CN106675577A - Biphenyl liquid crystal compound containing pyridine end group and preparation method and application thereof - Google Patents
Biphenyl liquid crystal compound containing pyridine end group and preparation method and application thereof Download PDFInfo
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- CN106675577A CN106675577A CN201710005033.9A CN201710005033A CN106675577A CN 106675577 A CN106675577 A CN 106675577A CN 201710005033 A CN201710005033 A CN 201710005033A CN 106675577 A CN106675577 A CN 106675577A
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- 0 Cc1ccc(C(CC2)CCC2*#C)cc1 Chemical compound Cc1ccc(C(CC2)CCC2*#C)cc1 0.000 description 3
- FDEDJRHULYIJOR-UHFFFAOYSA-N C#Cc1ccncc1 Chemical compound C#Cc1ccncc1 FDEDJRHULYIJOR-UHFFFAOYSA-N 0.000 description 1
- ABGPTXBFJCYXCV-UHFFFAOYSA-N C[Ar](C1=NC1)=C Chemical compound C[Ar](C1=NC1)=C ABGPTXBFJCYXCV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
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- 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
- Y02E10/542—Dye sensitized solar cells
Abstract
The invention discloses a biphenyl liquid crystal compound containing a pyridine end group and a preparation method and application thereof. The structure formula of the compound is as shown in the specification, wherein CnH2n+1 replaces C2-C5 linear alkyl. The liquid crystal compound is obtained through Suzuki coupled reaction of pyridyl boron ester and aromatic hydrocarbon iodide. The synthesis method is simple, the cost is relatively low, and the liquid crystal compound is suitable for industrial production. The liquid crystal compound has positive dielectric anisotropy and a certain nematic phase liquid crystal interval, is relatively high in clearing point, can be applied to an IPS display mode and a TN display mode, and can be applied to a dye-sensitized solar cell as a dye sensitizer molecule.
Description
Technical field
The invention belongs to liquid-crystal compounds technical field, and in particular to a kind of biphenyls liquid crystal chemical combination of base containing pyridyl end
Thing, and the liquid-crystal compounds preparation method and application.
Background technology
Liquid crystal material is developed so far, in liquid crystal display, liquid crystal optical device, high strength elastic material, organic solar electricity
Application is had been obtained in the various fields such as pond material.Thus liquid crystal material is ground as the study hotspot of cross discipline
The persons of studying carefully widely study.The situation that the challenge constituted to Global Sustainable Development in energy crisis and environmental pollution increasingly sharpens
Under background, solar cell is increasingly paid much attention to by science with industrial quarters.Over the past two years, liquid crystal research person had done substantial amounts of
Attempt research, it is desired to be able to which liquid crystal material is applied to solar cell research field.Nowadays, existing some liquid crystal materials success
It is applied to area of solar cell.For example, Agnieszka Iwan report a kind of chiral photoactivated liquid crystal molecule (AZOX) doping
To in the active layer of organic solar batteries, improve device photovoltaic performance (Liquid Crystals, 2015,42 (7),
964-972)。
Fan Li report the anode that a kind of ion liquid crystal (6CNBP-N) is added to bulk heterojunction polymer solar battery
In cushion, phase separation, crystallinity and ordered structure induction of active layer increased the photovoltaic of polymer solar battery
Energy (RSC Adv.2015,5,52874-52881).
E.A.Soto-Bustamante reports a kind of liquid crystal (M6R8) nano particle and is doped to titania nanoparticles
In, the photoelectric current (J.Mater.Chem.C, 2015,3,8566--8573) of organic inorganic composite solar battery can be improved.
Kuan Sun report a kind of nematic liquid crystal (BTR) and are especially suitable for printable organic solar batteries, doping
The efficiency (Nature Communications, 2015,6,6013) of solar cell can be improved in active layer.
Takashi Kato report a kind of liquid crystal electrolytes (1/2-I2) apply in DSSC, can
So that battery normally runs (Chem.Mater.2014,26,6496-6502) at high temperature.
But do not have but on the report that display liquid crystal material is applied in solar cell.
The content of the invention
The technical problems to be solved by the invention are to provide one kind and only exist nematic phase and with larger positive dielectric respectively to different
The display liquid-crystal compounds of property, and for the display liquid-crystal compounds provides a kind of preparation method and application.
Solving the technical scheme that is used of above-mentioned technical problem is：The display liquid-crystal compounds is the connection of base containing pyridyl end
Benzene class liquid-crystal compounds, its structural formula is as follows：
C in formulanH2n+1Represent C2~C5Straight chained alkyl.
The preparation method of the above-mentioned biphenyls liquid crystal compounds of base containing pyridyl end is：By 4- pyridines acetylene and 4- bromobenzeneboronic acids
Pinacol ester prepares pyridine radicals boron ester 1 by Heck coupling reactions；Then with N,N-dimethylformamide and distilled water volume ratio
It is 5:1 mixture is solvent, under inert gas shielding, by pyridine radicals boron ester 1 and aromatic hydrocarbon iodo thing nI, tetra-n-butyl bromine
Change ammonium, four (triphenyl) phosphines to close palladium, potassium carbonate is in molar ratio 1:1~1.3:0.05~0.2:0.02~0.04:2~4,40
Stirring reaction 12~24 hours, isolate and purify product at~60 DEG C, obtain the biphenyls liquid crystal compounds of base containing pyridyl end, and its is anti-
Answer equation as follows：
In the preparation method of the above-mentioned biphenyls liquid crystal compounds of base containing pyridyl end, preferably pyridine radicals boron ester and aromatic hydrocarbon iodine
Palladium is closed for thing nI, tetra-n-butyl ammonium bromide, four (triphenyl) phosphines, the mol ratio of potassium carbonate is 1:1.2:0.1:0.03:3.
Aromatic hydrocarbon iodo thing of the invention is according to Publication No. CN 103805208A, entitled《Dicyclohexyl ethylene
Base substituted diphenylamine alkynes liquid-crystal compounds and preparation method thereof》Chinese invention patent application disclosed in method synthesis.
Purposes of the biphenyls liquid crystal compounds of base containing pyridyl end of the invention in DSSC is prepared, its
Specifically used method is as follows：
1st, electro-conductive glass pretreatment
By electro-conductive glass successively in detergent, ethanol, deionized water with the ultrasonic wave that frequency is 40Hz, power is 100W
Cleaning 30 minutes to 1 hour, dry for standby at 110 DEG C.
2nd, dye solution is prepared
It is 1 that the biphenyls liquid crystal compounds of base containing pyridyl end are dissolved in into acetonitrile with the volume ratio of the tert-butyl alcohol:1 mixed solvent
In, it is configured to the dye solution that concentration is 0.3mmol/L.
3rd, electrolyte solution is prepared
By tetrabutylammonium iodide, lithium iodide, iodine, to tert .-butylpyridine add acetonitrile in, be configured to electrolyte solution, be electrolysed
In matter solution tetrabutylammonium iodide, lithium iodide, iodine, the concentration to tert .-butylpyridine be respectively 0.6mol/L, 0.1mol/L,
0.05mol/L、0.5mol/L。
4th, light anode is prepared
It is 0.25cm to use and prepare area on screen printing technique electro-conductive glass after the pre-treatment2, thickness be 12~20 μ
The nanoporous TiO of m2Film, 450 DEG C sinter 30 minutes, are naturally cooling to room temperature, are prepared into light anode.
5th, preparation work electrode
Light anode is impregnated 12~24 hours in dye solution, the working electrode being sensitized.
6th, prepare to electrode
It is 0.25cm to use and prepare area on screen printing technique electro-conductive glass after the pre-treatment2, thickness be 4~6 μm
Platinum slurry, prepare paired electrode.
7th, seal
In the peripheral position of electrode, sarin heat-sealing film is homogeneously disposed in setting position by printing spraying, working electrode with
Electrode is closed and is sealed, electrolyte solution is irrigated by vacuum suck-back, sealed, DSSC is obtained.
The invention has the advantages that：
1st, liquid-crystal compounds of the present invention, with pyridine ring as terminal groups, is the liquid crystal of end group with traditional alkyl chain with flexibility
Compound phase ratio, it is with big positive dielectric anisotropy and interval with certain nematic liquid crystal, can be applied to TN display moulds
Formula and IPS display patterns.
2nd, the present invention will contain pyridyl end base biphenyls liquid crystal compounds as dye sensitizing agent first, apply quick in dyestuff
In change solar cell.
Brief description of the drawings
Fig. 1 is dye sensitization of solar electricity prepared by the biphenyls liquid crystal compounds of base containing pyridyl end prepared by embodiment 1
The J-V curve maps in pond.
Specific embodiment
The present invention is described in more detail with reference to the accompanying drawings and examples, but protection scope of the present invention is not limited only to
These embodiments.
Embodiment 1
Under nitrogen protection, by 2.58g (8.46mmol) 4- bromobenzeneboronic acids pinacol ester, 0.73g (7.05mmol) 4- pyrroles
Pyridine acetylene, 20mL triethylamines (TEA), 20mL DMF are added to tri- mouthfuls of the 100mL equipped with thermometer, condenser pipe, magnetic stir bar and burn
In bottle, stirring is warming up to 60 DEG C after 30 minutes at 40 DEG C, be subsequently adding 0.16g (0.14mmol) four (triphenyl) phosphine close palladium and
0.05g (0.28mmol) cuprous iodide, continues to react 6 hours at 100 DEG C, and reaction solution naturally cools to room temperature, uses dichloromethane
Alkane extractive reaction liquid in three times, finally merges organic phase, and with salt water washing organic phase 3 times, anhydrous magnesium sulfate dries half an hour, takes out
Recycling design after filter, then it is 5 with the volume ratio of ethyl acetate to use petroleum ether:1 eluant, eluent carries out column chromatography separating purification, obtains
To 0.65g white solids, i.e. pyridine radicals boron ester 1, its yield is 30%.
Under nitrogen protection, by 2.38g (7.8mmol) pyridine radicals boron ester 1,0.25g (0.78mmol) tetran-butylphosphonium bromide
Ammonium, 3.23g (23.4mmol) potassium carbonate, 30mL N,N-dimethylformamides and 6mL distilled water are added to equipped with thermometer, magnetic
In power stirrer, the there-necked flask of condenser pipe, there-necked flask is placed in oil bath pan, and is warming up to 40 DEG C, treat that solid is completely molten
Xie Hou, adds 3.33g (9.36mmol) 4- (trans- (4- n-propyls cyclohexyl) ethyl) iodobenzene 3I and 0.27g (0.23mmol) four
(triphenyl) phosphine closes palladium, is warming up to 60 DEG C, and constant temperature stirring reaction 12 hours terminates reaction, and reaction solution is cooled into room temperature, is used in combination
Diatomite is filtered, and filtrate is extracted with ethyl acetate, and organic phase is obtained after point liquid and is washed to neutrality, then with after anhydrous magnesium sulfate drying
Concentration, concentrate carry out column chromatography separating purification (with silica gel as fixing phase, with the volume ratio of petroleum ether and ethyl acetate be 5:1
Mixed liquor be eluent), after the liquid concentration after isolating and purifying use ethyl alcohol recrystallization, obtain white crystal --- containing pyridine
Terminal groups biphenyls liquid crystal compounds 3N, its yield is 60%, and chemical name is 1- { 4- [2- (4- n-propyls cyclohexyl) ethyl]
Xenyl } -2- [4- pyridine radicals] acetylene.
The structural characterization data of gained base containing pyridyl end biphenyls liquid crystal compounds are as follows：
13C-NMR(CDCl3It is solvent, is inside designated as TMS, 101MHz, ppm)：149.85,143.31,142.02,137.37,
132.43,131.64,129.03,127.03,127.00,125.63,120.61,94.20,87.29,39.88,39.45,
37.62,37.60,33.34,33.30,33.13,20.15,14.55.
1H-NMR(CDCl3It is solvent, is inside designated as TMS, 400MHz, ppm)：(8.59 d, J=5.3Hz, 2H), 7.59 (s,
4H), 7.51 (d, J=8.1Hz, 2H), 7.41-7.35 (m, 2H), 7.29-7.21 (m, 2H), 2.80-2.51 (m, 2H), 1.86-
1.70 (m, 4H), 1.58-1.47 (m, 2H), 1.32-1.13 (m, 6H), 0.97-0.83 (m, 7H).
With reference to above-mentioned analysis result, it was demonstrated that the white crystal for obtaining strictly compound 1- { 4- [2- (4- n-propyl hexamethylenes
Base) ethyl] xenyl } -2- [4- pyridine radicals] acetylene.
Using differential calorimetric scan instrument, the cold and hot test of Leika DM2500P petrographic microscopes and Linkam THMSE600
The hot property of compound 1- { 4- [2- (4- n-propyls cyclohexyl) ethyl] xenyl } -2- [4- pyridine radicals] acetylene of synthesis, knot
Fruit shows that the compound has liquid crystalline phase, and phase transition property represents crystal for 138.3 DEG C of Cr, 245.1 DEG C of N I, Cr, and N represents nematic
Phase, I represents isotropic liquid, and clearing point is 245.1 DEG C.Tested by petrographic microscope, it is found that the compound was heating up
There is typical nematic phase in journey.
Embodiment 2
In embodiment 1,4- used (trans- (4- n-propyls cyclohexyl) ethyl) iodobenzene 3I is (trans- with equimolar 4-
(4- pentyl cyclohexyls) ethyl) iodobenzene 5I replaces, and other steps are same as Example 1, obtain white crystal --- containing pyridine
Terminal groups biphenyls liquid crystal molecule 5N, its yield is 63%, and chemical name is that { 4- [2- (4- pentyl cyclohexyls) ethyl] joins 1-
Phenyl } -2- [4- pyridine radicals] acetylene, specific reaction equation is as follows：
The structural characterization data of gained base containing pyridyl end biphenyls liquid crystal compounds are as follows：
13C-NMR(CDCl3It is solvent, is inside designated as TMS, 101MHz, ppm)：149.85,143.31,142.02,137.35,
132.40,131.64,129.04,127.03,126.99,125.62,120.61,94.19,87.28,39.45,37.91,
37.61,37.54,33.34,33.32,33.12,32.33,26.79,22.83,14.24.
1H-NMR(CDCl3It is solvent, is inside designated as TMS, 400MHz, ppm)：8.59 (dd, J=4.5,1.6Hz, 2H), 7.59
(s, 4H), 7.51 (d, J=8.2Hz, 2H), 7.41-7.35 (m, 2H), 7.29-7.22 (m, 2H), 2.69-2.60 (m, 2H),
1.85-1.69 (m, 4H), 1.57-1.47 (m, 2H), 1.33-1.11 (m, 10H), 0.97-0.82 (m, 7H).
With reference to above-mentioned analysis result, it was demonstrated that the white crystal for obtaining strictly compound 1- { 4- [2- (4- n-pentyl hexamethylenes
Base) ethyl] xenyl } -2- [4- pyridine radicals] acetylene.
Using differential calorimetric scan instrument, the cold and hot test of Leika DM2500P petrographic microscopes and Linkam THMSE600
The hot property of compound 1- { 4- [2- (4- pentyl cyclohexyls) ethyl] xenyl } -2- [4- pyridine radicals] acetylene of synthesis, knot
Fruit shows that the compound has liquid crystalline phase, and phase transition property represents crystal for 86.5 DEG C of Cr, 163.5 DEG C of N I, Cr, and N represents nematic
Phase, I represents isotropic liquid, and clearing point is 163.5 DEG C.By polarized light microscope observing, the compound is in temperature-rise period
All there is typical nematic phase.
Embodiment 3
The biphenyls liquid crystal compounds of base containing pyridyl end prepared by embodiment 1 are in DSSC is prepared
Purposes, its specifically used method is：
1st, electro-conductive glass pretreatment
By electro-conductive glass successively in detergent, ethanol, deionized water with the ultrasonic wave that frequency is 40Hz, power is 100W
Cleaning 30 minutes to 1 hour, dry for standby at 110 DEG C.
2nd, dye solution is prepared
It is 1 that the biphenyls liquid crystal compounds of base containing pyridyl end are dissolved in into acetonitrile with the volume ratio of the tert-butyl alcohol:1 mixed solvent
In, it is configured to the dye solution that concentration is 0.3mmol/L.
3rd, electrolyte solution is prepared
By tetrabutylammonium iodide, lithium iodide, iodine, to tert .-butylpyridine add acetonitrile in, be configured to electrolyte solution, be electrolysed
In matter solution tetrabutylammonium iodide, lithium iodide, iodine, the concentration to tert .-butylpyridine be respectively 0.6mol/L, 0.1mol/L,
0.05mol/L、0.5mol/L。
4th, light anode is prepared
It is 0.25cm to use and prepare area on screen printing technique electro-conductive glass after the pre-treatment2, thickness be 15 μm
Nanoporous TiO2Film, 450 DEG C sinter 30 minutes, are naturally cooling to room temperature, are prepared into light anode.
5th, preparation work electrode
Light anode is impregnated 24 hours in dye solution, the working electrode being sensitized.
6th, prepare to electrode
It is 0.25cm to use and prepare area on screen printing technique electro-conductive glass after the pre-treatment2, the platinum that thickness is 6 μm
Slurry, prepares paired electrode.
7th, seal
In the peripheral position of electrode, sarin heat-sealing film is homogeneously disposed in setting position by printing spraying, working electrode with
Electrode is closed and is sealed, electrolyte solution is irrigated by vacuum suck-back, sealed, DSSC is obtained.
Using J-V characteristic test systems, (model IV Test Station2000 are given birth to by CROWNTECH companies of the U.S.
Producing) solar cell to preparing tests, and the short-circuit current density of battery is 0.22mA/cm2, open-circuit voltage be
459.91V, fill factor, curve factor are 0.59, electricity conversion 0.06%.
Claims (4)
1. a kind of biphenyls liquid crystal compounds of base containing pyridyl end, it is characterised in that the structural formula of the compound is as follows：
C in formulanH2n+1Represent C2~C5Straight chained alkyl.
2. the preparation method of the biphenyls liquid crystal compounds of base containing pyridyl end described in a kind of claim 1, it is characterised in that：Will
4- pyridines acetylene prepares pyridine radicals boron ester 1 with 4- bromobenzeneboronic acids pinacol ester by Heck coupling reactions；Then with N, N- diformazans
Base formamide is 5 with distilled water volume ratio:1 mixture is solvent, under inert gas shielding, by pyridine radicals boron ester 1 and virtue
It is in molar ratio 1 that fragrant hydrocarbon iodo thing nI, tetra-n-butyl ammonium bromide, four (triphenyl) phosphines close palladium, potassium carbonate:1~1.3:0.05~
0.2:0.02~0.04:2~4, stirring reaction 12~24 hours, isolate and purify product at 40~60 DEG C, obtain containing pyridine end
End group biphenyls liquid crystal compounds；
3. the preparation method of the biphenyls liquid crystal compounds of base containing pyridyl end according to claim 2, it is characterised in that：Institute
State pyridine radicals boron ester 1 and close palladium, the mol ratio of potassium carbonate with aromatic hydrocarbon iodo thing nI, tetra-n-butyl ammonium bromide, four (triphenyl) phosphines
It is 1:1.2:0.1:0.03:3.
4. the biphenyls liquid crystal compounds of base containing pyridyl end described in claim 1 are in DSSC is prepared
Purposes.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111286343A (en) * | 2020-02-12 | 2020-06-16 | 华南师范大学 | Bis-difluoromethoxy bridged biphenyl liquid crystal compound substituted by bis-fluorine-containing group as well as preparation method and application thereof |
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| CN111286343A (en) * | 2020-02-12 | 2020-06-16 | 华南师范大学 | Bis-difluoromethoxy bridged biphenyl liquid crystal compound substituted by bis-fluorine-containing group as well as preparation method and application thereof |
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| CN106675577B (en) | 2018-10-23 |
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