CN113637028B - Hydrostatic pressure fluorescent sensing material based on carborane, and preparation method and application thereof - Google Patents
Hydrostatic pressure fluorescent sensing material based on carborane, and preparation method and application thereof Download PDFInfo
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- CN113637028B CN113637028B CN202110887892.1A CN202110887892A CN113637028B CN 113637028 B CN113637028 B CN 113637028B CN 202110887892 A CN202110887892 A CN 202110887892A CN 113637028 B CN113637028 B CN 113637028B
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- 230000002706 hydrostatic effect Effects 0.000 title claims abstract description 21
- 239000011540 sensing material Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims abstract description 28
- VHCSAOOJEIAWFS-UHFFFAOYSA-N boric acid phenanthrene Chemical compound OB(O)O.c1ccc2c(c1)ccc1ccccc21 VHCSAOOJEIAWFS-UHFFFAOYSA-N 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 37
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 7
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- VMVNPVVMNDUEOA-UHFFFAOYSA-N phenanthren-1-ylboronic acid Chemical compound C1=CC2=CC=CC=C2C2=C1C(B(O)O)=CC=C2 VMVNPVVMNDUEOA-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 12
- 238000010791 quenching Methods 0.000 abstract description 3
- 230000000171 quenching effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 abstract 1
- 239000000523 sample Substances 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/05—Cyclic compounds having at least one ring containing boron but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N2021/6417—Spectrofluorimetric devices
Abstract
The invention discloses a hydrostatic pressure fluorescent sensing material based on carborane, a preparation method and application thereof, wherein the molecular formula of the material is C 22 H 24 B 10 The preparation method takes phenanthrene boric acid and 4-o-carborane bromobenzene as raw materials and is prepared through Suzuki coupling reaction. The material can be used as a force-induced fluorescence color-changing pressure sensing probe, solves the problem of force-induced fluorescence quenching of the traditional material, presents force-induced fluorescence enhancement property under lower pressure, and has great application potential in a pressure sensing system.
Description
Technical Field
The invention belongs to the technical field of chemistry, and particularly relates to a hydrostatic pressure fluorescent sensing material based on carborane, and a preparation method and application thereof.
Background
The pressure (force) electrochromic refers to a phenomenon that fluorescent color or/and intensity and the like are reversibly changed under the action of external mechanical force (friction, shearing and the like) or hydrostatic pressure. The hydrostatic pressure photochromic (Piezochromic fluorescence, PCF) material has great application potential in the fields of pressure sensing systems (such as deep sea diving vehicles, aircraft wind tunnel tests and the like), optical recording, anti-counterfeiting, information display, storage and the like because the fluorescence of the hydrostatic pressure photochromic (Piezochromic fluorescence, PCF) material can be continuously changed under the action of pressure.
The traditional organic luminescent material increases intermolecular interaction force under the action of static pressure, and pi-pi action is enhanced, so that fluorescence quenching is finally caused. In other words, the luminescence intensity of the molecules is continuously reduced under the action of hydrostatic pressure, and the sensitivity of the pressure sensing device is reduced. Therefore, the construction of the hydrostatic pressure fluorescence enhancement material is a key for improving the detection line and the sensitivity of pressure sensing. The amount of hydrostatic pressure-induced fluorescence enhancement material is then very small to date.
Disclosure of Invention
The invention aims to provide a hydrostatic pressure fluorescent sensing material based on carborane, a preparation method and application thereof.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
hydrostatic pressure fluorescent sensing material based on carborane, wherein the material is carborane derivative, and the chemical formula of the material is C 22 H 24 B 10 The structural formula is as follows:
in another aspect of the present invention, there is provided a process for preparing a carborane derivative of formula (III) above, comprising the steps of:
dissolving 4-o-carborane bromobenzene, phenanthrene boric acid, tetraphenylphosphine palladium and sodium carbonate in tetrahydrofuran; stirring and reacting for 18-24 h at 90-100 ℃ under the protection of nitrogen atmosphere, extracting with water and pure dichloromethane for several times after the raw materials are reacted completely, collecting an extract phase, drying and purifying to obtain white powder, namely the target product carborane derivative (III).
