CN111362809A - Chiral perovskite nanosheet, and preparation method and application thereof - Google Patents
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Abstract
The invention provides a chiral perovskite nanosheet, which has intrinsic chirality and has chiral optical response at the maximum excitation absorption position. Also provides a preparation method and application thereof. The peak value of the circularly polarized absorption asymmetry factor (g-factor) of the chiral perovskite nanosheet is higher than that of the chiral perovskite nanocrystalline reported at present. The synthesis method is simple, and the perovskite nanosheet with intrinsic chirality can be rapidly prepared.
Description
Technical Field
The invention belongs to the field of perovskite materials, and particularly relates to a chiral perovskite nanosheet, and a preparation method and application thereof.
Background
Chirality is a geometric property that is widely found in nature. Two enantiomers with different chiralities are identical in material composition and are in mirror symmetry with each other in structure, and the difference in structure enables the enantiomers with different chiralities to have obvious difference in optical and electrical performances. In terms of optical properties, chiral molecules and materials have different absorption capacities for circularly polarized light with different rotating electric field vectors, and show that different enantiomers have mutually symmetrical circular dichroism spectra (CD). For chiral materials with light-emitting capability, Circularly Polarized Light (CPL) is often emitted. Electrically, recent studies have shown that spintronics polarize when electrons move in chiral organic molecules, creating spin filtering, a phenomenon known as chirally induced self-selection (CISS).
The perovskite material is a semiconductor material with excellent performance and has wide application in the fields of photoelectricity, photovoltaics, luminescence and the like. The common component composition of perovskite is ABX3(three-dimensional) A2BX4(two-dimensional) in which the A-position is a monovalent organic cation (e.g. MA)+、FA+Etc.), inorganic cations divalent in position B (e.g., Pb)2+、Sn2+、Cu2+Etc.), X is a monovalent negative halide (e.g., I)-、Br-、Cl-). The perovskite material can realize continuous adjustment of the structure and the band gap by adjusting the organic and inorganic components of the perovskite material. With the addition of the chiral cations at the A site, the central inversion symmetry of the perovskite is broken, and the chirality is transferred from the A site ions into the perovskite crystal structure. The chiral perovskite has unique physical properties of chiral optical activity, nonlinear optical response, ferroelectricity and the like. The introduction of the new physical properties and the excellent photoelectric properties of the perovskite material enable the chiral perovskite to have potential wide application prospects in the fields of circular polarization detection, nonlinear optics, ferroelectrics, spintronics and the like.
The perovskite nanocrystal has the advantages of adjustable band gap, high fluorescence quantum yield, narrow spectrum half-peak width, simple preparation method and the like, and is paid more and more attention. Chirality is introduced into the chiral perovskite nanocrystal, so that the excellent photoelectric property of the perovskite nanocrystal is combined with the chiral optical activity of the chiral material. The chiral perovskite nanocrystalline has potential application in the fields of circular polarization luminescence, nonlinear optics, spintronics and the like. However, few reports on chiral perovskite nanocrystals exist, and the material system of the chiral perovskite nanocrystals needs to be further expanded. The prior art discloses a preparation method of chiral perovskite nanocrystalline, which comprises the steps of firstly preparing achiral CsPbX3The chiral calcium is obtained by connecting a chiral ligand to the surface of the nanocrystal through ligand exchangeThe chiral source of the titanium ore nanocrystal is a surface chiral defect, but the nanocrystal has no chiral optical response at the maximum absorption. In addition, in other prior art, chirality is introduced into the perovskite nanocrystal by means of co-assembly of achiral perovskite nanocrystals and chiral gel, use of chiral ligands in the preparation process and the like, so that optically corresponding nanocrystals are prepared at the maximum absorption position, and the chirality of the chiral perovskite nanocrystals is derived from the interaction of chiral surface ligands and the perovskite nanocrystals, and belongs to induced chirality. However, the preparation of perovskite nanocrystals with intrinsic chirality is still blank.
Therefore, how to prepare the perovskite nanocrystal with intrinsic chirality and expand the material system of the perovskite nanocrystal has very important significance.
Disclosure of Invention
Therefore, the invention aims to overcome the defects in the prior art and provides a chiral perovskite nanosheet, and a preparation method and application thereof.
Before setting forth the context of the present invention, the terms used herein are defined as follows:
the term "R-MPEA" means: (R) -2-phenyl-1-propylamine.
The term "S-MPEA" means: (S) -2-phenyl-1-propylamine.
To achieve the above object, a first aspect of the present invention provides a chiral perovskite nanosheet having intrinsic chirality with a chiral optical response at the maximum excitation absorption.
Chiral perovskite nanoplatelets according to the first aspect of the present invention, wherein the absolute value of the peak of the circularly polarized absorption asymmetry factor of said chiral perovskite nanoplatelets is higher than 2 × 10-3Preferably higher than 3 × 10-3More preferably higher than 3.5 × 10-3。
A second aspect of the present invention provides a method for preparing the chiral perovskite nanosheet described in the first aspect, which may include the steps of:
(1) preparing chiral ammonium salt: mixing chiral amine and isopropanol to obtain chiral amine dispersion liquid, dropwise adding halogen acid with the same molar weight as the chiral amine into the dispersion liquid under an ice bath condition for reaction, removing redundant solvent, washing and drying to obtain chiral ammonium salt;
(2) preparing a precursor solution: dissolving the chiral ammonium salt prepared in the step (1) and lead halide salt in a good solvent, adding a protective agent, and filtering to obtain a precursor solution;
(3) preparing chiral perovskite nanocrystals: and (3) adding the precursor solution prepared in the step (2) into a poor solvent to react to obtain the chiral perovskite nanosheet.
The production method according to the second aspect of the present invention, wherein, in the step (1), the chiral amine is selected from one or more of: (R) -2-phenyl-1-propylamine, (S) -2-phenyl-1-propylamine, (R) -2-naphthyl-1-propylamine, (S) -2-naphthyl-1-propylamine, (R) -2-cyclohexyl-1-propylamine, (S) -2-cyclohexyl-1-propylamine, (R) -2-cyclopentyl-1-propylamine, and (S) -2-cyclopentyl-1-propylamine.
The production method according to the second aspect of the present invention, wherein, in the step (1), the halogen acid is selected from one or more of: hydriodic acid, hydrobromic acid, hydrochloric acid;
preferably, the hydrohalic acid added to the dispersion in step (1) is an aqueous solution; more preferably, the mass percentage of the halogen acid in the aqueous solution is 30-60%.
The production method according to the second aspect of the invention, wherein the halogen in the lead halide in the step (2) is the same as the halogen in the hydrohalic acid in the step (1).
The production method according to the second aspect of the present invention, wherein the good solvent in the step (2) is selected from one or more of: n, N-dimethylformamide, dimethyl sulfoxide, gamma-butyrolactone and acetonitrile.
The preparation method according to the second aspect of the present invention, wherein the protecting agent in the step (2) is selected from one or more of the following: octylamine, oleylamine, oleic acid.
The production method according to the second aspect of the present invention, wherein the poor solvent in the step (3) is selected from one or more of: toluene, chlorobenzene, dichloromethane, chloroform.
The third aspect of the invention provides an application of the chiral perovskite nanosheet of the first aspect or the chiral perovskite nanosheet prepared according to the method of the second aspect in preparing a circularly polarized luminescent material, a nonlinear optical material and a spintronic material.
The invention provides a preparation method of a chiral perovskite nanosheet and the chiral perovskite nanosheet prepared by the same. The preparation method comprises the following steps: (1) providing chiral amine and halogen acid to synthesize chiral ammonium salt; (2) dissolving lead halide and chiral ammonium salt in a good solvent to prepare a precursor solution; (3) and injecting the precursor solution into the stirred poor solvent to obtain the chiral perovskite nanosheet.
Specifically, the application provides a preparation method of a chiral perovskite nanosheet, which comprises the following steps:
(1) halogenation of chiral amine: under the ice bath condition, adding hydrohalic acid into equimolar chiral organic amine isopropanol dispersion liquid dropwise, reacting for 2 hours, removing redundant solvent by rotary evaporation, washing for many times, and drying to obtain chiral ammonium salt.
Wherein the hydrohalic acid can be one or more of hydriodic acid, hydrobromic acid and hydrochloric acid; the chiral organic amine may be one or more of (R) -2-phenyl-1-propylamine, (S) -2-phenyl-1-propylamine, (R) -2-naphthyl-1-propylamine, (S) -2-naphthyl-1-propylamine, (R) -2-cyclohexyl-1-propylamine, (S) -2-cyclohexyl-1-propylamine, (R) -2-cyclopentyl-1-propylamine, (S) -2-cyclopentyl-1-propylamine; the rotary evaporation temperature may be between 50-80 degrees celsius.
(2) Preparing a precursor solution: and dissolving the chiral ammonium salt and lead halide salt in a good solvent, heating for 2 hours on a hot table, adding a protective agent, and filtering the solution by using a filter membrane to obtain a precursor solution.
Wherein the lead halide can be one or more of lead iodide, lead bromide and lead chloride; the good solvent can be one or more of N, N-dimethylformamide, dimethyl sulfoxide, gamma-butyrolactone and acetonitrile; the concentration of halogenated lead salt in the precursor solution is 0.01M-0.05M; the molar ratio of the chiral ammonium salt to the lead halide in the precursor solution can be 1.5-2.5; the protective agent can be one or more of octylamine, oleylamine and oleic acid.
(3) Preparing a chiral perovskite nanosheet: and (3) taking a precursor solution, quickly dropwise adding the precursor solution into a stirred poor solvent, reacting for 2-5 minutes, centrifuging the obtained solution at a low speed to remove an aggregation product, and then centrifuging the supernatant at a high speed to obtain the chiral perovskite nanosheet.
Wherein the poor solvent can be toluene, chlorobenzene, dichloromethane or chloroform; the low-speed centrifugation condition can be 3500rpm for 3 min; the high speed centrifugation condition can be 9000rpm for 5 min; the volume ratio of the poor solvent to the precursor solution may be between 250 and 1000.
The chiral perovskite nanoplatelets of the present invention may have, but are not limited to, the following beneficial effects:
the chiral perovskite nanosheet type perovskite nanosheet has intrinsic chirality, has chiral optical response at the maximum excitation absorption position, and has a circular polarization absorption asymmetric factor (g-factor) peak value higher than that of the chiral perovskite nanocrystalline reported at present. The synthesis method is simple, and the perovskite nanosheet with intrinsic chirality can be rapidly prepared.
Drawings
Embodiments of the invention are described in detail below with reference to the attached drawing figures, wherein:
fig. 1 shows a circular dichroism spectrum of chiral perovskite nanosheet material synthesized in example 1 of the present invention.
Fig. 2 shows a circular polarization absorption asymmetry factor plot of chiral perovskite nanoplatelet materials synthesized in example 1 of the present invention.
Fig. 3 shows absorption and emission spectra of chiral perovskite nanoplatelets synthesized in example 1 of the present invention.
Fig. 4 shows an XRD pattern of chiral perovskite nanoplatelet material synthesized in example 1 of the present invention.
Detailed Description
The invention is further illustrated by the following specific examples, which, however, are to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.
This section generally describes the materials used in the testing of the present invention, as well as the testing methods. Although many materials and methods of operation are known in the art for the purpose of carrying out the invention, the invention is nevertheless described herein in as detail as possible. It will be apparent to those skilled in the art that the materials and methods of operation used in the present invention are well within the skill of the art, provided that they are not specifically illustrated.
The reagents and instrumentation used in the following examples are as follows:
reagent:
(R) -2-phenyl-1-propylamine, (S) -2-phenyl-1-propylamine was purchased from: xienssi Biotechnology Ltd. Hydrobromic acid, hydroiodic acid, hydrochloric acid, PbBr2N, N-dimethylformamide, octylamine, oleic acid were purchased from Shanghai Allantin reagent. Isopropanol, diethyl ether, toluene were purchased from Beijing chemical plant.
The instrument comprises the following steps:
a circular dichroism spectrometer purchased from japan light splitting plant association, model number; JASCO-810
A fluorescence spectrometer, available from Horiba jobin-Yvon, model Fluorolog-III;
an ultraviolet visible absorption spectrometer purchased from Shimadzu, model UV-2550;
x-ray diffractometer, available from Rigaku, model D/MAX-TTRIII 3.
Example 1
This example is used to illustrate the preparation method of the chiral perovskite nanosheet of the present invention.
10mL of isopropanol and 1mL of (R) -2-phenyl-1-propylamine (R-MPEA) or (S) -2-phenyl-1-propylamine (S-MPEA) were added to a round-bottom flask under ice-bath conditions, and after the above solution was completely cooled, 0.79mL of hydrobromic acid (48 wt.% aqueous solution) was added dropwise thereto under magnetic stirring. Reacting for 2 hours to obtain chiral amine precursor solution, removing the solvent by using a rotary evaporator at 50 ℃ to obtain white powdery R-MPEABr or S-MPEABr, washing the white powdery R-MPEABr or S-MPEABr with diethyl ether for three times, then recrystallizing the white powdery R-MPEABr or S-MPEABr with isopropanol and diethyl ether, and finally drying the white powdery R-MPEABr or S-MPEABr in a vacuum drying oven for 24 hours to obtain the final dry pure R-MPEABr or S-MPEABr.
0.0216g (0.1mmol) of R-MPEABr or S-MPEABr,0.0147g(0.04mmol)PbBr2dissolved in 1mLN, N-dimethylformamide and the solution heated on a 70 deg.C hot plate for 2 h. Then adding 1.5 mu L of octylamine and 100 mu L of oleic acid into the solution, and filtering through a 0.2 mu m filter membrane to obtain the chiral perovskite precursor solution.
10mL of toluene was added to an open vial at room temperature, at which time magnetic stirring (800rpm) was turned on, and then 20. mu.L of the chiral perovskite precursor solution was rapidly injected into the toluene. And reacting for 2min to obtain the toluene dispersion liquid of the chiral perovskite nanosheets. And centrifuging the dispersion liquid at 3500rpm for 3min to remove an aggregation product, and centrifuging the supernatant at 9000rpm for 5min to obtain the chiral perovskite nanosheet.
The chiral perovskite nano-crystal obtained in example 1 is subjected to chiral optical test, as shown in figure 1, R-and S-MPEA chiral perovskite nano-sheets have strong circular dichroism spectrum signals and possess opposite Cotton effect, as shown in figures 1 and 3, when the circular dichroism spectrum and the absorption spectrum of the chiral perovskite nano-sheets are compared, the inventor finds that the mirror circular dichroism spectrum signal between 375nm and 425nm corresponds to the excitation absorption maximum value, meanwhile, R-and S-MPEA molecules have no obvious circular dichroism signals in a wave band larger than 300nm, so that the chiral perovskite nano-sheets can be considered to possess chiral crystal structures, as shown in figure 3, the circular polarization absorption asymmetry factor (g-factor) peaks of the R-and S-MPEA chiral perovskite nano-sheets are respectively-3.6 × 10-3And 3.7 × 10-3Is higher than the chiral perovskite nanocrystalline reported at present. As shown in FIG. 3, the R-and S-MPEA chiral perovskite type nanosheets have narrow absorption peaks and sharp fluorescence peaks.
Chiral perovskite nanoplates were further characterized using X-ray diffraction (XRD). As shown in FIG. 4, the drop-coated thin films of the R-and S-MPEA chiral perovskite nanosheets both have sharp periodic (002) peaks, and the peak positions and intensities of the R-MPEA perovskite nanosheets are the same as those of the S-MPEA perovskite nanosheets. The peak spacing in the XRD pattern may reflect the average stacking distance between nanoplatelets. The peak spacing of the R-and S-MPEA chiral perovskite nanoplates was 4.88 °, corresponding to an average spacing of 1.8 nm.
Example 2
This example is used to illustrate the preparation method of the chiral perovskite nanosheet of the present invention.
10mL of isopropanol and 1mL of (R) -2-phenyl-1-propylamine (R-MPEA) or (S) -2-phenyl-1-propylamine (S-MPEA) were added to a round-bottomed flask under ice-bath conditions, and after the above solution was completely cooled, 0.92mL of hydroiodic acid (57 wt.% aqueous solution) was added dropwise thereto under magnetic stirring. And (3) reacting for 2 hours to obtain a chiral amine precursor solution, removing the solvent at 50 ℃ by using a rotary evaporator to obtain white powdery R-MPEAI or S-MPEAI, washing the white powdery R-MPEAI or S-MPEAI with diethyl ether for three times, recrystallizing the white powdery R-MPEAI or S-MPEAI with isopropanol and diethyl ether, and finally drying the white powdery R-MPEAI or S-MPEAI in a vacuum drying oven for 24 hours to obtain the final dry pure R-MPEAI or S-MPEAI.
0.0263g (0.1mmol) of R-MPEAI or S-MPEAI, 0.0184g (0.04mmol) of PbI2Dissolved in 1mL of N, N-dimethylformamide and the solution heated on a 70 ℃ hot plate for 2 h. Then adding 1.5 mu L octylamine into the solution, and filtering the solution by a filter membrane of 0.2 mu m to obtain the chiral perovskite precursor solution.
10mL of toluene was added to an open vial at room temperature, at which time magnetic stirring (800rpm) was turned on, and then 20. mu.L of the chiral perovskite precursor solution was rapidly injected into the toluene. And reacting for 2min to obtain the toluene dispersion liquid of the chiral perovskite nanosheets. And centrifuging the dispersion liquid at 3500rpm for 3min to remove an aggregation product, and centrifuging the supernatant at 9000rpm for 5min to obtain the chiral perovskite nanosheet.
Example 3
This example is used to illustrate the preparation method of the chiral perovskite nanosheet of the present invention.
10mL of isopropanol and 1mL of (R) -2-phenyl-1-propylamine (R-MPEA) or (S) -2-phenyl-1-propylamine (S-MPEA) were added to a round-bottomed flask under ice-bath conditions, and after the above solution was completely cooled, 0.58mL of hydrochloric acid (37 wt.% aqueous solution) was added dropwise thereto under magnetic stirring. Reacting for 2 hours to obtain chiral amine precursor solution, removing the solvent by using a rotary evaporator at 50 ℃ to obtain white powdery R-MPEACl or S-MPEACl, washing the white powdery R-MPEACl or S-MPEACl with diethyl ether for three times, then recrystallizing the white powdery R-MPEACl or S-MPEACl with isopropanol and diethyl ether, and finally drying the white powdery R-MPEACl or S-MPEACl in a vacuum drying oven for 24 hours to obtain the final dry pure R-MPEACl or S-MPEACl.
0.0172g (0.1mmol) of R-MPEACl or S-MPEACl, 0.0111g (0.04mmol) of PbCl2Dissolved in 1mLN, N-dimethylformamide and the solution heated on a 70 deg.C hot plate for 2 h. Then adding 1.5 mu L of octylamine and 100 mu L of oleic acid into the solution, and filtering through a 0.2 mu m filter membrane to obtain the chiral perovskite precursor solution.
10mL of toluene was added to an open vial at room temperature, at which time magnetic stirring (800rpm) was turned on, and then 20. mu.L of the chiral perovskite precursor solution was rapidly injected into the toluene. And reacting for 2min to obtain the toluene dispersion liquid of the chiral perovskite nanosheets. And centrifuging the dispersion liquid at 3500rpm for 3min to remove an aggregation product, and centrifuging the supernatant at 9000rpm for 5min to obtain the chiral perovskite nanosheet.
Although the present invention has been described to a certain extent, it is apparent that appropriate changes in the respective conditions may be made without departing from the spirit and scope of the present invention. It is to be understood that the invention is not limited to the described embodiments, but is to be accorded the scope consistent with the claims, including equivalents of each element described.
Claims (10)
1. A chiral perovskite nanosheet, wherein the chiral perovskite nanosheet is intrinsic chiral with a chiral optical response at a maximum excitation absorption.
2. Chiral perovskite nanoplate as claimed in claim 1, wherein the absolute value of the peak of the circularly polarized absorption asymmetry factor of the chiral perovskite nanoplate is higher than 2 × 10-3Preferably higher than 3 × 10-3More preferably higher than 3.5 × 10-3。
3. A method of preparing chiral perovskite nanoplates as claimed in claim 1 or 2, comprising the steps of:
(1) preparing chiral ammonium salt: mixing chiral amine and isopropanol to obtain chiral amine dispersion liquid, dropwise adding halogen acid with the same molar weight as the chiral amine into the dispersion liquid under an ice bath condition for reaction, removing redundant solvent, washing and drying to obtain chiral ammonium salt;
(2) preparing a precursor solution: dissolving the chiral ammonium salt prepared in the step (1) and lead halide salt in a good solvent, adding a protective agent, and filtering to obtain a precursor solution;
(3) preparing chiral perovskite nanocrystals: and (3) adding the precursor solution prepared in the step (2) into a poor solvent to react to obtain the chiral perovskite nanosheet.
4. The method according to claim 3, wherein in the step (1), the chiral amine is selected from one or more of the following: (R) -2-phenyl-1-propylamine, (S) -2-phenyl-1-propylamine, (R) -2-naphthyl-1-propylamine, (S) -2-naphthyl-1-propylamine, (R) -2-cyclohexyl-1-propylamine, (S) -2-cyclohexyl-1-propylamine, (R) -2-cyclopentyl-1-propylamine, and (S) -2-cyclopentyl-1-propylamine.
5. The method according to claim 3 or 4, wherein in the step (1), the halogen acid is selected from one or more of: hydriodic acid, hydrobromic acid, hydrochloric acid;
preferably, the hydrohalic acid added to the dispersion in step (1) is an aqueous solution; more preferably, the mass percentage of the halogen acid in the aqueous solution is 30-60%.
6. The production method according to any one of claims 3 to 5, wherein the halogen in the lead halide in step (2) is the same as the halogen in the hydrohalic acid in step (1).
7. The production method according to any one of claims 3 to 6, wherein the good solvent in step (2) is selected from one or more of: n, N-dimethylformamide, dimethyl sulfoxide, gamma-butyrolactone and acetonitrile.
8. The method according to any one of claims 3 to 7, wherein the protective agent in step (2) is selected from one or more of: octylamine, oleylamine, oleic acid.
9. The production method according to any one of claims 3 to 8, wherein the poor solvent in step (3) is selected from one or more of: toluene, chlorobenzene, dichloromethane, chloroform.
10. Use of chiral perovskite nanoplates as defined in claim 1 or 2 or prepared according to the preparation method of any one of claims 3 to 9 for the preparation of circularly polarized luminescent materials, nonlinear optical materials, spintronic materials.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113308734A (en) * | 2021-04-09 | 2021-08-27 | 北京交通大学 | Chiral two-dimensional perovskite single crystal and preparation method and application thereof |
| CN113308734B (en) * | 2021-04-09 | 2022-03-25 | 北京交通大学 | Chiral two-dimensional perovskite single crystal and preparation method and application thereof |
| CN114605994A (en) * | 2022-02-28 | 2022-06-10 | 苏州大学 | Chiral perovskite luminescent material and preparation method and application thereof |
| CN114988463A (en) * | 2022-05-27 | 2022-09-02 | 郑州大学 | Halide perovskite patterning assembly method and application thereof |
| CN114988463B (en) * | 2022-05-27 | 2023-10-24 | 郑州大学 | Halide perovskite patterning assembly method and application thereof |
| CN115181565A (en) * | 2022-06-21 | 2022-10-14 | 温州大学 | Mixed cation chiral perovskite nanosheet and preparation method thereof |
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