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Preparation method of 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate

A technology of dimethylaminostyrene and p-toluenesulfonate, which is used in the preparation of 4-(4-dimethylaminostyryl)methylpyridine p-toluenesulfonate, and the preparation of high-quality organic nonlinear optics In the field of crystals, it can solve the problems of complicated synthesis steps, limited crystal growth, and long reaction time, and achieve the effects of simple preparation method, short reaction time, and simple reaction steps.

Inactive Publication Date: 2013-12-25
QINGDAO UNIV
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Problems solved by technology

4-(4-Dimethylaminostyryl)picoline p-toluenesulfonate (DAST) is an organic salt crystal formed by strong Coulomb force, which has a good nonlinear optical effect, and is currently used in DAST The research is mainly focused on the realization of THz radiation through DAST crystals. 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate is currently the nonlinear optical crystal with the highest THz efficiency. 4-(4 -Dimethylaminostyryl) picoline p-toluenesulfonate crystal has an asymmetric central structure, and its cation contains a benzene ring and a pyridine ring. It is a hyperconjugated ion with a large conjugated π bond, belonging to Monoclinic crystal system, the point group is m, the space group is Cc, and its unit cell parameters are: α=90°, β=92.24°, γ=90°, Z=4, although the prior art has successfully synthesized 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate , but its synthesis steps are cumbersome, the yield is low, and the reaction time is long, which greatly limits the later crystal growth

Method used

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  • Preparation method of 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate

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Embodiment

[0018] The specific steps for preparing 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate in this example include three steps: ion exchange reaction, condensation reaction, and filtration purification:

[0019] (1) Ion exchange reaction: at room temperature, mix 0.05mol 4-picoline (purity 98%) and 0.05mol methyl p-toluenesulfonate and place in 50-60ml anhydrous methanol (purity not less than 99.5 %), then mix the two solutions and put them in a 250ml three-hole flask, heat and stir slowly to 50°C, ion exchange reaction for 12-18h, and condense and reflux at the same time, the solution does not change color during the ion exchange reaction, and the reaction Obtain 4-methyl-N-methylpyridine p-toluenesulfonate;

[0020] (2) Condensation reaction: Weigh 0.05mol of p-dimethylaminobenzaldehyde (analytically pure) and dissolve it in 50-60ml of anhydrous methanol (purity not less than 99.5%), heat and stir until it is completely dissolved, Use a glass rod to drain and put it into ...

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Abstract

The invention belongs to the technical field of functional material synthesis, and relates to a preparation method of 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate, which comprises the following steps: mixing 4-methylpyridine and methyl-p-toluene sulfonate, putting in absolute methanol, and pouring into a three-hole flask to carry out ion-exchange reaction; dissolving dimethyl amino benzaldehyde in absolute methanol, and putting into the three-hole flask to carry out condensation reflux reaction to obtain a crystallized product; and flushing the crystallized product with trichloromethane, quickly filtering to obtain a solid with green metal luster, heating the solid with green metal luster to completely dissolve the solid in the absolute methanol, cooling, airing, and recrystallizing to obtain the 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate. The preparation method has the advantages of simpleness, simple reaction steps, short reaction time, low cost and high yield.

Description

Technical field: [0001] The invention belongs to the technical field of preparation of functional materials, and relates to a process for rapidly and efficiently synthesizing 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate, especially a 4-(4-dimethyl The preparation method of amino styryl) picoline p-toluene sulfonate is used to prepare high-quality organic nonlinear optical crystals. Background technique: [0002] Nonlinear optical crystals are widely used in technical and research fields. They can be made into electro-optic switches and realize laser modulation. Optical parameter oscillation can be used to achieve laser frequency tuning; some nonlinear optical effects can also be used. The phase conjugation characteristics of the nonlinear optical crystals are used for light processing; at present, the research on nonlinear optical crystals has developed into a nonlinear optical crystal material science. Actively carrying out research in this field will undoubtedly pla...

Claims

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Application Information

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IPC IPC(8): C07D213/38C07C303/32C07C309/30
Inventor 滕冰曹丽凤钟德高冯珂庄树杰史永鑫
Owner QINGDAO UNIV
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