Further, the molar ratio of the 4-o-carborane bromobenzene, the phenanthrene boric acid, the tetraphenylphosphine palladium and the sodium carbonate is 1:1.0-1.5:0.08-0.1:0.8-1.0.
Further, the molar concentration of the 4-o-carborane bromobenzene and tetrahydrofuran is 1/(30-45) mmol/ml.
Further, the purification adopts column chromatography, wherein the eluent consists of petroleum ether and dichloromethane according to the volume ratio of 8:1.
Further, the powder of carborane derivative was placed in a pressure test chamber for pressure sensing performance testing.
In a further aspect of the invention there is provided the use of the carborane derivative (III) in a pressure sensor, preferably a hydrostatic pressure sensor.
The crystal powder of the carborane derivative (III) of the present invention emits green fluorescence, and the brightness of the crystal increases as the fluorescence brightness increases with increasing pressure (1 atm-1.1 gPa).
The beneficial effects of the invention are as follows:
the crystal powder of the carborane derivative (III) emits green fluorescence under normal pressure, the fluorescence brightness is continuously enhanced along with the pressure increase (1 atm-1.1 gPa), the brightness of the crystal is also continuously enhanced, the problem of force-induced fluorescence quenching of the traditional material is overcome, the force-induced fluorescence enhancement property is presented under lower pressure, and the crystal powder has huge application potential in a pressure sensing system.
Drawings
FIG. 1 is a molecular structure single crystal diagram of a carborane derivative of the present invention;
FIG. 2 is a photograph of fluorescence of carborane derivative crystals in the material of the present invention at a pressure ranging from 1atm to 1.1 gPa;
FIG. 3 is a luminescence spectrum of the carborane derivative (III) crystal of the present invention under a pressure range of 1atm to 1.1 gPa.
Detailed Description
The following description of the present invention will be made more complete and clear in view of the detailed description of the invention, which is to be taken in conjunction with the accompanying drawings that illustrate only some, but not all, of the embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a carborane-based hydrostatic pressure fluorescent sensing material, which is prepared by the following steps:
the synthetic route is as follows:
weighing 4-o-carborane bromobenzene (I), phenanthrene boric acid (II), tetraphenylphosphine palladium and sodium carbonate, and dissolving in tetrahydrofuran; wherein, 4-carborane bromobenzene (I): phenanthreneboronic acid (II): tetraphenylphosphine palladium: sodium carbonate: tetrahydrofuran is 1mmol to 1 to 1.5mmol to 0.08 to 0.1mmol to 0.8 to 1mmol to 30 to 45mL;
heating and stirring to react at 90-100 ℃ for 18-24 h under the protection of nitrogen atmosphere; determining the reaction progress by Thin Layer Chromatography (TLC), extracting the reaction system with water and a dichloromethane system for three times after terminating the reaction, collecting an extraction phase, performing column chromatography purification by using petroleum ether and dichloromethane 8:1 leacheate after spin drying to obtain white powder, namely a target product carborane derivative (III), wherein the molecular weight of 4-carborane bromobenzene (I) is 299g/mol; 222g/mol of phenanthreneboronic acid (II); carborane derivative (III) 779g/mol.
