CN104250845A - Construction method of low-dimensional organic frequency-doubling crystal - Google Patents
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Abstract
The invention discloses a simple construction method of a low-dimensional organic frequency-doubling crystal; a host-guest inclusion coordination self-assembly strategy is utilized, guest molecules are induced to be arranged in a non-centrosymmetric structure, and inclusion complex molecules are aggregated to form the low-dimensional organic frequency-doubling crystal by an anti-solvent diffusion method. The construction method particularly comprises three steps: synthesis of the inclusion complex; controllable synthesis of the low-dimensional organic crystal material, and characterization of second-order nonlinear optical properties of the low-dimensional organic crystal material. The construction method provided by the invention is simple in process, convenient to operate, and friendly to the environment, and has universality on synthesis of similar low-dimensional organic frequency-doubling crystals. The construction strategy can greatly broaden the material selection range of the second-order nonlinear optical material. The material is expected to be used as a micro/nano light source device in an integrated nano photonic circuit.
Description
Technical field
The present invention relates to a kind of construction method of low-dimensional organic double-frequency crystal.
Background technology
Photonics on research photon and the interactional basis of material, explores photon as the various function of energy and information carrier and application.21 century, the storage density needed in information transmission was increasing along with the development of the high-capacity and high-speed such as optical communication, optical oomputing information processing, and processing speed is more and more faster, and this requires that the size of unit component is little of submicron even nanometer scale.In order to realize above-mentioned target, there has been proposed a kind of new subject-nanophotonics.In nanophotonics field, a vital challenge is exactly the relevant laser emitting source of development one.Nonlinear optics studies the generation mechanism of the various new phenomenons occurred when being concerned with light-matter interaction, process rule and application approach, is a Ge Xin branch of the optics developed rapidly after laser occurs.Utilize the frequency multiplication of nonlinear optical material with frequently, the non-linear process such as difference frequency and optically erasing can obtain the frequency laser different from incident light frequency, reach the object of light frequency conversion, widen the wavelength region of LASER Light Source, thus obtain new relevant LASER Light Source.Second harmonic (frequency multiplication) is more and more paid close attention to widely as the basis of non-linear optical field.Colinearity two-phonon process is compared, and second harmonic has the advantages such as wavelength restriction, high polarization selectivity, of short duration time of response that are not stimulated.Recently, nano material, because of having wide second harmonic response scope, need not meeting strict phase matched restriction and high photochemical stability, has developed in order to potential double-frequency material.Compare with inorganic materials, organic materials, owing to having high nonlinear optical property, fast time of response, high damage threshold and easily design and prepare the advantages such as simple, is extensively used as nonlinear optical material.But because most of organic crystal is centrosymmetric, body phase material does not have second harmonic response, thus limit their application in actual procedure.Therefore, obtain having high efficiency of conversion, the low-dimensional organic double-frequency crystal of easily preparation become a new challenge.
Summary of the invention
The object of the present invention is to provide a kind of construction method of low-dimensional organic double-frequency crystal, to solve the above-mentioned problems in the prior art.
The invention discloses a kind of construction method of low-dimensional organic double-frequency crystal of novelty, by selecting suitable host molecule, utilize the strategy of host-guest inclusion Coordinate self-assembly, induction guest molecule is with non-centrosymmetrical structural arrangement, and the method spread by anti-solvent makes inclusion complex molecular aggregates become low-dimensional organic double-frequency crystal.
The present invention is achieved through the following technical solutions:
(1) construct a method for low-dimensional organic double-frequency crystal, it is characterized in that, described method comprises the steps:
1) the guest molecule system with nonlinear optical response is selected, with the host molecule system can effectively inducing the non-centrosymmetry of nonlinear optics guest molecule to arrange, by two kinds of molecular meltings in same solvent, vigorous stirring (preferably stir and spend the night), forms stable inclusion complex solution;
2) substrate in substrate, and is put into the container (as beaker) that is equipped with a certain amount of anti-solvent by inclusion complex solution-cast step 1) obtained;
3) select suitable anti-solvent, utilize anti-solvent diffusion process to prepare low-dimensional organic crystal material.
Anti-solvent method is a kind of universal method prepared by crystalline material.Be combined with anti-solvent by main solvent, thus reduce thing to be crystallized solvability in a solvent, solute is separated out.
According to the present invention, also comprise the steps:
4) characterisation step 3) Nonlinear Second order Optical Properties of low-dimensional organic crystal material that obtains.
According to the present invention, step 4) is characterized by following experimental installation: select wavelength to be the pulse titanium precious stone laser of 830nm, utilize the object lens of 50 times to be that the hot spot of 2 μm is to excite single low-dimensional organic crystal this laser focusing.
According to the present invention, above-mentioned steps 4) in the intensity of exciting light change by regulating Neutral density filter, and its intensity can be detected by energy meter.And, utilize half-wave plate can change the polarization direction of exciting light, thus change the second harmonic intensity of the low-dimensional organic double-frequency crystal collected.
(2) method Gen Ju (1), the molecule with nonlinear optical property used in step 1) is the molecule of D-π-A structure, as N-methyl-p-nitroaniline, Disperse Red, DISPERSE ORANGE 30 200 and pyridines guest molecule system etc.
Preferably, described guest molecule is p-Nitroaniline.
(3) according to (1) or the construction method described in (2), the macrocylc compound molecule that guest molecule can be induced to arrange used in step 1), as cyclodextrin, calixarene and Septochol human subject molecular system etc.
Preferably, described host molecule is beta-cyclodextrin.
(4) construction method according to any one of (1)-(3), it is characterized in that: described principle comprises the strategy utilizing host-guest inclusion Coordinate self-assembly, induction guest molecule is with non-centrosymmetrical structural arrangement, and the method spread by anti-solvent makes inclusion complex molecular aggregates become low-dimensional organic double-frequency crystal.
(5) construction method according to any one of (1)-(4), it is characterized in that, in step 1), the mol ratio of described guest molecule and host molecule is 10:1-1:10, is preferably 1:1-1:5, is more preferably 1:1.
Preferably, guest molecule is p-Nitroaniline, and host molecule is beta-cyclodextrin, and the mol ratio of described guest molecule and host molecule is 1:1.
(6) according to the construction method described in any one of (1)-(5), it is characterized in that, step 2) described in substrate be substrate of glass, quartz substrate or monocrystal silicon substrate.
(7) construction method according to any one of (1)-(6), is characterized in that, in step 3), selects the preparation of anti-solvent diffusion process, the aqueous solvent that preferred different polarities is large and ethanol.
The construction method that the present invention relates to has following actively useful effect:
1. provide that a kind of low-dimensional organic double-frequency crystal is simple, the construction method of universality.
2. expand the research field of supramolecular chemistry, be conducive to the application of development low-dimensional organic double-frequency crystalline material in the middle of the integrated nanometer photon circuit in future.
Accompanying drawing explanation
Fig. 1 be low-dimensional organic double-frequency crystal provided by the invention construct schematic diagram.
Fig. 2 is the transmission electron microscope photo of low-dimensional organic crystal material and the electron scanning micrograph of the different structure prepared by embodiment 1.Wherein:
The stereoscan photograph of a low-dimensional supramolecular complex that () water obtains as anti-solvent, scale is 20 μm;
The stereoscan photograph of b low-dimensional supramolecular complex that () ethanol obtains as anti-solvent, scale is 20 μm;
The transmission electron microscope photo of c low-dimensional supramolecular complex that () water obtains as anti-solvent, scale is 3 μm;
The transmission electron microscope photo of d low-dimensional supramolecular complex that () ethanol obtains as anti-solvent, scale is 3 μm.Fig. 3 is the principle schematic that low-dimensional organic crystal provided by the invention produces second harmonic.
The Nonlinear Second order Optical Properties of the single low-dimensional organic double-frequency crystal that Fig. 4 is prepared by embodiment 1.Wherein:
(a) when fundamental frequency light wavelength is 830nm, the second harmonic emission spectrum of different low-dimensional supramolecular complex;
The second harmonic intensity of (b, c) different low-dimensional supramolecular complex and the dependence of fundamental frequency light energy;
The experimental installation schematic diagram of (d) polarization measurement;
Second harmonic intensity and the dependence exciting polarizing angle of (e, f) different low-dimensional supramolecular complex.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described, but it will be appreciated by those skilled in the art that the present invention is not limited to following examples, and any improvement of making on basis of the present invention and change are all within the scope of the present invention.
The experimental technique used in following embodiment if no special instructions, is ordinary method.
Material used in following embodiment, reagent etc., if no special instructions, all can obtain from commercial channels.
The controlledly synthesis of the low-dimensional organic double-frequency crystal of embodiment 1, different structure
Be dissolved in 20 ml waters under ultrasonic for the beta-cyclodextrin of the p-Nitroaniline of 0.1 mmole and 0.1 mmole, form the stable aqueous solution.By this aqueous solution vigorous stirring overnight, the inclusion complex aqueous solution that p-Nitroaniline and beta-cyclodextrin mol ratio are 1:1 can be formed.Then the inclusion complex solution taking out 20 microlitres drips in monocrystal silicon substrate, monocrystal silicon substrate is put in the beaker that 3 milliliters of anti-solvent ethanol are housed airtight.In order to the growth of stable low-dimensional organic crystal material, allow water solvent at room temperature slowly volatilize 2-3 days.Within 4 hours, remove remaining solvent by dry in the vacuum drying oven of 60 degrees Celsius for the low-dimensional organic crystal material obtained, and be used for doing later nonlinear optical test.
Be dissolved in 20 ml waters under ultrasonic for the beta-cyclodextrin of the p-Nitroaniline of 0.1 mmole and 0.1 mmole, form the stable aqueous solution.By this aqueous solution vigorous stirring overnight, the inclusion complex aqueous solution that p-Nitroaniline and beta-cyclodextrin mol ratio are 1:1 can be formed.Then the inclusion complex solution taking out 20 microlitres drips in monocrystal silicon substrate, monocrystal silicon substrate is put in the beaker that 3 milliliters of anti-solvent water are housed airtight.In order to the growth of stable low-dimensional organic crystal material, allow water solvent at room temperature slowly volatilize 2-3 days.Within 4 hours, remove remaining solvent by dry in the vacuum drying oven of 60 degrees Celsius for the low-dimensional organic crystal material obtained, and be used for doing later nonlinear optical test.
As shown in Figure 1, the method shown in this figure is a kind of method of constructing the universality of low-dimensional organic double-frequency crystal to the construction method of corresponding low-dimensional organic double-frequency crystal.The transmission electron microscope photo of the low-dimensional organic crystal material of the different structure that Fig. 2 is prepared by embodiment 1 and electron scanning micrograph, the stereoscan photograph of the low-dimensional supramolecular complex that (a) water obtains as anti-solvent, scale is 20 μm; The stereoscan photograph of b low-dimensional supramolecular complex that () ethanol obtains as anti-solvent, scale is 20 μm; The transmission electron microscope photo of c low-dimensional supramolecular complex that () water obtains as anti-solvent, scale is 3 μm; The transmission electron microscope photo of d low-dimensional supramolecular complex that () ethanol obtains as anti-solvent, scale is 3 μm.
As known in the figure, different anti-solvent is selected can to obtain the low-dimensional organic double-frequency crystal of different structure.
Embodiment 2, other nlo molecule and host molecule is selected to construct low-dimensional organic double-frequency crystal
Be dissolved in 20 ml waters under ultrasonic for the γ-cyclodextrin of the p-Nitroaniline of 0.1 mmole and 0.1 mmole, form the stable aqueous solution.By this aqueous solution vigorous stirring overnight, the inclusion complex aqueous solution that p-Nitroaniline and γ-cyclodextrin mol ratio are 1:1 can be formed.Then the inclusion complex solution taking out 20 microlitres drips in monocrystal silicon substrate, monocrystal silicon substrate is put in the beaker that 3 milliliters of anti-solvent ethanol are housed airtight.In order to the growth of stable low-dimensional organic crystal material, allow water solvent at room temperature slowly volatilize 2-3 days.Within 4 hours, remove remaining solvent by dry in the vacuum drying oven of 60 degrees Celsius for the low-dimensional organic crystal material obtained, and be used for doing later nonlinear optical test.
Be dissolved in 20 ml waters under ultrasonic for the γ-cyclodextrin of the p-Nitroaniline of 0.1 mmole and 0.1 mmole, form the stable aqueous solution.By this aqueous solution vigorous stirring overnight, the inclusion complex aqueous solution that p-Nitroaniline and γ-cyclodextrin mol ratio are 1:1 can be formed.Then the inclusion complex solution taking out 20 microlitres drips in monocrystal silicon substrate, monocrystal silicon substrate is put in the beaker that 3 milliliters of anti-solvent water are housed airtight.In order to the growth of stable low-dimensional organic crystal material, allow water solvent at room temperature slowly volatilize 2-3 days.Within 4 hours, remove remaining solvent by dry in the vacuum drying oven of 60 degrees Celsius for the low-dimensional organic crystal material obtained, and be used for doing later nonlinear optical test.
Be dissolved in 20 ml waters under ultrasonic for the beta-cyclodextrin of the Disperse Red of 0.1 mmole and 0.1 mmole, form the stable aqueous solution.By this aqueous solution vigorous stirring overnight, the inclusion complex aqueous solution that Disperse Red and beta-cyclodextrin mol ratio are 1:1 can be formed.Then the inclusion complex solution taking out 20 microlitres drips in monocrystal silicon substrate, monocrystal silicon substrate is put in the beaker that 3 milliliters of anti-solvent ethanol are housed airtight.In order to the growth of stable low-dimensional organic crystal material, allow water solvent at room temperature slowly volatilize 2-3 days.Within 4 hours, remove remaining solvent by dry in the vacuum drying oven of 60 degrees Celsius for the low-dimensional organic crystal material obtained, and be used for doing later nonlinear optical test.
Be dissolved in 20 ml waters under ultrasonic for the beta-cyclodextrin of the Disperse Red of 0.1 mmole and 0.1 mmole, form the stable aqueous solution.By this aqueous solution vigorous stirring overnight, the inclusion complex aqueous solution that Disperse Red and beta-cyclodextrin mol ratio are 1:1 can be formed.Then the inclusion complex solution taking out 20 microlitres drips in monocrystal silicon substrate, monocrystal silicon substrate is put in the beaker that 3 milliliters of anti-solvent water are housed airtight.In order to the growth of stable low-dimensional organic crystal material, allow water solvent at room temperature slowly volatilize 2-3 days.Within 4 hours, be used for removing remaining solvent by dry in the vacuum drying oven of 60 degrees Celsius for the low-dimensional organic crystal material obtained, and be used for doing later nonlinear optical test.
The test of the Nonlinear Second order Optical Properties of embodiment 3, single low-dimensional organic double-frequency crystal
For the organic molecule with nonlinear optical property, assemble due to them and be assembled into centrosymmetric crystalline structure, thus their crystalline material does not have second harmonic response.By selecting suitable host molecule, utilize the strategy of host-guest inclusion Coordinate self-assembly that the non-centrosymmetry of guest molecule can be induced to arrange.Meanwhile, select different anti-solvent systems, guest molecule can be induced to be gathered into the low-dimensional organic double-frequency crystal of different structure.These low-dimensional organic double-frequency crystalline materials have very strong second harmonic response.Fig. 3 is the principle schematic that low-dimensional organic crystal produces second harmonic.
The Nonlinear Second order Optical Properties of low-dimensional organic double-frequency crystal is that the nanophotonics test platform utilizing oneself to build carries out testing.Select wavelength to be the pulse titanium precious stone laser of 830nm, utilize the object lens of 50 times to be that the hot spot of 2 μm is to excite single low-dimensional organic crystal this laser focusing.The intensity of exciting light changes by regulating Neutral density filter, and its intensity can be detected by energy meter.Utilize half-wave plate can change the polarization direction of exciting light, thus change the second harmonic intensity of the low-dimensional organic double-frequency crystal collected.Fig. 4 is the Nonlinear Second order Optical Properties figure of the single low-dimensional organic double-frequency crystal by example 1 preparation.(a) when fundamental frequency light wavelength is 830nm, the second harmonic emission spectrum of different low-dimensional supramolecular complex; The second harmonic intensity of (b, c) different low-dimensional supramolecular complex and the dependence of fundamental frequency light energy; The experimental installation schematic diagram of (d) polarization measurement; Second harmonic intensity and the dependence exciting polarizing angle of (e, f) different low-dimensional supramolecular complex.
Claims (7)
1. construct a method for low-dimensional organic double-frequency crystal, comprise the steps:
1) the guest molecule system with nonlinear optical response is selected, with the host molecule system can effectively inducing non-linear guest molecule non-centrosymmetry to arrange, by two kinds of molecular meltings in same solvent, vigorous stirring overnight, forms stable inclusion complex solution;
2) substrate in substrate (as monocrystalline silicon piece, sheet glass, quartz plate), and is put into the beaker that is equipped with a certain amount of anti-solvent by inclusion complex solution-cast step 1) obtained;
3) select suitable anti-solvent, utilize anti-solvent diffusion process to prepare low-dimensional organic crystal material;
4) experimental installation built by oneself characterizes the Nonlinear Second order Optical Properties of the low-dimensional organic crystal material obtained.
2. construction method according to claim 1, the molecule with the D-π-A structure of nonlinear optical property used in step 1), as p-Nitroaniline, Disperse Red, DISPERSE ORANGE 30 200 and pyridines guest molecule system; Other the guest molecule system with nonlinear optical property is all in the protection domain of this patent.
3. construction method according to claim 1 and 2, the macrocylc compound molecule that guest molecule can be induced to arrange used in step 1), as cyclodextrin, calixarene and Septochol human subject molecular system; Other the host molecule system that guest molecule can be induced to arrange is all in the protection domain of this patent.
4. the construction method according to any one of claim 1-3, it is characterized in that: described principle comprises the strategy utilizing host-guest inclusion Coordinate self-assembly, induction guest molecule is with non-centrosymmetrical structural arrangement, and the method spread by anti-solvent makes inclusion complex molecular aggregates become low-dimensional organic double-frequency crystal.
5. the construction method according to any one of claim 1-4, is characterized in that: in step 1), and the mol ratio of described molecule p-Nitroaniline and beta-cyclodextrin is 1:1.
6. the construction method according to any one of claim 1-5, is characterized in that: step 2) described in substrate be glass substrate, quartz substrate or monocrystalline silicon substrate.
7. the construction method according to any one of claim 1-6, is characterized in that: in step 3), selects the preparation of anti-solvent diffusion process, the aqueous solvent that preferred different polarities is large and ethanol.
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| CN107450125A (en) * | 2017-08-03 | 2017-12-08 | 河北科技大学 | A kind of preparation method and applications of low dimensional organic optical diode material |
| CN110837196A (en) * | 2019-11-13 | 2020-02-25 | 上海理工大学 | Light-resistant supermolecule organic crystal material and preparation method thereof |
| CN111628394A (en) * | 2020-06-12 | 2020-09-04 | 燕山大学 | Echo wall mode organic special-shaped resonant cavity and preparation method and application thereof |
| CN113106550A (en) * | 2021-04-07 | 2021-07-13 | 南京大学 | Electrochemical preparation method of frequency doubling crystal |
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| CN105780125A (en) * | 2016-01-18 | 2016-07-20 | 上海多磨新材料科技有限公司 | Preparation method of mesoscale line-shaped organic crystal |
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| CN106222752A (en) * | 2016-08-29 | 2016-12-14 | 上海理工大学 | A kind of method preparing organic crystal thin film |
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| CN107450125A (en) * | 2017-08-03 | 2017-12-08 | 河北科技大学 | A kind of preparation method and applications of low dimensional organic optical diode material |
| CN110837196A (en) * | 2019-11-13 | 2020-02-25 | 上海理工大学 | Light-resistant supermolecule organic crystal material and preparation method thereof |
| CN111628394A (en) * | 2020-06-12 | 2020-09-04 | 燕山大学 | Echo wall mode organic special-shaped resonant cavity and preparation method and application thereof |
| CN113106550A (en) * | 2021-04-07 | 2021-07-13 | 南京大学 | Electrochemical preparation method of frequency doubling crystal |
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