CN111732949A - Application of azaanthracene derivative as single-photon weak light up-conversion luminescent agent material - Google Patents
Application of azaanthracene derivative as single-photon weak light up-conversion luminescent agent material Download PDFInfo
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- CN111732949A CN111732949A CN202010739634.4A CN202010739634A CN111732949A CN 111732949 A CN111732949 A CN 111732949A CN 202010739634 A CN202010739634 A CN 202010739634A CN 111732949 A CN111732949 A CN 111732949A
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Abstract
The invention relates to application of a azaanthracene derivative as a single-photon weak light up-conversion luminescent agent material; the azaanthracene derivative is used as a luminescent agent material for single photon absorption up-conversion, so that the excitation of red light 655 nm can be realized, the red-to-yellow single photon absorption up-conversion fluorescent color change effect of orange light about 610 nm can be obtained, the up-conversion color change can be obtained without removing oxygen, and the type of the luminescent agent material in the field of single photon absorption up-conversion is enriched.
Description
Technical Field
The invention relates to a heterocyclic compound, in particular to an application of a azaanthracene derivative as a single-photon absorption up-conversion light-emitting agent material.
Background
Organic up-conversion (UC) refers to a phenomenon in which an organic molecular system emits light of a short wavelength (high energy) by absorbing light of a long wavelength (low energy). Depending on the separation of the excitation light source from the strong light and the weak light, the up-conversion is also called strong light up-conversion and weak light up-conversion. The former is such as strong Two-photon absorption up-conversion (TPA-UC), and the excitation light source intensity is required to be as high as MW cm in the process of TPA-UC-2Even GW cm-2Of order (i.e., more than one million times the intensity of sunlight), it is clear that such a high intensity excitation light source limits the practical application of strong two-photon absorption upconversion. The weak light up-conversion is in mW-W.cm-2Under the irradiation of an excitation light source with magnitude, an organic molecular system emits high-energy light by absorbing low-energy light. The intensity of the exciting light required for weak light up-conversion is close to the intensity of sunlight (100 mW cm)-2) The technology has potential application value in high-technology fields such as up-conversion lasing, three-dimensional fluorescence microscopy/imaging, solar cells, photocatalysis and photoelectric devices, and the like, so that the technology is more popular in the scientific and technological field, stimulates researchers to have great research enthusiasm, and becomes a hot topic in the field of organic photoelectricity.
The organic weak light up-conversion mechanism includes two mechanisms, namely Triplet-Triplet annihilation up-conversion (TTA-UC) and single-photon thermal band absorption up-conversion (OPA-UC). The TTA-UC weak light up-conversion material is composed of two parts, namely photosensitizer molecules (also called donor) and luminescent agent molecules (also called acceptor). Under the mechanism of TTA-UC, the upconversion phenomenon can be generated by many microscopic mechanisms through intermolecular energy transfer by the cooperation of a photosensitizer and a luminescent agent. Whereas in the mechanism of OPA-UC only one component (i.e. the luminescent agent molecule itself) is needed to generate the up-conversion phenomenon. Therefore, the system is also called a two-component up-conversion system and a single-component up-conversion system.
As can be seen from the TTA-UC mechanism, the wavelength of the up-converted excitation light and the emitted light can be conveniently tuned by selecting different photosensitizers and luminescent agents, but this tuning is in view of the efficient matching of the triplet energy levels of the photosensitizers and luminescent agents. Since the triplet energy levels of the photosensitizer and the luminescent agent are mostly difficult to measure, the difficulty of material preparation and performance research is greatly increased. On the other hand, the energy transfer between the photosensitizer and the luminescent agent of TTA-UC needs to be carried out under the condition of removing oxygen, so that the practical application of the material is greatly limited; and OPA-UC can be carried out without oxygen removal, which greatly improves the up-conversion application value.
At present, most of researches on conversion directions of weak light are developed around TTA-UC, few reports are made on the research on OPA-UC, and the research on the structure-performance relationship of OPA-UC materials is blank.