Example 1
A preparation method of a pressure fluorescence sensing material based on carborane comprises the following steps:
0.299g (1 mmol) of 4-carborane bromobenzene (I), 0.222g (1 mmol) of phenanthrene boric acid (II), 0.091g (0.08 mmol) of tetraphenylphosphine palladium and 0.084g (0.8 mmol) of sodium carbonate are weighed and dissolved in 30mL of tetrahydrofuran; heating and stirring at 90 ℃ for reaction for 18h under the protection of nitrogen atmosphere; simultaneously, determining the reaction process by combining Thin Layer Chromatography (TLC), extracting the reaction system with water and a dichloromethane system for three times after terminating the reaction, and then using petroleum ether and dichloromethane eluent with the volume ratio of 8:1 as column chromatography for purification to obtain 0.273g of white powder, wherein the yield is 35%, namely the target product carborane derivative (III).
Characterization data are as follows: 1H NMR (400 MHz, chloroform-d) δ8.84 (d, J=2.0 hz, 1H), 8.74 (d, J=8.1 hz, 1H), 7.97 (d, J=8.2 hz, 1H), 7.92 (dd, J=7.8, 1.6hz, 1H), 7.78 (d, J=7.3 hz, 3H), 7.74 (d, J=1.8 hz, 1H), 7.72 (d, J=2.0 hz, 1H), 7.70-7.65 (m, 1H), 7.63 (d, J=2.4 hz, 2H), 7.61 (d, J=2.2 hz, 1H), 4.02 (s, 1H), 2.74 (d, J=142.5 hz, 10H).
The single crystal structure of the molecule is shown in figure 1, and the carborane derivative (III) prepared by the invention is a brand new structural substance.
Example 2
A preparation method of a pressure fluorescence sensing material based on carborane comprises the following steps:
0.299g (1 mmol) of 4-carborane bromobenzene (I), 0.267g (1.2 mmol) of phenanthrene boric acid (II), 0.091g (0.08 mmol) of tetraphenylphosphine palladium and 0.084g (0.8 mmol) of sodium carbonate are weighed and dissolved in 30mL of tetrahydrofuran; heating and stirring at 90 ℃ for reaction for 18h under the protection of nitrogen atmosphere; simultaneously, the reaction process is determined by combining Thin Layer Chromatography (TLC), after the reaction is stopped, the reaction system is extracted for three times by using water and methylene dichloride system, and then petroleum ether and methylene dichloride 8:1 leaching solution are used for column chromatography purification, so that 0.288g of white powder is obtained, and the yield is 37%, namely the target product carborane derivative (III).
Example 3
A preparation method of a pressure fluorescence sensing material based on carborane comprises the following steps:
0.299g (1 mmol) of 4-carborane bromobenzene (I), 0.244g (1.1 mmol) of phenanthrene boric acid (II), 0.091g (0.8 mmol) of tetraphenylphosphine palladium and 0.084g (0.8 mmol) of sodium carbonate are weighed and dissolved in 40mL of tetrahydrofuran; heating and stirring at 100 ℃ for reaction for 18h under the protection of nitrogen atmosphere; simultaneously, the reaction process is determined by combining Thin Layer Chromatography (TLC), after the reaction is stopped, the reaction system is extracted for three times by using water and methylene dichloride system, and then petroleum ether and methylene dichloride 8:1 leaching solution are used for column chromatography purification, so that 0.280g of white powder is obtained, and the yield is 36%, namely the target product carborane derivative (III).
Example 4
A preparation method of a pressure fluorescence sensing material based on carborane comprises the following steps:
0.299g (1 mmol) of 4-carborane bromobenzene (I), 0.267g (1.2 mmol) of phenanthrene boric acid (II), 0.114g (0.1 mmol) of tetraphenylphosphine palladium and 0.105g (1 mmol) of sodium carbonate are weighed and dissolved in 40mL of tetrahydrofuran; heating and stirring for reaction for 18h at 95 ℃ under the protection of nitrogen atmosphere; simultaneously, determining the reaction progress by combining Thin Layer Chromatography (TLC), extracting the reaction system with water and dichloromethane system for three times after terminating the reaction, and purifying by using petroleum ether and dichloromethane 8:1 leacheate as column chromatography to obtain 0.312g of white powder, wherein the yield is 40%, namely the target product carborane derivative (III).
