CN115611820A - Preparation of organic photothermal material based on phenazine anthraquinone derivative receptor and water and electricity co-production application - Google Patents
Preparation of organic photothermal material based on phenazine anthraquinone derivative receptor and water and electricity co-production application Download PDFInfo
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000000463 material Substances 0.000 title abstract description 24
- 230000005611 electricity Effects 0.000 title abstract description 10
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- 239000007787 solid Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 claims description 3
- WPEJBJRFPBMVGJ-UHFFFAOYSA-N 3,6-dibromophenanthrene-9,10-dione Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3C(=O)C(=O)C2=C1 WPEJBJRFPBMVGJ-UHFFFAOYSA-N 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 abstract description 8
- 230000008020 evaporation Effects 0.000 abstract description 8
- 238000010521 absorption reaction Methods 0.000 abstract description 7
- 230000003595 spectral effect Effects 0.000 abstract description 3
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract 1
- 230000010354 integration Effects 0.000 abstract 1
- 230000008859 change Effects 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000002803 fossil fuel Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000002918 waste heat Substances 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
- C02F1/14—Treatment of water, waste water, or sewage by heating by distillation or evaporation using solar energy
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- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of an organic photothermal material based on a phenazine anthraquinone derivative receptor and application of the organic photothermal material in the field of water and power cogeneration. The invention combines two strong electron-withdrawing groups into one molecule, and constructs the organic photo-thermal material DDPA-PDN by using the rigid plane receptor PDN with strong electron-withdrawing capability. The novel compound has strong intramolecular charge transfer characteristics and a conjugated rigid planar skeleton, thus having broad spectral absorption of 300-850nm in the solid state, and having excellent photothermal effect and light/heat stability. Under 655nm laser irradiation, the solid photothermal conversion efficiency of the DDPA-PDN molecule can reach 56.23%. In addition, the integration of the DDPA-PDN cellulose paper with abundant water flow micro-channels with a thermoelectric device enables the evaporation efficiency to reach 61.06% under the light intensity of sunlight, and meanwhile, the open-circuit voltage of 43mV is generated. Our invention demonstrates the ability of organic photothermal materials to collect and utilize solar energy, thereby providing useful value for them in the field of cogeneration of water and electricity.
Description
Technical Field
The invention belongs to the technical energy field of water and power cogeneration, and particularly relates to a preparation method of an organic photo-thermal material based on a phenazine anthraquinone derivative receptor and application of the organic photo-thermal material in the water and power cogeneration field.
Background
With the rapid growth of the population and the increasing requirements of living standard, the consumption of fossil fuels is more and more serious, and meanwhile, the water purification system depending on the fossil fuels is difficult to continue. Therefore, there is a need to develop an eco-friendly technology to achieve the goal of sustainable development. Solar energy, as a replacement for fossil fuels, is a renewable, green, pollution-free energy source and can therefore be used to vaporize water and generate electricity without consuming fossil fuels. In the solar photo-thermal conversion process, the evaporation mode of water has a crucial influence on the photo-thermal conversion efficiency and the evaporation rate. At present, a selective heating system in the form of interfacial evaporation provides a challenge for the feasibility of thermoelectric conversion in solving the energy crisis, and therefore, the development of a high-efficiency photothermal material for constructing a solar-driven hydroelectric integrated device is urgently needed.
Currently, the commonly used photo-thermal materials mainly include carbon-based inorganic materials, metal-based inorganic materials, organic polymers, organic small molecule materials, and the like. Among them, organic small molecule photothermal materials are receiving more and more attention due to their unique advantages such as processability, structural diversity and adjustability. The organic micromolecule photo-thermal material is used as a solar energy absorption material, can collect waste heat in the water evaporation process to generate electricity, and has wide application prospect. Although organic photothermal small molecules have a wide application prospect in solar energy acquisition and conversion, further research is needed to broaden their absorption spectra and promote their photothermal conversion, thereby enabling their application in high-performance water evaporation/thermoelectric devices. Generally, organic conjugated molecules with donor-acceptor (D-A) structure can make absorption spectra undergo large red shift by effective electron delocalization. Furthermore, the conjugated rigid planar structure helps to increase the pi-pi stacking of the aggregated states, thereby further broadening the absorption spectrum. More interestingly, the resulting small energy gap may contribute to the generation of heat by non-radiative decay, according to the energy gap law. Therefore, the development of organic small molecule materials with D-a structure and conjugated rigid planar backbone is crucial for high performance evaporation/thermoelectric devices.
Disclosure of Invention
The invention aims to solve the problems of shortage of fresh water resources and low utilization rate of novel renewable energy sources at present, and provides a preparation method of an organic photo-thermal material based on a phenazine anthraquinone derivative receptor and application of the organic photo-thermal material in the field of cogeneration.
In order to achieve the purpose, the organic photothermal material is prepared by adopting the following steps:
the invention provides an organic photothermal material DDPA-PDN based on a phenazine anthraquinone derivative receptor, which has a structural formula shown as the following (formula I):
the synthetic route adopted by the invention can be represented by the following reaction formula:
preparing DDPA-PDN as shown in formula I:
first, 3, 6-dibromophenanthrene-9, 10-dione, diphenylamine, tris (dibenzylideneacetone) dipalladium (0) (Pd) 2 (dba) 3 ) Cesium carbonate (Cs) 2 CO 3 ) 1.0M of tri-tert-butylphosphine (P (t-Bu) 3 ) And sequentially adding the toluene solution into a three-necked bottle containing the toluene solution, and stirring for dissolving.
Next, the reaction mixture was reacted at an elevated temperature of 110 ℃ under a nitrogen atmosphere for 24 hours.
Finally, the mixture was cooled to room temperature and distilled water was added to quench the reaction.
The mixture was then extracted with dichloromethane, the combined organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure.
Separating and purifying the obtained crude product by column chromatography to obtain a deep red solid and a compound DDPA-PD;
and step 2, synthesizing a compound DDPA-PDN:
firstly, the deep red solid DDPA-PD synthesized in the step 1 and 5, 6-diaminoanthraquinone are poured into a dry three-mouth bottle, and acetic acid is added for full dissolution.
Next, the reaction mixture was reacted at an elevated temperature of 120 ℃ under nitrogen for 12 hours.
Finally, the mixture was cooled to room temperature and poured into water, and filtered, and then the filter cake was dissolved in dichloromethane, dried over anhydrous sodium sulfate, and then removed of water under reduced pressure to obtain a crude product.
And separating and purifying the crude product by column chromatography to obtain a deep red solid DDPA-PDN.
The invention has the beneficial effects that:
(1) The organic photothermal material DDPA-PDN has a small molecular structure, a simple and convenient synthetic route and high yield (about 50 percent), and can realize large-scale commercial production;
(2) The organic photothermal material DDPA-PDN can be used as a light absorption material, has the broad spectrum absorption of 350-850nm, has the photothermal conversion efficiency of 56.23 percent, and lays a feasible foundation for the water and electricity cogeneration application driven by solar energy;
(3) The DDPA-PDN filter paper can simultaneously carry out water-electricity cogeneration, the solar water evaporation efficiency under the intensity of sunlight reaches 61.06%, and meanwhile, 43mV open circuit voltage can be generated, which shows that the material can be well applied to the technical energy field of water-electricity cogeneration.
Drawings
FIG. 1 is a diagram of a synthesized DDPA-PDN circuit;
FIG. 2 is a laser stabilization diagram of DDPA-PDN;
FIG. 3 is a thermogravimetric analysis plot of DDPA-PDN;
FIG. 4 is a scanning electron micrograph of DDPA-PDN filter paper;
FIG. 5 is a graph of the UV absorption of DDPA-PDN filter paper;
FIG. 6 is a temperature difference diagram of DDPA-PDN water and electricity cogeneration;
FIG. 7 is a voltage diagram of DDPA-PDN water-electricity cogeneration;
FIG. 8 is a diagram of the rate of DDPA-PDN co-generation of water and electricity;
Detailed Description
The technical scheme of the invention is further explained by combining the drawings in the specification.
The first embodiment of the invention:
synthesis of Compound DDPA-PD: first, 3, 6-dibromophenanthrene-9, 10-dione (3.66g, 10mmol), diphenylamine (4.22g, 25mmol), tris (dibenzylideneacetone) dipalladium (0) (Pd) 2 (dba) 3 ) (275mg, 0.3mmol), cesium carbonate (Cs) 2 CO 3 ) (13.04g, 40mmol), 1.0M tri-tert-butylphosphine (P (t-Bu) 3 ) The toluene solution (3 ml) was added to a three-necked flask containing the toluene solution (100 ml) in this order, and dissolved by stirring.
Next, the reaction mixture was reacted at an elevated temperature of 110 ℃ under a nitrogen atmosphere for 24 hours.
Finally, the mixture was cooled to room temperature and distilled water was added to quench the reaction.
The mixture was then extracted with dichloromethane, the combined organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure.
Separating and purifying the obtained crude product by column chromatography, and using dichloromethane as an eluent to obtain a deep red solid and a compound DDPA-PD;
synthesis of Compound DDPA-PDN: first, DDPA-PD (2.17g, 4 mmol), which was a deep red solid synthesized in step 1, and 5, 6-diaminoanthraquinone (4.80g, 20mmol) were poured into a dry three-necked bottle, and 30ml of acetic acid was further added thereto to sufficiently dissolve.
Next, the reaction mixture was reacted at an elevated temperature of 120 ℃ under nitrogen for 12 hours.
Finally, the mixture was cooled to room temperature and poured into water, followed by filtration, and then the filter cake was dissolved in dichloromethane, dried over anhydrous sodium sulfate, and then removed under reduced pressure to obtain a crude product.
The crude product was purified by column chromatography using dichloromethane as eluent to give DDPA-PDN as a dark red solid.
Optical stability of DDPA-PDN: testing the temperature change condition of DDPA-PDN-4mg solid powder under continuous five times of on-off laser cycle irradiation, adopting a 730nm laser, and having an energy density of 0.8W/cm 2 Switching on and off the laser every 60s, and recording the temperature every 2 s;
thermal stability of DDPA-PDN: measuring the change in mass of the DDPA-PDN solid powder by heating from 25 ℃ to 800 ℃ at a rate of 10K/min in a nitrogen atmosphere using a TA Q500 thermogravimetric analyzer;
photothermal conversion performance of DDPA-PDN: the ultraviolet absorption spectrum of the DDPA-PDN solid powder is firstly measured by an ultraviolet spectrophotometer to obtain the absorbance of the DDPA-PDN solid powder at 655 nm. Secondly, uniformly spin-coating DDPA-PDN on a quartz plate to form a film, and opening the quartz plate to be 0.8W/cm 2 And (3) irradiating the material with 655nm laser to the maximum temperature, closing the laser to start timing, recording the temperature once every 5s, measuring the cooling condition of the DDPA-PDN film in 0-350s, and making a T-T cooling curve. And finally, calculating the photothermal conversion efficiency of the DDPA-PDN.
The second embodiment of the invention:
preparation of DDPA-PDN filter paper: firstly, dissolving DDPA-PDN 5mg in a small amount of DCM solvent, dripping the solution on the surface of filter paper by using a liquid-transferring gun, repeatedly operating, successfully dipping the DDPA-PDN on the filter paper, and finally airing the filter paper in natural wind to prepare the photothermal absorption layer DDPA-PDN filter paper;
loading of DDPA-PDN filter paper: observing the shapes of blank filter paper and 5 mg-loaded DDPA-PDN filter paper by adopting an EM-30plus type scanning electron microscope;
absorption characteristics of DDPA-PDN filter paper: measuring the ultraviolet absorption conditions of blank filter paper and DDPA-PDN filter paper at 300-1000nm by using a Hitachi U-4100 ultraviolet/visible/near-infrared spectrophotometer;
temperature difference change condition of water and electricity cogeneration: DDPA-PDN filter paper is irradiated by a CEL-S500/350 xenon lamp light source with a standard AM 1.5G spectral filter under the light intensity of 1,2,5 sunlight, and the surface temperature and the water temperature change of the temperature filter paper are recorded by using a thermal infrared imager (TESTO-869). Recording the surface temperature and the water temperature of the filter paper every 30s, and testing the change condition of the temperature difference within 5 min;
the application condition of water and electricity cogeneration is as follows: the water and power cogeneration experiment is carried out by adopting a CEL-S500/350 xenon lamp light source with a standard AM 1.5G spectral filter. Irradiating DDPA-PDN filter paper under the light intensity of 1 sunlight, monitoring the mass loss of water by using an analytical balance, and simultaneously recording open-circuit voltage data by a Keithley 6514 system;
in summary, the preferred embodiments of the present invention are described, and any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (2)
1. Preparation of compound DDPA-PD:
first, 3, 6-dibromophenanthrene-9, 10-dione, diphenylamine, tris (dibenzylideneacetone) dipalladium (0) (Pd) 2 (dba) 3 ) Cesium carbonate (Cs) 2 CO 3 ) 1.0M of tri-tert-butylphosphine (P (t-Bu) 3 ) And sequentially adding the toluene solution into a three-neck flask containing the toluene solution, and stirring for dissolving.
Next, the reaction mixture was reacted at an elevated temperature of 110 ℃ under a nitrogen atmosphere for 24 hours.
Finally, the mixture was cooled to room temperature and distilled water was added to quench the reaction.
The mixture was then extracted with dichloromethane, the combined organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure.
And separating and purifying the obtained crude product by column chromatography to obtain a deep red solid and a compound DDPA-PD.
2. Preparation of Compound DDPA-PDN:
first, the synthesized deep red solid DDPA-PD, 5, 6-diaminoanthraquinone, was poured into a dry three-necked bottle, and acetic acid was added thereto for sufficient dissolution.
Next, the reaction mixture was reacted at 120 ℃ under nitrogen for 12 hours.
Finally, the mixture was cooled to room temperature and poured into water, and filtered, and then the filter cake was dissolved in dichloromethane, dried over anhydrous sodium sulfate, and then removed of water under reduced pressure to obtain a crude product.
And separating and purifying the crude product by column chromatography to obtain a dark red solid DDPA-PDN.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080121870A1 (en) * | 2004-06-14 | 2008-05-29 | Marder Seth | Transition-Metal Charge Transport Materials, Methods Of Fabrication Thereof, And Methods Of Use Thereof |
| CN101379110A (en) * | 2006-02-10 | 2009-03-04 | 西巴控股有限公司 | Novel polymers |
| KR20140131133A (en) * | 2013-05-03 | 2014-11-12 | 삼성디스플레이 주식회사 | Compound and organic light emitting device comprising same |
| CN112457313A (en) * | 2020-12-18 | 2021-03-09 | 深圳大学 | Naphthalimide-azacyclo-luminescent material and application thereof |
-
2021
- 2021-07-16 CN CN202110804096.7A patent/CN115611820A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080121870A1 (en) * | 2004-06-14 | 2008-05-29 | Marder Seth | Transition-Metal Charge Transport Materials, Methods Of Fabrication Thereof, And Methods Of Use Thereof |
| CN101379110A (en) * | 2006-02-10 | 2009-03-04 | 西巴控股有限公司 | Novel polymers |
| KR20140131133A (en) * | 2013-05-03 | 2014-11-12 | 삼성디스플레이 주식회사 | Compound and organic light emitting device comprising same |
| CN112457313A (en) * | 2020-12-18 | 2021-03-09 | 深圳大学 | Naphthalimide-azacyclo-luminescent material and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| DEEPALI N. KANEKAR等: "Synthesis and investigation of the photophysical, electrochemical and theoretical properties of phenazine–amine based cyan blue-red fluorescent materials for organic electronics", NEW J. CHEM., vol. 44, 22 January 2020 (2020-01-22), pages 3278 - 3293 * |
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