CN114573532A - Synthesis and luminescence of bis-benzophenanthrofuran discotic liquid crystal compound - Google Patents
Synthesis and luminescence of bis-benzophenanthrofuran discotic liquid crystal compound Download PDFInfo
- Publication number
- CN114573532A CN114573532A CN202011376436.2A CN202011376436A CN114573532A CN 114573532 A CN114573532 A CN 114573532A CN 202011376436 A CN202011376436 A CN 202011376436A CN 114573532 A CN114573532 A CN 114573532A
- Authority
- CN
- China
- Prior art keywords
- bis
- drying
- reaction
- liquid crystal
- biphenyl
- 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 49
- 239000004985 Discotic Liquid Crystal Substance Substances 0.000 title claims abstract description 19
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 13
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 13
- IAUBQDZFQACACC-UHFFFAOYSA-N 20-oxanonacyclo[19.16.0.02,19.03,16.04,9.010,15.022,35.023,28.029,34]heptatriaconta-1(21),2(19),3(16),4,6,8,10,12,14,17,22(35),23,25,27,29,31,33,36-octadecaene Chemical compound C1=CC=CC2=C3C=CC=CC3=C3C(=C12)C=1C2=C(OC1C=C3)C3=C1C=CC=CC1=C1C=CC=CC1=C3C=C2 IAUBQDZFQACACC-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000004020 luminiscence type Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- 238000001035 drying Methods 0.000 claims description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 25
- 239000003208 petroleum Substances 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 229960001701 chloroform Drugs 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000003480 eluent Substances 0.000 claims description 18
- 238000001914 filtration Methods 0.000 claims description 17
- 238000010898 silica gel chromatography Methods 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000005303 weighing Methods 0.000 claims description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- 229910052786 argon Inorganic materials 0.000 claims description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 238000001816 cooling Methods 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 5
- -1 bis-benzophenanthrofuran compound Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 3
- 229910002666 PdCl2 Inorganic materials 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000000499 gel Substances 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract description 2
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture 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
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to synthesis and optical property research of a dibenzophenanthrofuran discotic liquid crystal compound. It is characterized by having general formulas (I) and (II). Wherein R is C8~C16The compounds of the general formula (I) and (II) can self-assemble into a hexagonal columnar liquid crystal intermediate phase in a wide temperature range, and the compounds of the general formula (I) are gels of various polar/non-polar organic solvents. The invention also provides a preparation method of the bis-benzophenanthrofuran discotic liquid crystal compound, the synthetic route is simple and quick, the conditions are mild, and the compounds of general formulas (I) and (II) can be prepared in FeCl through the compounds of general formulas (III) and (IV)3Intramolecular oxidation ring closure.
Description
Technical Field
The invention relates to synthesis and luminescence of a bis-benzophenanthrofuran discotic liquid crystal compound.
Background
At present, discotic liquid crystal is a unique material which has remarkable electric conduction and photoconduction performance and can form a nano microstructure through self-assembly, liquid crystal molecules can be assembled into a close-packed molecular arrangement, which is beneficial to the rapid transmission of current carriers, therefore, the organic liquid crystal molecules can be used as an unconventional organic semiconductor, and the organic liquid crystal semiconductor material has unique properties such as charge transmission, orderly self-assembly can be carried out in the interphase, the processability is good, the film forming property is good, the defect repairability is good, the cost is low, and the like, thus, discotic liquid crystals have been used for some applications in the fields of molecular electronics, photonics, photoconductivity, photovoltaics, and electroluminescent devices, and are considered promising organic semiconductors, however, columnar internal accumulation of the mesophase of polymeric liquid crystals may also have some influence on the parameters of charge carrier flow efficiency due to topological defects, thermal fluctuations, and molecular diffusion. The improvement of these properties requires that the desired molecular ordering be achieved by various methods, such as very stable sensor materials, suitable temperatures, and ideal operating environments, so that the reaction can be handled easily, thereby improving the charge transport performance. The discotic liquid crystal micromolecules are concise and efficient in design and synthesis, self-assemble into a stable columnar intermediate phase, and are easy to dissolve in various common organic solvents, so that the possibility of processing the discotic liquid crystal micromolecules into a film is provided. In order to explore the differences among discotic liquid crystal compounds in different configurations, liquid crystallinity, optical properties and semiconductor properties of the same compound, the following compounds were designed and synthesized on the basis of furan.
