CN113293439A - Organic nonlinear optical crystal material DOBT and preparation method thereof - Google Patents
Organic nonlinear optical crystal material DOBT and preparation method thereof Download PDFInfo
- Publication number
- CN113293439A CN113293439A CN202110434584.3A CN202110434584A CN113293439A CN 113293439 A CN113293439 A CN 113293439A CN 202110434584 A CN202110434584 A CN 202110434584A CN 113293439 A CN113293439 A CN 113293439A
- Authority
- CN
- China
- Prior art keywords
- dobt
- crystal
- solution
- methanol
- nonlinear optical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 48
- 239000000463 material Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 230000003287 optical effect Effects 0.000 title abstract description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 45
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 claims abstract description 12
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 230000006911 nucleation Effects 0.000 claims abstract description 4
- 238000010899 nucleation Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 230000002269 spontaneous effect Effects 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 4
- -1 3, 4-dimethoxybenzaldehyde-N-methyl-2-methylbenzothiazole-p-toluenesulfonate Chemical compound 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000002178 crystalline material Substances 0.000 claims 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000008204 material by function Substances 0.000 abstract description 2
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/54—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
- C30B7/14—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions the crystallising materials being formed by chemical reactions in the solution
-
- 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
- G02F1/3551—Crystals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Abstract
The invention belongs to the technical field of functional materials and preparation thereof, and relates to an organic nonlinear optical crystal material DOBT and a preparation method thereof, wherein methanol is used as a solvent to prepare equimolar methyl p-toluenesulfonate and 2-methylbenzothiazole solutions, the two prepared solutions are mixed to react, then equimolar 3, 4-dimethoxybenzaldehyde is added, a catalyst is added to react to obtain a crystal growth raw material, then a spontaneous nucleation method is adopted to carry out DOBT crystal growth, the obtained crystal belongs to a nonlinear optical crystal, and a molecule with a benzothiazole ring is arranged in the structure, so that the non-central symmetry degree of the crystal is further improved, and a larger second-order nonlinear optical coefficient is favorably generated; the second-order nonlinear optical property of the optical material is about 6 times of KDP, and the optical material also has good electro-optical performance. The preparation method of the crystal is simple and convenient, has good nonlinear performance and has a good application prospect.
Description
The technical field is as follows:
the invention belongs to the technical field of functional materials and preparation thereof, and relates to an organic nonlinear crystal material DOBT and a preparation method thereof.
Background art:
in recent years, with the continuous development of THz technology, basic research has been transformed into application research, so that a THz research heat surge is raised internationally. At present, materials for generating and detecting THz waves are mainly inorganic nonlinear and organic nonlinear optical materials, and compared with inorganic materials, organic nonlinear optical materials are high in nonlinear optical coefficient, high in response speed, easy to modify optical damage threshold values, high in molecular variability and wide in application prospect in aspects of laser frequency doubling, integration, communication and the like. DAST crystals are the most representative of organic nonlinear optical materials, and are used as the most effective THz radiation sources, which have important significance for promoting the development of THz technology, but the process for growing high-quality and large-size DAST crystals is not mature; the stability is poor, the deliquescence is easy, and the THz performance is not achieved after the deliquescence; in addition, in the process of converting the optical-THz wave, a strong absorption peak exists at the position of 1.1THz, namely, the continuous tunable THz wave can not be generated near the position of 1 THz. Therefore, based on the DAST molecular structure, researchers at home and abroad begin to explore new crystals with large second-order nonlinearity, high stability, strong growth capability and good phase matching at different pump wavelengths. I.e. new crystals are synthesized by changing the donor, acceptor and anion in the cation in DAST crystals in an attempt to overcome these disadvantages.
The invention content is as follows:
the invention aims to overcome the defects in the prior art, and provides a novel organic nonlinear optical crystal material and a preparation method thereof, wherein the prepared crystal SHG has the signal intensity 6 times that of KDP, and has higher solubility, so that high-quality crystals can be easily grown.
In order to achieve the purpose, the chemical formula of the organic nonlinear optical crystal material DOBT is C25H25NO5S2And the name: 3, 4-dimethoxybenzaldehyde-N-methyl-2-methylbenzothiazole-p-toluenesulfonate salt.
The organic nonlinear optical crystal material DOBT is of a cation-anion structure, has a pi electron conjugated system in a cation chromophore and is beneficial to enhancing the second-order nonlinear optical property.
The preparation process of the organic nonlinear optical crystal material DOBT comprises the following steps:
(1) adding 0.05-0.2 mol of methyl p-toluenesulfonate into 20-80 ml of methanol solution, and uniformly mixing to obtain a mixed solution;
(2) pouring the mixed solution obtained in the step (1) into a three-neck flask with a condensation reflux device, adding magnetons, and stirring;
(3) adding 0.05-0.2 mol of 2-methylbenzothiazole and 40-160 ml of methanol into the three-neck flask obtained in the step (2), setting the temperature to be 50-70 ℃, and reacting for 60-80 h;
(4) dissolving 0.05-0.2 mol of 3, 4-dimethoxybenzaldehyde in 50-200 ml of methanol;
(5) adding the solution obtained in the step (4) into the solution after the reaction in the step (3), adding a catalyst, and continuing the reaction for 48-96 hours to obtain a dark red solution, wherein red precipitate is generated at the bottom of the solution;
(6) recrystallizing the solution obtained in the step (5) for 3 times to obtain a DOBT crystal growth raw material;
(7) and (2) carrying out DOBT crystal growth by adopting a spontaneous nucleation method, taking methanol as a solvent, preparing a DOBT solution with the concentration of 2-4 g/100ml from the DOBT crystal growth raw material, pouring the DOBT solution into a crystal growing bottle, keeping the solution at 50 ℃, stabilizing for 12-24 h, then cooling at the speed of 0.3-1 ℃/day, and obtaining the DOBT crystal after 10-30 days.
The purity of the 2-methylbenzothiazole is more than 98%, the purity of methyl p-toluenesulfonate is more than 98%, the purity of 3, 4-dimethoxybenzaldehyde is more than 95%, and the purity of anhydrous methanol is more than 99.5%.
Compared with the prior art, the preparation method is simple, raw materials are easy to obtain, the prepared molecules with benzothiazole rings in the crystal structure further improve the non-centrosymmetry degree of the crystal, and are favorable for generating larger second-order nonlinear optical coefficients, the second-order nonlinear optical properties of the crystal are about 6 times of KDP, the nonlinear performance is better, and meanwhile, the crystal has good electro-optical performance and higher application prospect.
Description of the drawings:
fig. 1 is an XRD pattern of DOBT powder prepared in accordance with the present invention.
Fig. 2 is a graph comparing the SHG intensity of dott prepared according to the present invention with that of existing KDP.
FIG. 3 is a diagram of a DOBT crystal obtained in the present invention.
Fig. 4 is a structural diagram of a DOBT crystal according to the present invention.
The specific implementation mode is as follows:
the invention is further illustrated by the following examples in conjunction with the accompanying drawings.
Example (b):
the specific process for preparing the DOBT crystal in the embodiment comprises the following steps:
(1) adding 0.1mol of methyl p-toluenesulfonate into 40ml of methanol solution, and uniformly mixing;
(2) pouring the solution obtained in the step (1) into a three-neck flask with a condensation reflux device, adding magnetons and stirring;
(3) adding 0.1mol of 2-methylbenzothiazole and 40ml of methanol into the three-neck flask obtained in the step (2), keeping the rotation speed of magnetons unchanged, and reacting for 72 hours at the temperature of 60 ℃;
(4) 0.1mol of 3, 4-dimethoxybenzaldehyde is dissolved in 100ml of methanol;
(5) adding the solution obtained in the step (4) into the solution after the reaction in the step (3), adding a catalyst, and continuing the reaction for 72 hours to obtain a dark red solution, wherein a red precipitate is generated at the bottom of the solution;
(6) recrystallizing the solution obtained in the step (5) for 3 times to obtain a DOBT crystal growth raw material;
(7) adopting a spontaneous nucleation method to grow DOBT crystals, using methanol as a solvent, preparing a DOBT solution with the concentration of 4g/100ml, pouring the DOBT solution into a crystal growing bottle, keeping the temperature of the solution at 50 ℃, stabilizing the solution for 24 hours, then cooling the solution at the speed of 0.6 ℃/day, and obtaining the DOBT crystals after 20 days, wherein the DOBT crystals are shown in figure 3.
The purity of 2-methylbenzothiazole, methyl p-toluenesulfonate, 3, 4-dimethoxybenzaldehyde and anhydrous methanol involved in this example were > 98%, 95% and 99.5%, respectively.
The catalyst described in this example was piperidine.
The crystal of DOBT prepared in this example has the chemical formula C25H25NO5S2And the name: 3, 4-dimethoxybenzaldehyde-N-methyl-2-methylbenzothiazole-p-toluenesulfonate, which has an XRD pattern and a molecular structure as shown in figure 1 and figure 4, respectively.
In this example, the SHG intensity of the prepared DOBT crystal is compared with that of the existing KDP crystal, and the result is shown in fig. 2, and it can be seen from the figure that the SHG signal intensity of the DOBT crystal is 6 times that of KDP.
Claims (2)
1. An organic nonlinear crystal material DOBT, which is characterized in that the chemical formula is as follows: c22H24N2O4S is 3, 4-dimethoxybenzaldehyde-N-methyl-2-methylbenzothiazole-p-toluenesulfonate, is of an anion-cation structure, and has a pi electron conjugated system in a cation chromophore.
2. A method for preparing organic nonlinear crystalline material DOBT as claimed in claim 1, characterized in that the preparation process comprises the following steps:
(1) adding 0.05-0.2 mol of methyl p-toluenesulfonate into 20-80 ml of methanol solution, and uniformly mixing to obtain a mixed solution;
(2) pouring the mixed solution obtained in the step (1) into a three-neck flask with a condensation reflux device, adding magnetons, and stirring;
(3) adding 0.05-0.2 mol of 2-methylbenzothiazole and 40-160 ml of methanol into the three-neck flask obtained in the step (2), setting the temperature to be 50-70 ℃, and reacting for 60-80 h;
(4) dissolving 0.05-0.2 mol of 3, 4-dimethoxybenzaldehyde in 50-200 ml of methanol;
(5) adding the solution obtained in the step (4) into the solution after the reaction in the step (3), adding a catalyst, and continuing the reaction for 48-96 hours to obtain a dark red solution, wherein red precipitate is generated at the bottom of the solution;
(6) recrystallizing the solution obtained in the step (5) for 3 times to obtain a DOBT crystal growth raw material;
(7) and (2) carrying out DOBT crystal growth by adopting a spontaneous nucleation method, taking methanol as a solvent, preparing a DOBT solution with the concentration of 2-4 g/100ml from the DOBT crystal growth raw material, pouring the DOBT solution into a crystal growing bottle, keeping the solution at 50 ℃, stabilizing for 12-24 h, then cooling at the speed of 0.3-1 ℃/day, and obtaining the DOBT crystal after 10-30 days.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110434584.3A CN113293439A (en) | 2021-04-22 | 2021-04-22 | Organic nonlinear optical crystal material DOBT and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110434584.3A CN113293439A (en) | 2021-04-22 | 2021-04-22 | Organic nonlinear optical crystal material DOBT and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113293439A true CN113293439A (en) | 2021-08-24 |
Family
ID=77321682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110434584.3A Pending CN113293439A (en) | 2021-04-22 | 2021-04-22 | Organic nonlinear optical crystal material DOBT and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113293439A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111960993A (en) * | 2020-08-28 | 2020-11-20 | 青岛大学 | Preparation method of 4- (3, 4-dimethoxystyryl) methylpyridine p-toluenesulfonate |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05113587A (en) * | 1991-02-18 | 1993-05-07 | Matsushita Electric Ind Co Ltd | Nonlinear optical material, its production and optical wavelength converter |
| CN104389023A (en) * | 2014-11-26 | 2015-03-04 | 中国科学院福建物质结构研究所 | Anti-deliquesce terahertz non-linear optical crystal 4-(4-dimethyl amino styryl)methylpyridine 2-amino-5-toluenesulfonate |
| WO2016086425A1 (en) * | 2014-12-05 | 2016-06-09 | 中国科学院福建物质结构研究所 | Nonlinear optical crystal material, method for preparation thereof, and application thereof |
| CN111793828A (en) * | 2020-08-28 | 2020-10-20 | 青岛大学 | Organic benzothiazole crystal material and preparation method thereof |
| CN111960993A (en) * | 2020-08-28 | 2020-11-20 | 青岛大学 | Preparation method of 4- (3, 4-dimethoxystyryl) methylpyridine p-toluenesulfonate |
| CN112279818A (en) * | 2020-11-12 | 2021-01-29 | 青岛大学 | Preparation method of 2- (4-hydroxy) -styryl-5-chlorobenzothiazole p-toluenesulfonate |
| CN112341388A (en) * | 2020-11-12 | 2021-02-09 | 青岛大学 | 3, 4-dimethoxybenzaldehyde-N-methyl 2-methylquinoline-p-toluenesulfonate and preparation method thereof |
-
2021
- 2021-04-22 CN CN202110434584.3A patent/CN113293439A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05113587A (en) * | 1991-02-18 | 1993-05-07 | Matsushita Electric Ind Co Ltd | Nonlinear optical material, its production and optical wavelength converter |
| CN104389023A (en) * | 2014-11-26 | 2015-03-04 | 中国科学院福建物质结构研究所 | Anti-deliquesce terahertz non-linear optical crystal 4-(4-dimethyl amino styryl)methylpyridine 2-amino-5-toluenesulfonate |
| WO2016086425A1 (en) * | 2014-12-05 | 2016-06-09 | 中国科学院福建物质结构研究所 | Nonlinear optical crystal material, method for preparation thereof, and application thereof |
| CN111793828A (en) * | 2020-08-28 | 2020-10-20 | 青岛大学 | Organic benzothiazole crystal material and preparation method thereof |
| CN111960993A (en) * | 2020-08-28 | 2020-11-20 | 青岛大学 | Preparation method of 4- (3, 4-dimethoxystyryl) methylpyridine p-toluenesulfonate |
| CN112279818A (en) * | 2020-11-12 | 2021-01-29 | 青岛大学 | Preparation method of 2- (4-hydroxy) -styryl-5-chlorobenzothiazole p-toluenesulfonate |
| CN112341388A (en) * | 2020-11-12 | 2021-02-09 | 青岛大学 | 3, 4-dimethoxybenzaldehyde-N-methyl 2-methylquinoline-p-toluenesulfonate and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| SEUNG-HEON LEE，ET AL: "Benzothiazolium Single Crystals: A New Class of Nonlinear Optical Crystals with Efficient THz Wave Generation", ADVANCED MATERIALS, vol. 29, no. 30, pages 1 - 7 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111960993A (en) * | 2020-08-28 | 2020-11-20 | 青岛大学 | Preparation method of 4- (3, 4-dimethoxystyryl) methylpyridine p-toluenesulfonate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang et al. | Synthesis, structure and properties of a new nonlinear optical material: zinc cadmium tetrathiocyanate | |
| Aggarwal et al. | Solution growth of a novel nonlinear optical material: L-histidine tetrafluoroborate | |
| Rajkumar et al. | Synthesis, structural, thermal, mechanical, second harmonic generation efficiency and laser damage threshold studies of 4-dimethylaminopyridinium-3, 5-dicarboxybenzoate trihydrate single crystal | |
| CN113293439A (en) | Organic nonlinear optical crystal material DOBT and preparation method thereof | |
| CN101514479A (en) | Large size hydrate potassium borate nonlinear optical crystal, preparation and use thereof | |
| Wenbo et al. | A new organometallic nonlinear optical material—triallylthiourea mercury bromide (ATMB) crystal: growth and structure | |
| CN113955792B (en) | Preparation method of copper-cesium halide crystal | |
| CN111793828A (en) | Organic benzothiazole crystal material and preparation method thereof | |
| CN103467366A (en) | Preparation method of 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate | |
| Raj et al. | Growth and characterization of nonlinear optical active l-alanine formate crystal by modified Sankaranarayanan–Ramasamy (SR) method | |
| Wang et al. | Crystal growth, spectral and thermal properties of nonlinear optical crystal: MnHg (SCN) 4 | |
| CN111960993A (en) | Preparation method of 4- (3, 4-dimethoxystyryl) methylpyridine p-toluenesulfonate | |
| CN101921196B (en) | Organic amine phosphate nonlinear optical crystal [C6H9N3O2][HPO4] | |
| Thangaraj et al. | Ethylenediaminium di (2-nitrophenolate) single crystals as materials for optical second harmonic generation | |
| CN112279818A (en) | Preparation method of 2- (4-hydroxy) -styryl-5-chlorobenzothiazole p-toluenesulfonate | |
| Wang et al. | Growth and properties of UV nonlinear optical crystal ZnCd (SCN) 4 | |
| CN105274621B (en) | A kind of molybdophosphate fluorine potassium compound, its nonlinear optical crystal and its production and use | |
| CN106521632B (en) | Inorganic-organic hybridization supermolecule type nonlinear optical crystal and its preparation method and purposes | |
| Bharthasarathi et al. | Crystal growth, thermal and optical studies on a metalorganic nonlinear optical material dipotassium boro maleate (DKBM) | |
| CN112341388A (en) | 3, 4-dimethoxybenzaldehyde-N-methyl 2-methylquinoline-p-toluenesulfonate and preparation method thereof | |
| CN101818377A (en) | Room-temperature solution growth method of nonlinear optical crystal hydrated rubidium borate | |
| CN115287741A (en) | Perovskite crystal black-phase formamidine lead iodide crystal form and preparation method thereof | |
| CN100562792C (en) | The growing method of a kind of second-order non-linear laser material 4-nitro-N-oxygen-2-pyridine carboxylic acid two generation crystals | |
| CN101469449A (en) | Method for preparing potassium titanium oxide phosphate crystal by liquid phase coprecipitation sythesis of growth material | |
| CN107056678A (en) | A kind of organic nonlinear optical crystal material PBSB and its preparation technology |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |