CN109824615B - Organic long-afterglow material, application thereof, and detection method and detection system of ultraviolet light wavelength - Google Patents
Organic long-afterglow material, application thereof, and detection method and detection system of ultraviolet light wavelength Download PDFInfo
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Abstract
The invention provides an organic long afterglow material, application thereof, and a detection method and a detection system of ultraviolet light wavelength. The organic long afterglow material is a compound with a structure shown in a formula I or a formula II. The detection method comprises the following steps: (1) Exciting an ultraviolet detection composition containing the organic long afterglow material by using a series of ultraviolet light with known wavelength, stopping excitation, observing afterglow color, and establishing a standard corresponding relation between the excitation light wavelength and the afterglow color; (2) And (2) exciting the ultraviolet detection composition in the step (1) by using ultraviolet light to be detected, stopping excitation, observing afterglow color, and obtaining the wavelength of the ultraviolet light to be detected according to the standard corresponding relation established in the step (1). The organic long afterglow material provided by the invention has the property that the luminescent color changes along with the change of the wavelength of the exciting light, and the ultraviolet wavelength detection method based on the organic long afterglow material can realize the visual detection of the wavelength of the ultraviolet light.
Description
Technical Field
The invention belongs to the technical field of organic long afterglow materials, and relates to an organic long afterglow material, an application thereof, and a detection method and a detection system of ultraviolet light wavelength.
Background
The luminescent material with color tunable characteristic has potential application value in many photoelectric fields. For example, the colorful coded micro-nano ions can be used for high-density information storage, anti-counterfeiting and multiplexed biological detection. Colorful nano particles are successfully applied to the field of stereoscopic display through an up-conversion technology. The multicolored luminophores can be used as biomarkers for multifunctional biological imaging. In the field of material science, although the regulation and control of realizing multicolor luminescence for the fluorescent substance of the luminescent material have been developed, a huge challenge still exists in the aspect of developing a novel intelligent response material.
In recent years, photoelectric functional materials having a long-life excited state have been favored in the fields of display, emergency signal, data encryption, bio-imaging, and the like, as well as basic scientific research. The long afterglow material is a photoluminescent material with long life excited state property, can absorb the energy of the exciting light and can still give out light after the excitation is stopped.
At present, the long afterglow materials are mainly inorganic materials, such as rare earth element doped aluminate materials. However, the inorganic long afterglow material has the disadvantages of harsh processing conditions, scarce material source, heavy metal biotoxicity and the like, and the application of the inorganic long afterglow material is limited. Therefore, people utilize the strategies of constructing H-type aggregates, crystal induction, host-guest doping, MOF (metal organic framework) and the like to realize long-afterglow luminescence of a series of organic materials to replace inorganic long-afterglow luminescent materials. Compared with inorganic long afterglow materials, the organic long afterglow material has the advantages of flexibility, easy synthesis, easy modification and the like. For example, spin coupling is increased by introducing heavy atoms (such as halogen, deuteron and the like) or special organic modification structural units (aromatic groups containing heteroatoms), intersystem crossing of photogenerated excitons from singlet states to triplet states is promoted, and long-life phosphorescence emission is realized.
CN 108117541A discloses a high-efficiency phosphorescent pure organic long afterglow material, which forms different halogen bonds through isomerization, and improves the phosphorescent quantum efficiency. CN 108047035A discloses a long afterglow organic salt material which can display different afterglow colors after being treated by ammonia gas or hydrogen chloride gas and can be used for visual detection of the gas. However, at present, the variety of organic long afterglow materials is few, and novel organic long afterglow materials still need to be developed.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide an organic long afterglow material, application thereof, and a detection method and a detection system of ultraviolet light wavelength. The organic long afterglow material can absorb ultraviolet light energy, continues to emit light after excitation is stopped, has the property that the light emitting color changes along with the change of the wavelength of the excitation light, and can be used for colorful display, anti-counterfeiting or ultraviolet light detection.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an organic long afterglow material, wherein the organic long afterglow material is a compound having the structure of formula I or formula II as follows:
wherein X is carbon or nitrogen;
R 1 、R 2 、R 3 each independently selected from a hydrogen atom, -C n H 2n+1 、-OC n H 2n+1 、-SC n H 2n+1 、-NHC n H 2n+1 、-N(CH 3 ) 2 、-O(C 6 H 5 )、-NH(C 6 H 5 )、-N(C 6 H 5 ) 2 -COOH or a halogen atom, n is an integer from 1 to 6 (e.g. 1, 2, 3, 4, 5 or 6, etc.).
The inventor synthesizes the compound with the structure shown in the formula I or the formula II, and researches show that the compound can continue to emit light after being excited by ultraviolet light and stopped, is an organic long afterglow material, and the afterglow color can be regulated and controlled by changing the wavelength of the excitation light.
The halogen atom may be F, cl, br or I.
As a preferred technical scheme of the invention, X in the formula I is nitrogen.
As a preferred technical scheme of the invention, R in the formula I 1 、R 2 、R 3 Each independently selected from a hydrogen atom, -OC n H 2n+1 、-SC n H 2n+1 Or a halogen atom, and not all are selected from a halogen atom and a hydrogen atom.
As a preferred technical scheme of the invention, R in the formula I 1 、R 2 、R 3 Each independently selected from a hydrogen atom, -OCH 3 、-SCH 3 Or a halogen atom, and not all of them are selected from halogen atoms and hydrogen atoms.
As a preferred technical scheme of the invention, the organic long afterglow material is a compound with any one of the following structures:
in a second aspect, the invention provides a use of the organic long afterglow material, wherein the organic long afterglow material is used for multicolor display, anti-counterfeiting or ultraviolet light detection.
In a third aspect, the invention provides an ultraviolet detecting composition, which comprises any one of the compounds with the structure shown in formula I or formula II as an organic long afterglow material.
The present invention is not particularly limited to the other components added to the ultraviolet detecting composition, and for example, functional additives such as a binder and the like may be added.
In a fourth aspect, the present invention provides a method for detecting ultraviolet wavelength, comprising the following steps:
(1) Exciting the ultraviolet detecting composition provided by the third aspect of the present invention with a series of ultraviolet light of known wavelength, stopping excitation, observing the afterglow color, and establishing a standard correspondence between the excitation light wavelength and the afterglow color;
(2) And (2) exciting the ultraviolet detection composition in the step (1) by using ultraviolet light to be detected, stopping excitation, observing afterglow color, and obtaining the wavelength of the ultraviolet light to be detected according to the standard corresponding relation established in the step (1).
Preferably, the wavelength gradient of the series of ultraviolet light of known wavelengths is 5-10nm; for example, it may be 5nm, 6nm, 7nm, 8nm, 9nm or 10nm.
It should be noted that, when the standard corresponding relationship is established, the larger the gradient of the wavelength of the ultraviolet light is, the more inaccurate the obtained standard corresponding relationship is, and the larger the error of the wavelength of the ultraviolet light is measured; the smaller the gradient of the wavelength of the ultraviolet light used, the smaller the error of the wavelength of the ultraviolet light measured. However, when the wavelength gradient is too small, the afterglow colors of two uv-excitations that differ by one wavelength gradient may be difficult to distinguish. Thus, the wavelength gradient of the series of known wavelengths of UV light in the present invention is preferably 5-10nm
In a fifth aspect, the present invention provides an ultraviolet test paper, which comprises a substrate and the ultraviolet detecting composition provided by the third aspect of the present invention coated on the substrate.
The material of the substrate of the ultraviolet test paper is not particularly limited, and those skilled in the art can select the substrate according to needs, and for example, paper, a PET (polyethylene terephthalate) film, a PE (polyethylene) film, or the like can be used.
In a sixth aspect, the present invention provides a system for detecting a wavelength of ultraviolet light, including the ultraviolet test paper and the color chart provided in the fifth aspect of the present invention;
the color comparison card comprises a background plate, color blocks printed on the background plate and wavelength marks matched with the color blocks;
the color of the color block and the wavelength of the wavelength mark respectively correspond to the afterglow color and the excitation light wavelength of the ultraviolet detection composition provided by the third aspect of the invention.
