CN104250845B - Construction method of low-dimensional organic frequency-doubling crystal - Google Patents
Construction method of low-dimensional organic frequency-doubling crystal Download PDFInfo
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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
Photonic propulsion is that photon is explored on the basis of research photon with material interaction as energy and information carrier
Various functions and application.21 century, with the development of the high-capacity and high-speed information processing such as optic communication, optical oomputing, is needed in information transfer
The memory density wanted is increasing, and processing speed is more and more faster, and this requires that the size of unit component is little to submicron even nanometer
Magnitude.In order to realize above-mentioned target, there has been proposed a kind of new subject-nanophotonics.In nanophotonics field,
One vital challenge is exactly to develop a relevant laser emitting source.Nonlinear optics is research coherent light and material phase
The generation mechanism of the various new phenomenons occurred during interaction, process rule and application approach, are developed rapidly after laser occurs
The optical Ge Xin branches got up.It is non-linear using the frequency multiplication and frequency of nonlinear optical material, difference frequency and optically erasing etc.
Process can obtain the frequency laser different from incident light frequency, reach the purpose of light frequency conversion, widened LASER Light Source
Wave-length coverage, so as to obtain new relevant LASER Light Source.Second harmonic（Frequency multiplication）As non-linear optical field basis
Jing is more and more widely paid close attention to.Synteny two-phonon process is compared, and there is second harmonic the wavelength that is not stimulated to limit, height
Polarization selectivity, the advantage such as of short duration response time.Recently, nano material because have wide second harmonic response scope,
Limit without meeting strict phase matched, and high photochemical stability, have developed into for potential double-frequency material.Together
Inorganic material is compared, organic material due to high nonlinear optical property, quick response time, high damage threshold and
The advantages of which easily designs and prepares simple, has extensively been used as nonlinear optical material.But, due to most of organic crystalline
Body is centrosymmetric, and body phase material does not have second harmonic response, thus limits their applications in real process.Cause
This, obtains having become a new challenge with high conversion efficiency, the low-dimensional organic double-frequency crystal for easily preparing.
The content of the invention
It is an object of the invention to provide a kind of construction method of low-dimensional organic double-frequency crystal, to solve to deposit in prior art
The problems referred to above.
The invention discloses a kind of construction method of novel low-dimensional organic double-frequency crystal, by selecting suitable main body point
Son, includes the strategy of Coordinate self-assembly using host-guest, induces guest molecule with non-centrosymmetrical structural arrangement, by anti-
The method of solvent diffuse assembles inclusion complex molecule becomes low-dimensional organic double-frequency crystal.
The present invention is achieved through the following technical solutions：
（1）A kind of method for constructing low-dimensional organic double-frequency crystal, it is characterised in that methods described comprises the steps：
1）The guest molecule system with nonlinear optical response is selected, and can effectively induce nonlinear optics guest molecule
The host molecule system of sub- non-centrosymmetry arrangement, by two kinds of molecular meltings in same solvent, is stirred vigorously（It is preferred that stirred
Night）, form stable inclusion complex solution；
2）By step 1）The inclusion complex solution-cast for obtaining is in substrate, and substrate is put into one equipped with certain
The container of amount anti-solvent（Such as beaker）In；
3）Suitable anti-solvent is selected, and low-dimensional organic crystal material is prepared using anti-solvent diffusion method.
Anti-solvent method is a kind of universal method prepared by crystalline material.Will main solvent be used in combination with anti-solvent, so as to
Thing to be crystallized dissolubility in a solvent is reduced, separates out solute.
According to the present invention, also comprise the steps：
4）Characterize step 3）The Nonlinear Second order Optical Properties of the low-dimensional organic crystal material for obtaining.
According to the present invention, step 4）Characterized by following experimental provision：Swashed from pulse Ti∶Sapphire laser of the wavelength for 830nm
Light, using 50 times of object lens the hot spot that the laser focusing is 2 μm exciting single low-dimensional organic crystal.
