CN106480506B - Organic molecule ferroelectric crystal di-n-butylamine difluoro chloroacetate salt and its preparation method and purposes - Google Patents
Organic molecule ferroelectric crystal di-n-butylamine difluoro chloroacetate salt and its preparation method and purposes Download PDFInfo
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- CN106480506B CN106480506B CN201610888927.2A CN201610888927A CN106480506B CN 106480506 B CN106480506 B CN 106480506B CN 201610888927 A CN201610888927 A CN 201610888927A CN 106480506 B CN106480506 B CN 106480506B
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- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/03—Monoamines
- C07C211/07—Monoamines containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three
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- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/16—Halogenated acetic acids
- C07C53/18—Halogenated acetic acids containing fluorine
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- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
- C30B7/14—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions the crystallising materials being formed by chemical reactions in the solution
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Abstract
Invention is related to organic molecule ferroelectric crystal di-n-butylamine difluoro chloroacetate salt and its preparation method and purposes, pass through the ferroelectric hysteresis loop of Sawyer-Tower circuit test organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt of the present invention, the result shows that: it presents good ferroelectric properties in ferroelectric phase, with biggish saturated polarization, reach 3.9 μ C/cm2, moderate coercive field, about 12.4kV cm‑1.Alternating temperature it is non-linear survey the result shows that, the material does not have apparent second nonlinear frequency-doubled signal in paraelectric phase, when temperature is down to Curie temperature (243K), there is apparent second nonlinear frequency-doubled signal, with the reduction of temperature, nonlinear properties intensity value reaches saturation, and excellent non-linear "ON" "Off" performance is presented in entire Range of measuring temp, on-off ratio reaches~28, and repeatability is preferably.Reaction is simple, mild condition.
Description
Technical field
The present invention relates to organic molecule ferroelectric crystal di-n-butylamine difluoro chloroacetate salt and its preparation methods and purposes, belong to function
Energy Material Field, the in particular to preparation and its application of the ferroelectric crystal materials.
Background technique
Ferroelectric material is a kind of special polar material, inside there are spontaneous polarization effect, and spontaneous polarization direction
It under the action of outfield (such as electric field, magnetic field, pressure), can overturn or reorientation, so that polarization intensity and electricity
The loop line relationship that field action exhibits hysteresis.Based on the characteristic, ferroelectric material shows some special photoelectric functional characteristics, such as
Ferroelectric effect, nonlinear switching effect, pyroelectric effect, piezoelectric effect, electrooptic effect and photorefractive effect etc..Therefore, ferroelectricity
Material has been obtained in fields such as microelectric technique, photoelectron technology, sensing technology and laser technologies and is widely applied, and pushes
The rapid developments of hyundai electronics information industries.Traditional inorganic ferroelectrics are due to biggish polarization intensity and higher Curie
Temperature and have been favored by people, still, inorganic ferroelectric material preparation process is relative complex, and synthesis condition is harsh, simultaneously synthesizing
The environmentally harmful heavy metal element such as lead is often used in the process, is constrained it to a certain extent and is widely applied.
Compared with traditional pure inorganic ferroelectrics, not only synthesis condition is mild for organic molecule ferroelectric crystal materials, is easy to cut
It cuts out, it is environmental-friendly, and its spontaneous polarization overturning response time is faster, in addition can pass through the side of MOLECULE DESIGN and crystal engineering
Method, the structure and composition of decorating molecule, and then performance improvement more effectively can be carried out to it.So in a sense,
Organic molecule ferroelectric crystal is a kind of functional material with development potential, provides good machine for the innovation of photoelectric technology
It meets.
Utilize the big saturated polarization of ferroelectric material, it is possible to produce the nonvolatile memory of various high capacity；Together
When, it is mutated according to ferroelectric crystal materials optical property in phase transformation temperature points, i.e., material does not have second nonlinear in paraelectric phase
Optical signalling shows apparent second nonlinear optic signal in ferroelectric phase, shows unique nonlinear optical property, can
To be used to design frequency doubling non-linear's switch.Therefore, organic molecule ferroelectric crystal materials data communication, data storage, it is non-thread
Property switch etc. fields have huge application prospect.In recent years, with the fast development of synthesis chemistry and crystal engineering, ferroelectricity material
The application range of material constantly expands.But existing organic molecule ferroelectric crystal materials type is still less, and spontaneous polarization is strong
Spend less than normal, while the stability of material is poor so that its device preparation and in terms of be limited by very large.
Therefore, synthesize and prepare big saturated polarization, the organic molecule ferroelectric material of high stability has important practical value.
Summary of the invention
The first purpose of this invention is to provide an organic molecular species ferroelectric crystal di-n-butylamine difluoro chloroacetate salt；
Second object of the present invention is to provide an organic molecular species ferroelectric crystal di-n-butylamine difluoro chloroacetate salt
Preparation method；
Third object of the present invention is to provide an organic molecular species ferroelectric crystal di-n-butylamine difluoro chloroacetate salt
Purposes.
Di-n-butylamine difluoro chloroacetate salt of the invention is a kind of high stability, and saturated polarization is larger, coercive
The moderate organic molecule ferroelectric crystal in field, and organic molecule ferroelectric crystal preparation method of the invention is simple, low in cost, anti-
Answer mild condition.
One organic molecular species ferroelectric crystal di-n-butylamine difluoro chloroacetate salt, it is characterised in that: the di-n-butylamine
The chemical formula of difluoro chloroacetate salt is C10H20ClF2NO2, its structural formula is
The di-n-butylamine difluoro chloroacetate salt belongs to rhombic system, Pnma space group in room temperature；When temperature drops
When to 243K, ferroelectric phase transition occurs for material, and space group is changed into Pna21。
Cell parameter of the di-n-butylamine difluoro chloroacetate salt in room temperature be Work as temperature
When degree is down to 243K, cell parameter is
The preparation method of organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt:
At room temperature, di-n-butylamine is dissolved in deionized water, then adds difluoro chloroacetic acid, at 40-60 DEG C
It is sufficiently stirred after all dissolutions, filtrate is placed in 35-45 DEG C of baking oven by filtering, and slowly crystallization is to get the two positive fourths
The molar ratio of amine difluoro chloroacetate salt, the di-n-butylamine and difluoro chloroacetic acid is 1:1.
Beneficial effects of the present invention:
(1) pass through Sawyer-Tower circuit test one chlorine of organic molecule ferroelectric crystal materials di-n-butylamine difluoro of the present invention
The ferroelectric hysteresis loop of acetate, the results showed that it presents good ferroelectric properties in ferroelectric phase, has biggish saturated polarization strong
Degree, reaches 3.9 μ C/cm2, moderate coercive field, about 12.4kV cm-1。
(2) alternating temperature it is non-linear survey the result shows that, which does not have apparent second nonlinear frequency-doubled signal in paraelectric phase, when
When temperature is down to Curie temperature (243K), there is apparent second nonlinear frequency-doubled signal, with the reduction of temperature, non-linear letter
Number intensity value reaches saturation, excellent non-linear "ON" "Off" performance is presented in entire Range of measuring temp, on-off ratio reaches
To~28, and repeatability is preferably.
(3) reaction is simple, mild condition.
Detailed description of the invention
The organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt that Fig. 1 is prepared for embodiment 1 shows differential thermal
Scanning amount Thermal test curve.
Fig. 2 is that the electric hysteresis of organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt prepared by embodiment 1 returns
Line.
Fig. 3 is that the second order of organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt prepared by embodiment 1 is non-
Linear frequency-doubled signal varies with temperature curve.
Specific embodiment
The present invention is further described below in conjunction with the drawings and specific embodiments.
(1) specific embodiment
At room temperature, di-n-butylamine is dissolved in deionized water, then adds difluoro chloroacetic acid, it is (excellent at 40-60 DEG C
Select 50 DEG C) under be sufficiently stirred after all dissolution after, filtering, filtrate is placed in 35-45 DEG C of (preferably 40 DEG C) baking oven, slowly tie
For crystalline substance to get the di-n-butylamine difluoro chloroacetate salt, the molar ratio of the di-n-butylamine and difluoro chloroacetic acid is 1:
1.The molar ratio of the di-n-butylamine and difluoro chloroacetic acid may be the ratio on the periphery 1:1.
(2) specific embodiment
Embodiment 1
The preparation of organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt
At room temperature, by di-n-butylamine (5 × 10-3) and difluoro chloroacetic acid (5 × 10 mol-3Mol) it is dissolved in 50mL distillation
In water, 50 DEG C are heated to, stirring 20min reacts it sufficiently.Solution is after crystallisation by cooling, filtering, drying to get described two
N-butylamine difluoro chloroacetate salt.Then powder solid is redissolved in 50mL distilled water again, recrystallization three times, is slowly waved
Hair, finally colorless and transparent strip target product, i.e. di-n-butylamine difluoro chloroacetic acid salt compound, yield 96.2%.
Through detecting, the chemical formula of the di-n-butylamine difluoro chloroacetate salt is C10H20ClF2NO2, its structural formula is
The di-n-butylamine difluoro chloroacetate salt belongs to rhombic system, Pnma space group in room temperature；When temperature drops
When to 243K, ferroelectric phase transition occurs for material, and space group is changed into Pna21。
Cell parameter of the di-n-butylamine difluoro chloroacetate salt in room temperature be Work as temperature
When degree is down to 243K, cell parameter is
Embodiment 2
Application of the organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt in ferroelectricity field of storage
Hysteresis is carried out to the obtained di-n-butylamine difluoro chloroacetate salt of embodiment 1, as shown in Figure 1,
245K, test frequency 20Hz, the material polarization intensity and electric field are linear relationship；In temperature-fall period, same test frequency
Under, apparent ferroelectric hysteresis loop feature is shown between 240K polarization intensity and electric field；Temperature continues to reduce, and polarization intensity continues
Increase, while coercive field also constantly increases, and reaches 3.9 μ C/cm of saturation value in 236K saturated polarization2, coercive field is
12.4kV cm-1.Biggish saturated polarization and moderate coercive field, so that the organic molecule ferroelectric crystal materials, which become, to be had
The candidate material of machine nonvolatile memory preparation.
Embodiment 3
Organic molecule ferroelectric crystal materials di-n-butylamine difluoro chloroacetate salt is in non-linear optical field using to reality
Apply the obtained di-n-butylamine difluoro chloroacetate salt of case 1 carry out the test of alternating temperature non-linear behaviour, frequency doubling non-linear's signal with
The change curve of temperature is as shown in Figure 3, the results showed that: more than phase transition temperature, material does not have nonlinear properties, temperature-fall period
In, in 243K significant change occurs for the nonlinear properties of material, shows apparent frequency doubling non-linear's signal, continues to cool down, non-thread
Property frequency-doubled signal, which gradually increases, is finally reached saturation.The material nonlinearity optical signalling shows uniqueness in Range of measuring temp
Switch performance, and its on-off ratio reaches 28；By multiple loop test, nonlinear properties do not weaken significantly, table
Repeatability is preferable in the bright material application process.Can the variation of frequency doubling non-linear's signal not only further confirm material herein
Nearby ferroelectric phase transition occurs for temperature, and shows that material has potential application in nonlinear optics field of switches.
Above-mentioned specific embodiment is only explained in detail technical solution of the present invention, the present invention not only only office
Be limited to above-described embodiment, it will be understood by those skilled in the art that it is all according to above-mentioned principle and spirit on the basis of the present invention
It improves, substitution, it all should be within protection scope of the present invention.
Claims (4)
1. an organic molecular species ferroelectric crystal di-n-butylamine difluoro chloroacetate salt, it is characterised in that: the di-n-butylamine two
The chemical formula of fluorine chloroacetate salt is C10H20ClF2NO2, its structural formula is
The di-n-butylamine difluoro chloroacetate salt belongs to rhombic system, Pnma space group in room temperature；When temperature is down to
When 243K, ferroelectric phase transition occurs for material, and space group is changed into Pna21；
Cell parameter of the di-n-butylamine difluoro chloroacetate salt in room temperature be α=β=γ=90.0 °, Z=4,When temperature drops
When to 243K, cell parameter isα=β=γ=
90.0 °, Z=4,
2. the preparation method of organic molecule ferroelectric crystal di-n-butylamine difluoro chloroacetate salt according to claim 1,
It is characterized in that: the following steps are included:
At room temperature, di-n-butylamine is dissolved in deionized water, then adds difluoro chloroacetic acid, at 40-60 DEG C sufficiently
Stirring is after all dissolutions, and filtrate is placed in 35-45 DEG C of baking oven by filtering, and slowly crystallization is to get the di-n-butylamine two
The molar ratio of fluorine chloroacetate salt, the di-n-butylamine and difluoro chloroacetic acid is 1:1.
3. the application of organic molecule ferroelectric crystal di-n-butylamine difluoro chloroacetate salt according to claim 1, feature
Be: the di-n-butylamine difluoro chloroacetate salt is applied in ferroelectricity field of storage.
4. the application of organic molecule ferroelectric crystal di-n-butylamine difluoro chloroacetate salt according to claim 1, feature
Be: the di-n-butylamine difluoro chloroacetate salt is applied in second nonlinear frequency multiplication field of switches.
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| CN112981540B (en) * | 2021-02-18 | 2022-02-01 | 江苏建筑职业技术学院 | Diisopropylpropylamine tetrafluoroborate crystal material and preparation method and application thereof |
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| CN101544611A (en) * | 2008-03-25 | 2009-09-30 | 中国科学院福建物质结构研究所 | Substituted 1,2,4-triazole complex and application thereof as nonlinear optical and ferroelectric material |
| CN101560218A (en) * | 2008-04-18 | 2009-10-21 | 中国科学院福建物质结构研究所 | Organometallic complex of nonlinear optical and ferroelectric material, synthesis and application thereof |
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