CN118064162A - Synthesis and mesogenic research of aryl trifluoro benzophenanthrene discotic liquid crystal compound - Google Patents
Synthesis and mesogenic research of aryl trifluoro benzophenanthrene discotic liquid crystal compound Download PDFInfo
- Publication number
- CN118064162A CN118064162A CN202211463021.8A CN202211463021A CN118064162A CN 118064162 A CN118064162 A CN 118064162A CN 202211463021 A CN202211463021 A CN 202211463021A CN 118064162 A CN118064162 A CN 118064162A
- Authority
- CN
- China
- Prior art keywords
- discotic liquid
- liquid crystal
- benzophenanthrene
- general formula
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 title claims abstract description 13
- -1 aryl trifluoro benzophenanthrene Chemical compound 0.000 title claims abstract description 13
- 238000011160 research Methods 0.000 title abstract description 3
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 claims abstract description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 3
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 7
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005442 molecular electronic Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- 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
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to research on chemical structure, synthesis method, mesogenic property and application of aryl trifluoro benzophenanthrene discotic liquid crystal compound. It is characterized by having the general formula (I). Ar is naphthalene, pyrene, benzophenanthrene, tetraphenyl ethylene or benzothiophene, and the compound shown in the general formula (I) can be self-assembled into a columnar liquid crystal mesophase in a certain temperature range. The invention also provides a preparation method of the aryl trifluoro benzophenanthrene discotic liquid crystal compound, which has a simple and quick synthetic route, and the compound in the general formula (I) can be obtained by carrying out nucleophilic substitution reaction of aryl on 1,2,3, 4-tetrafluoro-6, 7,10, 11-tetra (octyloxy) benzophenanthrene and Ar through a one-pot method.
Description
Technical Field
The invention relates to an aryl trifluoro benzophenanthrene discotic liquid crystal compound structure and mesogenic property.
Background
The discotic liquid crystal is a planar discotic molecule with pi conjugated polycyclic aromatic hydrocarbon, and due to the columnar accumulation of one-dimensional molecules, the discotic liquid crystal can self-assemble into a columnar structure, particularly a hexagonal columnar phase, which provides a unique molecular path for one-dimensional charge carrier transmission. Therefore, discotic liquid crystals are a promising class of organic semiconductor materials in applications in the fields of molecular electronics, optoelectronics, photoconductivity, photovoltaics, electroluminescent devices, and the like. Since fluorine atoms have special properties such as a large electron withdrawing effect and a small blocking effect, the physical properties of the liquid crystal molecules are greatly changed by introducing fluorine atoms into the liquid crystal molecules. If the viscosity is reduced, the driving voltage is reduced, the response speed is accelerated, the dielectric constant is improved, the temperature range of the liquid crystal phase is widened, and the like. To investigate the effect of conjugated size, positional isomerism and S atom in conjugated ring on the photophysical properties of aryl fluorine-containing derivatives. The aromatic nucleus compounds with different centers are changed, and the electronic and steric effects of molecules have great influence on self-assembly behaviors, photophysical properties and semiconductor characteristics.
Disclosure of Invention
Based on the design, aryl trifluoro benzophenanthrene discotic liquid crystal compound is synthesized. The compound is obtained through nucleophilic substitution reaction of polyfluoroaromatic hydrocarbon in synthesis. The target compound is obtained by a one-pot method through nucleophilic substitution reaction of aryl by 1,2,3, 4-tetrafluoro-6, 7,10, 11-tetra (octyloxy) benzophenanthrene and Ar. Tests show that the compounds form stable columnar liquid crystal in a certain temperature range.
In addition, the invention provides a preparation method of the aryl trifluoro-benzophenanthrene discotic liquid crystal compound.
An aryltrifluorobenzophenanthrene discotic liquid crystal compound is characterized by having a structure shown in a general formula (I):
wherein Ar is naphthalene, pyrene, benzophenanthrene, tetraphenyl ethylene, benzothiophene.
An aryltrifluorobenzophenanthrene of the general formula (i) as claimed in claim 2, which is synthesized by the steps of:
synthesis of aryl trifluorobenzophenanthrene:
4-Bromotetraphenyl ethylene (0.25 g, 0.61 mmol) was weighed into a 50 mL reaction tube, and solvent THF (10 mL) was added thereto, n-BuLi (2.5M in Hexane, 1.22 mmol) was slowly injected into the reaction tube by syringe at-78℃and reacted at-78℃continuously for 0.5 h, followed by reaction for 3 h at room temperature, and tetrafluorobenzophenanthrene (0.25 g, 0.30 mmol) was then weighed into the reaction tube and reacted at 55℃for 10 h. After the reaction, the organic phase was dried over anhydrous MgSO4, filtered, concentrated, and the crude product was purified by column chromatography on silica gel (eluent: V Dichloromethane (dichloromethane) : V Petroleum ether =1:3) and recrystallized from ethyl acetate and ethanol to give a white solid.