Compared with the prior art, the invention has the following beneficial effects:
the organic long-afterglow material provided by the invention has the advantages of simple preparation method, low raw material price and longer luminescence life, and the luminescence color of the material can be regulated and controlled by changing the wavelength of exciting light, so that the material has more intelligent characteristics than a monochromatic organic long-afterglow material, and is suitable for the fields of multicolor display, anti-counterfeiting, ultraviolet light detection and the like.
The detection method and the detection system for the ultraviolet wavelength provided by the invention utilize the characteristic that the luminescent color of the organic long afterglow material changes along with the change of the excitation wavelength, realize the visual detection of the ultraviolet wavelength and conveniently obtain the wavelength of the ultraviolet light.
Drawings
FIG. 1 is a fluorescence spectrum of compound TMO under the excitation of 310nm ultraviolet light.
FIG. 2 is a phosphorescence spectrum diagram of compound TMO after being excited by ultraviolet light with different wavelengths.
FIG. 3a is a graph showing the phosphorescence lifetime of a compound TMO after excitation by 245nm ultraviolet light.
FIG. 3b is a phosphorescence lifetime chart of compound TMO after 365nm ultraviolet light excitation
FIG. 4 is a phosphorescence spectrum of a compound CYAD after being excited by ultraviolet light with different wavelengths;
wherein the wavelengths of the excitation light from left to right are 270nm, 280nm, 290nm, 300nm, 310nm, 320nm, 330nm, 340nm, 350nm and 360nm respectively.
Fig. 5 is a photograph of a color chart provided in example 1.
FIG. 6 is a color photograph of a TMO pattern after being excited by ultraviolet light of different wavelengths.
Detailed Description
The technical scheme of the invention is further explained by the specific implementation mode in combination with the attached drawings. It should be understood by those skilled in the art that the specific embodiments are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Preparation example 1
Compound (I)
Preparation of (noted TMO):
in a 50mL flask, 2.10g of metallic sodium (89.47 mmol) was weighed, 15mL of dry methanol was added, and stirring was carried out at room temperature for 15min to prepare sodium methoxide. 5.0g (27.11 mmol) of trichlorotriazine as a white solid is weighed into a 50mL flask, 70mL of dry tetrahydrofuran is added, and the sodium methoxide solution prepared above is extracted and slowly added to the system, and stirred at room temperature for 15min. Column chromatography (petroleum ether: dichloromethane = 2:1) gave TMO as a white solid in 65.2% yield.
The structure is characterized as follows: 1 H NMR(CDCl 3 )：δ4.02(s,9H)； 13 C NMR(CDCl 3 )：δ173.55,55.25。
preparation example 2
Compound (I)
Preparation of (denoted as DMO):
in a 50mL flask, 0.8g of metallic sodium (35.78 mmol) was weighed, and 15mL of dry methanol was added, followed by stirring at room temperature for 15min to prepare sodium methoxide. 3.0g (16.27 mmol) of white solid trichlorotriazine was weighed into a 50mL flask, 30mL of dried tetrahydrofuran was added, the sodium methoxide solution prepared above was extracted and slowly added to the system, and stirred at room temperature for 15min. Column chromatography (petroleum ether: dichloromethane = 2:1) gave DMO as a white solid in 71.0% yield.
The structure is characterized as follows: 1 H NMR(CDCl 3 )：δ3.99(s,6H)； 13 C NMR(CDCl 3 )：δ172.58,171.74,5,6.46。
preparation example 3
Compound (I)
Preparation of (denoted SMO):
in a 50mL flask, 0.4g of metallic sodium (17.39 mmol) was weighed, and 15mL of dry methanol was added, followed by stirring at room temperature for 15min to prepare sodium methoxide. 3.2g (17.39 mmol) of white solid trichlorotriazine is weighed into a 50mL flask, 30mL of dry tetrahydrofuran is added, the prepared sodium methoxide solution is extracted and slowly added into the system, and the mixture is stirred at minus 25 ℃ for 15min. Column chromatography (petroleum ether: dichloromethane = 2:1) gave SMO as a white solid in 56% yield.
