CN108277020A - Utilize the multiaxis liquid crystal refrigerating material and preparation method of the synthesis of click chemistry method - Google Patents
Utilize the multiaxis liquid crystal refrigerating material and preparation method of the synthesis of click chemistry method Download PDFInfo
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- CN108277020A CN108277020A CN201810074017.XA CN201810074017A CN108277020A CN 108277020 A CN108277020 A CN 108277020A CN 201810074017 A CN201810074017 A CN 201810074017A CN 108277020 A CN108277020 A CN 108277020A
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- 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
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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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
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
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Abstract
It is a kind of to be using the multiaxis liquid crystal refrigerating material and preparation method, multiaxis liquid crystal refrigerating material structure of click chemistry method synthesis：Preparation method is that terminal alkyne compound and nitrine hydride compounds and N, N dimethylformamide are added in the reaction vessel, and catalyst CuI is added, is stirred to react 15 hours under conditions of 100 DEG C；After the completion of reaction, reaction dissolvent is removed, crude product is purified using the method for column chromatography, obtains multiaxis liquid crystal refrigerating material；The made multiaxis liquid crystal refrigerating material of the present invention has excellent refrigeration performance.
Description
Technical field
The present invention relates to liquid crystal refrigerating material fields, and in particular to a kind of multiaxis liquid crystal synthesized using click chemistry method
Refrigerating material and preparation method.
Background technology
Click chemistry is that one kind that the Americanized scholar Sharpless of Nobel chemistry Prize winner in 2001 is proposed quickly is closed
It is the another synthesis that significant innovation is brought to traditional Synthetic Organic Chemistry after combinatorial chemistry at the new method of a large amount of compounds
Technology.Currently, the technology has penetrated into the fields such as the foundation in lead compound library, the synthesis of new drug development and polymer.It clicks
Chemical essence refers to selecting the raw material that is easy to get, and realizes that heteroatoms connect by reliable, efficient and selective chemical reaction
It connects, low cost, a set of powerful and practical synthetic method of a large amount of noval chemical compounds of Fast back-projection algorithm.Its core be using it is a series of can
Reaction lean on, modular, which generates, contains heteroatomic compound.These reactions usually have following feature：It is raw materials used to be easy to get；Instead
Easy to operate, mild condition is answered, it is insensitive to oxygen, water；Product yield high, selectivity are good；Product easy purification, post-processing are simple.
Liquid crystal refrigerating material not only has the conversion of higher electric heating as a kind of New Refrigerating material without using compressor
Performance and no any pollution.Liquid crystal refrigerating material mainly occurs second order phase transition under electric field action using liquid crystal and generates
Thermodynamic entropy, and then cause the principle of the variation of environment temperature, there is wider foreground in refrigerating material.Before inventor
Phase has studied refrigeration characteristic (the Chinese patent CN201410336316.8 of liquid crystal refrigerating material；CN201410816332.7 it) sends out
It is existing：Twin shaft mixed liquid crystal has better refrigeration performance than uniaxial mixed liquid crystal.So, for multiaxis (being more than twin shaft) liquid crystal
Refrigeration performance, no document discloses in the world at present.
Invention content
In order to overcome the disadvantages of the above prior art, it is an object of the present invention to provide it is a kind of using click chemistry method synthesis
Multiaxis liquid crystal refrigerating material and preparation method, made multiaxis liquid crystal refrigerating material have excellent refrigeration performance.
In order to achieve the above object, the technical solution that the present invention takes is：
A kind of multiaxis liquid crystal refrigerating material synthesized using click chemistry method, compound structure are：
Wherein, R1=CnH2n+1(n=1~18)；
R2=F, CF3、CN、NO2、NCS、
A kind of preparation method of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method, reaction equation are：
Wherein, R1=CnH2n+1(n=1~18)；
R2=F, CF3, CN, NO2, NCS,
A kind of preparation method of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method, includes the following steps：
Terminal alkyne compound and nitrine hydride compounds and n,N-Dimethylformamide (DMF), end are added in the reaction vessel
The molar ratio 1 of alkine compounds and nitrine hydride compounds:2.5, the ratio of terminal alkyne compound and n,N-Dimethylformamide (DMF) is
1g:10mL is added the catalyst CuI of terminal alkyne compound quality 3.0%, is stirred to react 15 hours under conditions of 100 DEG C；It has reacted
Cheng Hou removes reaction dissolvent, and crude product is purified using the method for column chromatography, obtains multiaxis liquid crystal refrigerating material.