Disclosure of Invention
Based on the design, the bis-benzophenanthrene benzofuran discotic liquid crystal compound is synthesized. The compound is mainly obtained by Suzuki coupling in synthesis. The ring closure occurs mainly through Suzuki coupling of 4,4,5, 5-tetramethyl-2- (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl ] -2-yl) -1,3, 2-dioxaborane with 2, 8-dibromofuran and 4, 6-dibromofuran, respectively. The target compound is obtained, and researches show that the compound forms a stable columnar phase in a wider temperature range and is a liquid crystal with excellent performance. Meanwhile, the compound has good luminous performance, and the absolute quantum yield can reach 60%.
Further, it is necessary to provide a method for producing a bis-benzophenanthrofuran discotic liquid crystal compound, characterized by having a structure represented by general formula (i), (ii):
wherein R is CnH2n+1And n represents an integer of 8 to 16 carbon atoms.
A bis (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl ] -2-yl) dibenzo [ b, d ] furan of formula 2, 8-position (III), 3, 4-position (IV) according to claim 2, characterized in that it comprises the following steps.
The method comprises the following steps: the intermediate is the preparation of the compound b:
taking a compound shown as a formula a as a raw material, weighing the compound and bromine in a molar ratio of 1:1 in a 250ml round-bottom flask, adding 150ml of trichloromethane, sleeving a constant pressure dropping funnel, adding trichloromethane (20 ml) and bromine into the dropping funnel, putting the round-bottom flask into a room temperature environment, controlling the solution in the constant pressure dropping funnel to be 2 seconds per drop, tracking the solution at intervals of 15 minutes, adding sodium bisulfite to terminate the reaction after the reaction is finished, filtering, spin-drying, performing silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2), and recrystallizing with ethanol and ethyl acetate to obtain a product b, wherein R is a compound shown as a formula b, and R is a compound shown as a formula b, wherein R is a compound shown as a formula b1is-CnH2n+1And n represents an integer of 6 to 16 carbon atoms.
Step two: synthesis of intermediate 4,4,5, 5-tetramethyl-2- (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl ] -2-yl) -1,3, 2-dioxaborane (c):
2-bromo-3 ',4,4', 5-tetra (alkoxy) -1,1' -biphenyl (b): bis (valerylboron: CH) in a molar ratio in a 100ml reaction tube3COOK: PdCl2(dppf) =1: 1.5: 0.05: 3 and 1, 4-dioxygen is weighed and addedHexacyclic ring 25 ml, reacting under argon protection at 90 ℃ for 24h, cooling to room temperature, extracting with dichloromethane, extracting the organic phase with anhydrous MgSO4Drying, filtering, spin-drying, and recrystallizing by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 3) with ethyl acetate and methanol to obtain white solid (C), wherein R is CnH2n+1，n represents a carbon number of 8 to 16.
Step three:
(a) synthesis of 2, 8-bis (3 ',4,4', 5-tetrakis (alkoxy) - [1,1' -biphenyl ] -2-yl) dibenzo [ b, d ] furan (iii):
in a 50ml reaction tube, in a molar ratio of c: 2, 8-dibromofuran: K2CO3 : Pd(PPh3)4 Weighing and adding mixed solvent water (3 ml)/THF (10 ml) under the protection of argon, reacting at 70 deg.C for 48 h, cooling to room temperature, extracting with dichloromethane, and collecting organic phase with anhydrous MgSO4Drying, filtering, spin-drying, and recrystallizing with ethyl acetate and ethanol by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 3) to obtain white solid (III), wherein R is CnH2n+1，n represents a carbon number of 8 to 16.
(b) Synthesis of 4, 6-bis (3 ',4,4', 5-tetrakis (alkoxy) - [1,1' -biphenyl ] -2-yl) dibenzo [ b, d ] furan (iv):
in a 50ml reaction tube, in molar ratio c: 4, 6-dibromofuran: K2CO3 : Pd(PPh3)4 Weighing and adding mixed solvent water (3 ml)/THF (10 ml) under the protection of argon, reacting at 70 deg.C for 48 h, cooling to room temperature, extracting with dichloromethane, and collecting organic phase with anhydrous MgSO4Drying and filteringSpin-drying, and recrystallizing with ethyl acetate and ethanol by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 3) to obtain white solid (IV), wherein R is CnH2n+1，n represents a carbon number of 8 to 16.