Disclosure of Invention
The invention provides an application of a azaanthracene derivative as a single-photon absorption up-conversion luminescent agent, which can realize fluorescent color change of red light irradiation yellow light emission without oxygen removal environment and low-power excitation, further enriches the types of luminescent agent materials in the field of single-photon absorption up-conversion materials, and provides reference for molecular design of an OPA-UC material. The azaanthracene derivative material is traditionally used as a dye, can be used as a biological dyeing reagent and can also be used as an acid-base indicator, but no report of the application of the azaanthracene derivative material to a single-photon absorption up-conversion luminescent material exists at present, and 3 kinds of azaanthracene derivatives are commercially available, namely Safranine (PSF), Safranine T (SFT) and methylene violet (MTV), and the fluorescent color change of red light irradiation and yellow light emission can be realized without an oxygen removal environment and by low-power excitation.
In order to achieve the purpose of the invention, the invention adopts the technical scheme that:
the azaanthracene derivative is applied as a single-photon weak light up-conversion luminescent agent material.
The single-photon weak light up-conversion system consists of azaanthracene derivative and solvent.
According to the preparation method of the single-photon weak light up-conversion system, the azaanthracene derivative is added into a solvent to obtain the single-photon weak light up-conversion system.
The azaanthracene derivative has the following chemical structural formula:
wherein R is1Is NH2Or N (CH)2CH3）2，R2Is NH2Or N (CH)2CH3）2，R3Is H or CH3，R4Is H or CH3. Preferably, the chemical structural formula of the azaanthracene derivative is R1And R2At least one of them is NH2，R3And R4At least one of which is H.
Further preferably, the azaanthracene derivative of the present invention has the following chemical structure:
。
in the present invention, the solvent is any one of DMSO, DMF and THF, and preferably, the solvent is DMSO.
In the single-photon weak light up-conversion system, the concentration of the azaanthracene derivative is 1 × 10-5~5×10-3M, preferably 1 × 10-5M。
The power density of exciting light of the single-photon weak light up-conversion system is 500-2000 mW/cm2Preferably 1000 mW/cm2(ii) a The excitation wavelength was 655 nm.
Compared with the prior art, the invention has the following progress:
the azaanthracene derivative is used as a single photon absorption up-conversion luminescent material, so that up-conversion fluorescence discoloration can be carried out without removing oxygen and only by low-power light excitation, and the research on the structure-performance relation of the OPA-UC material is enriched.
Drawings
FIG. 1 shows UV-visible absorption spectra of azaanthracene derivatives in different solvents (a: PSF, b: SFT, c: MTV, concentration: 1 × 10-5M）；
FIG. 2 is a UV-visible absorption spectrum of azaanthracene derivatives at various concentrations (a: PSF, b: SFT, c: MTV, solvent: DMSO);
FIG. 3 shows fluorescence spectra of azaanthracene derivatives in different solvents (a: PSF, b: SFT, c: MTV, concentration: 1 × 10-5M，λex= respective maximum absorption peak position);
FIG. 4 shows fluorescence spectra of azaanthracene derivatives at different concentrations (a: PSF, b: SFT, c: MTV, solvent: DMSO, lambda)ex= respective maximum absorption peak position);
FIG. 5 is a graph of the Power Density-Up-conversion spectra (a and b) of azaanthracene derivatives and the corresponding log-linear plots (c and d) (a: PSF, b: MTV, concentration: 50. mu.M, solvent: DMSO,. lambda.ex= 655 nm）；
FIG. 6 shows a spectrum (left) of the azaanthracene derivative OPA-UC and a corresponding actual image (right);
FIG. 7 is an upconversion spectrum of a azaanthracene derivative at different concentrations (solvent: DMSO, lambda)ex=655 nm）；
FIG. 8 shows the excitation spectrum of the azaanthracene derivative (solvent: DMSO, ZnPc intensity reduced by 10 times);
FIG. 9 is a graph of the conversion efficiency on azaanthracene derivatives at different concentrations (solvent: DMSO).
Detailed Description
The invention will be further described with reference to examples of embodiments shown in the drawings to which the invention is attached. However, the present invention is not limited to the following examples. The implementation conditions adopted in the embodiments can be further adjusted according to different requirements of specific use, and the implementation conditions not mentioned are conventional conditions in the industry. The technical features related to the embodiments of the present invention may be combined with each other as long as they do not conflict with each other; the whole process does not need to remove oxygen.
Commercially available 3 azaanthracene derivatives, Phenol Safranine (PSF), Safranine T (SFT), and Methylene Violet (MTV), respectively:
example 1
In this example, the UV-visible absorption spectrum was measured by a UV-2600 UV-visible spectrometer from Shimadzu corporation, Japan; the fluorescence spectra were measured on a fluorescence/phosphorescence emission spectrometer model FLS 920 from edinburgh.
FIG. 1 is a graph of the solvent effect UV-VIS absorption spectrum of a azaanthracene derivative at the same concentration (concentration 1 × 10)-5M), the absorption peak positions of the three compounds are red-shifted, PSF is red-shifted from 530 nm to 537nm by 7nm, SFT is red-shifted from 532 nm to 538 nm by 6 nm, MTV is red-shifted from 556 nm to 560 nm by 4 nm, and the three azaanthracene derivatives are shown to generate pi-pi*And (4) transition.
FIG. 2 shows the UV-vis absorption spectra of the azaanthracene derivatives at different concentrations in the solvent DMSO, the absorption values of the three azaanthracene derivatives increased with increasing concentration, when the concentration increased to 1 × 10-4A platform peak appears when M is generated, aggregate characteristics appear, and 1 × 10 is selected when the molecular state performance is tested-5The concentration of M.
As shown in FIG. 3, the fluorescence spectra of the azaanthracene derivatives in different solvents were tested at concentrations of 1 × 10-5And (3) exciting the three azaanthracene derivative solutions of M by using light with wavelengths of 530 nm, 535 nm and 556 nm (the respective maximum absorption wavelengths) respectively, and testing the fluorescence spectrum properties of the three solutions.
FIG. 4 shows nitrogenIn DMSO as solvent, light with 537nm, 539 nm and 560 nm wavelength (respective maximum absorption wavelength) is used to perform excitation test on the three to obtain fluorescence spectra, it can be seen from the figure that the fluorescence peak positions of the three azaanthracene derivatives are all red-shifted with increasing concentration, at the concentration from 1 × 10-6M to 1 × 10-5As M increases, the fluorescence intensity of all three azaanthracene derivatives increases with increasing concentration, with increasing concentration going to 1 × 10-4In the course of M, the fluorescence intensity of the three azaanthracene derivatives gradually decreased.
Example 2
The azaanthracene derivatives were tested for single component up conversion (OPA-UC) spectra. In this embodiment, a diode-pumped solid-state red laser from new technologies electro-optical limited, vinpocetine, and a spectral scan spectrometer PR655 from photossearch, usa are used for testing the up-conversion spectrum. Comparative tests were performed with PSF and MTV to study the effect on OPA-UC, with DMSO (dimethyl sulfoxide) as solvent.
The upconversion spectra (concentration 50 μ M) of the two azaanthracene derivatives were measured using a 655 nm CW semiconductor laser as the light source, as shown in fig. 5. Where fig. 5 (a and b) are the power density-upconversion spectra of PSF and MTV, respectively, it can be seen that the upconversion intensity of each of the azaanthracene derivatives increases with increasing power density. Fig. 5 (c and d) are logarithmic linear plots of up-converted integrated intensity versus power density for PSF and MTV, respectively. At power density of 500 mW cm-2Increase to 2W cm-2In the process, the up-conversion integrated intensity and the logarithm of the power density of the aza-anthracene derivative present a linear relation, the slopes are respectively 0.98 and 0.99, which are close to 1, and the up-conversion process of the aza-anthracene derivative can be proved to be a direct single photon absorption process.
At the same concentration (1 × 10)-5M) and the same solvent (DMSO), and two azaanthracene derivatives are excited by light with the wavelength of 655 nm to obtain the OPA-UC structure effect spectrum (as shown in figure 6). As can be seen from the figure, the up-conversion intensity sequence is MTV>PSF. Can demonstrate a strong intramolecular chargeTransfer (ICT) facilitates enhancement of single photon absorption up-conversion. From the physical picture, the OPA-UC process of the two azaanthracene derivatives can be observed by naked eyes to change from red to yellow, and the yellow light of MTV is more obvious.
FIG. 7 is a graph of the OPA-UC spectra of different concentrations of azaanthracene derivatives in DMSO solvents with increasing red shift of their up-conversion peak positions, with PSF red-shifted from 615 nm to 619 nm by 4 nm and MTV red-shifted from 613 nm to 617 nm by 4 nm, and additionally, with concentration from 1 × 10-5M increases to 1 × 10-3M, their up-conversion intensity increased continuously, PSF and MTV increased 9.2 times and 15.7 times, respectively, as the concentration continued to increase to 5 × 10-3At M, the up-conversion intensity rapidly decreases (black dashed line in the figure).
Example 3
Single component up-conversion (OPA-UC) efficiency versus performance of the azaanthracene derivatives.
The fluorescence quantum yield in DMF solvent is phi with ZnPc as referencer= 32%. The excitation spectra of the azaanthracene derivatives were tested by figure 8 to give excitation intensity values at 655 nm for each, and substituted into the following formula to calculate the up-conversion efficiency at different concentrations for each.
The different concentrations are listed in Table 1 (low concentration 1 × 10 was selected)-5M and high concentration 1 × 10-3M) efficiency of the azaanthracene derivative OPA-UC. As can be seen from the concentration-upconversion efficiency curves of fig. 9, the upconversion efficiency increases significantly as the solution concentration of the azaanthracene derivative increases. From low to high concentrations, the OPA-UC efficiency of PSF increased by 1.6 times and the MTV increased by 4.0 times. The method can prove that under a certain concentration range, the conversion efficiency on single photon absorption is increased along with the increase of the concentration of the solution.
In table 2, the OPA-UC basic properties of the azaanthracene derivatives are listed at different concentrations, and comparing their respective up-conversion efficiencies at different concentrations, it can be found that their respective up-conversion efficiencies are increased at high concentrations, because the thermal vibrational energy level of the molecular ground state is possibly activated due to the enhanced intermolecular interaction, thereby promoting the electron transition to increase the up-conversion efficiency.
It will be understood by those skilled in the art that the foregoing is only a preferred embodiment of the present invention, and is not intended to limit the invention, and that any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (7)
1. The application of the azaanthracene derivative as a single-photon weak light up-conversion luminescent agent material is characterized in that: the azaanthracene derivative has the following chemical structural formula:
wherein R is1Is NH2Or N (CH)2CH3）2，R2Is NH2Or N (CH)2CH3）2，R3Is H or CH3，R4Is H or CH3。
2. Use according to claim 1, characterized in that: in the chemical structural formula of the azaanthracene derivative, R1And R2At least one of them is NH2，R3And R4At least one of which is H.
3. Use according to claim 1, characterized in that: the azaanthracene derivative has the following chemical structural formula:
4. use according to claim 1, characterized in that: when the azaanthracene derivative is used as a single-photon weak light up-conversion light-emitting agent material, the solvent is any one of DMSO, DMF and THF.
5. The use according to claim 4, wherein the concentration of said azaanthracene derivative is 1 × 10-5~5×10-3M。
6. The use according to claim 5, wherein the concentration of said azaanthracene derivative is 1 × 10-5M。
7. Use of the azaanthracene derivative of claim 1 in the preparation of a red to yellow upconverter material.
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| PCT/CN2020/127396 WO2022021662A1 (en) | 2020-07-28 | 2020-11-08 | Azaanthracene derivative upconversion system, preparation method therefor and use thereof |
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| WO2022021662A1 (en) * | 2020-07-28 | 2022-02-03 | 苏州科技大学 | Azaanthracene derivative upconversion system, preparation method therefor and use thereof |
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| CN110229165A (en) * | 2019-05-31 | 2019-09-13 | 苏州科技大学 | Up-conversion fluorescence probe Rhodamine Derivatives and its application |
| CN110724167A (en) * | 2018-09-05 | 2020-01-24 | 苏州科技大学 | Triplet-triplet annihilation up-conversion photosensitizer and application thereof |
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| CN102037115A (en) * | 2008-05-20 | 2011-04-27 | 荷兰联合利华有限公司 | Shading composition |
| CN110724167A (en) * | 2018-09-05 | 2020-01-24 | 苏州科技大学 | Triplet-triplet annihilation up-conversion photosensitizer and application thereof |
| CN110229165A (en) * | 2019-05-31 | 2019-09-13 | 苏州科技大学 | Up-conversion fluorescence probe Rhodamine Derivatives and its application |
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| WO2022021662A1 (en) * | 2020-07-28 | 2022-02-03 | 苏州科技大学 | Azaanthracene derivative upconversion system, preparation method therefor and use thereof |
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