According to the present invention, above-mentioned steps 4）In the intensity of exciting light be by adjusting Neutral density filter changing
, and its intensity can be detected by energy meter.And, the polarization direction of exciting light can be changed using half-wave plate, from
And change the second harmonic intensity of the low-dimensional organic double-frequency crystal collected.
（2）According to（1）Described method, step 1）In the molecule with nonlinear optical property used be D- π-A knots
The molecule of structure, such as nitroaniline, disperse red, disperse orange and pyridines guest molecule system etc..
Preferably, the guest molecule is paranitroanilinum.
（3）According to（1）Or（2）Described construction method, step 1）In used can induce the big of guest molecule arrangement
Cycle compound molecule, such as cyclodextrin, calixarenes and deoxycholic acid human subject molecular system etc..
Preferably, the host molecule is beta-schardinger dextrin-.
（4）According to（1）-（3）Construction method described in any one, it is characterised in that：The principle includes utilizing host-guest
The strategy of inclusion Coordinate self-assembly, induction guest molecule is with non-centrosymmetrical structural arrangement, the method spread by anti-solvent
Assembling inclusion complex molecule becomes low-dimensional organic double-frequency crystal.
（5）According to（1）-（4）Construction method described in any one, it is characterised in that step 1）In, the guest molecule with
The mol ratio of host molecule is 10:1-1:10, preferably 1:1-1:5, more preferably 1:1.
Preferably, guest molecule is paranitroanilinum, and host molecule is beta-schardinger dextrin-, the guest molecule and host molecule
Mol ratio be 1:1.
（6）According to（1）-（5）Construction method described in any one, it is characterised in that step 2）Described in substrate be glass
Substrate, quartz substrate or monocrystal silicon substrate.
（7）According to（1）-（6）Construction method described in any one, it is characterised in that step 3）In, select anti-solvent diffusion
Method preparation, the big aqueous solvent of preferred different polarities and ethanol.
Construction method according to the present invention has following positive beneficial effect：
1. provide that a kind of low-dimensional organic double-frequency crystal is simple, the construction method of universality.
2. the research field of supramolecular chemistry is extended, is conducive to developing low-dimensional organic double-frequency crystalline material following integrated
Application in the middle of nano-photon loop.
Description of the drawings
Fig. 1 constructs schematic diagram for the low-dimensional organic double-frequency crystal for providing of the invention.
Fig. 2 be by embodiment 1 prepare different structure low-dimensional organic crystal material transmission electron microscope photo and
Electron scanning micrograph.Wherein：
The stereoscan photograph of a low-dimensional supramolecular complex that () water is obtained as anti-solvent, scale are 20 μm；
The stereoscan photograph of b low-dimensional supramolecular complex that () ethanol is obtained as anti-solvent, scale are 20 μm；
The transmission electron microscope photo of c low-dimensional supramolecular complex that () water is obtained as anti-solvent, scale are 3 μm；
The transmission electron microscope photo of d low-dimensional supramolecular complex that () ethanol is obtained as anti-solvent, scale are 3 μm.Fig. 3 is this
The low-dimensional organic crystal that invention is provided produces the principle schematic of 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) in the case of a length of 830nm of fundamental light wave, the second harmonic emission spectra of different low-dimensional supramolecular complexes；
The dependence of the second harmonic intensity and fundamental frequency light energy of (b, c) difference low-dimensional supramolecular complex；
The experimental provision schematic diagram of (d) polarization measurement；
The second harmonic intensity and the dependence for exciting the angle of polarization of (e, f) difference low-dimensional supramolecular complex.
Specific embodiment
With reference to specific embodiment, the invention will be further described, it will be appreciated by those skilled in the art that the present invention is simultaneously
Following examples are not limited to, any improvement made on the basis of the present invention and change are within the scope of the present invention.
Experimental technique used in following embodiments if no special instructions, is conventional method.
In following embodiments, material used, reagent etc., if no special instructions, commercially obtain.