Preparation of bis-benzophenanthrofuran discotic liquid crystal compounds (I) and (II).
(a) A discotic liquid crystalline bis-benzophenanthrofuran compound of the general formula (I) as defined in claim 1, which is prepared by:
in a 100ml round-bottomed flask with compound (III): FeCl3 Weighing at a molar ratio of 1: 6, adding trichloromethane (60 ml) and nitromethane (5ml), reacting at room temperature, tracking the reaction by a point plate every 15min, adding methanol to stop the reaction after the reaction is finished, extracting with trichloromethane, and MgSO4Drying, filtering, spin-drying, and recrystallizing with toluene and petroleum ether by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2) to obtain a tan solid (I), wherein R is CnH2n+1，n represents a carbon number of 8 to 16.
(b) A discotic liquid crystalline bis-benzophenanthrofuran compound of the general formula (II) as defined in claim 1, which is prepared by:
in a 100ml round-bottom flask with compound (IV): FeCl3 Weighing at a molar ratio of 1: 6, adding trichloromethane (60 ml) and nitromethane (5ml), reacting at room temperature, tracking the reaction by a point plate every 15min, adding methanol to stop the reaction after the reaction is finished, extracting with trichloromethane, and MgSO4Drying, filtering, spin-drying, and recrystallizing with toluene and petroleum ether by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2) to obtain white solidA compound of formula (II) wherein R is CnH2n+1，n represents a carbon number of 8 to 16.
The preparation method of the bis-benzophenanthrofuran discotic liquid crystal compound has a simple and quick synthesis route and mild conditions, the compound is subjected to ring closing after Suzuki coupling is carried out on 4,4,5, 5-tetramethyl-2- (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl ] -2-yl) -1,3, 2-dioxaborane and 4, 6-dibromofuran, a plurality of aryl groups are connected together in a condensation mode, and under the regulation action of a plurality of peripheral alkoxy flexible chains, the compound can be self-assembled into a stable hexagonal columnar liquid crystal intermediate phase in a wider temperature range and at room temperature, and has a good application value in the aspect of liquid crystal materials.
Drawings
FIG. 1R obtained in example 1 is C10H21Nuclear magnetic hydrogen spectrum of intermediate b (2).
FIG. 2R obtained in example 2 is C10H21Nuclear magnetic hydrogen spectrum of intermediate c.
FIG. 3R obtained in example 3 is C10H21Nuclear magnetic hydrogen spectrum of the general formula (III).
FIG. 4R obtained in example 4 is C10H21Nuclear magnetic hydrogen spectrum of general formula (I).
FIG. 5R obtained in example 5 is C10H21Nuclear magnetic hydrogen spectrum of general formula (IV).
FIG. 6R obtained in example 6 is C10H21Nuclear magnetic hydrogen spectrum of the general formula (II).
FIG. 7. R obtained in example 4 is C10H21DSC profile of the general formula (I).
FIG. 8 shows that R obtained in example 6 is C10H21DSC profile of the general formula (II).
FIG. 9 shows that R obtained in example 4 is C10H21A polarized light weave pattern of the general formula (I).
FIG. 10 shows that R in example 6 is C10H21A polarizing weave pattern of the general formula (II).
FIG. 11 is an XRD diffractogram with curves beingR obtained in example 4 is C10H21The XRD diffractogram of the mesophase of formula (I).
FIG. 12 is an XRD diffractogram having the curve that R is C obtained in example 610H21The XRD diffractogram of the mesophase of the general formula (II).
FIG. 13 shows a fluorescence emission spectrum, wherein curve F1 shows that R is C in example 410H21The fluorescence emission spectrum of the general formula (I) and curve F2, where R is C as obtained in example 610H21Fluorescence emission spectrum of general formula (II).
FIG. 14 is a graph of an ultraviolet absorption spectrum, and curve F1 shows that R is C in example 410H21The ultraviolet absorption spectrum of formula (I) and curve F2 for the R value C obtained in example 610H21Ultraviolet absorption spectrum of the general formula (II).
FIG. 15 is a photograph of an inverted gel in which R is C as obtained in example 410H21The gel picture of the compound of the general formula (I) formed in an organic solvent by dichloromethane, ethyl acetate, tetrahydrofuran, toluene, hexane and cyclohexane in sequence.
Detailed Description
The following examples are given to illustrate the invention in detail, it being emphasized that the examples given below are only illustrative of the invention and are not intended to limit the scope of the invention. In the practical implementation, the skilled person in the art may still be able to make modifications or adaptations to the invention based on the above disclosure, without substantial changes.
The synthesis methods used in the following embodiments are all prior art:
T. Yasuda, T. Shimizu, F. Liu, G. Ungar, T. Kato, J. Am. Chem. Soc. 2011, 133, 13437–13444.
example 1.
This example provides the preparation of compound intermediate b, wherein R is C10H21，The preparation reaction is as follows:
taking 3,3',4,4' -tetra (decaalkoxy) -1,1' -biphenyl (a) (0.63 mg, 0.80 mmol) as a raw material, weighing the raw material and bromine (0.11 g, 0.80 mmol) in a 1:1 molar ratio in a 250ml round-bottom flask, adding 150ml of trichloromethane, covering a constant pressure dropping funnel, adding the trichloromethane (20 ml) and the bromine into the trichloromethane, placing the round-bottom flask into a room-temperature environment, controlling the solution in the constant pressure dropping funnel to be 2 seconds per drop, tracing the plate every 15 minutes, stopping the reaction by adding sodium bisulfite after the reaction is finished, filtering, spin-drying, performing silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2), and recrystallizing by using ethanol and ethyl acetate to obtain a product b (0.65 g, 94% of yield).
Nuclear magnetic hydrogen spectrum1H NMR(CDCl3, TMS, 400 MHz), 1H NMR(CDCl3, TMS, 400 MHz), δ:7.10(s, 1H, ArH), 6.95(s, 1H, ArH), 6.89(d, J = 4 Hz, 2H, ArH),6.84(s, 1H, ArH), 4.02(t, J = 2.8 Hz, 8H, OCH2), 1.76-1.87(m, 8H, CH2), 1.27-1.57(m, 56H, CH2), 0.88(t, J = 2.8Hz, 12H, CH3)。
Example 2.
4,4,5, 5-tetramethyl-2- (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl)]Preparation of (e) -2-yl) -1,3, 2-dioxaborane (C) wherein R is C10H21，The preparation reaction is as follows:
2-bromo-3 ',4,4', 5-tetra (alkoxy) -1,1' -biphenyl, bis (valeryl) diboron (b) CH in a molar ratio in a 100ml reaction tube3COOK: PdCl2(dppf) =1 (1.2 g) = 1.5 (0.53 g): 0.05 (0.06 g): 3 (0.4 g) was weighed and added to 25 ml of 1, 4-dioxane, reacted at 90 ℃ for 24h under argon protection, cooled to room temperature, extracted with dichloromethane, and the organic phase was extracted with dichloromethaneAnhydrous MgSO (MgSO)4Drying, filtration, spin-drying, and recrystallization from ethyl acetate and methanol by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 3) gave (c) as a white solid (1.27 g, 40% yield).
Nuclear magnetic hydrogen spectrum1H NMR(CDCl3, TMS, 400 MHz), 1H NMR(CDCl3, TMS, 400 MHz), δ:7.21(s, 1H, ArH), 6.92(s, 1H, ArH), 6.85(s, 3H, ArH), 4.0-4.05(m, 8H, OCH2),1.80-1.85(m, 8H, CH2), 1.27-1.50(m, 56H, CH2), 1.19(s, 12H, CH3),0.88(t, J = 4Hz, 12H, CH3)。
Example 3.
This example provides the preparation of a compound of formula (III) wherein R is C10H21The preparation reaction is as follows:
in a 50ml reaction tube, in a molar ratio of c: 2, 7-dibromofuran: K2CO3 : Pd(PPh3)4 = 2.5 (0.35): 1 (0.05): 30 (0.64): 0.2 (0.04) by weight and adding mixed solvent water (3 ml)/THF (10 ml), reacting at 70 ℃ for 48 h under argon protection, cooling to room temperature, extracting with dichloromethane, and using anhydrous MgSO for organic phase4Drying, filtration, spin-drying, and recrystallization from ethyl acetate and ethanol by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 3) gave (iii) (0.20 g, 76% yield) as a white solid.
Nuclear magnetic hydrogen spectrum1H NMR(CDCl3, TMS, 400 MHz), δ:7.73 (s, 2H, ArH), 7.31 (d, J = 8.0 Hz,2H, ArH), 7.10(d, J = 8.0 Hz, 2H, ArH), 6.99 (d, J = 4.0 Hz, 4H, ArH), 6.70 (s, 4H, ArH), 6.59 (s, 2H, ArH),4.10- 4.06 (m , 8H , OCH2), 3.91 (t, J = 8.0 Hz, 4H, OCH2), 3.61 (t, J = 8.0 Hz , 4H, OCH2), 1.88-1.73 (m, 14H, CH2), 1.58-1.48 (m, 14H, CH2),1.38-1.19 (m, 100H, CH2), 0.88 (t, J = 8.0 Hz, 24H, CH3)。
Example 4.
The compounds provided in this example are of formula (I) wherein R1Is C10H21，The preparation reaction is as follows:
in a 100ml round-bottomed flask with compound (III): FeCl3 Weighing according to the molar ratio of =1 (0.140) to 6 (0.08), adding trichloromethane (60 ml) and nitromethane (5ml), reacting at room temperature, performing plate tracking reaction every 15min, adding methanol to stop the reaction after the reaction is finished, extracting with trichloromethane, and performing MgSO (MgSO) after the reaction is finished4Drying, filtration, spin-drying, and recrystallization from silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2), toluene and petroleum ether gave a tan solid (I), (0.90 g, 65% yield).
Nuclear magnetic hydrogen spectrum1H NMR(CDCl3, TMS, 400 MHz), 1H NMR(CDCl3, TMS, 400 MHz), δ:9.02 (s, 2H, ArH), 8.41 (s, 2H, ArH), 8.18(s, 2H, ArH), 7.92 (s, 2H, ArH), 7.75 (s, 2H, ArH), 7.73 (s, 2H, ArH), 4.38-4.21 (m, 16H, OCH2), 2.01-1.94 (m, 16H, CH2), 1.66-1,57 (m ,16H, CH2), 1.45-1.26 (m, 96H, CH2), 0.91-0.86 (m, 24H, CH3)。
Example 5.
This example provides the preparation of a compound of formula (IV) wherein R is C10H21The preparation reaction is as follows:
k in a molar ratio of c: 2, 7-dibromofuran in a 50ml reaction tube2CO3 : Pd(PPh3)4 = 2.5 (0.35): 1 (0.05): 30 (0.64): 0.2 (0.04) by weight and adding mixed solvent water (3 ml)/THF (10 ml), reacting at 70 ℃ for 48 h under argon protection, cooling to room temperature, extracting with dichloromethane, and using anhydrous MgSO for organic phase4Drying, filtration, spin-drying, and recrystallization from silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 3) with ethyl acetate and ethanol gave white solid (iv), (0.20 g, 77% yield).
Nuclear magnetic hydrogen spectrum1H NMR (CDCl3, TMS, 400 MHz) δ: 7.71-7.69 (m, 2H, ArH), 7.13 (t, J = 4.0 Hz, 4H, ArH), 7.02 (s, 2H, ArH), 6.96 (s, 2H, ArH), 6.50-6.44 (m, 4H, ArH), 6.33 (d, J = 4.0 Hz, 2H, ArH), 4.09 (t, J = 8.0 Hz, 4H, OCH2), 3.90 (t, J = 8.0 Hz, 4H, OCH2), 3.73 (t, J = 8.0 Hz, 4H, OCH2), 3.31 (t, J = 4.0 Hz, 4H, OCH2), 1.92-1.74 (m, 12H, CH2), 1.69-1.64 (m, 4H, CH2), 1.54-1.48 (m, 6H, CH2), 1.41-1.17 (m, 106H, CH2), 0.89-0.86 (m, 24H, CH3)。
Example 6.
The compounds provided in this example are of the general formula (II) wherein R1Is C10H21，The preparation reaction is as follows:
in a 100ml round-bottomed flask with compound (IV): FeCl3 Weighing the mixture according to the molar ratio of =1 (0.16) to 6 (0.09), adding dichloromethane (60 ml) and nitromethane (5ml) to react at room temperature, carrying out plate tracking reaction every 15min, adding methanol to stop the reaction after the reaction is finished, extracting with chloroform, and carrying out MgSO (MgSO) through extraction with chloroform4Drying, filtration, spin-drying, and recrystallization from silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2), toluene and petroleum ether gave (ii) (0.20 g, 85% yield) as a white solid.
