CN116789518A - 2-position phenyl substituted triarylethylene photochromic material and preparation method and application thereof - Google Patents
2-position phenyl substituted triarylethylene photochromic material and preparation method and application thereof Download PDFInfo
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- CN116789518A CN116789518A CN202310673293.9A CN202310673293A CN116789518A CN 116789518 A CN116789518 A CN 116789518A CN 202310673293 A CN202310673293 A CN 202310673293A CN 116789518 A CN116789518 A CN 116789518A
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- 239000000463 material Substances 0.000 title claims abstract description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 239000005977 Ethylene Substances 0.000 claims abstract description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- 238000003860 storage Methods 0.000 claims abstract description 12
- 230000003287 optical effect Effects 0.000 claims abstract description 9
- 239000000654 additive Substances 0.000 claims abstract description 8
- 230000000996 additive effect Effects 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000007639 printing Methods 0.000 claims abstract description 8
- 230000001105 regulatory effect Effects 0.000 claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 8
- 238000005034 decoration Methods 0.000 claims abstract description 7
- 238000012632 fluorescent imaging Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 230000009471 action Effects 0.000 claims description 12
- 150000001491 aromatic compounds Chemical class 0.000 claims description 12
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- SBWKQMCGTSWDPE-UHFFFAOYSA-N 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(F)C=C1 SBWKQMCGTSWDPE-UHFFFAOYSA-N 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 10
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 9
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 238000001308 synthesis method Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 7
- 230000004048 modification Effects 0.000 claims description 7
- 238000012986 modification Methods 0.000 claims description 7
- ALMFIOZYDASRRC-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(F)(F)F)C=C1 ALMFIOZYDASRRC-UHFFFAOYSA-N 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical group BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 5
- 150000008366 benzophenones Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- 238000007239 Wittig reaction Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 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 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 2
- 230000004044 response Effects 0.000 abstract description 8
- 238000012984 biological imaging Methods 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 11
- 238000002835 absorbance Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 230000008859 change Effects 0.000 description 9
- -1 diaryl ethylene compound Chemical class 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 7
- 238000005286 illumination Methods 0.000 description 7
- 238000000985 reflectance spectrum Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 230000004298 light response Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- MKYQPGPNVYRMHI-UHFFFAOYSA-N Triphenylethylene Chemical group C=1C=CC=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 MKYQPGPNVYRMHI-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000013461 design Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000008033 biological extinction Effects 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 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 description 2
- 238000006349 photocyclization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- GQFITODJWOIYPF-UHFFFAOYSA-N 1-(bromomethyl)-2-iodobenzene Chemical compound BrCC1=CC=CC=C1I GQFITODJWOIYPF-UHFFFAOYSA-N 0.000 description 1
- 238000010146 3D printing Methods 0.000 description 1
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- HCIMXTXCDVBLOA-UHFFFAOYSA-N [4-(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC=C(C(F)(F)F)C=C1 HCIMXTXCDVBLOA-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001988 diarylethenes Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
-
- 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
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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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a 2-position phenyl substituted triaryl ethylene photochromic material, a preparation method and application thereof, and the prepared photochromic material can realize remarkable regulation and control on the photochromic performance of triaryl ethylene by regulating the steric hindrance and electron withdrawing capacity of a 2-position substituent. The material has the advantages of low raw material price, simple synthesis steps, quick response and excellent fatigue resistance, so that the triaryl ethylene material which has single original stimulus response and no obvious rule between the structure and the photochromic property is improved, and the material is expected to have wide application prospect in the fields of high-speed information storage, quick biological imaging and the like. In addition, the invention adjusts the photochromic color saturation through different steric hindrance and electron withdrawing substituents, and is suitable for the fields of anti-counterfeiting, photosensitive decoration, optical information storage, single-molecule logic gate, super-resolution fluorescent imaging, green printing, additive manufacturing and the like.
Description
Technical Field
The invention belongs to the technical field of organic photochromic materials, and relates to a 2-bit phenyl substituted triaryl vinyl photochromic material, a preparation method and application thereof, in particular to a 2-bit phenyl substituted triaryl vinyl photochromic material, a preparation method thereof and application thereof in the fields of anti-counterfeiting, photosensitive decoration, optical information storage, single-molecule logic gate, super-resolution fluorescent imaging, green printing, additive manufacturing and the like.
