CN102211973A - Orientation-controllable benzophenanthrene disc-shaped liquid crystal molecule and preparation method thereof - Google Patents
Orientation-controllable benzophenanthrene disc-shaped liquid crystal molecule and preparation method thereof Download PDFInfo
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- CN102211973A CN102211973A CN2011100899610A CN201110089961A CN102211973A CN 102211973 A CN102211973 A CN 102211973A CN 2011100899610 A CN2011100899610 A CN 2011100899610A CN 201110089961 A CN201110089961 A CN 201110089961A CN 102211973 A CN102211973 A CN 102211973A
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Abstract
The invention belongs to the technical fields of a disc-shaped liquid crystal molecule and preparation thereof, and in particular relates to an orientation-controllable benzophenanthrene disc-shaped liquid crystal molecule and a preparation method thereof. The structure of the liquid crystal molecule is shown in a general formula (I), wherein R represents -CnH2n+1 or other structural formulas as shown in the specification, and n is an integral of 4-18. The liquid crystal molecule has the beneficial effects that the disc-shaped liquid crystal can be self-assembled into a hexagonal prism phase and shows excellent properties such as high conductivity and the like in a molecule stacking direction. Thus, the orientation-controllable benzophenanthrene disc-shaped liquid crystal molecule has a wide basic research value and a wide practicable application range.
Description
Technical field
The invention belongs to discotic liquid-crystalline molecules and preparing technical field thereof, be specifically related to be orientated controlled benzophenanthrene class discotic liquid-crystalline molecules and preparation method thereof; This discotic liquid-crystalline molecules is to be rigid central with the benzophenanthrene, enlarges the molecule discotic liquid-crystalline molecules that its conjugative effect preparation has self-assembly and liquid crystal property by alkynyl and phenyl ring.
Background technology
Discotic mesogenic was found in 1977, and existing up till now 14 classes, about 1000 disc liquid-crystal compounds are synthesized.Discotic liquid-crystalline molecules is generally by the plane or approach planar rigidity reality and six of centering on or more soft chain are formed.Discotic mesogenic all shows the characteristics that show with rod shaped liquid crystal that are different from aspects such as molecular structure, transformation behavior and photoelectric properties.Their shape of molecule, packing of molecules mode, charge transfer dimension difference.Its optical birefringence value difference presents negative value, be used in the visual angle of improving indicating meter in the liquid crystal display device so can be used as optical compensation films to liquid crystal to the row plate-like, therefore Japanese fuji company just once used a kind of polymkeric substance of benzophenanthrene, and this also is first application example of discotic mesogenic.Its mesomorphic phase is more prone to the column phase by the high-sequential of molecule self-assembly formation, interact along axis of a cylinder direction aromatic hydrocarbons π-π, therefore have higher electric charge and energy transfer rate along the post direction, having good application prospects at aspects such as organic electronic transmission apparatus, a ballistic transistor, photoelectrical solar devices.Discotic mesogenic is optical conductor and semiconductor material preferably, thereby causes that people study interest greatly.
Nobel chemistry Prize was authorized U.S. scientist Richard F He Ke, Japanese scientist's root bank English one and Suzuki chapter in 2010, to commend the outstanding contribution that they make in " palladium catalysis cross-coupling in the organism building-up process ".Chemistry prize evaluation committee says that three people's achievements in research are stopped work by " exquisite instrument " to chemists, promotes the possibility of synthetic complicated chemical material greatly.By the linked reaction under the palladium catalysis, we can directly link to each other alkynyl with the benzophenanthrene rigid disk, and at alkynyl the other end connection phenyl ring, can enlarge the π-pi-conjugated effect of molecule significantly, make the interaction between disklike molecule strengthen, thereby molecule is arranged the formation column mutually with the molecule stacking.
In the discotic mesogenic of report, the benzophenanthrene material that fixing rigid central nuclear arranged owing to it is easy to synthesize relatively, good solubility, abundant mesomorphic phase type, heat and chemical property are stablized, are easy to process and become in the discotic mesogenic material along the higher advantages such as charge transfer speed of axis of a cylinder be studied at most, a class the most widely.There have been 500 above benzophenanthrene disc liquid-crystal compounds to be synthesized up till now.A series of outstanding work of novel discotic liquid-crystalline molecules synthetic based on benzophenanthrene are recently also delivered, utilize the hexabromo benzophenanthrene to synthesize by the Sonogashira linked reaction as Michael M.Haley and have big ring discoid structure novel molecular; Dong Hoon Choi etc. also utilizes it to synthesize novel discotic liquid-crystalline molecules, is used to organic field effect tube (OFET).So, based on benzophenanthrene design and synthesize comprise different topological frameworks, peripheral side-chain radical, give electronics or electron-withdrawing group, the Multifunction of the controlled crosslinked group of different condition, stable discotic liquid-crystalline molecules, be one of very potential and feasible approach of preparation organic photoelectrical material.Our work is exactly under mentality of designing instructs, and has synthesized a series of controlled benzophenanthrene class discotic liquid-crystalline molecules of novel orientation with side-chain radical structure.
Summary of the invention
In order to address the above problem,, purpose of the present invention on the benzophenanthrene centronucleus, contains benzophenanthrene symmetric form disc liquid-crystal compounds and preparation method thereof by introducing π-pi-conjugated interaction induced liquid crystalline phase that alkynyl and phenyl ring increase substantially between the disklike molecule thereby providing a kind of.
Technical scheme of the present invention is: the controlled benzophenanthrene class of a kind of orientation discotic liquid-crystalline molecules, and this compound structure is shown in general formula (1):
Wherein, R is expressed as-C
nH
2n+1,
And n is the integer of 4-18.
The present invention also provides the preparation method of the controlled benzophenanthrene class of above-mentioned orientation discotic liquid-crystalline molecules, and the reaction mechanism of compound of the present invention is:
, this method has following steps:
The preparation of bromo dish nuclear:
1. a certain amount of benzophenanthrene is dissolved in the oil of mirbane, places in the reactor, add certain proportion Fe powder, dropping liquid Br gradually under the room temperature
2, be 120-150 ℃ in temperature, behind the reaction 12-16h, be chilled to room temperature, obtain product A; Wherein, benzophenanthrene: Fe powder: Br
2Mol ratio is 1: 2-5: 1-9;
2. product A is added and fills in the solution of sodium bisulfite, stirred 1 hour, remove distill water layer after, change distilled water once every 10min, repeat 5 times, colourless until solution, separatory is removed the distillation water layer; The adding dehydrated alcohol produces the particulate state precipitation, through behind the suction filtration, the powder on the filter paper is coated with filter paper, puts into the fat extraction device with distilled water extracting one day, uses the dehydrated alcohol extracting again one day, gets purifying bromination product B after the drying;
The Sonogashira linked reaction prepares discotic mesogenic:
1. above-mentioned steps is obtained being dissolved in tetrahydrofuran (THF) and the Diisopropylamine mixing solutions of bromination product B, place reactor to lead to argon shield, ultrasonic time is 20-60min, and the complete protected gas of dissolved oxygen is replaced;
With add alkyl acetylene among the purified product B, to alkylbenzene acetylene or to alkylamine phenylacetylene reactant, be heated to the 80-120 degree, the cuprous iodide catalyst of the normal molar weight 4-8% of the triphenyl phosphorus palladium chloride of the normal molar weight 4-8% of adding product B and adding product B, back flow reaction 12-16h under the argon shield; Underpressure distillation removes the rear pillar chromatography purified product of desolvating, and adding normal hexane and methylene dichloride mol ratio are 1: 4 developping agent, obtains final product and is the controlled benzophenanthrene class discotic liquid-crystalline molecules of orientation, and productive rate is 50%-60%.
The advantage of discotic liquid-crystalline molecules is among the present invention:
1 has wide intermediate phase temperature, and can control the scope of phase transition temperature and intermediate phase temperature range with crossing the length of adjusting alkyl chain.
2. because the molecular structure of its electron rich has big electronic mobility on the molecule minor axis, has great potential in the application facet of photoelectric device.
Description of drawings
Fig. 1 is the FTIR collection of illustrative plates of embodiment 1 molecule
Fig. 2 is the FTIR collection of illustrative plates of embodiment 2 molecules.
Fig. 3 is the FTIR collection of illustrative plates of embodiment 3 molecules.
Embodiment
Below in conjunction with specific embodiment technical scheme of the present invention is described further.
With the hexabromo benzo luxuriant and rich with fragrance with
Reaction is introduced such discotic mesogenic preparation methods for example:
A. the preparation of bromo dish nuclear:
(1) with raw material benzophenanthrene 6.00g (26.28mmol), is dissolved in the 120ml oil of mirbane, places in the 250ml single port bottle, add Fe powder 3.00g (53.55mmol), drip 12ml liquid Br under the room temperature gradually
2(236.52mmol), after dripping, temperature is raised to 120 ℃ of degree, reacts stopped reaction after 14 hours, be chilled to room temperature;
(2) product is poured into saturated sodium bisulfite distilled water solution and layering occurred, stirred 1 hour, remove the distillation water layer after, change distilled water and stirred 1 hour, remove the distillation water layer again, this process repeats 5 times;
(3) dehydrated alcohol is poured into, precipitation occurred, through behind the suction filtration powder on the filter paper is coated with filter paper, put into the fat extraction device with distilled water extracting one day, used the dehydrated alcohol extracting again one day, drying had both got white powder bromination product 10.80g, productive rate 90%;
The B.Sonogashira linked reaction prepares discotic mesogenic:
(4) be dissolved in 150ml tetrahydrofuran (THF) and the 150ml Diisopropylamine mixing solutions obtaining hexabromo product 1.5g among the A, place 500ml single port bottle to lead to argon shield, and the complete protected gas of dissolved oxygen is replaced;
(5) add hexyl phenylacetylene 4.74g (25.50mmol), be warmed up to 80 ℃; Add catalyzer 0.53mmol triphenyl phosphorus palladium chloride (0.38g), 1.05mmol cuprous iodide (0.20g) and 1.05mmol triphenyl phosphorus (0.27g).Back flow reaction is 12 hours under the argon shield;
(6) behind the stopped reaction, after underpressure distillation removed and desolvates, product was purified through 2 column chromatographies, using for the first time methylene dichloride to remove as eluent desalts, use for the second time methylene dichloride: the mixed solvent of normal hexane=1: 4 obtains 1.27 gram light yellow product, productive rate 55% as developping agent.
As shown in Figure 1, the spectroscopic data that records of this monomer is as follows:
Infrared FTIR (KBr), v (cm
-1): 2960cm
-1(CH
3Stretching), 2930cm
-1And 2850cm
-1(CH
2, stretching).
Embodiment 2
With the hexabromo benzo luxuriant and rich with fragrance with
Reaction is introduced such discotic mesogenic preparation methods for example:
A. the preparation of bromo dish nuclear:
(1) with raw material benzophenanthrene 4.00g (17.52mmol), is dissolved in the 80ml oil of mirbane, places in the 250ml single port bottle, drip 8ml liquid Br gradually under adding Fe powder 2.50g (44.64mmol) room temperature
2(157.68mmol), after dripping, temperature is raised to 130 ℃ of degree, reacts stopped reaction after 15 hours, be chilled to room temperature;
(2) product is poured into saturated sodium bisulfite distilled water solution and layering occurred, stirred 1 hour, remove the distillation water layer after, change distilled water and stirred 1 hour, remove the distillation water layer again, this process repeats 5 times;
(3) dehydrated alcohol is poured into, precipitation occurred, through behind the suction filtration powder on the filter paper is coated with filter paper, put into the fat extraction device with distilled water extracting one day, used the dehydrated alcohol extracting again one day, drying had both got white powder bromination product 10.80g, productive rate 90%;
The B.Sonogashira linked reaction prepares discotic mesogenic:
(4) be dissolved in 100ml tetrahydrofuran (THF) and the 100ml Diisopropylamine mixing solutions obtaining hexabromo product 1g among the A, place 500ml single port bottle to lead to argon shield, and the complete protected gas of dissolved oxygen is replaced;
(5) add Phenylacetylene butyl ether 2.96g (17.00mmol), be warmed up to 95 ℃; Add catalyzer 0.35mmol triphenyl phosphorus palladium chloride (0.25g), 0.70mmol cuprous iodide (0.13g) and 0.70mmol triphenyl phosphorus (0.18g).Back flow reaction is 14 hours under the argon shield;
(6) behind the stopped reaction, after underpressure distillation removed and desolvates, product was purified through 2 column chromatographies, using for the first time methylene dichloride to remove as eluent desalts, use for the second time methylene dichloride: the mixed solvent of normal hexane=1: 4 obtains 794 milligrams of light yellow product, productive rate 55% as developping agent.
As shown in Figure 2, the spectroscopic data that records of this monomer is as follows:
Infrared FTIR (KBr), v (cm
-1): 2209cm
-1(C ≡ C stretching), 1250cm
-1(C-O-C, stretching).
Embodiment 3
With the hexabromo benzophenanthrene with
Introduce the preparation of such discotic mesogenic material for example:
The preparation of bromo dish nuclear:
(1) with raw material benzophenanthrene 2.00g (8.76mmol), is dissolved in the 40ml oil of mirbane, places in the 100ml single port bottle, drip 1.35ml liquid Br gradually under adding Fe powder 1.47g (26.28mmol) room temperature
2(26.28mmol), after dripping, temperature is raised to 150 ℃ of degree, reacts stopped reaction after 16 hours, be chilled to room temperature;
(2) product is poured into saturated sodium bisulfite distilled water solution and layering occurred, stirred 1 hour, remove the distillation water layer after, change distilled water and stirred 1 hour, remove the distillation water layer again, this process repeats 5 times;
(3) dehydrated alcohol is poured into, precipitation occurred, through behind the suction filtration powder on the filter paper is coated with filter paper, put into the fat extraction device with distilled water extracting one day, used the dehydrated alcohol extracting again one day, drying had both got white powder bromination product 3.57g, productive rate 88%.
The B.Sonogashira linked reaction prepares discotic mesogenic:
(4) be dissolved in 12ml tetrahydrofuran (THF) and the 12ml Diisopropylamine mixing solutions obtaining hexabromo product 140mg (0.20mmol) among the A, place 100ml single port bottle to lead to argon shield, and the complete protected gas of dissolved oxygen is replaced;
(5) add N, N-two decyls are warmed up to 115 ℃ to acetylene aniline 900mg (2.40mmol), add 0.04mmol triphenyl phosphorus palladium chloride (0.028g), 0.07mmol cuprous iodide (0.013g) and 0.07mmol triphenyl phosphorus (0.018g) catalyzer.Back flow reaction is 16 hours under the argon shield;
(6) behind the stopped reaction, after underpressure distillation removed and desolvates, product was purified through 2 column chromatographies, using for the first time methylene dichloride to remove as developping agent desalts, use for the second time methylene dichloride: the mixed solvent of normal hexane=1: 4 obtains the 716mg light yellow product as developping agent, productive rate 60%.
As shown in Figure 3, the spectroscopic data that records of this monomer is as follows:
Infrared FTIR (KBr), v (cm
-1): 1360cm
-1(RR ' N-Ar, stretching), 1193cm
-1(RR ' N-Ar, stretching).
Embodiment 4:
In general formula, when
The time, we synthesize, and to have obtained the linear alkyl chain chain length be the different discotic liquid-crystalline molecules of n=4～18, adopts differential scanning calorimeter (DSC) that their phase transition temperature is tested and characterized.Resulting phase transition temperature is as shown in table 1:
The phase transition temperature of the symmetric form discotic liquid-crystalline molecules of table 1 different lengths straight-chain paraffin
Embodiment 5:
In general formula, when
We synthesize, and to have obtained the linear alkyl chain chain length be the different discotic liquid-crystalline molecules of n=4～18, and its carrier mobility is as shown in table 2:
The charge mobility of the symmetric form discotic liquid-crystalline molecules of table 2 different lengths straight-chain paraffin
| The C atomicity | Charge mobility * 10 -4(cm 2.V -1.s -1) |
| 4 | 0.9 |
| 5 | 0.93 |
| 6 | 0.97 |
| 7 | 0.99 |
| 8 | 1.01 |
| 9 | 1.03 |
| 10 | 1.07 |
| 11 | 1.09 |
| 12 | 1.1 |
| 13 | 1.13 |
| 14 | 1.16 |
| 15 | 1.18 |
| 16 | 1.21 |
| 17 | 1.22 |
| 18 | 1.24 |
Claims (2)
1. one kind is orientated controlled benzophenanthrene class discotic liquid-crystalline molecules, it is characterized in that this liquid crystal molecule structure is shown in general formula (1):
（1）
Wherein, R is expressed as-C
nH
2n+1,
,
,
Or
, and n is the integer of 4-18.
2. the preparation method of the controlled benzophenanthrene class of orientation according to claim 1 discotic liquid-crystalline molecules is characterized in that, specifically may further comprise the steps:
The preparation of bromo dish nuclear:
(1) .. is dissolved in a certain amount of benzophenanthrene in the oil of mirbane, places in the reactor, adds certain proportion Fe powder, dropping liquid Br gradually under the room temperature
2, be 120-150 in temperature
OC, behind the reaction 12-16 h, be chilled to room temperature, obtain product A; Wherein, benzophenanthrene: Fe powder: Br
2Mol ratio is 1:2-5:1-9;
(2). product A added fill in the solution of sodium bisulfite, stirred 1 hour, remove distill water layer after, change distilled water once every 10min, repeat 5 times, colourless until solution, separatory is removed the distillation water layer; The adding dehydrated alcohol produces the particulate state precipitation, through behind the suction filtration, the powder on the filter paper is coated with filter paper, puts into the fat extraction device with distilled water extracting one day, uses the dehydrated alcohol extracting again one day, gets purifying bromination product B after the drying;
The Sonogashira linked reaction prepares discotic mesogenic:
(1). above-mentioned steps is obtained being dissolved in tetrahydrofuran (THF) and the Diisopropylamine mixing solutions of bromination product B, place reactor to lead to argon shield, ultrasonic time is 20-60 min, and the complete protected gas of dissolved oxygen is replaced;
(2). with add alkyl acetylene among the purified product B, to alkylbenzene acetylene or to alkylamine phenylacetylene reactant, be heated to 80-120
OC, the cuprous iodide catalyst of the normal molar weight 4-8% of the triphenyl phosphorus palladium chloride of the normal molar weight 4-8% of adding product B and adding product B, back flow reaction 12-16 h under the argon shield; Underpressure distillation removes the rear pillar chromatography purified product of desolvating, and adding normal hexane and methylene dichloride mol ratio is the developping agent of 1:4, obtains final product and is the controlled benzophenanthrene class discotic liquid-crystalline molecules of orientation, and productive rate is 50%-60%.
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| CN102516185A (en) * | 2011-11-15 | 2012-06-27 | 北京科技大学 | Benzophenanthrene asymmetrical disk compound and preparation method thereof |
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| CN102902094A (en) * | 2012-09-28 | 2013-01-30 | 北京京东方光电科技有限公司 | TN-typed liquid crystal display panel and manufacturing method thereof |
| CN109231159A (en) * | 2018-09-10 | 2019-01-18 | 电子科技大学中山学院 | Method for changing orientation of benzophenanthrene discotic liquid crystal molecules |
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| WO2012115369A2 (en) * | 2011-02-24 | 2012-08-30 | 한국화학연구원 | Triphenylene-based reactive mesogen containing acetylene |
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| CN102503854A (en) * | 2011-12-19 | 2012-06-20 | 北京科技大学 | Symmetric discotic pyrene compounds and preparation method thereof |
| CN102902094A (en) * | 2012-09-28 | 2013-01-30 | 北京京东方光电科技有限公司 | TN-typed liquid crystal display panel and manufacturing method thereof |
| CN102902094B (en) * | 2012-09-28 | 2015-03-25 | 北京京东方光电科技有限公司 | TN-typed liquid crystal display panel and manufacturing method thereof |
| CN109231159A (en) * | 2018-09-10 | 2019-01-18 | 电子科技大学中山学院 | Method for changing orientation of benzophenanthrene discotic liquid crystal molecules |
| CN109231159B (en) * | 2018-09-10 | 2020-06-02 | 电子科技大学中山学院 | Method for changing orientation of benzophenanthrene discotic liquid crystal molecules |
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Application publication date: 20111012 |