-pi transitions caused by c=o/c=n functions, respectively. Fig. 1b can determine that ca@cds have peaks at 332 nm and 268 nm, representing n-pi transitions caused by c=o functions and pi-pi transitions caused by c=c functions, respectively. It is inferred that the phosphorescence behavior of the materials prepared according to the present invention is caused by the combination of a large conjugated structure and a surface functional group.
2. Raman spectra (fig. 2a, b) show that the raman spectral peak positions of bi@cds and ca@cds have similarities, located at 1404 and 1625 cm -1, respectively, corresponding to disordered D-bands and graphite G-bands. The D-band and G-band intensity ratios (I D/IG) of Bi@CDs and CA@CDs were 1.11 and 1.09, respectively, which indicates that both CDs have certain structural defects.
3. The invention analyzes the elements and chemical components of Bi@CDs and CA@CDs through XRD. Figures 3a, b show that the XRD spectra of both CDs have three peaks, bi@cds and ca@cds with one prominent peak at 23 °, corresponding to the (002) crystal plane of carbon. One distinct spike at 24 ° for bi@cds and ca@cds indicates the presence of the (002) crystal plane in the graphitic carbon. On the other hand, the narrow diffraction peaks of Bi@CDs and CA@CDs at about 28 degrees also indicate that the graphite has obvious graphite structural characteristics. This indicates that both materials have good crystallinity and both exhibit highly graphitized structures.
4. The chemical bonds of Bi@CDs and CA@CDs were analyzed by Fourier transform infrared spectroscopy (FTIR). As shown in fig. 4a, the absorption peak at 3412 cm -1 of bi@cds is the stretching vibration caused by the N-H functional group, the absorption peaks at 1714 and 1497 cm -1 are the stretching vibration caused by the c=o functional group, and the absorption peaks at 1609 and 831 cm -1 are the stretching vibration caused by the C-N and C-H functional groups, respectively. On the other hand, fig. 4b characterizes the infrared absorption peaks of ca@cds, such as 1714, 1637 and 1399 cm -1, mostly due to the stretching vibration of the c=o functional group. Peaks at 1181 and 837cm -1 of CA@CDs are due to the stretching vibrations of the C-O and C-H functional groups. The Fourier transform infrared spectrum results show that Bi@CDs and CA@CDs consist of sp 2 conjugated carbon cores and surface functional groups.
5. The presence of elements and functional groups in Bi@CDs and CA@CDs was further confirmed by X-ray photoelectron spectroscopy (XPS). As shown in FIG. 5a, bi@CDs consist of C, O, N elements. Peaks of C1s, O1s and N1s are 281 eV, 529 eV and 396 eV, respectively, with atomic ratio C: O: n=49: 27:24. wherein the C1s XSP spectrum of bi@cds has three peaks at 283.3 eV, 284.8 eV and 288 eV, belonging to C-C/C-H, C =c and c=o, respectively (fig. 5C). The O1s XSP spectrum of bi@cds has a peak at 527.5 eV, belonging to c=o (fig. 5 d). The N1s XSP spectrum of Bi@CDs has two peaks at 398.4 eV and 399.4 eV, belonging to N-C and N-H, respectively (FIG. 5 e). On the other hand, the C1s and O1s peaks of ca@cds were 282 eV and 529 eV, respectively, with an atomic ratio C: o=67:36 (fig. 5 b). The C1s XSP spectrum of ca@cds has three peaks at 280.7 eV, 282 eV and 284.9 eV, belonging to C-C/c= C, C-O and c=o, respectively (fig. 5 f). The O1s XSP spectrum of ca@cds has two peaks at 528 eV and 529.2 eV, belonging to o=c and O-C, respectively. The similarity of FTIR and XPS data indicates that the material surface has a wide range of functional groups, which have a significant impact on its optical properties. Furthermore, these findings verify the molecular basis necessary to achieve phosphorescence at the structural level.
6. Fig. 6 shows the fluorescence emission under 360 nm excitation and the phosphorescence emission with stopped excitation for both materials. Bi@CDs-C-PMMA and CA@CDs-H-MMA both have blue emission at 393 nm, and after excitation is turned off, their phosphorescent emission peaks are at 656 nm and 674 nm, resulting in a wavelength difference of about 260 nm, indicating that the material achieves phosphorescent emission from blue to red.
Claims (9)
1. The preparation method of the temperature response type red phosphorescent material is characterized by comprising the following steps of:
(1) Uniformly grinding pyrene, a control material and AlCl 3-6H2 O after being mixed to obtain a solid mixture, then carrying out microwave treatment on the solid mixture until the reaction is complete, cooling to room temperature to obtain control material@CDs powder, and washing and purifying with deionized water for later use;
(2) Dissolving PMMA in DMF solution, and standing to obtain PMMA solution;
(3) Adding control material @ CDs into PMMA solution, performing ultrasonic treatment until the control material @ CDs is completely dissolved, dripping the mixed solution, cooling and solidifying to obtain a sample film, and drying the sample film to obtain a product.
2. The method according to claim 1, wherein in the step (1), the mass ratio of pyrene, the control material and AlCl 3-6H2 O is 1.36:18-34:5.7.
3. The method of claim 1 or 2, wherein in step (1), the control material is biuret or citric acid.
4. A method according to any one of claims 1 to 3, wherein in step (1), the microwave treatment is carried out by first treating for 30min at a power of 280 to 290W and then treating for 20 to 30min at a power of 350 to 360W.
5. The method of claim 1, wherein in step (2), the concentration of the PMMA solution is 0.2g/mL.
6. The method of any one of claims 1-5, wherein in step (3), the ratio of control materials @ CDs to PMMA is 1 mg/1 g.
7. The method according to claim 1 or 6, wherein the drying treatment is a treatment at 70 ℃ for 60min.
8. A temperature-responsive red phosphorescent material prepared by the method of any one of claims 1 to 7.
9. Use of the temperature-responsive red phosphorescent material according to claim 8 in the field of information encryption anti-counterfeiting.
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|---|---|---|---|---|
| CN106916587A (en) * | 2017-03-20 | 2017-07-04 | 上海大学 | Oil-soluble carbon quantum dot (OCDs), PMMA@OOCDs, its preparation method and its application |
| US9738827B1 (en) * | 2016-04-28 | 2017-08-22 | Savannah River Nuclear Solutions, Llc | Carbon quantum dots and a method of making the same |
| CN110564414A (en) * | 2019-10-08 | 2019-12-13 | 河北工业大学 | Preparation method of carbon dots with adjustable force-induced fluorescence color |
| CN114015441A (en) * | 2021-12-10 | 2022-02-08 | 兰州大学 | Green solid fluorescent carbon dot and preparation method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9738827B1 (en) * | 2016-04-28 | 2017-08-22 | Savannah River Nuclear Solutions, Llc | Carbon quantum dots and a method of making the same |
| CN106916587A (en) * | 2017-03-20 | 2017-07-04 | 上海大学 | Oil-soluble carbon quantum dot (OCDs), PMMA@OOCDs, its preparation method and its application |
| CN110564414A (en) * | 2019-10-08 | 2019-12-13 | 河北工业大学 | Preparation method of carbon dots with adjustable force-induced fluorescence color |
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| Title |
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