Background
Photochromic refers to a phenomenon in which a chemical substance undergoes a reversible color change upon irradiation with light of a certain wavelength (Pure and Applied chemistry 2001, 73-4, 639-665), during which there is a significant change in the absorption spectrum. The photochromic process is a reversible chemical change, and some substances undergo irreversible reactions after illumination, resulting in a color change, which is not within the photochromic category. In recent years, the photochromic material has wide application in the fields of photosensitive decoration, optical information storage, single-molecule logic gates, photoelectric devices and the like, and has important application prospects in the fields of super-resolution fluorescent imaging, green printing, additive manufacturing and the like. The photochromic materials are classified into organic, inorganic and organic-inorganic hybrid, and compared with inorganic photochromic materials, the organic photochromic materials have the advantages of easy modification and processing, excellent fatigue resistance, capability of being prepared into flexible devices, good biocompatibility and the like, and become the focus of research on future development of the photochromic materials.
Organic photochromic materials can be divided into four classes according to molecular structure, i.e. spiropyran, diarylethene, azobenzene and fulgide. The compound containing azobenzene molecules is a light response material based on cis-reflective isomerization, and macroscopically can generate shrinkage, bending and other photo-induced deformation phenomena, but has small difference of color change before and after illumination and poor fatigue resistance, which is not beneficial to practical application in the field of photochromism. The spiropyran compound undergoes isomerism and rearrangement of molecules before and after ultraviolet light irradiation, the color of the compound is changed from colorless to colored, but spiropyran is easy to be oxidized and degraded, so that the stability and fatigue resistance of the material are reduced, and the practical application of the material is limited. The diaryl ethylene compound can change the color of the reversible photocyclization reaction before and after ultraviolet irradiation, has excellent photochromic property, good thermal stability and fatigue resistance, but only cis-conformation diaryl ethylene can be photochromic, so that the cis-conformation is fixed by bridging five-membered rings on an olefinic bond, the molecular structure of the diaryl ethylene is complex and difficult to synthesize, and the application is limited. Based on this, the present invention proposes to design the triarylethylene structure to simplify the photochromic molecule synthesis procedure.
At present, the triaryl vinyl compound reported by Yu et al mostly introduces different substituents at the 4-position of benzene ring at the same side of alkene hydrogen to adjust the photochromic performance (J.Mater.chem.C, 2021,9,11126-11131), the reported compound has single structure and photo-response property, and no obvious rule exists between the structure and the photochromic property. The 4-position triaryl vinyl compound is also reported to be used for 3D printing (Research, 2022, 9834140), and other substituted positions of the triaryl are relatively less researched, but the 2-position substitution has a significant effect on the property adjustment of the triaryl vinyl photochromic molecules, and is expected to realize significant adjustment and control on the photochromic property of the triaryl vinyl by adjusting the steric hindrance and electron withdrawing capacity of the 2-position substituent.
Disclosure of Invention
Technical problem to be solved
In order to avoid the defects of the prior art, the invention provides a 2-position phenyl substituted triaryl ethylene photochromic material, a preparation method and application thereof, and solves the technical problem that the researches on other substitution positions except for the 4-position of triaryl ethylene are relatively less.
The invention aims to design and synthesize a series of novel triphenylethylene compounds with simple synthesis process and high yield by introducing phenyl, 4-fluorophenyl and 4- (trifluoromethyl) benzene substituent groups with different electron withdrawing capacities and relatively smaller steric hindrance into the 2-position of benzene rings on the same side as alkene hydrogen in triarylethylene.
The second purpose of the invention is to research the influence of the 2-substituent on the photochromic property of the triaryl vinyl compound by means of ultraviolet-visible absorption spectrum, time resolution spectrum, X-ray diffraction, single crystal analysis and the like, and provide a reasonable molecular design strategy to realize the regulation and control of the photochromic property of the triaryl vinyl compound.
