CN111732949B - 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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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 53
- 239000000463 material Substances 0.000 title claims abstract description 22
- 239000000891 luminescent agent Substances 0.000 title claims abstract description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 20
- 230000005284 excitation Effects 0.000 abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 abstract description 7
- 239000001301 oxygen Substances 0.000 abstract description 7
- 230000008859 change Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- ALJHHTHBYJROOG-UHFFFAOYSA-N 7-(dimethylamino)phenothiazin-3-one Chemical compound C1=CC(=O)C=C2SC3=CC(N(C)C)=CC=C3N=C21 ALJHHTHBYJROOG-UHFFFAOYSA-N 0.000 description 18
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- 238000002189 fluorescence spectrum Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 230000007246 mechanism Effects 0.000 description 6
- 239000003504 photosensitizing agent Substances 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000001831 conversion spectrum Methods 0.000 description 2
- 238000000695 excitation spectrum Methods 0.000 description 2
- 238000000799 fluorescence microscopy Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- DDNCQMVWWZOMLN-IRLDBZIGSA-N Vinpocetine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OCC)N5C2=C1 DDNCQMVWWZOMLN-IRLDBZIGSA-N 0.000 description 1
- 239000002696 acid base indicator Substances 0.000 description 1
- -1 and preferably Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229960000744 vinpocetine Drugs 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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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 as strong Two-photon absorption up-conversion (Two-TPA-UC) requiring excitation light source intensity up to 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 multiplied by 10-5~5×10-3M; preferably 1X 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: 1X 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: 1X 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 1X 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 various concentrations. In the solvent DMSO, the absorption values of the three azaanthracene derivatives increase with increasing concentration, when the concentration increases to 1X 10-4When M appears a platform peak, the aggregate characteristics appear, when testing the molecular state performance, 1 × 10 is selected-5The concentration of M.
The fluorescence spectra of the azaanthracene derivatives in different solvents were tested as in fig. 3. The preparation concentrations are all 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 the fluorescence spectra of the azaanthracene derivatives at different concentrations. In a solvent DMSO, the three are respectively excited by light with wavelengths of 537nm, 539 nm and 560 nm (the respective maximum absorption wavelengths) to test the fluorescence spectra. As can be seen from the figure, the fluorescence peak positions of the three azaanthracene derivatives are all red-shifted with increasing concentration. At a concentration of 1X 10-6M to 1X 10-5In the process of increasing M, the fluorescence intensity of the three azaanthracene derivatives is increased along with the increase of the concentration. As the concentration continued to rise to 1X 10-4In the course of M, the fluorescence intensities of the three azaanthracene derivativesAnd gradually weakens.
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 (1X 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. It can be shown that stronger Intramolecular Charge Transfer (ICT) is beneficial to the 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 shows the OPA-UC spectra of different concentrations of the azaanthracene derivative in DMSO solvent. Their up-conversion peak position is continuously red-shifted during the course of increasing concentration. Wherein PSF is red-shifted by 4 nm from 615 nm to 619 nm, and MTV is red-shifted by 4 nm from 613 nm to 617 nm. In addition, the concentration is changed from 1X 10-5M is increased to 1X 10-3M, their up-conversion intensity is increased continuously, PSF and MTV are respectively increased by 9.2 times and 15.7 times, when the concentration is increased to 5X 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 (low concentrations 1X 10 were selected) are listed in Table 1-5M and high concentration 1X 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. Use according to claim 4, characterized in that: the concentration of the azaanthracene derivative is 1 x 10-5~5×10-3M。
6. Use according to claim 5, characterized in that: the concentration of the azaanthracene derivative is 1 x 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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| CN102037115A (en) * | 2008-05-20 | 2011-04-27 | 荷兰联合利华有限公司 | Shading composition |
| 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 |
Non-Patent Citations (3)
| Title |
|---|
| Photochemical reactions of triplet state of safranine-T studied by transient absorption spectroscopy in visible/near-IR regions;Shafiqul D.-M. Islam 等;《Physical Chemistry Chemical Physics》;19991231;3737-3742页 * |
| Photoinduced Energy and Electron Transfer between Ketone Triplets and Organic Dyes;S. Jockusch 等;《The Journal of Physical Chemistry A》;19961215;440-445页 * |
| Solvatochromic effects on the fluorescence and triplet–triplet absorption of phenosafranine in protic and aprotic solvents;Martin F. Broglia 等;《Journal of Photochemistry and Photobiology A: Chemistry》;20051115;143-149页 * |
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