Prepared multiaxis liquid crystal refrigerating material is poured into 10um No yield point liquid crystal cells, in 1000MV/m electric field actions
Under, ferroelectric hysteresis loop is measured, the relation curve between polarizability and temperature under electric field action is obtained, utilizes Maxwell equation calculations
The maximum cryogenic temperature that this kind of liquid crystal generates under electric field action.
Advantages of the present invention is：
1, method using the present invention prepares thiophene-based multiaxis liquid-crystal compounds, reaction conversion simple with preparation method
Rate height, the thorough of reaction progress, click chemistry can the remarkable advantages such as 100% completely reaction.
2, a kind of utilization click chemistry prepared by the present invention, which prepares thiophene-based multiaxis liquid-crystal compounds, has longer π-electricity
Sub- conjugated system, exposed terminated groups have electron-withdrawing group and electron-donating group equimolecular architectural characteristic, are a kind of function admirables
Liquid crystal refrigerating material, does not find relevant report at home and abroad so far.
Description of the drawings
Fig. 1 is multiaxis liquid crystal refrigerating material Fourier transform infrared spectroscopy figure prepared by embodiment 1.
Fig. 2 is multiaxis liquid crystal refrigerating material Fourier transform infrared spectroscopy figure prepared by embodiment 2.
Fig. 3 is multiaxis liquid crystal refrigerating material Fourier transform infrared spectroscopy figure prepared by embodiment 3.
Specific implementation mode
The preparation method of the present invention is specifically described below by embodiment.
Embodiment 1, a kind of preparation method of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method, including it is following
Step：
Be added in the reaction vessel 3.00g to trifluoromethyl terminal alkyne compound and 2.13g azidos propane and
30mLDMF is added 0.09g CuI as catalyst, is stirred to react 15 hours under conditions of 100 DEG C；After the completion of reaction, removal is anti-
Solvent, crude product is answered to be purified using the method for column chromatography, solvent is dichloromethane:Petroleum ether=3:1 (vt), obtains multiaxis liquid
Brilliant refrigerating material, yield 65.2%.
The multiaxis liquid crystal refrigerating material Fourier transform infrared spectroscopy figure of the present embodiment referring to Fig.1, as can be seen from Figure 1
Prepared product is target thiophene-based multiaxis liquid-crystal compounds.
Multiaxis liquid crystal refrigerating material prepared by the present embodiment is poured into 10um No yield point liquid crystal cells, in 1000MV/m electricity
Under field action, ferroelectric hysteresis loop is measured, the relation curve between polarizability and temperature under electric field action is obtained, utilizes the side Maxwell
Journey calculates this kind of liquid crystal producible maximum 6.72K cryogenic temperatures under electric field action.
Embodiment 2, a kind of preparation method of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method, including it is following
Step：
3.00g is added in the reaction vessel to trifluoromethyl terminal alkyne compound, 2.83g nitrine pentane and 30mLDMF, adds
Enter 0.09g CuI as catalyst, is stirred to react 15 hours under conditions of 100 DEG C；After the completion of reaction, reaction dissolvent is removed, slightly
Product is purified using the method for column chromatography, and solvent is dichloromethane:Petroleum ether=3:1 (vt) obtains multiaxis liquid crystal refrigeration material
Material, yield 68.5%.
The multiaxis liquid crystal refrigerating material Fourier transform infrared spectroscopy figure of the present embodiment is with reference to Fig. 2, as can be seen from the figure
Prepared product is target thiophene-based multiaxis liquid-crystal compounds.
