CN109824615A - The detection method and detection system of a kind of organic long-afterglow material, its purposes and ultraviolet wavelength - Google Patents
The detection method and detection system of a kind of organic long-afterglow material, its purposes and ultraviolet wavelength Download PDFInfo
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Abstract
The present invention provides the detection methods and detection system of a kind of organic long-afterglow material, its purposes and ultraviolet wavelength.Organic long-afterglow material is the compound with Formulas I or Formula II structure.The detection method includes the following steps: that (1) includes the ultraviolet detection composition of organic long-afterglow material using a series of ultraviolet excitation of known wavelengths, stop excitation, twilight sunset color is observed, the standard corresponding relationship of excitation wavelength and twilight sunset color is established;(2) using ultraviolet detection composition described in ultraviolet excitation step (1) to be measured, stop excitation, observe twilight sunset color, the wavelength of the ultraviolet light to be measured is obtained according to the standard corresponding relationship that step (1) is established.The property that there is organic long-afterglow material provided by the invention luminescent color to change with the variation of excitation wavelength, can be realized the Visual retrieval of ultraviolet wavelength based on its ultraviolet wavelength detection method.
Description
Technical field
The invention belongs to organic long-afterglow material technical field, it is related to a kind of organic long-afterglow material, its purposes and ultraviolet
The detection method and detection system of optical wavelength.
Background technique
Luminescent material with Color tunable characteristic makes it in many photoelectric fields, and there is potential application values.Such as
The micro-nano ion of colorful coding can be used for highdensity information storage, anti-fake and multiplexing biological detection.Colorful
Nanoparticle has been used successfully to field of stereoscopic display by upper switch technology.Colorful illuminator can be used as biomarker and be used for
Multi-functional bio-imaging.In materials science field, although realizing that multi-colour luminous regulation is existing to the fluorescent substance of luminescent material
Developed, but remains huge challenge in terms of developing novel intelligent responsive materials.
In recent years, no matter the photoelectric functional material with long-life Excited State Properties is in basic scientific research, or is showing
Show, emergency lamp signal telegraph, the fields such as data encryption and bio-imaging are all by favor.Long-afterglow material is a kind of long-life excitation
The embedded photoluminescent material of state property matter can absorb the energy of exciting light, and continue to shine after excitation stops.
Currently, long-afterglow material is mainly inorganic material, such as rare earth doped aluminate materials.But without more than captain
Brightness material has the shortcomings that processing conditions is harsh, material source is rare and heavy metal biological toxicity, and application is restricted.Institute
One is realized using strategies such as building H-type aggregation, crystal induction, host-guest system, MOF frames (metal organic frame) with people
Serial organic material it is long-persistence luminous, to replace inorganic long after glow luminous material.Compared with inorganic long-afterglow material, there is captain
Afterglowing material has many advantages, such as flexibility, is easily-synthesized and easy modification.Such as by introducing heavy atom (such as halogen and deuterated member
Element etc.) or special organic decoration structural unit (containing heteroatomic aromatic group) increase spin coupling effect, promote photoproduction to swash
Son from singlet to triplet state between be between pass through, realize the phosphorescent emissions of long-life.
CN 108117541A discloses a kind of pure organic long-afterglow material of high efficiency phosphorescent, forms difference by isomerization
Halogen key, improve phosphorescence quantum efficiency.CN 108047035A discloses a kind of organic salt material of long afterglow, through ammonia or chlorine
After changing hydrogen processing, it can show different twilight sunset colors, can be used for the Visual retrieval of the gas.But it is organic at present
The type of long-afterglow material is less, and novel organic long-afterglow material is still up for research and development.
Summary of the invention
In view of the deficiencies of the prior art, the present invention intends to provide a kind of organic long-afterglow material, its purposes
And the detection method and detection system of ultraviolet wavelength.Organic long-afterglow material can absorb UV energy, and excite
Stop subsequent supervention light, and with the property that luminescent color changes with the variation of excitation wavelength, can be used for colorful display, prevents
Pseudo- or ultraviolet light detection.
To achieve this purpose, the present invention adopts the following technical scheme:
In a first aspect, the present invention provides a kind of organic long-afterglow material, organic long-afterglow material is that have such as following formula I
Or the compound of Formula II structure:
Wherein, X is carbon or nitrogen;
R1、R2、R3It is each independently selected from hydrogen atom ,-CnH2n+1、-OCnH2n+1、-SCnH2n+1、-NHCnH2n+1、-N
(CH3)2、-O(C6H5)、-NH(C6H5)、-N(C6H5)2, one of-COOH or halogen atom, n is 1-6 (such as 1,2,3,4,5
Or 6 etc.) integer.