The third purpose of the invention is to apply the 2-position phenyl substituted triaryl ethylene photochromic material with quick light response to the fields of high-speed information storage, quick biological imaging, green printing, anti-counterfeiting, additive manufacturing and the like.
Technical proposal
A2-position phenyl substituted triaryl ethylene photochromic material is characterized by having a molecular structural general formula:
wherein R0 and R1 are different modification groups, R1 is selected from fluorine, and R0 is selected from benzene, 4-fluorobenzene or 4- (trifluoromethyl) benzene.
A method for synthesizing the 2-position phenyl substituted triarylvinyl photochromic material according to claim 1, which is characterized by comprising the steps of: phenyl, 4-fluorobenzene or 4- (trifluoromethyl) benzene is introduced into the 2-position of the triarylethylene photochromic material, and the steric hindrance and electron withdrawing capability of the 2-position substituent are regulated, so that the triarylethylene photochromic material has pink, pink or deep pink respectively after ultraviolet irradiation relative to a compound with the phenyl, 4-fluorobenzene or 4- (trifluoromethyl) benzene introduced into the 2-position.
The synthesis method according to claim 2, characterized in that: the method comprises the following steps:
step 1: preparing a phosphorus ylide reagent by reacting an aromatic ring, an aromatic heterocycle or a derivative thereof with triethyl phosphite, wherein one end of the aromatic ring contains a benzyl bromide substituent;
step 2: adding carbonyl, tetrahydrofuran solution and potassium tert-butoxide into a phosphorus ylide reagent by adopting a Witting reaction, and reacting under the action of strong alkali potassium tert-butoxide to obtain a triaryl vinyl skeleton; the pH of the solution was 13;
step 3: through Suzuki coupling reaction, the triaryl vinyl skeleton is respectively reacted with phenylboronic acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid under the action of palladium catalyst to obtain the target compound, namely the 2-phenyl substituted triaryl vinyl photochromic material.
The reaction mole ratio of the aromatic ring, the aromatic heterocycle or the derivative thereof with one end containing the benzyl bromide substituent group in the step 1 to the triethyl phosphite is 1:1.5.
The molar ratio of the phosphorus ylide reagent to the carbonyl in the step 2 is 1:1.2.
The molar ratio of the triaryl vinyl skeleton to phenylboronic acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid is 1:0.5.
The other synthesis method is characterized by comprising the following steps:
step 1): the diphenyl ketone derivative and an aromatic compound or a heterocyclic compound containing triethyl phosphite group are subjected to Wittig reaction in tetrahydrofuran solution under the action of potassium tert-butoxide to obtain difluoro substituent;
step 2): the difluoro substituent is respectively mixed with an aromatic compound or heterocyclic compound containing boric acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid pinacol borate ester group, and under the action of potassium carbonate in tetrahydrofuran solution, the target compound, namely the 2-position phenyl substituted triaryl ethylene photochromic material is obtained through catalysis of tetraphenylphosphine palladium.
The molar ratio of the aromatic compound containing triethyl phosphite to the benzophenone derivative in the step 1) is 1:1.2.
The molar ratio of difluoro substituent to aromatic compound or heterocyclic compound containing boric acid or pinacol borate ester group in the step 2) is 1:0.5.
The application of the 2-position phenyl substituted triaryl vinyl photochromic material is characterized in that: the fluorescent dye is used in the fields of anti-counterfeiting, photosensitive decoration, optical information storage, single-molecule logic gate, super-resolution fluorescent imaging, green printing and additive manufacturing.
Advantageous effects
The 2-position phenyl substituted triaryl ethylene photochromic material, the preparation method and the application thereof provided by the invention can realize remarkable regulation and control on the photochromic performance of triaryl ethylene by regulating the steric hindrance and electron withdrawing capacity of the 2-position substituent. The material has the advantages of low raw material price, simple synthesis steps, quick response and excellent fatigue resistance, so that the triaryl ethylene material which has single original stimulus response and no obvious rule between the structure and the photochromic property is improved, and the material is expected to have wide application prospect in the fields of high-speed information storage, quick biological imaging and the like. In addition, the invention adjusts the photochromic color saturation through different steric hindrance and electron withdrawing substituents, and is suitable for the fields of anti-counterfeiting, photosensitive decoration, optical information storage, single-molecule logic gate, super-resolution fluorescent imaging, green printing, additive manufacturing and the like.