The structure is characterized as follows: 1 H NMR(CDCl 3 )：δ3.83(s,3H)； 13 C NMR(CDCl 3 )：δ179.4,169.1,54,7。
preparation example 4
Compound (I)
Preparation of (denoted as TMS):
0.20g of metallic sodium (8.69 mmol) was weighed into a 20mL flask, 10mL of dry methyl mercaptan was added, and the mixture was stirred at room temperature for 15min to prepare sodium thiomethoxide. 0.53g (2.89 mmol) of trichlorotriazine as a white solid was weighed into a 20mL flask, 15mL of dried tetrahydrofuran was added, and the sodium methoxide solution prepared above was extracted and slowly added to the system, followed by stirring at room temperature for 15min. Column chromatography (petroleum ether: dichloromethane = 2:1) gave TMS as a white solid in 49.8% yield.
The structure is characterized as follows: 1 H NMR(CDCl 3 )：δ2.53(s,9H)； 13 C NMR(CDCl 3 )：δ179.5,14.8。
preparation example 5
Compound (I)
Preparation of (denoted DMS):
0.18g of metallic sodium (7.82 mmol) was weighed into a 20mL flask, 10mL of dry methyl mercaptan was added, and the mixture was stirred at room temperature for 15min to prepare sodium thiomethoxide. 0.72g (3.91 mmol) of white solid trichlorotriazine is weighed into a 20mL flask, 15mL of dried tetrahydrofuran is added, the sodium methoxide solution prepared above is extracted and slowly added to the system, and stirring is carried out at room temperature for 15min. Chromatography column (petroleum ether: dichloromethane = 2:1) gave DMS as a white solid in 53.8% yield.
The structure is characterized as follows: 1 H NMR(CDCl 3 )：δ2.56(s,6H)； 13 C NMR(CDCl 3 )：δ183.5,167.6,14.4。
and (3) performance testing:
use of Steady/transient fluorescence Spectroscopy on Compounds obtained in preparation examples 1-5 and Compounds
(denoted CYAD) was tested for performance. Wherein the test results of the TMO are shown in FIG. 1, FIG. 2, FIG. 3a and FIG. 3 b. It can be seen from fig. 1 that the emission of the TMO can cover the blue and green regions under the excitation of uv light. As can be seen from FIGS. 2, 3a and 3b, the wavelength of the emission light of TMO excited by 245nm ultraviolet light is 470nm, which is blue light, and the lifetime is 582ms; the wavelength of the emission light of TMO excited by 365nm ultraviolet light is 510nm, the emission light is green light, and the service life is 745ms. Phosphorescence spectra of CYAD after excitation with uv light of different wavelengths are shown in fig. 4, and it can be seen from fig. 4 that the emission wavelength of CYAD is red-shifted as the laser wavelength increases.
The change range of the emitted light wavelength and the change range of the afterglow color of the compounds after being excited by ultraviolet light with different wavelengths (190-400 nm) are shown in the following table 1:
TABLE 1
| Name (R) | Range of emitted light wavelength variation | Range of variation of afterglow color |
| TMO | 450-505nm | Blue purple-green |
| DMO | 420-470nm | Purple-blue |
| SMO | 458-508nm | Blue-green |
| TMS | 430-540nm | Purple-green |
| DMS | 410-500nm | Purple-green |
| CYAD | 370-430nm | Purple-blue-purple |
As can be seen from the results in table 1, the afterglow color of each compound changes with the wavelength of the excitation light, and thus the compound can be used in the fields of multicolor display, ultraviolet light detection, and the like.
Example 1
The embodiment provides a detection system for ultraviolet wavelength, which comprises ultraviolet test paper and a colorimetric card;
the preparation method of the ultraviolet test paper comprises the following steps: grinding the compound TMO into powder in an agate mortar, adding a little aloe gel, and uniformly stirring to form pasty TMO. Then, paste TMO is poured onto one end of a screen plate having a stripe pattern, and a squeegee is used to apply a uniform pressure to a portion of the screen plate on which the paste TMO is applied while pushing the squeegee toward the other end. The pasty TMO is pressed onto the filter paper from the mesh of the pattern while moving. And after the aloe gel is dried, removing the screen printing plate to obtain filter paper printed with TMO material strip patterns, namely the ultraviolet test paper.
