CN111253206A - Pyrene unit-containing mechanochromic fluorene derivative and preparation method and application thereof - Google Patents
Pyrene unit-containing mechanochromic fluorene derivative and preparation method and application thereof Download PDFInfo
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- CN111253206A CN111253206A CN202010139151.0A CN202010139151A CN111253206A CN 111253206 A CN111253206 A CN 111253206A CN 202010139151 A CN202010139151 A CN 202010139151A CN 111253206 A CN111253206 A CN 111253206A
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- 125000005581 pyrene group Chemical group 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title claims abstract 10
- 239000000463 material Substances 0.000 claims abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 238000004440 column chromatography Methods 0.000 claims description 8
- MWEKPLLMFXIZOC-UHFFFAOYSA-N pyren-1-ylboronic acid Chemical compound C1=C2C(B(O)O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 MWEKPLLMFXIZOC-UHFFFAOYSA-N 0.000 claims description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
- 239000010931 gold Substances 0.000 claims description 5
- 229910052737 gold Inorganic materials 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 230000002441 reversible effect Effects 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000002845 discoloration Methods 0.000 abstract description 2
- 230000015654 memory Effects 0.000 abstract description 2
- 239000011540 sensing material Substances 0.000 abstract description 2
- 150000002220 fluorenes Chemical class 0.000 description 41
- 239000007787 solid Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 14
- 238000005424 photoluminescence Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000005284 excitation Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/62—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing four rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
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- 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
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
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- 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
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- Engineering & Computer Science (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a pyrene unit-containing mechanochromic fluorene derivative and a preparation method and application thereof, belonging to the field of mechanochromic materials. The compound provided by the invention is a novel mechanical color-changing fluorene derivative containing pyrene units and having a mechanochromic property, and the compound also has a reversible mechanochromic property. The high-contrast force-induced discoloration phenomenon is beneficial to becoming a novel high-efficiency force sensing material and is applied to the fields of force sensors, memories, anti-counterfeiting marks and the like.
Description
Technical Field
The invention relates to the technical field of mechanochromic materials, in particular to a pyrene unit-containing mechanochromic fluorene derivative and a preparation method and application thereof.
Background
Force-induced color-changing materials responding to mechanical force have a potential application value in the fields of mechanical sensors, anti-counterfeiting, information storage and the like, thereby arousing extensive research interest of scientific personnel. Under the action of external mechanical force, the optical property of the intelligent material with the mechanochromic characteristic can be changed. To date, a number of pure organic compounds having uv-vis mechanochromic properties have been reported, and the number of organic compounds having near-ir mechanochromic properties is very limited in comparison. This is very helpful for the practical application of mechanochromic materials, since mechanochromic materials with a high solid state luminescence facilitate the realization of mechanochromic materials with a distinct color contrast before and after mechanical grinding. Therefore, it is very interesting to develop intelligent luminescent materials with the preparation and application of the novel trichromatic mechanical color-changing fluorene derivatives containing pyrene units.
Disclosure of Invention
In view of the above, the present invention aims to provide a mechanochromic fluorene derivative containing a pyrene unit, and a preparation method and an application thereof. The pyrene unit-containing mechanochromic fluorene derivative provided by the invention is a novel compound with reversible force-induced color change property.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a pyrene unit-containing mechanochromic fluorene derivative, which has a structure shown in a formula I:
the invention also provides a preparation method of the pyrene unit-containing mechanochromic fluorene derivative, which comprises the following steps:
under the nitrogen atmosphere, carrying out coupling reaction on a fluorene derivative with a structure shown in a formula 2, 1-pyreneboric acid, tetrakistriphenylphosphine palladium gold and potassium carbonate in N, N-dimethylformamide to obtain the pyrene unit-containing mechanochromic fluorene derivative;
preferably, the coupling reaction time is 10-12 hours.
Preferably, the molar ratio of the fluorene derivative having the structure shown in formula 2 to 1-pyreneboronic acid is 1: 2.1-1: 2.2.
Preferably, after the coupling reaction, the method further comprises the steps of sequentially carrying out suction filtration and column chromatography on the obtained coupling reaction product, wherein an eluent for column chromatography is a mixed solvent of petroleum ether and dichloromethane in a volume ratio of 1: 1.
The invention also provides the application of the pyrene unit-containing mechanochromic fluorene derivative prepared by the preparation method in the technical scheme or the pyrene unit-containing mechanochromic fluorene derivative prepared by the preparation method in the technical scheme in preparation of mechanochromic luminescent materials.
The invention provides a pyrene unit-containing mechanochromic fluorene derivative, and the compound provided by the invention is a novel pyrene unit-containing mechanochromic fluorene derivative with mechanochromic property, and the compound also has reversible mechanochromic property. The high-contrast force-induced discoloration phenomenon is beneficial to becoming a novel high-efficiency force sensing material and is applied to the fields of force sensors, memories, anti-counterfeiting marks and the like.
Drawings
FIG. 1 is a nuclear magnetic spectrum of the mechanically discolored fluorene derivative containing pyrene units;
FIG. 2 is a photoluminescence spectrum (excitation wavelength is 365nm) of a solid powder of a mechanically discolored fluorene derivative containing pyrene units, a solid powder after mechanical grinding and a solid powder after grinding and then fumigating by dichloromethane, which are shown in formula I;
FIG. 3 is a photoluminescence fluorescence map (excitation wavelength is 365nm) of a solid powder of a pyrene unit-containing mechanochromic fluorene derivative represented by formula I, a solid powder after mechanical grinding and a solid powder after grinding and then fumigating by dichloromethane, wherein (a) is a photoluminescence fluorescence map of a pyrene unit-containing mechanochromic fluorene derivative represented by formula I, b is a photoluminescence fluorescence map of a mechanical grinding solid powder of a pyrene unit-containing mechanochromic fluorene derivative represented by formula I, and (c) is a photoluminescence fluorescence map of a methylene chloride fumigating solid powder after grinding of a pyrene unit-containing mechanochromic fluorene derivative represented by formula I.
Detailed Description
The invention provides a pyrene unit-containing mechanochromic fluorene derivative, which has a structure shown in a formula I:
the invention also provides a preparation method of the pyrene unit-containing mechanochromic fluorene derivative, which comprises the following steps:
under the nitrogen atmosphere, carrying out coupling reaction on a fluorene derivative with a structure shown in a formula 2, 1-pyreneboric acid, tetrakistriphenylphosphine palladium gold and potassium carbonate in N, N-dimethylformamide to obtain the pyrene unit-containing mechanochromic fluorene derivative;
the reaction equation for preparing the pyrene unit-containing mechanochromic fluorene derivative is shown as the following formula:
in the invention, the coupling reaction time is preferably 10-12 hours, the temperature is preferably room temperature, and no additional heating or cooling is required.
In the invention, the molar ratio of the fluorene derivative having the structure shown in formula 2 to 1-pyreneboronic acid is preferably 1: 2.1-1: 2.2. In the present invention, the source of the fluorene derivative having the structure represented by formula 2 and 1-pyreneboronic acid is not particularly limited, and commercially available products known to those skilled in the art may be used.
In the invention, after the coupling reaction, the method preferably further comprises the steps of sequentially carrying out suction filtration and column chromatography on the obtained coupling reaction product, wherein an eluent for column chromatography is a mixed solvent of petroleum ether and dichloromethane in a volume ratio of 1: 1.
In a specific embodiment of the present invention, it is preferable that 0.64g (1.92mmol) of the fluorene derivative having the structure represented by formula 2, 1.0g (4.05mmol) of 1-pyreneboronic acid, and tetrakistriphenylphosphine palladium gold Pd (PPh)3)4(0.192mmol), potassium carbonate (3.0g) and 30mL of N, N-dimethylformamide were added and the mixture was evacuated and charged with N2And reacting at room temperature for 10-12 hours in a subsequent reaction container, after the reaction is finished, performing suction filtration, and performing column chromatography to separate and elute a mixed solvent of petroleum ether and dichloromethane in a volume ratio of 1:1) to obtain the pyrene unit-containing mechanochromic fluorene derivative.
The invention also provides the application of the pyrene unit-containing mechanochromic fluorene derivative prepared by the preparation method in the technical scheme or the pyrene unit-containing mechanochromic fluorene derivative prepared by the preparation method in the technical scheme in preparation of mechanochromic luminescent materials.
In order to further illustrate the present invention, the mechanochromic fluorene derivatives containing pyrene units and the preparation method and application thereof provided by the present invention are described in detail below with reference to examples, but they should not be construed as limiting the scope of the present invention.
Example 1
0.64g (1.92mmol) of fluorene derivative with a structure shown in formula 2, 1.0g (4.05mmol) of 1-pyreneboronic acid and tetrakistriphenylphosphine palladium gold Pd (PPh)3)4(0.192mmol), potassium carbonate (3.0g) and 30mL of N, N-dimethylformamide were added and the mixture was evacuated and charged with N2And reacting at room temperature for 10-12 hours in a subsequent reaction container, after the reaction is finished, performing suction filtration, and performing column chromatography to separate and elute a mixed solvent of petroleum ether and dichloromethane at a volume ratio of 1:1) to obtain 0.46g of the pyrene unit-containing mechanochromic fluorene derivative.
The structure of the mechanically discolored fluorene derivative containing pyrene units is determined by nuclear magnetic hydrogen spectroscopy, fig. 1 is a nuclear magnetic spectrum of the mechanically discolored fluorene derivative containing pyrene units, m/z is 578.20, found 578.5, and as can be seen from fig. 1, the structure of the mechanically discolored fluorene derivative containing pyrene units prepared by the invention is shown as a formula I.
Fig. 2 is a photoluminescence spectrogram (excitation wavelength is 365nm) of solid powder of a pyrene unit-containing mechanochromic fluorene derivative shown in formula I, solid powder after mechanical grinding and solid powder after grinding and then fumigating with dichloromethane, and it can be seen from fig. 2 that after the solid sample of the pyrene unit-containing mechanochromic fluorene derivative shown in formula I is ground by mechanical force, a photoluminescence signal is subjected to red shift, and then further fumigating with dichloromethane solvent, and the photoluminescence signal is generated and returns to an initial state.
FIG. 3 is a photoluminescence fluorescence (excitation wavelength is 365nm) of a solid powder of a mechanically discolored fluorene derivative containing pyrene units, a solid powder after mechanical grinding and a solid powder after grinding and then fumigating by dichloromethane shown in formula I, the fluorescent picture is restored to the state of (a) after the dichloromethane fumigation, and as can be seen from fig. 3, the mechanical color-changing fluorene derivative containing the pyrene unit shown in the formula I shows rare bicolor mechanical color-changing property.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner. It should be noted that, for those skilled in the art, without departing from the principle of the present invention, several improvements and modifications can be made, and these improvements and modifications should also be construed as the protection scope of the present invention.
Claims (6)
1. A pyrene unit-containing mechanochromic fluorene derivative is characterized by having a structure shown in formula I:
2. the method for producing a mechanochromic fluorene derivative containing a pyrene unit according to claim 1, comprising the steps of:
under the nitrogen atmosphere, carrying out coupling reaction on a fluorene derivative with a structure shown in a formula 2, 1-pyreneboric acid, tetrakistriphenylphosphine palladium gold and potassium carbonate in N, N-dimethylformamide to obtain the pyrene unit-containing mechanochromic fluorene derivative;
3. the method according to claim 2, wherein the coupling reaction time is 10 to 12 hours.
4. The preparation method according to claim 2, wherein the molar ratio of the fluorene derivative having the structure represented by formula 2 to 1-pyreneboronic acid is 1:2.1 to 1: 2.2.
5. The preparation method according to claim 2, further comprising performing suction filtration and column chromatography on the obtained coupling reaction product in sequence after the coupling reaction, wherein an eluent for the column chromatography is a mixed solvent of petroleum ether and dichloromethane in a volume ratio of 1: 1.
6. Use of the pyrene unit-containing mechanochromic fluorene derivative of claim 1 or the pyrene unit-containing mechanochromic fluorene derivative prepared by the preparation method of any one of claims 2 to 5 in preparation of a mechanochromic luminescent material.
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| CN202010139151.0A CN111253206A (en) | 2020-03-03 | 2020-03-03 | Pyrene unit-containing mechanochromic fluorene derivative and preparation method and application thereof |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007227152A (en) * | 2006-02-23 | 2007-09-06 | Idemitsu Kosan Co Ltd | White color group organic electroluminescent element |
| JP2007230887A (en) * | 2006-02-28 | 2007-09-13 | Idemitsu Kosan Co Ltd | Heterocyclic perylene derivative and organic electroluminescent device |
| CN101331627A (en) * | 2005-11-07 | 2008-12-24 | 出光兴产株式会社 | Organic electroluminescent element |
| CN107109212A (en) * | 2014-11-18 | 2017-08-29 | 国立研究开发法人科学技术振兴机构 | Power mutagens color luminescent material, make the power mutagens color luminescent material be crosslinked obtained by power mutagens chromoresin and the manufacture method of the two |
| CN108947933A (en) * | 2018-08-17 | 2018-12-07 | 天津师范大学 | The diethyl terephthalate class compound and preparation method and purposes of power mutagens color |
-
2020
- 2020-03-03 CN CN202010139151.0A patent/CN111253206A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101331627A (en) * | 2005-11-07 | 2008-12-24 | 出光兴产株式会社 | Organic electroluminescent element |
| JP2007227152A (en) * | 2006-02-23 | 2007-09-06 | Idemitsu Kosan Co Ltd | White color group organic electroluminescent element |
| JP2007230887A (en) * | 2006-02-28 | 2007-09-13 | Idemitsu Kosan Co Ltd | Heterocyclic perylene derivative and organic electroluminescent device |
| CN107109212A (en) * | 2014-11-18 | 2017-08-29 | 国立研究开发法人科学技术振兴机构 | Power mutagens color luminescent material, make the power mutagens color luminescent material be crosslinked obtained by power mutagens chromoresin and the manufacture method of the two |
| CN108947933A (en) * | 2018-08-17 | 2018-12-07 | 天津师范大学 | The diethyl terephthalate class compound and preparation method and purposes of power mutagens color |
Non-Patent Citations (2)
| Title |
|---|
| GUOFENG ZHANG ET AL: "Efficient green-red piezofluorochromism of bisanthracene-modified dibenzfulvene", 《RSC ADVANCES》 * |
| 刘庆俭著: "《有机化学上册》", 30 November 2018 * |
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