Wherein Ar is naphthalene, pyrene, benzophenanthrene, tetraphenyl ethylene or benzothiophene.
The Ar is naphthalene, pyrene, benzophenanthrene, tetraphenyl ethylene and benzothiophene discotic liquid crystal compound preparation method, the synthetic route is simple and quick, the compound takes nucleophilic substitution reaction of aryl by 1,2,3, 4-tetrafluoro-6, 7,10, 11-tetra (octyloxy) benzophenanthrene and Ar, and the compound can self-assemble into stable columnar liquid crystal mesophase under a certain temperature range and has good application value in the aspect of liquid crystal materials.
Drawings
FIG. 1 shows the nuclear magnetic resonance spectrum of example 1 (I).
FIG. 2 shows the nuclear magnetic resonance fluorine spectrum of (I) in example 1.
FIG. 3 is a DSC graph of (I) in example 1.
FIG. 4 shows the polarizing texture of (I) in example 1.
Detailed Description
The examples given below are specific descriptions of the invention, it being emphasized that the examples given below are merely further illustrative of the invention and are not intended to limit the scope of the invention. Modifications and adaptations of the invention involving those skilled in the art will be within the scope of the invention without materially departing from the novel teachings and advantages thereof.
Example 1.
The compounds provided in this example are prepared as follows:
4-Bromotetraphenyl ethylene (0.25 g, 0.61 mmol) was weighed into a 50mL reaction tube, and solvent THF (10 mL) was added thereto, n-BuLi (2.5M in Hexane, 1.22 mmol) was slowly injected into the reaction tube by syringe at-78℃and reacted at-78℃continuously for 0.5h, followed by reaction for 3 h at room temperature, and tetrafluorobenzophenanthrene (0.25 g, 0.30 mmol) was then weighed into the reaction tube and reacted at 55℃for 10 h. After the reaction was completed, extraction was performed with methylene chloride, and the organic phase was dried over anhydrous MgSO4, filtered, concentrated, and the crude product was separated and purified by silica gel column chromatography (eluent: V Dichloromethane (dichloromethane) : V Petroleum ether =1:3), and recrystallized from ethyl acetate and ethanol to give a white solid (0.24: 0.24 g, yield 75%).
Nuclear magnetic hydrogen spectrum 1H NMR (400 MHz, TMS, CDCl3) δ 8.50 (d, J = 5.9 Hz, 1H, ArH), 8.44 (d, J = 6.3 Hz, 1H, ArH), 7.83 (s, 2H, ArH), 7.57 – 7.52 (m, 1H, ArH), 7.44 – 7.42 (m, 2H, ArH), 7.38 – 7.27 (m, 5H, ArH), 7.15 – 7.06 (m, 5H, ArH), 7.00 (t, J = 6.2 Hz, 3H, ArH), 6.84 – 6.76 (m, 3H, ArH), 4.28 – 4.12 (m, 8H, OCH2), 1.99 – 1.85 (m, 8H, CH2), 1.57 – 1.27 (m, 40H, CH2), 0.95 – 0.83 (m, 12H, CH3).
19F NMR (565 MHz, TMS, CDCl3) δ -115.34 – -115.61 (m, 1F, ArF), -141.25 – -141.48 (m, 1F, ArF), -142.48 (t, J = 14.5 Hz, 1F, ArF).
Claims (5)
1. The aryl trifluoro benzophenanthrene discotic liquid crystal compound is characterized by having a structure shown in a general formula (I):
The aryltrifluorotriphenylene discotic liquid-crystalline compound (I) as claimed in claim 1, wherein Ar is naphthalene, pyrene, benzophenanthrene, tetraphenylethylene, benzothiophene.
2. An aryltrifluorotriphenylene discotic liquid-crystalline compound of the general formula (i) as claimed in claim 2, which is prepared by:
4-Bromotetraphenyl ethylene (0.25 g, 0.61 mmol) was weighed into a 50mL reaction tube, and solvent THF (10 mL) was added thereto, n-BuLi (2.5M in Hexane, 1.22 mmol) was slowly injected into the reaction tube by syringe at-78℃and reacted at-78℃continuously for 0.5 h, followed by reaction for 3h at room temperature, and tetrafluorobenzophenanthrene (0.25 g, 0.30 mmol) was then weighed into the reaction tube and reacted at 55℃for 10h.
3. After the reaction, the organic phase was dried over anhydrous MgSO4, filtered, concentrated, and the crude product was purified by column chromatography on silica gel (eluent: V Dichloromethane (dichloromethane) : V Petroleum ether =1:3) and recrystallized from ethyl acetate and ethanol to give a white solid.
4. A chemical structure of an aryltrifluorotriphenylene discotic liquid-crystalline compound of the general formula (I) as defined in claim 1 and a method for synthesizing the same.
5. A mesogenic property of an aryltrifluorotriphenylene discotic liquid-crystalline compound of the general formula (I) as claimed in claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211463021.8A CN118064162A (en) | 2022-11-22 | 2022-11-22 | Synthesis and mesogenic research of aryl trifluoro benzophenanthrene discotic liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211463021.8A CN118064162A (en) | 2022-11-22 | 2022-11-22 | Synthesis and mesogenic research of aryl trifluoro benzophenanthrene discotic liquid crystal compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN118064162A true CN118064162A (en) | 2024-05-24 |
Family
ID=91094189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211463021.8A Pending CN118064162A (en) | 2022-11-22 | 2022-11-22 | Synthesis and mesogenic research of aryl trifluoro benzophenanthrene discotic liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118064162A (en) |
-
2022
- 2022-11-22 CN CN202211463021.8A patent/CN118064162A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111362783A (en) | Tetratetrafluoro tetraalkoxy benzophenanthrene discotic liquid crystal compound and preparation method thereof | |
| CN111825598A (en) | Carbazole-containing discotic liquid crystal compound and preparation method thereof | |
| CN111662196A (en) | Triphenylene discotic liquid crystal compound and preparation method thereof | |
| CN113528148A (en) | Liquid crystal medium for high-frequency technology and assembly thereof | |
| CN102051184A (en) | Symmetrical discotic liquid crystal molecule taking pyrene as rigid core and preparation method thereof | |
| CN112409374B (en) | Preparation method of rigid core direct-connected graphene-like benzophenanthrene discotic liquid crystal and mesomorphism | |
| CN113528149B (en) | Liquid crystal compound, composition thereof and high-frequency component comprising liquid crystal compound | |
| CN118064162A (en) | Synthesis and mesogenic research of aryl trifluoro benzophenanthrene discotic liquid crystal compound | |
| Reghu et al. | Synthesis and properties of hole-transporting triphenylamine-derived dendritic compounds | |
| CN114015459B (en) | Liquid crystal containing dinaphthyl monomer, and preparation method and application thereof | |
| JP3763495B2 (en) | Pyridinium-type ionic compound derivative, its production method and liquid crystal substance | |
| CN109054862A (en) | Benzo [b] thiophene-based liquid-crystal compounds with luminescent properties and preparation method thereof | |
| JP5439647B2 (en) | Novel diamantane compound, liquid crystal compound and liquid crystal composition | |
| CN115477572A (en) | Preparation method of trifluoromethyl trifluoro-triphenylene discotic liquid crystal compound | |
| CN115806542A (en) | 2,5-bis (1,3,4-trifluorotetra (alkoxy) triphenylen-2-yl) thiophene discotic liquid crystals and synthesis | |
| KR20140107975A (en) | Bent-core reactive mesogenic compounds and low birefringence liquid crystalline orientation film of their mixture | |
| CN115477571A (en) | 2-phenyl-1, 3, 4-trifluoro-6, 7,10, 11-tetra (alkoxy) triphenylene discotic liquid crystal and synthesis | |
| CN115806476A (en) | Difluoro octaalkoxy triphenyl tetracene discotic liquid crystal compound and preparation method thereof | |
| Tang et al. | The fluorescent liquid crystal and spiro-silicon bridged compounds based on silafluorene core | |
| CN114350378A (en) | Alkyne liquid crystal compound containing thiophene and preparation method and application thereof | |
| Ji et al. | Synthesis and mesomorphism of diacetylene-bridged triphenylene discotic liquid crystal dimers | |
| CN101880219A (en) | Liquid crystal compound and preparation method thereof | |
| EP0314735A1 (en) | Liquid crystal material | |
| CN118085886A (en) | Preparation method of terphenyl phenanthrene discotic liquid crystal compound | |
| JP4007462B2 (en) | Pyridinium-type ionic compound derivative, its production method and liquid crystal substance |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |