CN112812021A - Organic molecule-based antiferroelectric material, preparation method and application thereof - Google Patents

Organic molecule-based antiferroelectric material, preparation method and application thereof Download PDF

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CN112812021A
CN112812021A CN202011580741.3A CN202011580741A CN112812021A CN 112812021 A CN112812021 A CN 112812021A CN 202011580741 A CN202011580741 A CN 202011580741A CN 112812021 A CN112812021 A CN 112812021A
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organic molecule
antiferroelectric material
based antiferroelectric
antiferroelectric
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孙志华
徐豪杰
韩世国
刘艺
罗军华
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Fujian Institute of Research on the Structure of Matter of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/16—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings
    • C07C211/17—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings other than six-membered aromatic rings containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/353—Frequency conversion, i.e. wherein a light beam is generated with frequency components different from those of the incident light beams
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/35—Non-linear optics
    • G02F1/355—Non-linear optics characterised by the materials used
    • G02F1/361—Organic materials
    • G02F1/3611—Organic materials containing Nitrogen
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/22—Electrodes
    • H01G11/30—Electrodes characterised by their material
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/84—Processes for the manufacture of hybrid or EDL capacitors, or components thereof
    • H01G11/86—Processes for the manufacture of hybrid or EDL capacitors, or components thereof specially adapted for electrodes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
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    • 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
    • Y02E10/549—Organic PV cells

Abstract

The invention relates to an organic molecule-based antiferroelectric material, a preparation method and application thereof, wherein the chemical formula of the organic molecule-based antiferroelectric material is C7H16NBr is an orthorhombic Pbca space group at room temperature, and has unit cell parameters a-8.1818 (2), b-7.9363 (3),
Figure DDA0002865187670000011
Z＝8，
Figure DDA0002865187670000012
Figure DDA0002865187670000013
when the temperature is raised to 354K, the organic molecule-based antiferroelectric material is converted into a ferroelectric phase, and when the temperature is raised to be higher than 364K, the organic molecule-based antiferroelectric material is converted into a paraelectric phase. The organic molecule-based antiferroelectric material has the advantages of simple synthesis method, low cost, mild reaction conditions and higher stability, and is an organic molecule antiferroelectric compound with higher saturation polarization intensity.

Description

Organic molecule-based antiferroelectric material, preparation method and application thereof
Technical Field
The invention belongs to the field of functional materials, and particularly relates to an organic molecule-based antiferroelectric material, a preparation method and application thereof.
Background
Antiferroelectric is an important functional material, and has wide application in the fields of energy storage capacitors, transducers, voltage modulation elements and the like. The adjacent unit cells of the material are arranged in an antiparallel manner in a certain temperature range, and the polarization strength on a macroscopic scale is zero. The discovery of antiferroelectric and antiferroelectric materials originated in the fifties of the last century, 1951, by american physicist c.kittle, based on the theory of phenomenology, proposed that "the basic concept of antiferroelectric" (similar to ferroelectric), ions of crystal lattice in antiferroelectric crystal undergo displacement type spontaneous polarization, but the spontaneous polarization directions of ions in adjacent sub-lattices are opposite, so that the spontaneous polarization intensity of antiferroelectric crystal is zero macroscopically, and the existence and characteristics of antiferroelectric are predicted. Lead zirconate (PbZrO) was reported by Shirane, Sawaguchi and Takagi et al in the same year3) The antiferroelectric property of (1). From now on, antiferroelectric materials have entered the research field of people, and with the continuous development of microscopic characterization means and the great potential exhibited by antiferroelectric materials in the aspects of electric power, electronic equipment and the like, people have conducted more intensive research on antiferroelectric materials. To date, researchers have discovered and reported a variety of antiferroelectric materialsThe materials are still far behind the research on ferroelectric materials, wherein the antiferroelectric materials with potential application value are much less. The conventional inorganic antiferroelectric material has high saturation polarization, small remnant polarization and suitable phase transition electric field, so that the conventional inorganic antiferroelectric material is favored. However, the application of inorganic antiferroelectric materials is often limited by the problems that high-temperature sintering is needed in the preparation process, the preparation cost is expensive, phase separation and precipitation are easily generated, and the like, and meanwhile, lead and other heavy metal elements harmful to the environment are often involved in the synthesis process, so that the development of the inorganic antiferroelectric materials is restricted.
Compared with the traditional inorganic material, the pure organic molecular antiferroelectric has the characteristics of mild synthesis conditions, easy molecular cutting and structural design and environmental friendliness, and can modify the structure and composition of molecules by the methods of molecular design and crystal engineering, thereby more effectively improving the performance of the antiferroelectric. In addition, molecular antiferroelectric materials are expected to be strong candidates for flexible electronic devices due to their unique advantages in biocompatibility, thin film fabrication, and the like. Therefore, the antiferroelectric of organic molecules is a functional material with great development potential, and is expected to provide new opportunities for the innovation of photoelectric technology and the development of electrically ordered materials.
Based on the large saturation polarization strength of the antiferroelectric material, a miniaturized and lightweight super capacitor can be manufactured; meanwhile, the material has abrupt change near the phase transition temperature point according to the nonlinear optical properties (particularly frequency doubling effect), and can be used for designing and assembling nonlinear optical frequency doubling switching devices. Therefore, the organic molecule antiferroelectric crystal material has good application prospect in the fields of large displacement sensors, explosive transducers, energy storage capacitors, infrared pyroelectric sensors, data communication, data storage, nonlinear switches and the like, and the application range of the material is continuously expanded along with the gradual development of the technology. In summary, the chemical synthesis and preparation of the organic molecule antiferroelectric material with high performance have important practical value.
Disclosure of Invention
The organic molecule-based antiferroelectric material has the advantages of simple synthesis method, low cost, mild reaction conditions and higher stability, and is an organic molecule antiferroelectric compound with higher saturation polarization strength.
The invention is realized by the following technical scheme:
scheme I)
An organic molecule-based antiferroelectric material, the chemical formula of the organic molecule-based antiferroelectric material is C7H16NBr, molecular structure:
Figure BDA0002865187650000021
furthermore, the organic molecule-based antiferroelectric material is an orthorhombic Pbca space group at room temperature, the unit cell parameters are a-8.1818 (2), b-7.9363 (3),
Figure BDA0002865187650000022
Z＝8，
Figure BDA0002865187650000023
further, when the temperature is raised to 354K, the organic molecule-based antiferroelectric material is transformed into a ferroelectric phase, i.e., tetragonal system P4mm space group, with the cell parameter of
Figure BDA0002865187650000024
Figure BDA0002865187650000025
Further, when the temperature rises to be higher than 364K, the organic molecule-based antiferroelectric material is converted into a paraelectric phase, the space group is converted into P4/nmm, and the unit cell parameter is
Figure BDA0002865187650000026
Figure BDA0002865187650000031
Scheme two)
The preparation method of the organic molecule-based antiferroelectric material comprises the following steps: at room temperature, dripping cyclohexylmethylamine into hydrobromic acid according to the stoichiometric ratio of 1:1, heating to 60-100 ℃, stirring until the cyclohexylmethylamine is dissolved to form a clear solution, then placing the obtained solution into a thermostat at 80 ℃, and then slowly reducing the temperature of the thermostat to 30-45 ℃ to obtain the organic molecule-based antiferroelectric material.
Scheme three)
The application of the organic molecule-based antiferroelectric material in a transducer, wherein the transducer comprises the organic molecule-based antiferroelectric material.
Scheme four)
The application of the organic molecule-based antiferroelectric material in a memory device comprises the organic molecule-based antiferroelectric material.
Scheme five)
The application of the organic molecule-based antiferroelectric material in a second-order nonlinear frequency doubling switch comprises the organic molecule-based antiferroelectric material.
Scheme six)
The application of the organic molecule-based antiferroelectric material in an electric card refrigerating device comprises the organic molecule-based antiferroelectric material.
Compared with the prior art, the invention creatively provides an organic molecule-based antiferroelectric material. The organic molecule-based antiferroelectric material has the advantages of simple synthesis method, low cost, mild reaction conditions and higher stability, and is an organic molecule antiferroelectric compound with higher saturation polarization intensity. The method has application prospects in energy converters, memory devices, second-order nonlinear frequency doubling switches and electric card refrigeration devices.
Drawings
FIG. 1 is a molecular schematic diagram of organic antiferroelectric cyclohexylmethylamine bromide
FIG. 2 is a crystal structure stacking diagram of organic molecule antiferroelectric cyclohexylmethylamine bromide
FIG. 3 is a differential scanning calorimetry test curve of cyclohexylmethylamine bromide of organic molecule antiferroelectric
FIG. 4 shows the hysteresis loop of organic molecule antiferroelectric cyclohexylmethylamine bromide in antiferroelectric phase
FIG. 5 shows the hysteresis loop of organic molecule antiferroelectric cyclohexylmethylamine bromide in ferroelectric phase
Detailed Description
The invention is further described below with reference to the accompanying drawings and the detailed description.
Example 1
The preparation method of the organic molecule-based antiferroelectric material comprises the following steps: at room temperature, dripping cyclohexylmethylamine into hydrobromic acid according to the stoichiometric ratio of 1:1, heating to 80 ℃, stirring until the cyclohexylmethylamine is dissolved to form a clear solution, then placing the obtained solution in an incubator at 80 ℃ to slowly reduce the temperature to 30 ℃, thus obtaining the organic molecular-based antiferroelectric material, namely the cyclohexylmethylamine bromide, wherein the yield is 95%, the organic molecular-based antiferroelectric material is shown in figures 1 and 2, the organic molecular-based antiferroelectric material is an orthorhombic Pbca space group at room temperature, the unit cell parameters are a-8.1818 (2), b-7.9363 (3),
Figure BDA0002865187650000041
Z＝8，
Figure BDA0002865187650000042
Figure BDA0002865187650000043
when the temperature is raised to 354K, the phase is converted into a ferroelectric phase, the tetragonal system P4mm space group has the cell parameter of
Figure BDA0002865187650000044
Figure BDA0002865187650000045
When the temperature rises to above 364K, the phase is changed into paraelectric phase, the space group is changed into P4/nmm, and the unit cell parameter is
Figure BDA0002865187650000046
Example 2
The preparation method of the organic molecule-based antiferroelectric material comprises the following steps: dripping cyclohexylmethylamine into hydrobromic acid at the stoichiometric ratio of 1:1 at room temperature, heating to 60 ℃, stirring until the cyclohexylmethylamine is dissolved to form a clear solution, then placing the obtained solution in a thermostat at 80 ℃ to slowly reduce the temperature to 40 ℃, thus obtaining the organic molecular antiferroelectric material which is an orthorhombic Pbca space group at room temperature, wherein the unit cell parameters are a-8.1818 (2), b-7.9363 (3),
Figure BDA0002865187650000047
Z＝8，
Figure BDA0002865187650000048
Figure BDA0002865187650000049
when the temperature is raised to 354K, the phase is converted into a ferroelectric phase, the tetragonal system P4mm space group has the cell parameter of
Figure BDA00028651876500000410
Figure BDA00028651876500000411
When the temperature rises to above 364K, the phase is changed into paraelectric phase, the space group is changed into P4/nmm, and the unit cell parameter is
Figure BDA00028651876500000412
Example 3
The preparation method of the organic molecule-based antiferroelectric material comprises the following steps: dripping cyclohexylmethylamine into hydrobromic acid at the stoichiometric ratio of 1:1 at room temperature, heating to 100 ℃, stirring until the cyclohexylmethylamine is dissolved to form a clear solution, and slowly placing the clear solution in an incubator at 80 DEG CCooling to 45 ℃ to obtain the organic molecule-based antiferroelectric material which is an orthorhombic Pbca space group at room temperature, wherein the unit cell parameters are a-8.1818 (2), b-7.9363 (3),
Figure BDA0002865187650000051
Z＝8，
Figure BDA0002865187650000052
Figure BDA0002865187650000053
when the temperature is raised to 354K, the phase is converted into a ferroelectric phase, the tetragonal system P4mm space group has the cell parameter of
Figure BDA0002865187650000054
Figure BDA0002865187650000055
When the temperature rises to above 364K, the phase is changed into paraelectric phase, the space group is changed into P4/nmm, and the unit cell parameter is
Figure BDA0002865187650000056
Application of organic molecule antiferroelectric crystal material cyclohexylmethylamine bromide prepared in the above example 1 in the field of energy storage materials
The cyclohexylmethylamine bromide obtained in example 1 was subjected to the hysteresis loop test, as shown in FIG. 4, at 340K, under the same applied electric field, with a saturation polarization of about 8 μ C/cm2And the test frequency is changed, and the material has better stability, so that the organic molecular antiferroelectric material becomes a candidate material for refrigerating an energy storage device and an electric card.
The application of organic molecule antiferroelectric cyclohexylmethylamine bromide in the fields of nonlinear optics and electric card refrigeration.
When the temperature rise test hysteresis loop of the cyclohexylmethylamine bromide obtained in the embodiment 1 is carried out, after the structure of the antiferroelectric-ferroelectric phase is transformed, an obvious ferroelectric hysteresis loop appears in the material, as shown in fig. 5. The test result shows that: above the phase transition temperature, the material is changed from a centrosymmetric structure to a non-centrosymmetric structure, the temperature is continuously raised, and after the transition temperature of the ferroelectric phase and the paraelectric phase is reached, the material is changed into the centrosymmetric structure again. The nonlinear optical signal of the material shows unique switching performance in a test temperature range, namely from absence to existence to disappearance again. The related results show that the material has potential application value in the field of nonlinear optical switches.

Claims (10)

1. An organic molecule-based antiferroelectric material, characterized in that: the chemical formula of the organic molecule-based antiferroelectric material is C7H16NBr, molecular structure diagram:
Figure FDA0002865187640000011
。
2. the organic molecule-based antiferroelectric material of claim 1, wherein: at room temperature, the organic molecule-based antiferroelectric material is an orthorhombic Pbca space group at room temperature, the unit cell parameters are a-8.1818 (2), b-7.9363 (3),
Figure FDA0002865187640000012
Z＝8，
Figure FDA0002865187640000013
Figure FDA0002865187640000014
3. the organic molecule-based antiferroelectric material of claim 1, wherein: when the temperature is raised to 354K, the organic molecule-based antiferroelectric material is converted into a ferroelectric phase, a tetragonal system P4mm space group and the unit cell parameter is
Figure FDA0002865187640000015
Figure FDA0002865187640000016
4. The organic molecule-based antiferroelectric material of claim 1, wherein: when the temperature rises to be higher than 364K, the organic molecule-based antiferroelectric material is converted into paraelectric phase, the space group is converted into P4/nmm, and the unit cell parameter is
Figure FDA0002865187640000017
Figure FDA0002865187640000018
5. A method for preparing an organic molecule based antiferroelectric material according to any of claims 1-4, characterized in that: the method comprises the following steps: at room temperature, dripping cyclohexylmethylamine into hydrobromic acid according to the stoichiometric ratio of 1:1, heating to 60-100 ℃, stirring until the cyclohexylmethylamine is dissolved to form a clear solution, then placing the obtained solution into a thermostat at 80 ℃, and then slowly reducing the temperature of the thermostat to 30-45 ℃ to obtain the organic molecule-based antiferroelectric material.
6. The method of claim 5, wherein the temperature reduction rate is reduced by 1-2 ℃ every two days.
7. The application of the organic molecule-based antiferroelectric material on the transducer is characterized in that: the transducer comprises the organic molecule-based antiferroelectric material of any one of claims 1-4.
8. The application of the organic molecule-based antiferroelectric material on the memory device is characterized in that: the memory device comprising the organic molecule-based antiferroelectric material of any one of claims 1-4.
9. The application of the organic molecule-based antiferroelectric material in the second-order nonlinear frequency doubling switch is characterized in that: the second-order nonlinear frequency-doubling switch comprises the organic molecule-based antiferroelectric material according to any one of claims 1 to 4.
10. The application of the organic molecule-based antiferroelectric material in the electric card refrigerating device is characterized in that: the electric card refrigeration device comprising the organic molecule-based antiferroelectric material of any one of claims 1-4.
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