Example 5
The white target product (III) prepared in example 3 was placed in a pressure chamber and tested for fluorescence spectra under different hydrostatic pressures. As shown in fig. 2, as the hydrostatic pressure increases, the crystal fluorescence intensity increases.
The white target product (III) prepared in example 4 was placed in a pressure chamber and tested for crystal fluorescence under different hydrostatic pressures. As shown in fig. 3, the intensity of the fluorescence spectrum is continuously increased as the hydrostatic pressure increases.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made to these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (6)
1. The hydrostatic pressure fluorescent sensing material based on carborane is characterized in that the hydrostatic pressure fluorescent sensing material is a carborane derivative, and the molecular formula is as follows: c (C) 22 H 24 B 10 The structural formula is shown as formula (III):
2. the method for preparing the hydrostatic pressure fluorescent sensing material according to claim 1, which is characterized in that 4-o-carborane bromobenzene, phenanthrene boric acid, tetraphenylphosphine palladium and sodium carbonate are dissolved in tetrahydrofuran, the mixture is heated and reacted under the protection of nitrogen atmosphere, water and pure methylene dichloride are used for extraction after the reaction is completed, an extraction phase is collected, and the white powder is obtained after drying and purification, namely the target product carborane derivative (III).
3. The preparation method according to claim 2, wherein the molar ratio of the 4-o-carborane bromobenzene, phenanthreneboronic acid, tetraphenylphosphine palladium and sodium carbonate is 1:1.0-1.5:0.08-0.1:0.8-1.0.
4. The preparation method according to claim 2, wherein the molar concentration of the 4-o-carborane bromobenzene and tetrahydrofuran is 1/(30-45) mmol/ml.
5. The method of claim 2, wherein the purification is by column chromatography, wherein the eluent consists of petroleum ether and dichloromethane in a volume ratio of 8:1.
6. Use of carborane derivatives of formula (III) according to claim 1 in pressure sensors.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866716A (en) * | 2017-04-28 | 2017-06-20 | 南京大学 | A kind of carborane derivative as well as preparation method and application thereof |
| CN109575062A (en) * | 2019-01-10 | 2019-04-05 | 济南大学 | Dinaphthyl caborane compounds and its preparation method and application |
| CN109651416A (en) * | 2018-12-19 | 2019-04-19 | 湖州师范学院 | Three fluorescence anti-fake material, preparation method and application based on excitation wavelength dependence |
| CN112851701A (en) * | 2021-01-11 | 2021-05-28 | 吉林大学 | Anthracene-based mechanoluminescence organic material and preparation method and application thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866716A (en) * | 2017-04-28 | 2017-06-20 | 南京大学 | A kind of carborane derivative as well as preparation method and application thereof |
| CN109651416A (en) * | 2018-12-19 | 2019-04-19 | 湖州师范学院 | Three fluorescence anti-fake material, preparation method and application based on excitation wavelength dependence |
| CN109575062A (en) * | 2019-01-10 | 2019-04-05 | 济南大学 | Dinaphthyl caborane compounds and its preparation method and application |
| CN112851701A (en) * | 2021-01-11 | 2021-05-28 | 吉林大学 | Anthracene-based mechanoluminescence organic material and preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| Deshuang Tu,et al.."Highly Emissive Organic Single-Molecule White Emitters by Engineering o-Carborane-Based Luminophores".《Angew. Chem. Int. Ed.》.2017,第56卷第11370 –11374页. * |
| Deshuang Tu,et al.."A carborane-triggered metastable charge transfer state leading to spontaneous recovery of mechanochromic luminescence".《Chem. Commun.》.2016,第52卷第12494--12497页. * |
| Xueyan Wu,et al.."Mechanically triggered reversible stepwise tricolor switching and thermochromism of anthracene-ocarborane dyad".《Chem. Sci.》.2018,第9卷第5270–5277页. * |
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