CN105542793A - Chiral room-temperature ironic liquid crystal compound and preparation method thereof - Google Patents

Chiral room-temperature ironic liquid crystal compound and preparation method thereof Download PDF

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CN105542793A
CN105542793A CN201610108345.8A CN201610108345A CN105542793A CN 105542793 A CN105542793 A CN 105542793A CN 201610108345 A CN201610108345 A CN 201610108345A CN 105542793 A CN105542793 A CN 105542793A
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halogenated aliphatic
aliphatic acid
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CN105542793B (en
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张静
马成乡
蔡瑾
吴立新
魏学红
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Shanxi University
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Abstract

The invention provides a chiral room-temperature ironic liquid crystal compound and a preparation method thereof. The general structural formula of the compound is C30H51NO2BrRmTn, wherein Rm is alkyl carbon chain -(CH2)m-, and m is 5, 7, 9 or 10; Tn is alkyl carbon chain -CnH2n+1, and n is 1, 4, 8 or 12. The method comprises preparation steps as follows: firstly, initial raw materials, namely, cholesterol and halogenated fatty acid have an esterification reaction to produce a liquid crystal intermediate, namely, halogenated fatty acid cholesterol ester; then the liquid crystal intermediate and tertiary amine have a quaterisation reaction to produce a target product. The chiral room-temperature ironic liquid crystal compound is designed and synthesized by using the steric-hindrance effect, the method is simple, raw materials are easy to obtain, and the material has chirality, can display the liquid crystal phase at the room temperature and is expected to be widely applied to aspects of liquid crystal display, solar cells, electrochemical devices and the like.

Description

A kind of chirality room-temperature ion liquid-crystalization compound and preparation method thereof
Technical field
The present invention relates to liquid crystal material field, be specifically related to a kind of chirality room-temperature ion liquid-crystalization compound and preparation method thereof.This type of room-temperature ion liquid crystal material not only has chirality, and at room temperature can demonstrate mesomorphic phase, is expected to be used widely in liquid-crystal display, solar cell, electrochemical device etc.
Background technology
Chiral liquid crystal forms spirane structure because of the existence of chiral centre in molecule, and these spirane structures make chiral liquid crystal have special optical characteristics, as the selective reflection, circular dichroism etc. of opticity, polarized light.Chiral liquid crystal is because of the optics of its uniqueness, electrical properties and being paid attention to widely.Chiral ion liquid crystal, as the functional materials of a class novelty, has the special property of ionic liquid and the assembling characteristic of chiral liquid crystal concurrently.Chiral ion liquid crystal has potential application prospect in the synthesis template etc. of anisotropic ionic conductor material, dye sensitization solar battery, chemical sensor and nano material.From the angle of practical application, the liquid crystal of low transition temperature gives chiral ion liquid crystal with great application space, at room temperature can show liquid crystal liquid crystal property and the chiral ion liquid crystal material had between wider liquid crystal area is required in practical application.But in view of the existence of electrostatic interaction, ionic is constructed between primitive has stronger microphase-separated, most of chiral ion liquid crystal is difficult to can show liquid crystal liquid crystal property at ambient temperature.
People attempt to carry out chemical cutting to reduce its liquid crystal transition temperature by the molecular structure of chiral ion liquid crystal, people's design and synthesis such as Meng Fanbao are containing the imidazoles salt form chiral ion liquid crystal (LiX of cholesterol, LanX, MaS, BaiL, MengF, TianM, Synthesisandcharacterizationofimidazolium-basedionicliqu idcrystalsbearingacholesterylmesogenicgroup, LiquidCrystals, 2014,41,1843-1853.), between its liquid crystal area be 67-129 DEG C; The people such as Warner report the chiral ion liquid crystal containing dysprosium, are 41.9-98 DEG C between its liquid crystal area, not only higher than (LuC narrow between room temperature but also liquid crystal area, DasS, SirajN, MagutPKS, LiM, WarnerIM, Spectralandphysicochemicalcharacterizationofdysprosium-b asedmultifunctionalionicliquidcrystals, J.Phys.Chem.A, 2015,119,4780-4786.).But up to the present, yet there are no the report of chirality room-temperature ion liquid crystal material.
Consider the microphase-separated of ion liquid crystal molecule, we utilize space steric effect, and end group cholesterol larger for volume being modified at quaternary ammonium salt molecule is tightly packed with what destroy between adjacent molecule, to reach the object reducing liquid crystal transition temperature.
Summary of the invention
The object of the present invention is to provide a kind of chirality room-temperature ion liquid-crystalization compound and preparation method thereof, preparation method is simple and easy to do, and raw material is easy to get, and conversion unit is simple, and operational condition is gentle, and the easily separated purifying of product, productive rate is high, and cost is low, is easy to suitability for industrialized production.
A kind of chirality room-temperature ion liquid-crystalization compound provided by the invention, its basic structure is made up of containing compared with the hydrophobic alkyl chain of macoradical cholesterol and counter anion bromine quaternary ammonium salt cationic polar head group, end, and its general structure is C 30h 51nO 2brR mt n, in formula: R mfor alkyl carbon chain-(CH 2) m-, wherein m=5,7,9 or 10; T nfor alkyl carbon chain-C nh 2n+1, wherein n=1,4,8 or 12.Its structural formula is:
The preparation method of a kind of chirality room-temperature ion liquid-crystalization compound provided by the invention, for raw material carries out esterification with cholesterol and halogenated aliphatic acid, the intermediate product of gained carries out quaterisation with tertiary amine again, prepares the chiral ionic compound that can show liquid crystal liquid crystal property at ambient temperature.Reaction formula is:
Preparation method comprises the following steps:
1) synthesis of intermediate halogenated aliphatic acid cholesteryl ester
Halogenated aliphatic acid is dissolved in anhydrous trichloromethane, keeps concentration to be 8-12 mg/ml, then add cholesterol, the consumption of both control, make the mol ratio of cholesterol and halogenated aliphatic acid be 1.2-1.6:1; At 0-4 DEG C, add catalyzer DMAP and water-retaining agent dicyclohexylcarbodiimide, make the mol ratio of dicyclohexylcarbodiimide and halogenated aliphatic acid be 1.2-1.6:1, there is white precipitate in magnetic agitation reaction 3-7 hour under nitrogen protection; Stirring reaction 17-21 hour is continued under normal temperature; Cross and filter the rear sherwood oil/methylene dichloride of precipitation (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain intermediate product 11-bromine undeeanoic acid cholesteryl ester;
Described halogenated aliphatic acid is that 6-bromocaproic acid, 8-bromine are sad, 10-bromine capric acid or 11-bromine undeeanoic acid.
2) synthesis of chirality room-temperature ion liquid-crystalization compound
By halogenated aliphatic acid cholesteryl ester heating for dissolving in acetone, keep concentration to be 5-8 mg/ml, then add tertiary amine, the consumption of both control, the mol ratio of tertiary amine and halogenated aliphatic acid cholesteryl ester is made to be 6-10:1, under nitrogen protection back flow reaction 24-48 hour; Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains the chiral quaternary ammonium salt compound containing cholesterol;
Described tertiary amine is Trimethylamine 99, N, N-dimethyl n butylamine, N, N-dimethyl n octylame or N, N-dimethyl dodecylamine.
Compared with prior art beneficial effect of the present invention: chirality room-temperature ion liquid-crystalization compound at room temperature shows chiral liquid crystal, wider between liquid crystal area.
The equipment that the present invention adopts is simple, and method operation is convenient, and preparation condition is gentle, obtains the ion liquid crystal material containing cholesterol chiral radicals.Characterize this material by circular dichroism spectrum, dsc, polarizing microscope and X-ray diffraction, in room temperature, there is chiral liquid crystal.Be expected to be used widely in liquid-crystal display, solar cell, electrochemical device etc.
Accompanying drawing explanation
Fig. 1: C 30h 51nO 2brR 10t 12infrared spectrogram;
Fig. 2: C 30h 51nO 2brR 10t 12nMR (Nuclear Magnetic Resonance) spectrum;
Fig. 3: C 30h 51nO 2brR 10t 12mass spectrum;
Fig. 4: C 30h 51nO 2brR 10t 12circular dichroism spectrogram;
Fig. 5: C 30h 51nO 2brR 10t 12differential scanning calorimetric curve;
Fig. 6: C 30h 51nO 2brR 10t 12x-ray diffraction pattern;
Fig. 7: C 30h 51nO 2brR 10t 12polarizing microscope photo;
Embodiment
Embodiment 1:
(1) get 1 gram of 11-bromine undeeanoic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.04 grams of cholesterol.A little catalyzer DMAP and 1.09 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 5 hours.Stirring reaction is continued 19 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 11-bromine undeeanoic acid cholesteryl ester, productive rate is 78%.
(2) by 1 gram of 11-bromine undeeanoic acid cholesteryl ester heating for dissolving in 170 milliliters of acetone, then add 2.70 grams of N, N-dimethyl dodecylamine, back flow reaction 36 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 10t 12, productive rate is 79%.
Fig. 1 is C 30h 51nO 2brR 10t 12and infrared spectrogram, 3365cm -1for O-H antisymmetric stretching vibration; 2923,2850cm -1for CH 2unsymmetrically and symmetrical stretching vibration; 1735cm -1for C-O stretching vibration; 1467cm -1for CH 2scissoring vibration.
Fig. 2 is C 30h 51nO 2brR 10t 12nMR (Nuclear Magnetic Resonance) spectrum figure, [ 1hNMR (500MHz, CDCl 3, δ): 0.675 (s, 3H), 0.854 – 1.845 (m, 78H), 1.939 – 2.02 (m, 2H), 2.262 (t, J=7Hz, 2H), 2.296 – 2.312 (d, J=8Hz, 2H), 3.408 (s, 6H), 3.506 – 3.533 (m, 4H), 4.571 – 4.636 (m, 1H), 5.362 – 5.371 (m, 1H)], the peak at 5.362 – 5.371ppm places is pointed out as the proton peak on unsaturated double-bond on cholesterol group, the peak at 4.571 – 4.636ppm places is pointed out as the proton on carbon adjacent with ester group on cholesterol group, 3.408ppm, the proton peak into quaternary ammonium salt head methyl and methylene radical is pointed out at the peak at 3.506 – 3.533ppm places, the peak at 2.296 – 2.312ppm places is pointed out as the proton peak on the methylene radical adjacent with ester group, the number of integral area and proton matches.
Fig. 3 is C 30h 51nO 2brR 10t 12mass spectrum, nucleo plasmic relation m/z is 766.7, consistent with the molecular weight of liquid crystalline cpd cationic moiety.In conjunction with infrared spectrogram, NMR (Nuclear Magnetic Resonance) spectrum figure and mass spectrum, determine the ion liquid crystalline cpd successfully synthesizing target.
Embodiment 2:
(1) get 1 gram of 11-bromine undeeanoic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 1.75 grams of cholesterol.A little catalyzer DMAP and 0.93 gram of dicyclohexylcarbodiimide is added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 3 hours.Stirring reaction is continued 21 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 11-bromine undeeanoic acid cholesteryl ester, productive rate is 76%.
(2) by 1 gram of 11-bromine undeeanoic acid cholesteryl ester heating for dissolving in 125 milliliters of acetone, then add 2.02 grams of N, N-dimethyl dodecylamine, back flow reaction 24 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 10t 12, productive rate is 72%.
Embodiment 3:
(1) get 1 gram of 11-bromine undeeanoic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.33 grams of cholesterol.A little catalyzer DMAP and 1.24 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 7 hours.Stirring reaction is continued 17 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 11-bromine undeeanoic acid cholesteryl ester, productive rate is 81%.
(2) by 1 gram of 11-bromine undeeanoic acid cholesteryl ester heating for dissolving in 200 milliliters of acetone, then add 3.37 grams of N, N-dimethyl dodecylamine, back flow reaction 48 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 10t 12, productive rate is 83%.
Embodiment 4:
(1) get 1 gram of 6-bromocaproic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.76 grams of cholesterol.A little catalyzer DMAP and 1.48 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 4 hours.Stirring reaction is continued 20 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 6-bromocaproic acid cholesteryl ester, productive rate is 82%.
(2) by 1 gram of 6-bromocaproic acid cholesteryl ester heating for dissolving in 170 milliliters of acetone, then add 3.03 grams of N, N-dimethyl dodecylamine, back flow reaction 36 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 5t 12, productive rate is 71%.
Embodiment 5:
(1) get 1 gram of 8-bromocaproic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.43 grams of cholesterol.A little catalyzer DMAP and 1.29 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 5 hours.Stirring reaction is continued 19 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain the sad cholesteryl ester of 8-bromine, productive rate is 81%.
(2) by 1 gram of sad cholesteryl ester heating for dissolving of 8-bromine in 170 milliliters of acetone, then add 2.88 grams of N, N-dimethyl dodecylamine, back flow reaction 36 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 7t 12, productive rate is 79%.
Embodiment 6:
(1) get 1 gram of 10-bromine capric acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.43 grams of cholesterol.A little catalyzer DMAP and 1.29 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 6 hours.Stirring reaction is continued 18 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 10-bromine capric acid cholesteryl ester, productive rate is 77%.
(2) by 1 gram of 10-bromine capric acid cholesteryl ester heating for dissolving in 170 milliliters of acetone, then add 2.75 grams of N, N-dimethyl dodecylamine, back flow reaction 36 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 9t 12, productive rate is 77%.
Embodiment 7:
(1) get 1 gram of 11-bromine undeeanoic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.04 grams of cholesterol.A little catalyzer DMAP and 1.09 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 5 hours.Stirring reaction is continued 19 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 11-bromine undeeanoic acid cholesteryl ester, productive rate is 78%.
(2) by 1 gram of 11-bromine undeeanoic acid cholesteryl ester heating for dissolving in 170 milliliters of acetone, then add the Trimethylamine 99 of 2.33 gram 40%, back flow reaction 36 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 10t 1, productive rate is 81%.
Embodiment 8:
(1) get 1 gram of 11-bromine undeeanoic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.04 grams of cholesterol.A little catalyzer DMAP and 1.09 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 5 hours.Stirring reaction is continued 19 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 11-bromine undeeanoic acid cholesteryl ester, productive rate is 78%.
(2) by 1 gram of 11-bromine undeeanoic acid cholesteryl ester heating for dissolving in 170 milliliters of acetone, then add 1.27 grams of N, N-dimethyl n butylamine, back flow reaction 36 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 10t 4, productive rate is 62%.
Embodiment 9:
(1) get 1 gram of 11-bromine undeeanoic acid to be dissolved in 100 milliliters of anhydrous trichloromethanes, then add 2.04 grams of cholesterol.A little catalyzer DMAP and 1.09 grams of dicyclohexylcarbodiimide are added at 3 DEG C.White precipitate is there is in nitrogen protection lower magnetic force stirring reaction after 5 hours.Stirring reaction is continued 19 hours under normal temperature.Cross after filtering white precipitate and be spin-dried for filtrate, with sherwood oil/methylene dichloride (volume ratio is 2:1) for eluent carries out column chromatography for separation, obtain 11-bromine undeeanoic acid cholesteryl ester, productive rate is 78%.
(2) by 1 gram of 11-bromine undeeanoic acid cholesteryl ester heating for dissolving in 170 milliliters of acetone, then add 1.98 grams of N, N-dimethyl n octylames, back flow reaction 36 hours under nitrogen protection.Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains quaternary ionic compound C 30h 51nO 2brR 10t 8, productive rate is 68%.
Embodiment 10:
We utilize circular dichroism spectrogram detailed examination Compound C 30h 51nO 2brR 10t 12optical activity (see Fig. 4) in acetonitrile solution, it to have shown negative, a positive gram effect respectively at 214nm, 337nm place, first negative gram signal (214nm) shows Compound C 30h 51nO 2brR 10t 12under the induction of cholesterol group, have optical activity, be S-configuration chipal compounds.
Embodiment 11:
Chirality room-temperature ion liquid-crystalization compound C 30h 51nO 2brR 10t 12differential scanning calorimetric curve (see Fig. 5) to heat up and multiple phase in version peaks of showing of temperature-fall period show that meaning has liquid crystal property and there is multiple phase; Wherein, lower the temperature up to 145 DEG C occur exothermic peaks point out as isotropy state is to mesomorphic phase in version peak, continue to be cooled to-1.7 DEG C and occur glassy transition peak; In temperature-rise period, have three phase in version peaks, wherein 3 DEG C is glassy transition peak, and 81 DEG C is the phase in version peak between different liquid crystal state, is warming up to 151 DEG C and occurs endotherm(ic)peak, and 151 DEG C is clearing point, shows that liquid crystal state disappears, and is now completely unordered liquid state.Illustrate this quarternary ammonium salt compound temperature-fall period-1.7 DEG C to 145 DEG C, temperature-rise period 3 DEG C has liquid crystal liquid crystal property to 151 DEG C.
Embodiment 12:
Chirality room-temperature ion liquid-crystalization compound C 30h 51nO 2brR 10t 12alternating temperature X-ray diffraction and polarizing microscope test show that it is chiral smectic phase ion liquid crystal.When being cooled to 120 DEG C from isotropy state first time, there are two equally spaced diffraction peaks 001 and 002 (see Fig. 6) in the little angular region of X-ray diffracting spectrum, be indicated as Rotating fields, interlamellar spacing d is 3.84nm; There is unrestrained bag instead of the diffraction peak of disperse in wide-angle district, shows that now alkyl chain is in unordered stacking states at 20 ° of places.Adopt sandwich type sample multidomain sample to be carried out to the observation of liquid crystal texture, the uniform sample of grinding that takes a morsel is placed in two-layer circular lid slide interlayer, light cap slide.Above-mentioned prepared sample is placed in the thermal station of polarizing microscope, utilizes the thermic assembly behavior of cross-polarized light to liquid crystal molecule to observe.Be cooled to 120 DEG C from isotropy state, have broken fan-shaped texture (a) to occur see in Fig. 7.X-ray diffracting spectrum and polarizing microscope show that the liquid crystal phase at 120 DEG C is chiral smectic A (SmA*) phase that the degree of order is lower;
Embodiment 13:
When being cooled to 60 DEG C from isotropy state first time, there are two equally spaced diffraction peaks 001 and 002 (see Fig. 6) in the little angular region of X-ray diffracting spectrum, be indicated as Rotating fields, interlamellar spacing d is 4.02nm; There is unrestrained bag instead of the diffraction peak of disperse in wide-angle district, shows that now alkyl chain is in unordered stacking states at 20 ° of places.Adopt sandwich type sample multidomain sample to be carried out to the observation of liquid crystal texture, the uniform sample of grinding that takes a morsel is placed in two-layer circular lid slide interlayer, light cap slide.Above-mentioned prepared sample is placed in the thermal station of polarizing microscope, utilizes the thermic assembly behavior of cross-polarized light to liquid crystal molecule to observe.Be cooled to 60 DEG C from isotropy state, have typical conical texture (b) to occur see in Fig. 7.X-ray diffracting spectrum and polarizing microscope show that the liquid crystal phase at 60 DEG C is chiral smectic A (SmA*) phase that the degree of order is lower;
Embodiment 14:
When second time is warming up to 50 DEG C, there are two equally spaced diffraction peaks 001 and 002 (see Fig. 6) in the little angular region of X-ray diffracting spectrum, be indicated as Rotating fields, interlamellar spacing d is 4.02nm; There is unrestrained bag instead of the diffraction peak of disperse in wide-angle district, shows that now alkyl chain is in unordered stacking states at 20 ° of places.Adopt sandwich type sample multidomain sample to be carried out to the observation of liquid crystal texture, the uniform sample of grinding that takes a morsel is placed in two-layer circular lid slide interlayer, light cap slide.Above-mentioned prepared sample is placed in the thermal station of polarizing microscope, utilizes the thermic assembly behavior of cross-polarized light to liquid crystal molecule to observe.Be warming up to 60 DEG C, have fan-shaped conical texture (c) to occur see in Fig. 7.X-ray diffracting spectrum and polarizing microscope show that the liquid crystal phase at 60 DEG C is chiral smectic C (SmC*) phase that the degree of order is higher;
Embodiment 15:
When second time is warming up to 110 DEG C, there are two equally spaced diffraction peaks 001 and 002 (see Fig. 6) in the little angular region of X-ray diffracting spectrum, be indicated as Rotating fields, interlamellar spacing d is 3.84nm; There is unrestrained bag instead of the diffraction peak of disperse in wide-angle district, shows that now alkyl chain is in unordered stacking states at 20 ° of places.Adopt sandwich type sample multidomain sample to be carried out to the observation of liquid crystal texture, the uniform sample of grinding that takes a morsel is placed in two-layer circular lid slide interlayer, light cap slide.Above-mentioned prepared sample is placed in the thermal station of polarizing microscope, utilizes the thermic assembly behavior of cross-polarized light to liquid crystal molecule to observe.Be warming up to 110 DEG C, have conical texture (d) to occur see in Fig. 7.X-ray diffracting spectrum and polarizing microscope show that the liquid crystal phase at 110 DEG C is chiral smectic A (SmA*) phase that the degree of order is lower.

Claims (4)

1. a chirality room-temperature ion liquid-crystalization compound, is characterized in that, structural formula is:
Wherein m=5,7,9 or 10, n=1,4,8 or 12.
2. the preparation method of a kind of chirality room-temperature ion liquid-crystalization compound as claimed in claim 1, is characterized in that, comprise the following steps:
1) synthesis of intermediate halogenated aliphatic acid cholesteryl ester
Halogenated aliphatic acid is dissolved in anhydrous trichloromethane, keeps concentration to be 8-12 mg/ml, then add cholesterol, the consumption of both control, make the mol ratio of cholesterol and halogenated aliphatic acid be 1.2-1.6:1; At 0-4 DEG C, add catalyzer DMAP and water-retaining agent dicyclohexylcarbodiimide, make dicyclohexylcarbodiimide and halogenated aliphatic acid and mol ratio be 1.2-1.6:1, there is white precipitate in magnetic agitation reaction 3-7 hour under nitrogen protection; Stirring reaction 17-21 hour is continued under normal temperature; Crossing and filtering the rear volume ratio of precipitation be the sherwood oil/methylene dichloride of 2:1 is that eluent carries out column chromatography for separation, obtains intermediate product halogenated aliphatic acid cholesteryl ester;
2) synthesis of chirality room-temperature ion liquid-crystalization compound
By halogenated aliphatic acid cholesteryl ester heating for dissolving in acetone, keep concentration to be 5-8 mg/ml, then add tertiary amine, the consumption of both control, the mol ratio of tertiary amine and halogenated aliphatic acid cholesteryl ester is made to be 6-10:1, under nitrogen protection back flow reaction 24-48 hour; Rotary evaporation except desolventizing, with chloroform/Diethyl ether recrystallization three times, obtains chirality room-temperature ion liquid-crystalization compound.
3. the preparation method of a kind of chirality room-temperature ion liquid-crystalization compound as claimed in claim 2, is characterized in that, step 1) described in halogenated aliphatic acid be that 6-bromocaproic acid, 8-bromine are sad, 10-bromine capric acid or 11-bromine undeeanoic acid.
4. the preparation method of a kind of chirality room-temperature ion liquid-crystalization compound as claimed in claim 2, is characterized in that, step 2) described in tertiary amine be Trimethylamine 99, N, N-dimethyl n butylamine, N, N-dimethyl n octylame or N, N-dimethyl dodecylamine.
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