The preparation method of the color comparison card comprises the following steps: in a dark environment, ultraviolet test paper is irradiated by a series of ultraviolet light with known wavelengths (the wavelengths are respectively 300nm, 310nm, 320nm, 330nm, 340nm, 350nm and 360 nm), then the light source is turned off, and a picture is taken. The color block with the same color as the color of the afterglow of the TMO and the corresponding excitation light wavelength mark are printed on the paper, and the colorimetric card with the detection range of 300-360nm can be obtained (as shown in FIG. 5, the color gradually changes from blue to green from 300-360 nm).
According to the method, the range of the ultraviolet wavelength can be expanded, and the gradient of the ultraviolet wavelength can be reduced by a person skilled in the art, so as to obtain the ultraviolet wavelength detection system with a larger detection range and a more accurate detection result.
Example 2
The embodiment provides a method for detecting ultraviolet wavelength, which includes that, by using the detection system provided in embodiment 1, ultraviolet test paper is irradiated by ultraviolet light to be detected, irradiation is stopped, a light-emitting color of the ultraviolet test paper is observed and compared with a color comparison card, and a wavelength of the ultraviolet light to be detected can be read.
Example 3
The embodiment provides an application of TMO in multicolor display:
the TMO is printed into a butterfly pattern by a screen printing technique, the pattern is irradiated with ultraviolet light having a wavelength of 245nm in a dark environment, the light source is turned off, and then the pattern is irradiated with ultraviolet light having a wavelength of 365nm, so that the color of the displayed pattern is changed from blue to green (as shown in fig. 6).
The applicant declares that the above description is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be understood by those skilled in the art that any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention disclosed herein fall within the scope and disclosure of the present invention.
Claims (5)
1. The application of the organic long afterglow material is characterized in that the organic long afterglow material is used for colorful display, anti-counterfeiting or ultraviolet light detection; the organic long afterglow material is a compound with any one of the following structures:
2. a detection method of ultraviolet light wavelength is characterized by comprising the following steps:
(1) Exciting the ultraviolet detection composition by using a series of ultraviolet light with known wavelength, stopping excitation, observing the afterglow color, and establishing a standard corresponding relation between the excitation wavelength and the afterglow color;
(2) Exciting the ultraviolet detection composition in the step (1) by using ultraviolet light to be detected, stopping excitation, observing the color of afterglow, and obtaining the wavelength of the ultraviolet light to be detected according to the standard corresponding relation established in the step (1);
the ultraviolet detection composition in the step (1) contains an organic long afterglow material; the organic long afterglow material is a compound with any one of the following structures:
3. the detection method according to claim 2, wherein the wavelength gradient of the series of ultraviolet light of known wavelengths is 5-10nm.
4. The ultraviolet test paper is characterized by comprising a base material and an ultraviolet detection composition coated on the base material;
the ultraviolet detection composition comprises an organic long afterglow material; the organic long afterglow material is a compound with any one of the following structures:
5. a uv wavelength measurement system comprising the uv strip of claim 4 and a color chart;
the color comparison card comprises a background plate, color blocks printed on the background plate and wavelength marks matched with the color blocks;
the color of the color block and the wavelength of the wavelength mark respectively correspond to the afterglow color and the excitation light wavelength of the ultraviolet detection composition.
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| CN101033347A (en) * | 2006-03-10 | 2007-09-12 | 龙彪 | Infrared-ultraviolet composite colorful false proof printing ink |
| CN106833622A (en) * | 2017-01-10 | 2017-06-13 | 南京工业大学 | A kind of pure organic long-afterglow material of excited by visible light and preparation method and application |
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| DE4114732A1 (en) * | 1991-05-06 | 1992-11-12 | Helmut Dr Bayer | Banknote security mark - uses 2 or more substances which are fluorescent under ultraviolet of different wavelengths |
| CN101033347A (en) * | 2006-03-10 | 2007-09-12 | 龙彪 | Infrared-ultraviolet composite colorful false proof printing ink |
| CN106833622A (en) * | 2017-01-10 | 2017-06-13 | 南京工业大学 | A kind of pure organic long-afterglow material of excited by visible light and preparation method and application |
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