The controlledly synthesis of the low-dimensional organic double-frequency crystal of embodiment 1, different structure
It is dissolved in 20 milliliters of water under will be the beta-schardinger dextrin-of 0.1 mM of paranitroanilinum and 0.1 mM ultrasonic, shape
Into stable aqueous solution.By the aqueous solution vigorous stirring overnight, it is 1 that can form paranitroanilinum and beta-schardinger dextrin-mol ratio:1
Inclusion complex aqueous solution.The inclusion complex solution for then taking out 20 microlitres is dripped in monocrystal silicon substrate, monocrystalline silicon substrate
Bottom is put into closed in the beaker equipped with 3 milliliters of anti-solvent ethanol.In order to stablize the growth of low-dimensional organic crystal material, aqueous solvent is allowed
Slowly volatilize 2-3 days at room temperature.By the low-dimensional organic crystal material for obtaining, in 60 degrees Celsius of vacuum drying oven, drying 4 is little
When remove remaining solvent, and for doing later nonlinear optical test.
It is dissolved in 20 milliliters of water under will be the beta-schardinger dextrin-of 0.1 mM of paranitroanilinum and 0.1 mM ultrasonic, shape
Into stable aqueous solution.By the aqueous solution vigorous stirring overnight, it is 1 that can form paranitroanilinum and beta-schardinger dextrin-mol ratio:1
Inclusion complex aqueous solution.The inclusion complex solution for then taking out 20 microlitres is dripped in monocrystal silicon substrate, monocrystalline silicon substrate
Bottom is put into closed in the beaker equipped with 3 milliliters of anti-solvent water.In order to stablize the growth of low-dimensional organic crystal material, aqueous solvent is allowed to exist
Slowly volatilize 2-3 days under room temperature.The low-dimensional organic crystal material for obtaining is dried 4 hours in 60 degrees Celsius of vacuum drying oven
Remaining solvent is removed, and for doing later nonlinear optical test.
The construction method of corresponding low-dimensional organic double-frequency crystal constructs low as shown in figure 1, the method shown in the figure is one kind
The method of the universality of dimension organic double-frequency crystal.Fig. 2 is saturating by the low-dimensional organic crystal material of the different structure of the preparation of embodiment 1
Electron micrograph and electron scanning micrograph are penetrated, (a) low-dimensional supramolecular complex that water is obtained as anti-solvent is swept
Electromicroscopic photograph is retouched, scale is 20 μm；The stereoscan photograph of b low-dimensional supramolecular complex that () ethanol is obtained as anti-solvent, mark
Chi is 20 μm；The transmission electron microscope photo of c low-dimensional supramolecular complex that () water is obtained as anti-solvent, scale are 3 μm；(d) ethanol
The transmission electron microscope photo of the low-dimensional supramolecular complex obtained as anti-solvent, scale are 3 μm.
It can be seen that selecting different anti-solvent obtain the low-dimensional organic double-frequency crystal of different structure.
Embodiment 2, low-dimensional organic double-frequency crystal is constructed from other nlo molecules and host molecule
It is dissolved in 20 milliliters of water under will be the gamma-cyclodextrin of 0.1 mM of paranitroanilinum and 0.1 mM ultrasonic,
Form stable aqueous solution.By the aqueous solution vigorous stirring overnight, paranitroanilinum can be formed and gamma-cyclodextrin mol ratio is
1:1 inclusion complex aqueous solution.The inclusion complex solution for then taking out 20 microlitres is dripped in monocrystal silicon substrate, monocrystal silicon
Substrate is put into closed in the beaker equipped with 3 milliliters of anti-solvent ethanol.In order to stablize the growth of low-dimensional organic crystal material, allow water-soluble
Agent is slowly volatilized 2-3 days at room temperature.By the low-dimensional organic crystal material for obtaining dry 4 in 60 degrees Celsius of vacuum drying oven
Hour removes remaining solvent, and for doing later nonlinear optical test.
It is dissolved in 20 milliliters of water under will be the gamma-cyclodextrin of 0.1 mM of paranitroanilinum and 0.1 mM ultrasonic,
Form stable aqueous solution.By the aqueous solution vigorous stirring overnight, paranitroanilinum can be formed and gamma-cyclodextrin mol ratio is
1:1 inclusion complex aqueous solution.The inclusion complex solution for then taking out 20 microlitres is dripped in monocrystal silicon substrate, monocrystal silicon
Substrate is put into closed in the beaker equipped with 3 milliliters of anti-solvent water.In order to stablize the growth of low-dimensional organic crystal material, aqueous solvent is allowed
Slowly volatilize 2-3 days at room temperature.By the low-dimensional organic crystal material for obtaining, in 60 degrees Celsius of vacuum drying oven, drying 4 is little
When remove remaining solvent, and for doing later nonlinear optical test.
It is dissolved in 20 milliliters of water under will be the beta-schardinger dextrin-of 0.1 mM of disperse red and 0.1 mM ultrasonic, forms steady
Fixed aqueous solution.By the aqueous solution vigorous stirring overnight, it is 1 that can form disperse red and beta-schardinger dextrin-mol ratio:1 inclusion is matched somebody with somebody
Compound aqueous solution.The inclusion complex solution for then taking out 20 microlitres is dripped in monocrystal silicon substrate, and monocrystal silicon substrate is put into dress
Have closed in the beaker of 3 milliliters of anti-solvent ethanol.In order to stablize the growth of low-dimensional organic crystal material, aqueous solvent is allowed at room temperature
Slowly volatilize 2-3 days.The low-dimensional organic crystal material for obtaining in 60 degrees Celsius of vacuum drying oven is dried to remove for 4 hours and is remained
Remaining solvent, and for doing later nonlinear optical test.
It is dissolved in 20 milliliters of water under will be the beta-schardinger dextrin-of 0.1 mM of disperse red and 0.1 mM ultrasonic, forms steady
Fixed aqueous solution.By the aqueous solution vigorous stirring overnight, it is 1 that can form disperse red and beta-schardinger dextrin-mol ratio:1 inclusion is matched somebody with somebody
Compound aqueous solution.The inclusion complex solution for then taking out 20 microlitres is dripped in monocrystal silicon substrate, and monocrystal silicon substrate is put into dress
Have closed in the beaker of 3 milliliters of anti-solvent water.In order to stablize the growth of low-dimensional organic crystal material, make aqueous solvent slow at room temperature
Slow vaporization 2-3 days.The low-dimensional organic crystal material for obtaining is dried into 4 hours for removing in 60 degrees Celsius of vacuum drying oven
Remaining solvent, and for doing later nonlinear optical test.
The test of embodiment 3, the Nonlinear Second order Optical Properties of single low-dimensional organic double-frequency crystal
For the organic molecule with nonlinear optical property, assembled due to them and be assembled into centrosymmetric crystalline substance
Body structure, thus their crystalline material is no second harmonic response.By selecting suitable host molecule, using master-
The strategy of guest inclusion Coordinate self-assembly can induce the non-centrosymmetry of guest molecule to arrange.Meanwhile, select different anti-molten
Agent system, can induce guest molecule to be gathered into the low-dimensional organic double-frequency crystal of different structure.These low-dimensional organic double-frequency crystal
Material has 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 are that the nanophotonics test built using oneself is flat
Platform is being tested.From wavelength for 830nm pulse titanium precious stone laser, using 50 times of object lens the laser focusing be 2 μ
The hot spot of m is exciting single low-dimensional organic crystal.The intensity of exciting light is changed by adjusting Neutral density filter, and
And its intensity can be detected by energy meter.The polarization direction of exciting light can be changed using half-wave plate, so as to change collection
The second harmonic intensity of the low-dimensional organic double-frequency crystal for arriving.Fig. 4 is the two of the single low-dimensional organic double-frequency crystal prepared by example 1
Rank nonlinear optical property figure.(a) in the case of a length of 830nm of fundamental light wave, different low-dimensional supramolecular complexes it is secondary humorous
Ripple emission spectra；The dependence of the second harmonic intensity and fundamental frequency light energy of (b, c) difference low-dimensional supramolecular complex；D () polarizes
The experimental provision schematic diagram of test；The second harmonic intensity of (e, f) difference low-dimensional supramolecular complex and the dependence for exciting the angle of polarization
Relation.
Claims (9)
1. a kind of method for constructing low-dimensional organic double-frequency crystal, comprises the steps：
1) the guest molecule system with nonlinear optical response is selected, and can effectively induces non-linear guest molecule non-central
The host molecule system of symmetric arrays, by two kinds of molecular meltings in same solvent, is stirred vigorously, and forms stable inclusion and coordinates
Thing solution；
2) by step 1) the inclusion complex solution-cast that obtains is in substrate, and substrate is put into into one equipped with a certain amount of anti-
In the container of solvent；
3) suitable anti-solvent is selected, low-dimensional organic crystal material is prepared using anti-solvent diffusion method,
Wherein, step 1) in the guest molecule system with nonlinear optical response used be the molecule of D- π-A structures, be selected from
Paranitroanilinum, disperse red and disperse orange guest molecule system；
Step 1) in the used macrocyclic compound molecule choosing that can effectively induce non-linear guest molecule non-centrosymmetry arrangement
From cyclodextrin and calixarenes host molecule system, wherein
The guest molecule is 10 with the mol ratio of host molecule:1-1:10.
2. method according to claim 1, it is characterised in that also comprise the steps：
4) characterize step 3) Nonlinear Second order Optical Properties of low-dimensional organic crystal material that obtain.
3. method according to claim 2, it is characterised in that step 4) by following experimental provision characterizing：From wavelength it is
The pulse titanium precious stone laser of 830nm, using 50 times of object lens the hot spot that the laser focusing is 2 μm exciting single low-dimensional organic
Crystal.
4. the method according to any one of claim 1-3, it is characterised in that：Principle includes being coordinated using host-guest inclusion
The strategy of self assembly, induction guest molecule match somebody with somebody inclusion with non-centrosymmetrical structural arrangement, the method spread by anti-solvent
Adduct molecule aggregation becomes low-dimensional organic double-frequency crystal.
5. the method according to any one of claim 1-3, it is characterised in that：Step 1) in, the guest molecule is selected from right
Nitroaniline, the host molecule are selected from beta-schardinger dextrin-, and wherein paranitroanilinum and the mol ratio of beta-schardinger dextrin-are 1:1.
6. the method according to any one of claim 1-3, it is characterised in that：Step 2) described in substrate be substrate of glass,
Quartz substrate or monocrystal silicon substrate.
7. the method according to any one of claim 1-3, it is characterised in that：Step 3) in, anti-solvent is selected from water and ethanol.
8. the method according to any one of claim 1-3, it is characterised in that the guest molecule and host molecule mole
Than for 1:1-1:5.
9. method according to claim 8, it is characterised in that the guest molecule is 1 with the mol ratio of host molecule:1.
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| CN105542753B (en) * | 2015-12-23 | 2019-05-17 | 上海多磨新材料科技有限公司 | The preparation method of organic nanocrystal |
| CN105780125B (en) * | 2016-01-18 | 2019-05-17 | 上海多磨新材料科技有限公司 | The preparation method of meso-scale linear organic crystal |
| CN106222752B (en) * | 2016-08-29 | 2019-02-15 | 上海理工大学 | A method of preparing organic crystal film |
| CN107450125B (en) * | 2017-08-03 | 2018-08-07 | 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 |
| CN111628394B (en) * | 2020-06-12 | 2021-08-03 | 燕山大学 | Echo wall mode organic special-shaped resonant cavity and preparation method and application thereof |
| CN113106550B (en) * | 2021-04-07 | 2022-08-19 | 南京大学 | Electrochemical preparation method of frequency doubling crystal |
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| JPH0369598A (en) * | 1989-08-10 | 1991-03-25 | Furukawa Electric Co Ltd:The | Method for growing organic nonlinear optical single crystal |
| CN101921196B (en) * | 2009-06-10 | 2013-05-22 | 宁波大学 | Organic amine phosphate nonlinear optical crystal [C6H9N3O2][HPO4] |
| CN101984152B (en) * | 2010-11-22 | 2012-05-23 | 中国科学院新疆理化技术研究所 | Nonlinear optical crystal of dimalic acid ammonium borate monohydrate compound and growing method and application thereof |
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