According to the invention, phenyl, 4-fluorobenzene and 4- (trifluoromethyl) benzene are introduced into the 2-position of the triarylethylene photochromic material, the photochromic performance of triarylethylene is obviously regulated and controlled by regulating the steric hindrance and electron withdrawing capacity of a 2-position substituent, and the defect that most of triarylethylene compounds are used for regulating the photochromic performance by introducing different substituents into the 4-position of benzene rings on the same side of alkene hydrogen is overcome. Lays a foundation for the deep research on how the substituent affects the photochromic performance of the triaryl vinyl compound.
The series of the triphenylethylene derivatives have fluorescence switch property, the luminous intensity of the compounds is reduced along with the increase of ultraviolet irradiation time, and the compounds can be restored to an initial state after the irradiation is stopped. Meanwhile, the compound shows quick light response on the photochromic property, and the quick light response material is expected to be used in the fields of high-speed information storage, biological imaging and the like.
According to the invention, electron withdrawing groups are introduced to stabilize the closed-loop structure of the compound, so that the saturated absorbance of the closed-loop isomer is improved, and the photochromic efficiency is further improved. The invention provides a reasonable molecular design strategy for developing functional materials with rapid response characteristics and high saturated absorbance.
The compound of the invention can also have good photochromic property in crystalline state, and crystal molecules are not usually provided with photochromic property due to ordered arrangement, but when the compound of the invention finds that substituent steric hindrance is small through single crystal analysis, the molecules are loosely arranged in space, and the compound is easy to twist in the molecule when being excited by ultraviolet light, so that the photochromic phenomenon is generated in the crystal state.
Drawings
FIG. 1 is a graph of the UV-visible absorption spectra of three end products of the invention in methylene chloride solution (1.0X10-5M). The absorption peaks of the three compounds were located at 304nm, 304nm and 305nm, respectively. The black line is the uv-vis absorption spectrum of the target product example 1, the dark gray line is the uv-vis absorption spectrum of the target product example 2, and the light gray line is the uv-vis absorption spectrum of the target product example 3.
FIG. 2 is a photograph of time resolved reflectance spectra of three end product powders of the present invention during photochromic recovery and their color change before and after powder illumination. The different absorbance values of the time resolved spectra represent the color saturation of the three compounds, with the absorbance of the three compounds increasing progressively, with the absorbance of example 3 being the largest and the color the deepest. (a) is the time-resolved reflectance spectrum of example 1, (b) is the time-resolved reflectance spectrum of example 2, and (c) is the time-resolved reflectance spectrum of example 3.
FIG. 3 is a photochromic cycle chart of three end product powders of the present invention. The photochromic cycle performance can reflect the fatigue resistance of the materials, and the cycle times of the three materials are more than 20 times, so that the fatigue resistance is proved to be strong. (a) is a cycle chart of example 1, (b) is a cycle chart of example 2, and (c) is a cycle chart of example 3.
Detailed Description
The invention will now be further described with reference to examples, figures:
the molecular general formula of the 2-position phenyl substituted triarylethylene photochromic material is shown as the general formula (1):
general formula (1):
wherein R0 and R1 are modification groups, R0 and R1 are different, the modification groups R1 in the structure are selected from fluorine, and R0 is selected from benzene, 4-fluorobenzene and 4- (trifluoromethyl) benzene.
The synthesis method comprises the following steps: phenyl, 4-fluorobenzene or 4- (trifluoromethyl) benzene is introduced into the 2-position of the triarylethylene photochromic material, and the steric hindrance and electron withdrawing capability of the 2-position substituent are regulated, so that the triarylethylene photochromic material has pink, pink or deep pink respectively after ultraviolet irradiation relative to a compound with the phenyl, 4-fluorobenzene or 4- (trifluoromethyl) benzene introduced into the 2-position.
One of the synthesis methods is as follows:
step 1: reacting an aromatic ring, an aromatic heterocycle or a derivative thereof with triethyl phosphite (80-100 degrees, example 85 degrees) with one end containing a benzyl bromide substituent to prepare a phosphorus ylide reagent; general SN 2 Reacting;
the ratio of the phosphorus ylide reagent to the carbonyl in the step 2 is 1:1.2.
Step 2: adding carbonyl, tetrahydrofuran solution and potassium tert-butoxide (ice bath, example 0 ℃) into a phosphorus ylide reagent by adopting a Witting reaction, and reacting under the action of strong alkali potassium tert-butoxide to prepare a triaryl vinyl skeleton; the pH of the solution was 13;
step 3: suzuki coupling reaction (80-100 degrees, example 85 degrees) is adopted, and the triaryl ethylene skeleton is respectively reacted with phenylboric acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboric acid under the action of palladium catalyst to obtain the target compound, namely the 2-position phenyl substituted triaryl ethylene photochromic material.
The ratio of the triaryl vinyl skeleton to phenylboronic acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid is 1:0.5.
The second synthesis method is as follows:
step 1): benzophenone derivatives and aromatic compounds or heterocyclic compounds containing triethyl phosphite groups are subjected to Wittig reaction in tetrahydrofuran solution under the action of potassium tert-butoxide to obtain difluoro substituents (80-100 ℃ C., example 85 ℃ C.);
the ratio of the aromatic compound containing triethyl phosphite to the benzophenone derivative in the step 1) is 1:1.2.
Step 2): the difluoro substituent is respectively mixed with an aromatic compound or heterocyclic compound containing boric acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid pinacol borate ester group, and under the action of potassium carbonate in tetrahydrofuran solution, the target compound, namely the 2-position phenyl substituted triaryl ethylene photochromic material is obtained through catalysis of tetraphenylphosphine palladium.
The reaction ratio of the difluoro substituent in the step 2) and the aromatic compound or the heterocyclic compound containing boric acid or pinacol boric acid ester group is 1:0.5.
The present invention will be further illustrated by the following specific examples of embodiments, but the present invention is not limited to these specific examples.
Example 1:
(1) Synthesis of intermediate [ 4,4' - (2- (2-iodophenyl) ethylene-1, 1-diyl) difluorobenzene ]
To a 250mL two-necked flask under argon atmosphere were added 2-iodobenzyl bromide (2.00 g,6.74 mmol) and triethyl phosphite (1.68 g,10.10 mmol), and after refluxing at 85℃for 6 hours, the heating was stopped to obtain phosphorus ylide reagent diethyl 2-iodobenzene phosphate. Tetrahydrofuran (50 mL) and 4,4' -difluorobenzophenone (1.78 g,8.08 mmol) were then added to the flask in an ice-water bath, and after the drug was completely dissolved, potassium tert-butoxide (2.27 g,20.21 mmol) was slowly added, and the reaction was stopped after stirring at room temperature for 3 hours. The reaction solution was concentrated by distillation under reduced pressure, and the extract was separated with methylene chloride and saturated brine, and the organic phase was collected and dried. The crude product was purified by silica gel column chromatography, and the eluent was n-hexane. 1.95g of pale yellow solid was obtained, and the yield was 69.14%.1H NMR (500 MHz, CDCl 3) delta 7.82 (d, J=7.9 Hz, 1H), 7.31 (dd, J=7.1, 5.5Hz, 2H), 7.25 (d, J=0.9 Hz, 1H), 7.07-6.97 (m, 5H), 6.91 (t, J=8.3 Hz, 2H), 6.84-6.76 (m, 3H).
(2) Synthesis of target product example 1
To a 250mL two-necked flask under argon atmosphere were added the intermediate [ 4,4' - (2- (2-iodophenyl) ethylene-1, 1-diyl) difluorobenzene ] (1.89 g,4.51 mmol) and phenylboronic acid (0.50 g,4.10 mmol), followed by tetrahydrofuran (50 mL), aqueous potassium carbonate (4.1M, 3 mL) and tetrakis (triphenylphosphine) palladium (0.05 g,0.06 mmol) as catalyst, and the reaction was stopped after refluxing at 85℃for 18 h. The reaction solution was concentrated by distillation under reduced pressure, and the extract was separated with methylene chloride and saturated brine, and the organic phase was collected and dried. The crude product was purified by silica gel column chromatography, and the eluent was n-hexane. 0.86g of white solid was obtained in 56.95% yield. 1H NMR (500 MHz, CDCl 3) delta 7.38-7.32 (m, 4H), 7.31-7.26 (m, 2H), 7.22 (td, J=7.5, 1.0Hz, 1H), 7.18-7.14 (m, 2H), 7.09-7.01 (m, 3H), 6.99 (d, J=7.8 Hz, 1H), 6.97-6.89 (m, 4H), 6.72 (s, 1H).
The product of this example was formulated to a concentration of 1.0X10 -5 M dichloromethane solution, the absorption peak of the compound is 304nm, and the corresponding molar extinction coefficient is 2.06×10 4 . The ultraviolet-visible absorption spectra of the compounds in methylene chloride solution are shown in the blue line of fig. 1.
The product of the embodiment has photochromic property in amorphous state under the irradiation of 365nm LED ultraviolet light source, the white powder gradually changes into pink, and the reflection spectrum gradually increases at the low energy absorption band of about 511nm due to the increase of the intramolecular conjugation; when the light was stopped, the color of the compound quickly recovered to white within 5 seconds. The time-resolved reflectance spectrum and the photo before and after powder illumination during the photochromic recovery are shown in fig. 3 (a).
The product of this example reached steady state under ultraviolet irradiation for 2s and recovered to its original state within 5s, and the fatigue resistance of the material was tested by drawing a photochromic cycle chart by collecting the highest and lowest points of the compound at the maximum absorption wavelength. The photochromic cycle chart is measured as shown in fig. 2 (a). After the compound is alternately irradiated by ultraviolet light and visible light for 20 times, the photochromic strength of the compound is not obviously weakened, and the compound shows good reversibility.
Example 2:
the objective compound, example 2, was synthesized with reference to step (2) of example 1 by substituting 4-fluorophenylboronic acid pinacol ester for phenylboronic acid. The crude reaction product was purified by silica column chromatography to give 0.95g of a white solid in 54.68% yield. 1H NMR (500 MHz, CDCl 3) delta 7.30-7.27 (m, 2H), 7.23 (qd, J=7.8, 1.4Hz, 2H), 7.18-7.14 (m, 2H), 7.09 (td, J=7.6, 1.8Hz, 1H), 7.04-6.89 (m, 9H), 6.68 (s, 1H).
The product of this example was formulated to a concentration of 1.0X10 -5 M dichloromethane solution, the absorption peak of the compound is 304nm, and the corresponding molar extinction coefficient is 1.80×10 4 . The ultraviolet-visible absorption spectra of the compounds in methylene chloride solution are shown in fig. 1 as black lines.
The product of the embodiment has photochromic property in an amorphous state under the irradiation of 365nm LED ultraviolet light source, and the compound gradually changes from white powder to pink, and the reflection spectrum gradually increases at the low-energy absorption band of about 509nm due to the increase of the intramolecular conjugation; when the light was stopped, the color of the compound quickly recovered to white within 6 s. The time-resolved reflectance spectrum and the photo before and after powder illumination during the photochromic recovery are shown in fig. 3 (b).
The product of this example reached steady state under ultraviolet irradiation for 4s and recovered to its original state within 6s, and the fatigue resistance of the material was tested by drawing a photochromic cycle chart by collecting the highest and lowest points of the compound at the maximum absorption wavelength. The photochromic cycle chart is measured as shown in fig. 2 (b). After the compound is alternately irradiated by ultraviolet light and visible light for 20 times, the photochromic strength of the compound is not obviously weakened, and the compound shows good reversibility.
Example 3:
the objective compound, example 3, was synthesized with reference to step (2) of example 1 using 4- (trifluoromethyl) phenylboronic acid instead of phenylboronic acid. The crude reaction product was purified by silica column chromatography to give 1.17g of a white solid in 63.59% yield. 1H NMR (500 MHz, CDCl 3) delta 7.56 (d, J=8.1 Hz, 2H), 7.40 (d, J=8.0 Hz, 2H), 7.24 (t, J=3.7 Hz, 2H), 7.18-7.13 (m, 3H), 7.08 (d, J=7.7 Hz, 1H), 6.99-6.93 (m, 2H), 6.93-6.85 (m, 4H), 6.70 (s, 1H).
The product of this example was formulated to a concentration of 1.0X10 -5 M dichloromethane solution, the absorption peak of the compound is 305nm, and the corresponding molar extinction coefficient is 1.80×10 4 . The ultraviolet-visible absorption spectrum of the compound in methylene chloride solution is shown in the red line of fig. 1.
The product of the embodiment has photochromic property under the irradiation of 365nm LED ultraviolet light source, the compound gradually changes from white powder to dark pink, and the reflection spectrum gradually increases at the low-energy absorption band of 509nm due to the increase of the intramolecular conjugation; when the light was stopped, the color of the compound quickly recovered to white within 52 s. In addition, the powder of example 3 was irradiated with an ultraviolet lamp for 2s, and its degree of photochromism was beyond the saturated absorbance of example 2. The time-resolved reflectance spectrum and the photo before and after powder illumination during the photochromic recovery are shown in fig. 3 (c).
The product of this example reached steady state at 15s under ultraviolet irradiation and recovered to its original state within 52s, and the fatigue resistance of the material was tested by plotting a photochromic cycle chart by collecting the highest and lowest points of the compound at the maximum absorption wavelength. The photochromic cycle chart is measured as shown in fig. 2 (c). After the compound is alternately irradiated by ultraviolet light and visible light for 20 times, the photochromic strength of the compound is not obviously weakened, and the compound shows good reversibility.
By comparing the photochromic properties of the three examples of the present invention, it was found that as the electron withdrawing ability of the substituents was enhanced, the saturated absorbance of the compound was gradually increased, the photochromic color was changed from pink to pink and finally to deep pink, the compound reached a steady state within 2s, 4s and 15s of ultraviolet irradiation, and was restored to the original state within 5s, 6s and 52s, respectively. This is because three compounds have a low energy barrier during the photochromic process, allowing the compounds to rapidly undergo a photocyclization reaction upon illumination. And example 3 exhibited extremely high saturated absorbance under short-time ultraviolet irradiation because trifluoromethyl group having strong electron withdrawing ability was introduced into the triphenylethylene structure, resulting in a remarkable improvement in the degree of photochromic of compound example 3. The photochromic cycle test shows that the photochromic strength of the three compounds is not obviously reduced after the three compounds are alternately irradiated by ultraviolet light and visible light for 20 times, and the three compounds show good reversibility.
Table 1: the maximum fluorescence emission wavelength, color change response time, recovery time, maximum color change UV absorption wavelength and number of photochromic cycles of the final product in the solid in each example
Note that: the emission spectrum and the cycle performance of the solid are measured by a marine optical QE65PRO spectrometer matched with a marine optical R600-125F reflection probe.
In summary, in the invention, a series of triphenylethylene derivatives are designed and synthesized by introducing benzene, 4-fluorobenzene and 4- (trifluoromethyl) benzene substituent groups with relatively small steric hindrance into the 2-position of benzene ring on the same side of hydrogen bond in the triphenylethylene. The rapid light response characteristics of the three compounds are researched through ultraviolet-visible absorption spectrum and time-resolved ultraviolet-visible reflection spectrum, and the rapid light response material is expected to have wide application prospects in the fields of high-speed information storage, rapid biological imaging and the like. Inventive example 3 exhibited excellent photochromic properties because the introduction of an electron withdrawing group can stabilize the closed-loop structure of the compound, thereby improving the photochromic efficiency of the compound. Therefore, the trifluoromethyl substituent with strong electron withdrawing capability is introduced into the triaryl ethylene structure, so that the saturated absorbance of the closed-loop isomer can be remarkably improved, and a reasonable molecular design strategy is provided for developing functional materials with quick response characteristics and high saturated absorbance. The preparation method disclosed by the invention is simple in process, and is suitable for application in the fields of anti-counterfeiting, photosensitive decoration, optical information storage, single-molecule logic gates, super-resolution fluorescent imaging, green printing, additive manufacturing and the like. In the above, those skilled in the art can make other corresponding changes and modifications according to the technical solutions and technical ideas of the present invention, and all such changes and modifications shall fall within the scope of the claims of the present invention.
Claims (10)
1. A2-position phenyl substituted triaryl ethylene photochromic material is characterized by having a molecular structural general formula:
wherein R0 and R1 are different modification groups, R1 is selected from fluorine, and R0 is selected from benzene, 4-fluorobenzene or 4- (trifluoromethyl) benzene.
2. A method for synthesizing the 2-position phenyl substituted triarylvinyl photochromic material according to claim 1, which is characterized by comprising the steps of: phenyl, 4-fluorobenzene or 4- (trifluoromethyl) benzene is introduced into the 2-position of the triarylethylene photochromic material, and the steric hindrance and electron withdrawing capability of the 2-position substituent are regulated, so that the triarylethylene photochromic material has pink, pink or deep pink respectively after ultraviolet irradiation relative to a compound with the phenyl, 4-fluorobenzene or 4- (trifluoromethyl) benzene introduced into the 2-position.
3. The synthesis method according to claim 2, characterized in that: the method comprises the following steps:
step 1: preparing a phosphorus ylide reagent by reacting an aromatic ring, an aromatic heterocycle or a derivative thereof with triethyl phosphite, wherein one end of the aromatic ring contains a benzyl bromide substituent;
step 2: adding carbonyl, tetrahydrofuran solution and potassium tert-butoxide into a phosphorus ylide reagent by adopting a Witting reaction, and reacting under the action of strong alkali potassium tert-butoxide to obtain a triaryl vinyl skeleton; the pH of the solution was 13;
step 3: through Suzuki coupling reaction, the triaryl vinyl skeleton is respectively reacted with phenylboronic acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid under the action of palladium catalyst to obtain the target compound, namely the 2-phenyl substituted triaryl vinyl photochromic material.
4. A synthetic method according to claim 3, characterized in that: the reaction mole ratio of the aromatic ring, the aromatic heterocycle or the derivative thereof with one end containing the benzyl bromide substituent group in the step 1 to the triethyl phosphite is 1:1.5.
5. The synthesis method according to claim 2, characterized by the steps of: the molar ratio of the phosphorus ylide reagent to the carbonyl in the step 2 is 1:1.2.
6. A synthetic method according to claim 3, characterized in that: the molar ratio of the triaryl vinyl skeleton to phenylboronic acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid is 1:0.5.
7. The synthesis method according to claim 2, characterized by the steps of:
step 1): the diphenyl ketone derivative and an aromatic compound or a heterocyclic compound containing triethyl phosphite group are subjected to Wittig reaction in tetrahydrofuran solution under the action of potassium tert-butoxide to obtain difluoro substituent;
step 2): the difluoro substituent is respectively mixed with an aromatic compound or heterocyclic compound containing boric acid, 4-fluorobenzeneboronic acid pinacol ester or 4- (trifluoromethyl) phenylboronic acid pinacol borate ester group, and under the action of potassium carbonate in tetrahydrofuran solution, the target compound, namely the 2-position phenyl substituted triaryl ethylene photochromic material is obtained through catalysis of tetraphenylphosphine palladium.
8. The method of synthesis according to claim 7, wherein: the molar ratio of the aromatic compound containing triethyl phosphite to the benzophenone derivative in the step 1) is 1:1.2.
9. The method of synthesis according to claim 7, wherein: the molar ratio of difluoro substituent to aromatic compound or heterocyclic compound containing boric acid or pinacol borate ester group in the step 2) is 1:0.5.
10. Use of a 2-position phenyl substituted triarylvinyl photochromic material according to claim 1, characterized in that: the fluorescent dye is used in the fields of anti-counterfeiting, photosensitive decoration, optical information storage, single-molecule logic gate, super-resolution fluorescent imaging, green printing and additive manufacturing.
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