CN115477572A - Preparation method of trifluoromethyl trifluoro-triphenylene discotic liquid crystal compound - Google Patents
Preparation method of trifluoromethyl trifluoro-triphenylene discotic liquid crystal compound Download PDFInfo
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Abstract
The invention discloses a 1,2, 4-trifluoro-6, 7,10, 11-tetra (alkoxy) -3-trifluoromethyltriphenylene discotic liquid crystal compoundAnd a novel method for preparing the same. Through the reaction of dibromo tetra alkoxy biphenyl and butyl lithium, and further reaction with perfluorotoluene (C) 6 F 5 ‑CF 3 ) Reacting to synthesize the trifluoromethyl trifluoro benzophenanthrene conjugated polycyclic aromatic hydrocarbon discotic liquid crystal in one pot. The synthesis method has the advantages of mild conditions, simple operation, short synthesis route, low synthesis cost, environmental friendliness and higher practical value. The invention also discloses physical properties of the trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compounds, and the compounds have liquid crystal performance, are columnar liquid crystal phases, have wide liquid crystal phase temperature range and moderate clearing point temperature, and are expected to be good liquid crystal semiconductor materials. The supermolecule columnar structure formed by stacking the compounds pi-pi can be used as a one-dimensional electron and hole transmission path, so that the supermolecule columnar structure can obtain higher charge carrier migration rate, and is expected to be used as an organic electronic material.
Description
Technical Field
The invention relates to a discotic liquid crystal compound of 1,2, 4-trifluoro-6, 7,10, 11-tetra (alkoxy) -3-trifluoromethyl-benzophenanthrene and a preparation method thereof.
Background
Discotic liquid crystals are a unique class of organic semiconducting materials with remarkable electrically and photoconducting properties that are capable of forming nano-micro ordered structures by self-assembly. Discotic liquid crystal molecules generally comprise two basic components: a rigid, planar or near-planar aromatic core and surrounding flexible aliphatic side chains. Such discotic molecules can undergo spontaneous self-assembly in a liquid crystal phase, and form an oriented nematic phase or a position-ordered columnar phase and lamellar phase through pi-pi interaction between aromatic rings. This provides a unique path for one-dimensional charge carrier transport. Triphenylene molecules are typically discotic liquid crystal molecules, which have been extensively studied, as well as derivatives thereof. Meanwhile, the research on the fluorine-containing rodlike liquid crystal molecules is very extensive, so that the researchers are interested in the research on the fluorine-containing discotic liquid crystal molecules, and various novel fluorine-containing discotic liquid crystal molecules are reported in succession. The radius of fluorine atom is similar to that of hydrogen atom, so that the replacement of hydrogen atom by fluorine atom will not affect the phase change of liquid crystal due to steric hindrance. In recent years, fluorine-containing liquid crystal materials have been applied to liquid crystal displays, which have been greatly noticed by scholars due to their unique physicochemical properties. Based on the background, the method for synthesizing the triphenylene discotic liquid crystal molecules by taking the perfluorotoluene as the raw material is designed, the triphenylene discotic liquid crystal molecules have excellent liquid crystal property, and the triphenylene discotic liquid crystal molecules are expected to have good application prospects in the aspects of photoelectric materials, organic transistors, photovoltaic solar cells and the like.
Disclosure of Invention
The invention aims to provide two preparation methods of trifluoromethyl trifluoro-benzotrifluorene discotic liquid crystal compounds. Researches show that the intermediate phase of the trifluoromethyl trifluoro-triphenylene discotic liquid crystal compound is a columnar liquid crystal phase in a wider temperature range, is liquid crystal at room temperature, shows good semiconductor properties and has better application prospect.
A trifluoromethyl trifluoro-triphenylene discotic liquid crystal compound is characterized by having a structure shown in a general formula I:
the invention realizes the first invention purpose, and adopts the technical scheme that: a trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compound (as general formula I, wherein R = C) n H 2n+1 N = 2,4, 6, 8, 10, 12).
The method comprises the following steps: putting 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl into a reaction tube, adding a proper amount of tetrahydrofuran to fully dissolve the tetrahydrofuran under the protection of nitrogen, putting the solution into a low-temperature environment of-78 ℃ to cool, adding n-butyllithium (the molar ratio of the 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl to the n-butyllithium is 1
The molar ratio of the compound to perfluorotoluene is 1. Extracting with dichloromethane and saturated brine, separating, and collecting organic phaseDrying with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, separating and purifying by column chromatography, and recrystallizing with anhydrous ethanol, small amount of ethyl acetate and methanol to obtain white solid.
The preparation method has short synthetic route and simple subsequent processing steps. The synthesized trifluoromethyl trifluoro triphenylene discotic liquid crystal molecules are in columnar phase accumulation, have a wider liquid crystal range and have high application value in the aspect of liquid crystal materials.
The invention realizes the second invention purpose, and the adopted technical scheme is as follows: a trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compound (as general formula I, wherein R = C) n H 2n+1 N = 2,4, 6, 8, 10, 12) (this process differs from the first process in terms of solvent, charge ratio, reaction temperature and butyllithium reagent).
The method comprises the following steps: putting 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl into a reaction tube, adding a proper amount of diethyl ether to fully dissolve the biphenyl under the protection of nitrogen, putting the solution into a low-temperature environment at-78 ℃ to cool, adding tert-butyl lithium (the molar ratio of the 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl to the tert-butyl lithium is 1 6 F 5 CF 3 (the molar ratio of the 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl to the perfluorotoluene was 1.5), and the reaction was carried out at room temperature for 12 hours. Extracting with dichloromethane and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, separating and purifying by column chromatography, and recrystallizing with anhydrous ethanol, small amount of ethyl acetate and methanol to obtain white solid.
The preparation method has the advantages of short synthetic route and simple subsequent treatment steps. The synthesized trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal molecules are in columnar phase accumulation, the liquid crystal range is wider, the application value in the aspect of liquid crystal materials is very high, the reaction condition is milder compared with that of the first method, and the yield is obviously improved.
The present invention will be described in further detail with reference to specific embodiments
Reference to the literature
Rebecca E. Yardley, Joseph A. Paquette, Hi Taing, Heather M. Gaebler, S. Holger Eichhorn, Ian P. Hamilton, and Kenneth E. Maly.Stabilization of Columnar Liquid Crystal Phases via Arene-Perfluoroarene Interactions[J].OrganicLetters,2019,21(24):10102-10105。
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the objective compound obtained in example 1.
FIG. 2 shows the NMR fluorine spectrum of the objective compound obtained in example 1.
FIG. 3 is a liquid crystal phase polarizing weave pattern of the objective compound obtained in example 1.
FIG. 4 is a DSC chart of the objective compound obtained in example 1.
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the objective compound obtained in example 2.
FIG. 6 is a nuclear magnetic resonance fluorine spectrum of the objective compound obtained in example 2.
FIG. 7 is a liquid crystal phase polarizing weave pattern of the objective compound obtained in example 2.
FIG. 8 is a DSC chart of the objective compound obtained in example 2.
Detailed Description
Example 1
R = C in formula I 4 H 9 The first preparation reaction formula of the trifluoromethyl trifluoro triphenylene discotic liquid crystal compound is as follows:
in the reaction formula, THF is tetrahydrofuran; n-BuLi is n-butyl lithium.
A trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compound with the general formulaStructure of I, wherein R = C 4 H 9 . The specific operation is as follows: 400 mg of 2,2 '-dibromo-4, 4',5 '-tetra (butoxy) -1,1' -biphenyl was weighed into a reaction tube, and 30 mL of tetrahydrofuran was added thereto under nitrogen protection to completely dissolve the 2,2 '-dibromo-4, 4',5 '-tetra (butoxy) -1,1' -biphenyl, and the solution was cooled in a low-temperature environment of-78 ℃ for 10 minutes, 1.33 mL of n-butyllithium (concentration: 2.5M) was added by a syringe with stirring, the reaction tube was taken out from the low-temperature environment and returned to room temperature, and then heated at 40 ℃ for 3 hours, 458 mg of perfluorotoluene was injected by a syringe with low-temperature conditions, and reacted at 40 ℃ for 12 hours. Extracting with dichloromethane and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, and purifying by column chromatography (eluent is V) (methylene chloride) : V (Petroleum ether) = 1: 2.5), recrystallization from absolute ethanol, small amounts of ethyl acetate and methanol gave 66.87 mg of a white solid in 16% yield. The following data show that the product prepared using the process of this example is structurally correct. 1 H NMR (400 MHz, TMS, CDCl 3 ) δ 8.39 (d, J = 5.0 Hz, 1H, ArH), 8.33 (d, J = 4.6 Hz, 1H, ArH), 7.76 (d, J = 4.1 Hz, 2H, ArH), 4.28-4.24 (m, 4H, OCH 2 ), 4.18 (t, J = 6.4 Hz, 4H, OCH 2 ), 1.99 -1.87 (m,8H, CH 2 ), 1.64-1.57 (m, 8H, CH 2 ), 1.07-1.02 (m, 12H, CH 3 ).
R = C in the general formula I 4 H 9 Another preparation reaction of the perfluorotolutriphenylene discotic liquid crystal compound of (1) is as follows:
in the reaction formula (C) 2 H 5 ) 2 O is diethyl ether; t-BuLi is tert-butyl lithium.
A trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compound has a structure shown in the general formula I, wherein R = C 4 H 9 . The specific operation is as follows: 300 mg of 2,2 '-dibromo-4, 4',5 '-tetra (butoxy) -1,1' -biphenyl was weighed into a reaction tube, and under the protection of nitrogen, 30 mL of diethyl ether was added to dissolve completely, and the solution was charged to-78 ℃ and cooledAfter cooling for 10 minutes at room temperature, 1.66 mL of t-butyllithium (concentration: 1.3M) was added with stirring by a syringe, the reaction tube was taken out from the low-temperature environment and returned to room temperature, followed by reaction at room temperature for 3 hours, and 177 mg of perfluorotoluene was injected with a syringe at room temperature and reacted at room temperature for 12 hours. Extracting with dichloromethane and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, and separating and purifying by column chromatography (eluent is V) (methylene chloride) : V (Petroleum ether) = 1: 2.5), recrystallisation from anhydrous ethanol, small amounts of ethyl acetate and methanol gave 144 mg of white solid in 45% yield. The following data indicate that the product prepared by the above method is structurally correct. The method has significantly improved yield compared with the first method. 1 H NMR (400 MHz, TMS, CDCl 3 ) δ 8.39 (d, J = 5.0 Hz, 1H, ArH), 8.33 (d, J = 4.6 Hz, 1H, ArH), 7.76 (d, J = 4.1 Hz, 2H, ArH), 4.28-4.24 (m, 4H, OCH 2 ), 4.18 (t, J = 6.4 Hz, 4H, OCH 2 ), 1.99 -1.87 (m,8H, CH 2 ), 1.64-1.57 (m, 8H, CH 2 ), 1.07-1.02 (m, 12H, CH 3 ).
The compound in this example was imaged by Differential Scanning Calorimetry (DSC) and hot stage polarization microscope (POM) and found to have a typical liquid crystal texture and a broad phase transition temperature range (62-223 ℃).
Example 2
R = C in formula I 8 H 17 The first preparation reaction formula of the trifluoromethyl trifluoro triphenylene discotic liquid crystal compound is as follows:
in the reaction formula, THF is tetrahydrofuran; n-BuLi is n-butyl lithium.
The perfluorotoluene benzophenanthrene discotic liquid crystal compound has a structure shown in the general formula I, wherein R = C 8 H 17 . The specific operation is as follows: 400 mg of 2,2 '-dibromo-4, 4',5 '-tetra (octyloxy) -1,1' -biphenyl was weighed into a reaction tube, and 30 mL of tetrahydrofuran was added under nitrogen protection to completely dissolve the biphenylAfter the reaction solution was cooled in a low-temperature environment of-78 ℃ for 10 min, 1 mL of n-butyllithium (concentration: 2.5M) was added with stirring by a syringe, the reaction tube was taken out from the low-temperature environment and returned to room temperature, and then heated at 40 ℃ for 3 hours, 343 mg of perfluorotoluene was injected with a syringe at low temperature and reacted at 40 ℃ for 12 hours. Extracting with dichloromethane and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, and purifying by column chromatography (eluent is V) (methylene chloride) : V (Petroleum ether) = 1: 4), recrystallization from absolute ethanol, small amounts of ethyl acetate and methanol gave 56 mg of a white solid in 19% yield. The following data show that the product obtained by the process of this example is structurally correct. 1 H NMR (400 MHz, TMS, CDCl 3 ) δ 8.39 (d, J = 4.5 Hz, 1H, ArH), 8.34 (d, J = 4.2 Hz, 1H, ArH), 7.76 (d, J = 4.1 Hz, 2H, ArH), 4.28 – 4.22 (m, 4H, OCH 2 ), 4.17 (d, J = 5.7 Hz, 4H, OCH 2 ), 1.95-1.90 (m, 8H, CH 2 ), 1.56 (d, J = 6.3 Hz, 8H, CH 2 ), 1.43 – 1.25 (m, 32H, CH 2 ), 0.89 (d, J = 6.4 Hz, 12H, CH 3 ).
R = C in formula I 8 H 17 Another preparation reaction of the perfluorotolutriphenylene discotic liquid crystal compound of (1) is as follows:
in the reaction formula (C) 2 H 5 ) 2 O is diethyl ether; t-BuLi is tert-butyl lithium.
A trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compound has a structure shown in the general formula I, wherein R = C 8 H 17 . The specific operation is as follows: 300 mg of 2,2 '-dibromo-4, 4',5 '-tetra (octyloxy) -1,1' -biphenyl was weighed in a reaction tube, and 30 mL of diethyl ether was added under nitrogen protection to dissolve it completely, and the solution was placed in a low temperature environment of-78 ℃ for cooling for 10 minutes, and 1.22 mL of t-butyllithium (concentration: 1.3M) was added by a syringe with stirring, and then the mixture was cooled from the low temperature environmentThe reaction tube was taken out and returned to room temperature, followed by reaction at room temperature for 3 hours, and 129 mg of perfluorotoluene was injected by a syringe at room temperature and reacted at room temperature for 12 hours. Extracting with dichloromethane and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, and separating and purifying by column chromatography (eluent is V) (methylene chloride) : V (Petroleum ether) = 1: 4), recrystallisation from anhydrous ethanol, small amounts of ethyl acetate and methanol gave 136 mg of a white solid in 43% yield. The method has significantly improved yield compared with the first method. The following data indicate that the product prepared by the above method is structurally correct. 1 H NMR (400 MHz, TMS, CDCl 3 ) δ 8.39 (d, J = 4.5 Hz, 1H, ArH), 8.34 (d, J = 4.2 Hz, 1H, ArH), 7.76 (d, J = 4.1 Hz, 2H, ArH), 4.28 – 4.22 (m, 4H, OCH 2 ), 4.17 (d, J = 5.7 Hz, 4H, OCH 2 ), 1.95-1.90 (m, 8H, CH 2 ), 1.56 (d, J = 6.3 Hz, 8H, CH 2 ), 1.43 – 1.25 (m, 32H, CH 2 ), 0.89 (d, J = 6.4 Hz, 12H, CH 3 ).
The compound of interest in this example was imaged by Differential Scanning Calorimetry (DSC) and hot stage polarization microscope (POM) and found to have a typical liquid crystal texture and a broad liquid crystal phase transition temperature range (-17-153 ℃).
The trifluoromethyl trifluoro triphenylene discotic liquid crystal compound has a typical liquid crystal texture (columnar phase texture) and a wide liquid crystal range by adopting a hot stage polarization microscope, differential scanning calorimetry and small-angle X-ray diffraction.
Claims (7)
1. A trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compound has a structure shown in the following general formula I, wherein R = C n H 2n+1 , n = 2, 4, 6, 8, 10, 12
A first process for the preparation of a discotic liquid crystalline compound of the general formula i trifluoromethyl benzotrifluorine according to claim 1:
the method comprises the following steps: weighing 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl in a reaction tube, adding a proper amount of tetrahydrofuran to fully dissolve the tetrahydrofuran under the protection of nitrogen, placing the solution in a low-temperature environment at-78 ℃ for cooling, adding n-butyl lithium (the molar ratio of the 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl to the n-butyl lithium is 1) by using an injector under the stirring condition, taking the reaction tube out from the low-temperature environment to return to the room temperature after reacting for 30 min at the low temperature, then heating and reacting for 3 h at 40 ℃, placing the reaction tube in the low-temperature environment at-78 ℃ for cooling, injecting perfluorotoluene C by using the injector, and reacting for 3 h 6 F 5 CF 3 (the molar ratio of the 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl to the perfluorotoluene is 1.
2. Extracting with dichloromethane and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, separating and purifying by column chromatography, and recrystallizing with anhydrous ethanol, small amount of ethyl acetate and methanol to obtain white solid.
3. An alternative process for the preparation of trifluoromethyltrifluoromethyltrifluoromethyltriphenylene discotic liquid crystal compounds of formula I as claimed in claim 1 (which differs from the first process in terms of solvent, charge ratio, reaction temperature and butyllithium reagent):
the method comprises the following steps: weighing 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl in a reaction tube, adding a proper amount of diethyl ether to fully dissolve the biphenyl under the protection of nitrogen, and dissolving the mixtureCooling the solution in a low-temperature environment at-78 ℃, adding tert-butyl lithium (the molar ratio of 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl to tert-butyl lithium is 1, 4) by using an injector under the stirring condition, taking out the reaction tube from the low-temperature environment to return to the room temperature after reacting for 30 min at the low temperature, then reacting for 3 h at the room temperature, and injecting perfluorotoluene C by using the injector 6 F 5 CF 3 (the molar ratio of the 2,2 '-dibromo-4, 4',5 '-tetraalkoxy-1, 1' -biphenyl to the perfluorotoluene was 1.5), and reacted at room temperature for 12 hours.
4. Extracting with dichloromethane and saturated saline solution, drying the organic phase with anhydrous magnesium sulfate, filtering, distilling under reduced pressure to obtain crude product, separating and purifying by column chromatography, and recrystallizing with anhydrous ethanol, small amount of ethyl acetate and methanol to obtain white solid.
5. The trifluoromethyl trifluoro benzophenanthrene discotic liquid crystal compound has a good application prospect in the aspects of liquid crystal materials and photoelectric materials.
6. The polyfluorobenzophene discotic liquid crystal compound has a certain liquid crystal range, has a liquid crystal phase presenting hexagonal columnar phase accumulation, is expected to be used as a liquid crystal semiconductor material, and has application in electronic devices such as organic light-emitting diodes, organic field effect transistors, organic solar cells and the like.
7. The polyfluorobenzophene discotic liquid crystal compound is accumulated into a columnar phase, can provide a one-dimensional electron or hole transmission path, further enables the polyfluorobenzophene discotic liquid crystal compound to obtain higher charge carrier mobility, and is expected to be used as an organic photoelectric material.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4307049A1 (en) * | 1993-03-08 | 1994-09-15 | Hoechst Ag | Discotic liquid crystals |
| JP2000336053A (en) * | 1999-05-26 | 2000-12-05 | Canon Inc | Triphenylene derivative compound |
| JP2003201263A (en) * | 2001-12-28 | 2003-07-18 | Sankio Chemical Co Ltd | Method for producing triphenylene compound |
| CN111362783A (en) * | 2018-12-26 | 2020-07-03 | 四川师范大学 | Tetratetrafluoro tetraalkoxy benzophenanthrene discotic liquid crystal compound and preparation method thereof |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4307049A1 (en) * | 1993-03-08 | 1994-09-15 | Hoechst Ag | Discotic liquid crystals |
| JP2000336053A (en) * | 1999-05-26 | 2000-12-05 | Canon Inc | Triphenylene derivative compound |
| JP2003201263A (en) * | 2001-12-28 | 2003-07-18 | Sankio Chemical Co Ltd | Method for producing triphenylene compound |
| CN111362783A (en) * | 2018-12-26 | 2020-07-03 | 四川师范大学 | Tetratetrafluoro tetraalkoxy benzophenanthrene discotic liquid crystal compound and preparation method thereof |
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