Inventor has synthesized the above-mentioned compound with Formulas I or Formula II structure, and pass through the study found that such compound by
It can continue to shine after ultraviolet excitation and stopping, be a kind of organic long-afterglow material, and twilight sunset color can pass through change and excite
Optical wavelength regulates and controls.
The halogen atom can be F, Cl, Br or I.
As the preferred technical solution of the present invention, X is nitrogen in Formulas I.
As the preferred technical solution of the present invention, R in Formulas I1、R2、R3It is each independently selected from hydrogen atom ,-OCnH2n+1、-
SCnH2n+1Or one of halogen atom, and it is not selected from halogen atom and hydrogen atom entirely.
As the preferred technical solution of the present invention, R in Formulas I1、R2、R3It is each independently selected from hydrogen atom ,-OCH3、-SCH3
Or it is a kind of in halogen atom, and it is not selected from halogen atom and hydrogen atom entirely.
As the preferred technical solution of the present invention, organic long-afterglow material is the change with any one following structure
Close object:
Second aspect, the present invention provide a kind of purposes of above-mentioned organic long-afterglow material, and organic long-afterglow material is used
In colorful display, anti-fake or ultraviolet light detection.
The third aspect, the present invention provides a kind of ultraviolet detection composition, comprising as any one of organic long-afterglow material
Kind has the compound of Formulas I or Formula II structure.
The other components that the present invention adds the ultraviolet detection composition are not particularly limited, illustratively, Ke Yitian
Add function additive, such as adhesive.
Fourth aspect, the present invention provide a kind of detection method of ultraviolet wavelength, include the following steps:
(1) the ultraviolet detection composition provided using a series of ultraviolet excitation third aspect present invention of known wavelengths,
Stop excitation, observes twilight sunset color, establish the standard corresponding relationship of excitation wavelength and twilight sunset color;
(2) using ultraviolet detection composition described in ultraviolet excitation step (1) to be measured, stop excitation, observe twilight sunset face
Color obtains the wavelength of the ultraviolet light to be measured according to the standard corresponding relationship that step (1) is established.
Preferably, a series of wavelength gradient of the ultraviolet light of known wavelengths is 5-10nm;Such as can be 5nm,
6nm, 7nm, 8nm, 9nm or 10nm etc..
It should be noted that the ultraviolet wavelength gradient of use is bigger, obtained mark when establishing the standard corresponding relationship
Quasi- corresponding relationship is more inaccurate, and the ultraviolet wavelength error measured is bigger;The ultraviolet wavelength gradient of use is smaller, then surveys
The ultraviolet wavelength error obtained is with regard to smaller.But when wavelength gradient is too small, two kinds of ultraviolet excitations of a wavelength gradient are differed
Twilight sunset color can be difficult to differentiate between.Therefore, a series of wavelength gradient of the ultraviolet light of heretofore described known wavelengths is preferably
5-10nm
5th aspect, the present invention provides a kind of ultraviolet test paper, and the present invention including substrate and coating on the substrate the
The ultraviolet detection composition that three aspects provide.
The present invention is not particularly limited the material of the substrate of ultraviolet test paper, and those skilled in the art can carry out as needed
Selection illustratively can be using paper, PET (polyethylene terephthalate) film, PE (polyethylene) film etc..
6th aspect, the present invention provide a kind of detection system of ultraviolet wavelength, provide including fifth aspect present invention
Ultraviolet test paper and colorimetric card;
The colorimetric card includes background board, and the color lump that is printed on the background board and with the matched wave of the color lump
Long mark;
The wavelength of the color of the color lump and wavelength mark respectively corresponds the ultraviolet inspection of third aspect present invention offer
Survey the twilight sunset color and excitation wavelength of composition.
Compared with prior art, the invention has the following advantages:
Organic long-afterglow material preparation method provided by the invention is simple, low in raw material price, has the longer luminous longevity
Life, and its luminescent color can be regulated and controled by changing excitation wavelength, show more intelligence than monochromatic organic long-afterglow material
Can characteristic, suitable for fields such as colorful display, anti-fake and ultraviolet light detections.
The detection method and detection system of ultraviolet wavelength provided by the invention are utilized organic long-afterglow material and shine
The characteristic that color changes with the variation of excitation wavelength, realizes the Visual retrieval of ultraviolet wavelength, can easily obtain
The wavelength of ultraviolet light out.
Detailed description of the invention
Fig. 1 is fluorescence spectra of the compound TMO under 310nm ultraviolet excitation.
Fig. 2 is phosphorescence spectrum figure of the compound TMO after the ultraviolet excitation of different wave length.
Fig. 3 a is phosphorescent lifetime figure of the compound TMO after 245nm ultraviolet excitation.
Fig. 3 b is phosphorescent lifetime figure of the compound TMO after 365nm ultraviolet excitation
Fig. 4 is phosphorescence spectrum figure of the compound CYAD after the ultraviolet excitation of different wave length;
Wherein, excitation wavelength from left to right be respectively 270nm, 280nm, 290nm, 300nm, 310nm, 320nm,
330nm、340nm、350nm、360nm。
Fig. 5 is the colorimetric card picture that embodiment 1 provides.
Fig. 6 is colorful photo of the TMO pattern after the ultraviolet excitation of different wave length.
Specific embodiment
To further illustrate the technical scheme of the present invention below with reference to the accompanying drawings and specific embodiments.Art technology
Personnel understand the present invention it will be clearly understood that the specific embodiment is only to aid in, and should not be regarded as a specific limitation of the invention.
Preparation example 1
CompoundThe preparation of (being denoted as TMO):
2.10g metallic sodium (89.47mmol) is weighed in the flask of 50mL, dry methanol 15mL is added, stirs at room temperature
It mixes 15min and prepares sodium methoxide.Three chlorotriazine of 5.0g (27.11mmol) white solid is weighed in 50mL flask, it is dry that 70mL is added
Dry tetrahydrofuran, the sodium methoxide solution for extracting above-mentioned preparation are slowly added in the system, stir 15min at room temperature.Chromatography
Column (petroleum ether: methylene chloride=2:1) separation, obtained white solid TMO, yield 65.2%.
Structural characterization is as follows:1H NMR(CDCl3): δ 4.02 (s, 9H);13C NMR(CDCl3): δ 173.55,55.25.
Preparation example 2
CompoundThe preparation of (being denoted as DMO):
0.8g metallic sodium (35.78mmol) is weighed in the flask of 50mL, dry methanol 15mL is added, stirs at room temperature
15min prepares sodium methoxide.Three chlorotriazine of 3.0g (16.27mmol) white solid is weighed in 50mL flask, it is dry that 30mL is added
Tetrahydrofuran, the sodium methoxide solution for extracting above-mentioned preparation is slowly added in the system, stirs 15min at room temperature.Chromatographic column
(petroleum ether: methylene chloride=2:1) separation, obtained white solid DMO, yield 71.0%.
Structural characterization is as follows:1H NMR(CDCl3): δ 3.99 (s, 6H);13C NMR(CDCl3): δ 172.58,171.74,5,
6.46。
Preparation example 3
CompoundThe preparation of (being denoted as SMO):
0.4g metallic sodium (17.39mmol) is weighed in the flask of 50mL, dry methanol 15mL is added, stirs at room temperature
15min prepares sodium methoxide.Three chlorotriazine of 3.2g (17.39mmol) white solid is weighed in 50mL flask, it is dry that 30mL is added
Tetrahydrofuran, the sodium methoxide solution for extracting above-mentioned preparation is slowly added in the system, lower stirs 15min in subzero 25 degree.Layer
Analyse column (petroleum ether: methylene chloride=2:1) separation, obtained white solid SMO, yield 56%.
Structural characterization is as follows:1H NMR(CDCl3): δ 3.83 (s, 3H);13C NMR(CDCl3): δ 179.4,169.1,54,
7。
Preparation example 4
CompoundThe preparation of (being denoted as TMS):
0.20g metallic sodium (8.69mmol) is weighed in the flask of 20mL, dry methyl mercaptan 10mL is added, stirs at room temperature
It mixes 15min and prepares sodium methyl mercaptide.Three chlorotriazine of 0.53g (2.89mmol) white solid is weighed in 20mL flask, 15mL is added
Dry tetrahydrofuran, the sodium methoxide solution for extracting above-mentioned preparation are slowly added in the system, stir 15min at room temperature.Layer
Analyse column (petroleum ether: methylene chloride=2:1) separation, obtained white solid TMS, yield 49.8%.
Structural characterization is as follows:1H NMR(CDCl3): δ 2.53 (s, 9H);13C NMR(CDCl3): δ 179.5,14.8.
Preparation example 5
CompoundThe preparation of (being denoted as DMS):
0.18g metallic sodium (7.82mmol) is weighed in the flask of 20mL, dry methyl mercaptan 10mL is added, stirs at room temperature
It mixes 15min and prepares sodium methyl mercaptide.Three chlorotriazine of 0.72g (3.91mmol) white solid is weighed in 20mL flask, 15mL is added
Dry tetrahydrofuran, the sodium methoxide solution for extracting above-mentioned preparation are slowly added in the system, stir 15min at room temperature.Layer
Analyse column (petroleum ether: methylene chloride=2:1) separation, obtained white solid DMS, yield 53.8%.
Structural characterization is as follows:1H NMR(CDCl3): δ 2.56 (s, 6H);13C NMR(CDCl3): δ 183.5,167.6,
14.4。
Performance test:
Using stable state/transient state Fluorescence Spectrometer to the obtained compound of preparation example 1-5 and compound
The performance of (being denoted as CYAD) is tested.Wherein the test result of TMO as shown in Figure 1, Figure 2, shown in Fig. 3 a and Fig. 3 b.It can be with by Fig. 1
Find out under the excitation of ultraviolet light, the transmitting of TMO can cover blue light and green wavelength.It can be seen by Fig. 2, Fig. 3 a and Fig. 3 b
Out, wavelength of transmitted light of the TMO after 245nm ultraviolet excitation is 470nm, is blue light, service life 582ms;TMO is through 365nm purple
Wavelength of transmitted light after outer light excitation is 510nm, is green light, service life 745ms.The ultraviolet excitation through different wave length of CYAD
Phosphorescence spectrum afterwards is as shown in figure 4, as seen from Figure 4, with the increase of optical maser wavelength, the wavelength of transmitted light of CYAD occurs red
It moves.
Above-mentioned each compound after the ultraviolet excitation of different wave length (190-400nm), wavelength of transmitted light variation range and
Twilight sunset color variation range is as shown in table 1 below:
Table 1
Title | Wavelength of transmitted light variation range | Twilight sunset color variation range |
TMO | 450-505nm | Royal purple-is green |
DMO | 420-470nm | It is purple-blue |
SMO | 458-508nm | Blue-green |
TMS | 430-540nm | It is purple-green |
DMS | 410-500nm | It is purple-green |
CYAD | 370-430nm | Purple-royal purple |
The twilight sunset color of above-mentioned each compound changes with the variation of excitation wavelength it can be seen from the result of table 1, can
For the fields such as colorful display and ultraviolet light detection.
Embodiment 1
The present embodiment provides a kind of detection systems of ultraviolet wavelength, including ultraviolet test paper and colorimetric card;
Wherein, ultraviolet test paper the preparation method is as follows: compound TMO is placed in agate mortar is ground to powdered, adds
It is a little to enter Aloe Vera Gel, stirs evenly, forms paste TMO.Then paste TMO is poured on one of the screen printing forme with strip pattern
End, the position for being coated with paste TMO on halftone with scraper plate applies uniform pressure, while pushing scraper plate to the other end.Paste TMO
It is extruded on filter paper from the mesh of pattern on the move.To remove halftone after Aloe Vera Gel drying, obtain being printed on TMO material
The filter paper of strip pattern, as ultraviolet test paper.
Colorimetric card the preparation method is as follows: in a dark environment, with the ultraviolet lights of known wavelengths a series of, (wavelength is respectively
300nm, 310nm, 320nm, 330nm, 340nm, 350nm, 360nm) the ultraviolet test paper of irradiation, it is then shut off light source, shoots photo.
Color lump identical with TMO twilight sunset color and corresponding excitation wavelength mark are printed out on paper, and detection can be obtained
The colorimetric card (as shown in figure 5, green is gradually become from blue from 300-360nm color) that range is 300-360nm.
Those skilled in the art can expand the range of ultraviolet wavelength according to the above method, reduce the ladder of ultraviolet wavelength
Degree, to obtain, detection range is bigger, the more accurate ultraviolet wavelength detection system of testing result.
Embodiment 2
The present embodiment provides a kind of detection method of ultraviolet wavelength, the detection system provided using embodiment 1, use is to be measured
The ultraviolet test paper of ultraviolet light stops irradiation, observes its luminescent color and compares with colorimetric card, that is, can be read to obtain to be measured ultraviolet
The wavelength of light.
Embodiment 3
The present embodiment provides a kind of application of TMO in colorful display:
TMO is printed as butterfly pattern, the ultraviolet light for being 245nm with wavelength under dark environment by screen printing technique
Irradiation patterns, close light source, and the ultraviolet light pattern for being then 365nm with wavelength can make the pattern color of display by indigo plant
Discoloration is green (as shown in Figure 6).
The Applicant declares that the foregoing is merely a specific embodiment of the invention, but protection scope of the present invention not office
It is limited to this, it should be clear to those skilled in the art, any to belong to those skilled in the art and take off in the present invention
In the technical scope of dew, any changes or substitutions that can be easily thought of, and all of which fall within the scope of protection and disclosure of the present invention.
Claims (10)
1. a kind of organic long-afterglow material, which is characterized in that organic long-afterglow material is that have such as following formula I or Formula II structure
Compound:
Wherein, X is carbon or nitrogen;
R1、R2、R3It is each independently selected from hydrogen atom ,-CnH2n+1、-OCnH2n+1、-SCnH2n+1、-NHCnH2n+1、-N(CH3)2、-O
(C6H5)、-NH(C6H5)、-N(C6H5)2, one of-COOH or halogen atom, n is the integer of 1-6.
2. organic long-afterglow material according to claim 1, which is characterized in that X is nitrogen.
3. organic long-afterglow material according to claim 1 or 2, which is characterized in that R1、R2、R3It is each independently selected from hydrogen
Atom ,-OCnH2n+1、-SCnH2n+1、-NHCnH2n+1Or one of halogen atom, and it is not selected from halogen atom and hydrogen atom entirely.
4. organic long-afterglow material according to claim 1-3, which is characterized in that R1、R2、R3Each independently
Selected from hydrogen atom ,-OCH3、-SCH3、-NHCH3Or it is a kind of in halogen atom, and it is not selected from halogen atom and hydrogen atom entirely.
5. organic long-afterglow material according to claim 1-4, which is characterized in that organic long-afterglow material
It is the compound with any one following structure:
6. a kind of purposes of organic long-afterglow material as described in any one in claim 1-5, which is characterized in that described to have captain
Afterglowing material is for colorful display, anti-fake or ultraviolet light detection.
7. a kind of ultraviolet detection composition, which is characterized in that the ultraviolet detection composition includes to be used as organic long-afterglow material
Any one compound with Formulas I or Formula II structure.
8. a kind of detection method of ultraviolet wavelength, which is characterized in that the detection method includes the following steps:
(1) using a series of ultraviolet excitation ultraviolet detection composition as claimed in claim 7 of known wavelengths, stop swashing
Hair observes twilight sunset color, establishes the standard corresponding relationship of excitation wavelength and twilight sunset color;
(2) using ultraviolet detection composition described in ultraviolet excitation step (1) to be measured, stop excitation, observe twilight sunset color, root
The wavelength of the ultraviolet light to be measured is obtained according to the standard corresponding relationship that step (1) is established;
Preferably, a series of wavelength gradient of the ultraviolet light of known wavelengths is 5-10nm.
9. a kind of ultraviolet test paper, which is characterized in that ultraviolet test paper include substrate and coating on the substrate such as claim 7
The ultraviolet detection composition.
10. a kind of detection system of ultraviolet wavelength, which is characterized in that the detection system includes as claimed in claim 9
Ultraviolet test paper and colorimetric card;
The colorimetric card includes background board, and the color lump that is printed on the background board and with the matched wavelength mark of the color lump
Know;
The wavelength of the color of the color lump and wavelength mark respectively corresponds ultraviolet detection composition as claimed in claim 7
Twilight sunset color and excitation wavelength.
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CN112940241A (en) * | 2021-02-08 | 2021-06-11 | 华南师范大学 | Triazine polymer and preparation method thereof |
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CN112940241B (en) * | 2021-02-08 | 2023-09-19 | 华南师范大学 | Triazine polymer and preparation method thereof |
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