Multiaxis liquid crystal refrigerating material prepared by the present embodiment is poured into 10um No yield point liquid crystal cells, in 1000MV/m electricity
Under field action, ferroelectric hysteresis loop is measured, the relation curve between polarizability and temperature under electric field action is obtained, utilizes the side Maxwell
Journey calculates this kind of liquid crystal producible maximum 6.28K cryogenic temperatures under electric field action.
Embodiment 3, a kind of preparation method of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method, including it is following
Step：
2.58g is added in the reaction vessel to cyano terminal alkyne compound, 2.13g nitrine propane and 25.8mLDMF, is added
0.08g CuI are stirred to react 15 hours under conditions of 100 DEG C as catalyst；After the completion of reaction, reaction dissolvent is removed, it is thick to produce
Product are purified using the method for column chromatography, and solvent is dichloromethane:Petroleum ether=3:1 (vt) obtains multiaxis liquid crystal refrigerating material,
Yield 59.6%.
The multiaxis liquid crystal refrigerating material Fourier transform infrared spectroscopy figure of the present embodiment is with reference to Fig. 3, as can be seen from the figure
Prepared product is target thiophene-based multiaxis liquid-crystal compounds.
Multiaxis liquid crystal refrigerating material prepared by the present embodiment is poured into 10um No yield point liquid crystal cells, in 1000MV/m electricity
Under field action, ferroelectric hysteresis loop is measured, the relation curve between polarizability and temperature under electric field action is obtained, utilizes the side Maxwell
Journey calculates this kind of liquid crystal producible maximum 7.86K cryogenic temperatures under electric field action.
All embodiments are served only for that the present invention is further detailed, and should not be understood as the limitation of protection domain, this
The person skilled in the art in field makes the protection that some nonessential modifications and adaptations also belong to the present invention according to the content of present invention
Range.
Claims (6)
1. a kind of multiaxis liquid crystal refrigerating material synthesized using click chemistry method, which is characterized in that compound structure is：
Wherein, R1=CnH2n+1(n=1~18)；
R2=-F ,-CF3 ,-CN ,-NO2、-NCS、
2. it is a kind of using click chemistry method synthesis multiaxis liquid crystal refrigerating material preparation method, which is characterized in that including with
Lower step：
Terminal alkyne compound and nitrine hydride compounds and n,N-Dimethylformamide (DMF), Terminal Acetylenes are added in the reaction vessel
Close the molar ratio 1 of object and nitrine hydride compounds:2.5, the ratio of terminal alkyne compound and n,N-Dimethylformamide (DMF) is 1g:
10mL is added the catalyst CuI of terminal alkyne compound quality 3.0%, is stirred to react 15 hours under conditions of 100 DEG C；Reaction is completed
Afterwards, reaction dissolvent is removed, crude product is purified using the method for column chromatography, obtains multiaxis liquid crystal refrigerating material.
3. a kind of preparation side of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method according to claim 2
Method, it is characterised in that：Prepared multiaxis liquid crystal refrigerating material is poured into 10um No yield point liquid crystal cells, in 1000MV/m electric fields
Under effect, ferroelectric hysteresis loop is measured, the relation curve between polarizability and temperature under electric field action is obtained, utilizes Maxwell equations
Calculate the maximum cryogenic temperature that this kind of liquid crystal generates under electric field action.
4. a kind of preparation side of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method according to claim 2
Method, it is characterised in that：
3.00g is added in the reaction vessel to trifluoromethyl terminal alkyne compound and 2.13g azidos propane and 30mL DMF, adds
Enter 0.09g CuI as catalyst, is stirred to react 15 hours under conditions of 100 DEG C；After the completion of reaction, reaction dissolvent is removed, slightly
Product is purified using the method for column chromatography, and solvent is dichloromethane:Petroleum ether=3:1 (vt) obtains multiaxis liquid crystal refrigeration material
Material, yield 65.2%.
5. a kind of preparation side of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method according to claim 2
Method, it is characterised in that：
3.00g is added in the reaction vessel to trifluoromethyl terminal alkyne compound, 2.83g nitrine pentane and 30mL DMF, is added
0.09g CuI are stirred to react 15 hours under conditions of 100 DEG C as catalyst；After the completion of reaction, reaction dissolvent is removed, it is thick to produce
Product are purified using the method for column chromatography, and solvent is dichloromethane:Petroleum ether=3:1 (vt) obtains multiaxis liquid crystal refrigerating material,
Yield 68.5%.
6. a kind of preparation side of multiaxis liquid crystal refrigerating material using the synthesis of click chemistry method according to claim 2
Method, it is characterised in that：
2.58g is added in the reaction vessel to cyano terminal alkyne compound, 2.13g nitrine propane and 25.8mL DMF, is added
0.08g CuI are stirred to react 15 hours under conditions of 100 DEG C as catalyst；After the completion of reaction, reaction dissolvent is removed, it is thick to produce
Product are purified using the method for column chromatography, and solvent is dichloromethane:Petroleum ether=3:1 (vt) obtains multiaxis liquid crystal refrigerating material,
Yield 59.6%.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20050012071A1 (en) * | 2003-07-17 | 2005-01-20 | Fuji Photo Film Co., Ltd. | Liquid crystalline compound, liquid crystalline composition and retardation film |
| DE102008063330A1 (en) * | 2008-12-30 | 2010-07-01 | Technische Universität Chemnitz | New biaxially nematic liquid crystal ring compounds, e.g. (2,5-bis-hexyloxy-4-pyridin-3-yl-ethynyl-phenylethynyl)-phenyl-(1,3,4)thiadiazol-2-yl-phenylethynyl-2,5-bis-hexyloxy-phenylethynyl-phenoxy-acetic acid ethyl ester, useful in LCD |
| CN102993107A (en) * | 2012-11-16 | 2013-03-27 | 西京学院 | Azobenzene liquid-crystal compound containing triazolyl and preparation method thereof |
| CN103044342A (en) * | 2013-01-08 | 2013-04-17 | 陕西科技大学 | Azobenzene liquid crystal compound and click chemistry preparation method thereof |
| CN104087307A (en) * | 2014-07-15 | 2014-10-08 | 西京学院 | Liquid crystal mixture for refrigerants |
| CN104531168A (en) * | 2014-12-24 | 2015-04-22 | 西京学院 | Giant electrothermal effect liquid crystal mixture based on biaxial liquid crystal molecules |
-
2018
- 2018-01-25 CN CN201810074017.XA patent/CN108277020A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050012071A1 (en) * | 2003-07-17 | 2005-01-20 | Fuji Photo Film Co., Ltd. | Liquid crystalline compound, liquid crystalline composition and retardation film |
| DE102008063330A1 (en) * | 2008-12-30 | 2010-07-01 | Technische Universität Chemnitz | New biaxially nematic liquid crystal ring compounds, e.g. (2,5-bis-hexyloxy-4-pyridin-3-yl-ethynyl-phenylethynyl)-phenyl-(1,3,4)thiadiazol-2-yl-phenylethynyl-2,5-bis-hexyloxy-phenylethynyl-phenoxy-acetic acid ethyl ester, useful in LCD |
| CN102993107A (en) * | 2012-11-16 | 2013-03-27 | 西京学院 | Azobenzene liquid-crystal compound containing triazolyl and preparation method thereof |
| CN103044342A (en) * | 2013-01-08 | 2013-04-17 | 陕西科技大学 | Azobenzene liquid crystal compound and click chemistry preparation method thereof |
| CN104087307A (en) * | 2014-07-15 | 2014-10-08 | 西京学院 | Liquid crystal mixture for refrigerants |
| CN104531168A (en) * | 2014-12-24 | 2015-04-22 | 西京学院 | Giant electrothermal effect liquid crystal mixture based on biaxial liquid crystal molecules |
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Application publication date: 20180713 |