Nuclear magnetic hydrogenSpectrum1H NMR(CDCl3, TMS, 600 MHz), δ:9.37 (s, 2H, ArH), 8.58 (d, J = 4.0 Hz, 2H, ArH), 8.24(d, J = 8.0 Hz, 2H, ArH), 8.13 (s, 2H, ArH), 7.98 (s, 2H, ArH), 7.93 (s, 2H, ArH), 4.32-4.15 (m, 16H, OCH2), 1.99-1.96 (m, 12H, CH2), 1.80-1,75 (m ,4H, CH2), 1.65-1.55 (m, 12H, CH2), 1.45-1.29 (m, 76H, CH2),1.21-1.14 (m, 24H, CH2), 0.90-0.82 (m, 24H, CH3)。
Claims (8)
1. A dibenzophenanthrofuran discotic liquid crystal compound is characterized by having a structure shown in general formulas (I) and (II):
2. bis (3 ',4,4', 5-tetrakis (alkoxy) - [1,1' -biphenyl ] -2-yl) dibenzo [ b, d ] furan characterized by the structure shown in positions (iii) 2,8 and (iv) 3,4 of the general formula:
3. the dibenzophenanthrofuran compounds (I), (II) according to claim 1 and bis (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl) at the 2, 8-position (III) or 3, 4-position (IV) according to claim 2]-2-yl) dibenzo [ b, d]Furan, characterized in that said R is-CnH2n+1And n represents an integer of 8 to 16 carbon atoms.
4. A bis (3 ',4,4', 5-tetrakis (alkoxy) - [1,1' -biphenyl ] -2-yl) dibenzo [ b, d ] furan of formula 2, 8-position (iii), 3, 4-position (iv) according to claim 2, prepared by:
the method comprises the following steps: preparation of intermediate b (2-bromo-3 ',4,4', 5-tetra (alkoxy) -1,1' -biphenyl),
taking a compound shown as a formula 3,3',4,4' -tetra (alkoxy) -1,1' -biphenyl (a) as a raw material, weighing the compound and bromine in a molar ratio of 1:1 in a 250ml round-bottom flask, adding 150ml of trichloromethane, sleeving a constant pressure dropping funnel, adding trichloromethane (20 ml) and bromine into the constant pressure dropping funnel, putting the round-bottom flask into a room temperature environment, controlling the solution in the constant pressure dropping funnel to be 2 seconds per drop, performing plate tracking every 15 minutes, adding sodium bisulfite to terminate the reaction after the reaction is finished, filtering, spin-drying, performing silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2), and recrystallizing with ethanol and ethyl acetate to obtain a product b, wherein R is1is-CnH2n+1N represents an integer of 8 to 16 carbon atoms;
step two: synthesis of intermediate 4,4,5, 5-tetramethyl-2- (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl ] -2-yl) -1,3, 2-dioxaborane (c):
2-bromo-3 ',4,4', 5-tetra (alkoxy) -1,1' -biphenyl to bis (valeryl) diboron CH in a molar ratio in a 100ml reaction tube3COOK: PdCl2(dppf) =1: 1.5: 0.05: 3 and adding 25 ml of 1, 4-dioxane, reacting at 90 ℃ for 24h under the protection of argon, cooling to room temperature, extracting with dichloromethane, and extracting the organic phase with anhydrous MgSO4Drying, filtering, spin-drying, and recrystallizing with ethyl acetate and methanol by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 3) to obtain a white solid (c);
step three:
(a) synthesis of bis (3 ',4,4', 5-tetrakis (alkoxy) - [1,1' -biphenyl ] -2-yl) dibenzo [ b, d ] furan (iii) in position 2, 8:
k in a molar ratio of c: 2, 8-dibromofuran in a 50ml reaction tube2CO3 : Pd(PPh3)4 Weighing and adding mixed solvent water (3 ml)/THF (10 ml) under the protection of argon, reacting at 70 deg.C for 48 h, cooling to room temperature, extracting with dichloromethane, and collecting organic phase with anhydrous MgSO4Drying, filtering, spin-drying, and recrystallizing with ethyl acetate and ethanol by silica gel column chromatography (eluent: V chloroform: V petroleum ether =1: 3) to obtain white solid (III);
(b) synthesis of 4, 6-bis (3 ',4,4', 5-tetra (alkoxy) - [1,1' -biphenyl ] -2-yl) dibenzo [ b, d ] furan (iv):
in a 50ml reaction tube, in molar ratio c: 4, 6-dibromofuran: K2CO3 : Pd(PPh3)4 = 2.5: 1: 30: 0.2 weigh and add mixed solvent water (3 ml)/THF (10 ml), react at 70 ℃ for 48 h under argon protection, cool to room temperature, extract with dichloromethane, use anhydrous MgSO for organic phase and use anhydrous MgSO for organic phase4Drying, filtering, spin-drying, and recrystallizing by silica gel column chromatography (eluent: V chloroform: V petroleum ether =1: 3) with ethyl acetate and ethanol to obtain white solid (IV).
(a) a discotic liquid crystal compound of bis-benzophenanthrofuran of the general formulae (I) and (II) as defined in claim 1, which is prepared by:
in a 100ml round-bottomed flask with compound (III) FeCl3 Weighing at a molar ratio of 1: 6, adding trichloromethane (60 ml) and nitromethane (5ml), reacting at room temperature, tracking the reaction by a point plate every 15min, adding methanol to stop the reaction after the reaction is finished, extracting with trichloromethane, and MgSO4Drying, filtering, spin-drying, and recrystallizing with toluene and petroleum ether by silica gel column chromatography (eluent: V dichloromethane: V petroleum ether =1: 2) to obtain a tan solid (I);
(b) a discotic liquid crystalline bis-benzophenanthrofuran compound of the general formula (II) as defined in claim 1, which is prepared by:
in a 100ml round-bottomed flask with compound (IV): FeCl3 Weighing at a molar ratio of 1: 6, adding trichloromethane (60 ml) and nitromethane (5ml), reacting at room temperature, tracking the reaction by a point plate every 15min, adding methanol to stop the reaction after the reaction is finished, extracting with trichloromethane, and MgSO4Drying, filtration, spin-drying, and recrystallization from toluene and petroleum ether by column chromatography on silica gel (eluent: V dichloromethane: V petroleum ether =1: 2) gave white solid (II).
6. Use of the discotic liquid crystal compounds of the general formulae (I) and (II) as defined in claim 1 as organic liquid crystal semiconductor materials.
7. Use of the bis-benzophenanthrofuran discotic liquid crystal compounds of the general formulae (I) and (II) as defined in claim 1 as organic photoluminescent materials.
8. Use of the bis-benzophenanthrofuran discotic liquid crystal compound in the general formula (i) as defined in claim 1 as an organogelator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011376436.2A CN114573532A (en) | 2020-11-30 | 2020-11-30 | Synthesis and luminescence of bis-benzophenanthrofuran discotic liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011376436.2A CN114573532A (en) | 2020-11-30 | 2020-11-30 | Synthesis and luminescence of bis-benzophenanthrofuran discotic liquid crystal compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114573532A true CN114573532A (en) | 2022-06-03 |
Family
ID=81767124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011376436.2A Pending CN114573532A (en) | 2020-11-30 | 2020-11-30 | Synthesis and luminescence of bis-benzophenanthrofuran discotic liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114573532A (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160204345A1 (en) * | 2015-01-13 | 2016-07-14 | Feng-wen Yen | Ditriphenylene derivative and organic electroluminescent device using the same |
| CN108368045A (en) * | 2015-12-04 | 2018-08-03 | 广州华睿光电材料有限公司 | Thermal excitation delayed fluorescence material, high polymer, mixture, composition and organic electronic device |
| CN109575046A (en) * | 2018-11-30 | 2019-04-05 | 四川师范大学 | A kind of four aryl of dithienothiophene replace and double luxuriant and rich with fragrance condensed compounds and preparation |
| CN109824691A (en) * | 2019-03-11 | 2019-05-31 | 四川师范大学 | Liquid-crystal compounds and its preparation based on cyclopentadiene 1,4-Dithiapentalene -4- ketone |
| CN109852397A (en) * | 2019-01-19 | 2019-06-07 | 四川师范大学 | A kind of preparation method of the disc liquid-crystal compounds of condensed-nuclei aromatics containing fluorenes |
| CN111320607A (en) * | 2018-12-17 | 2020-06-23 | 机光科技股份有限公司 | Organic compound with triphenylene-containing polycyclic heteroaromatic group as core and application thereof |
| CN111825598A (en) * | 2019-04-20 | 2020-10-27 | 四川师范大学 | Carbazole-containing discotic liquid crystal compound and preparation method thereof |
-
2020
- 2020-11-30 CN CN202011376436.2A patent/CN114573532A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160204345A1 (en) * | 2015-01-13 | 2016-07-14 | Feng-wen Yen | Ditriphenylene derivative and organic electroluminescent device using the same |
| CN108368045A (en) * | 2015-12-04 | 2018-08-03 | 广州华睿光电材料有限公司 | Thermal excitation delayed fluorescence material, high polymer, mixture, composition and organic electronic device |
| US20190214577A1 (en) * | 2015-12-04 | 2019-07-11 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Thermally activated delayed fluorescence material, polymer, mixture, formulation, and organic electronic device |
| CN109575046A (en) * | 2018-11-30 | 2019-04-05 | 四川师范大学 | A kind of four aryl of dithienothiophene replace and double luxuriant and rich with fragrance condensed compounds and preparation |
| CN111320607A (en) * | 2018-12-17 | 2020-06-23 | 机光科技股份有限公司 | Organic compound with triphenylene-containing polycyclic heteroaromatic group as core and application thereof |
| CN109852397A (en) * | 2019-01-19 | 2019-06-07 | 四川师范大学 | A kind of preparation method of the disc liquid-crystal compounds of condensed-nuclei aromatics containing fluorenes |
| CN109824691A (en) * | 2019-03-11 | 2019-05-31 | 四川师范大学 | Liquid-crystal compounds and its preparation based on cyclopentadiene 1,4-Dithiapentalene -4- ketone |
| CN111825598A (en) * | 2019-04-20 | 2020-10-27 | 四川师范大学 | Carbazole-containing discotic liquid crystal compound and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5940548B2 (en) | Novel spirobifluorene compounds | |
| JP6080870B2 (en) | Organic semiconductor material for solution process and organic semiconductor device | |
| 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 | |
| CN112409323A (en) | Preparation method and mesomorphism of graphene-like conjugated heterocyclic benzophenanthrene discotic liquid crystal | |
| CN112979434A (en) | Preparation method of triphenylene-pyrene-triphenylene discotic liquid crystal triad compound | |
| KR101851880B1 (en) | Novel branched oligoarylsilanes and method for producing same | |
| CN109879870B (en) | Synthesis and application of novel functional material based on benzothiadiazole | |
| CN112409374B (en) | Preparation method of rigid core direct-connected graphene-like benzophenanthrene discotic liquid crystal and mesomorphism | |
| RU2396290C1 (en) | Branched oligoarylsilanes and synthesis method thereof | |
| CN109575046A (en) | A kind of four aryl of dithienothiophene replace and double luxuriant and rich with fragrance condensed compounds and preparation | |
| Taneda et al. | Photochromism of polymorphic 4, 4′-methylenebis (N-salicylidene-2, 6-diisopropylaniline) crystals | |
| CN112409325A (en) | Synthesis and luminescence of bis-benzophenanthrene thiophene discotic liquid crystal compound | |
| CN114573532A (en) | Synthesis and luminescence of bis-benzophenanthrofuran discotic liquid crystal compound | |
| CN114507237B (en) | Azapolycyclic fused ring compound based on acenaphthopyrazinooxaline and synthetic method | |
| CN114516790A (en) | Synthesis and luminescence of bis-benzophenanthracenone pentanone discotic liquid crystal compound | |
| CN110105160B (en) | Preparation method based on triphenylene alkyne type precursor and polycyclic aromatic hydrocarbon derivative thereof | |
| RU2544863C2 (en) | Branched oligoarylsilanes with reactionable terminal groups and method of obtaining thereof | |
| Chai et al. | Synthesis, Crystal Structure and Fluorescence Behavior of 2, 6-Di (thiophen-2-yl)-benzo [1, 2-d: 4, 5-d] bisoxazole | |
| CN112300158A (en) | Synthesis and properties of luminescent discotic liquid crystals based on naphthalene anhydride | |
| CN115820264A (en) | Synthesis and performance research of bis-benzophenanthrene-pyrene discotic liquid crystal compound | |
| CN115626911B (en) | Trans-dithienylethylene derivative and preparation method and application thereof | |
| CN115477572A (en) | Preparation method of trifluoromethyl trifluoro-triphenylene discotic liquid crystal compound | |
| CN110256253B (en) | Biphenyl alkene derivative and preparation method thereof | |
| CN118085886A (en) | Preparation method of terphenyl phenanthrene discotic liquid crystal compound |
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 | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20220603 |