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D-pi-A structure nonlinear optical chromophore, and its synthesizing method

A technology of nonlinear light and synthesis method, which is applied in the field of nonlinear optical chromophore and its synthesis, which can solve the problems such as the decrease of molecular transparency, and achieve the effects of high yield, high nonlinear optical performance and good transparency

Inactive Publication Date: 2006-10-25
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, blindly increasing the intensity of the donor and acceptor will cause the maximum absorption wavelength to red shift, resulting in a decrease in the transparency of the molecule, which is the so-called "non-linear-light transmission contradiction". This requires finding the optimum intensity of the donor and acceptor Optimum combination to reduce the "non-linear-transparency contradiction"
Therefore, the design and synthesis of nonlinear optical molecules with both high nonlinear optical properties and excellent transparency are still challenging.

Method used

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  • D-pi-A structure nonlinear optical chromophore, and its synthesizing method
  • D-pi-A structure nonlinear optical chromophore, and its synthesizing method
  • D-pi-A structure nonlinear optical chromophore, and its synthesizing method

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Embodiment 1

[0019] R is a chlorine atom, and the synthetic route of the nonlinear optical chromophore 2,5-dimethyl-4-(2'-chloro-4'-nitroazo)phenol is as follows:

[0020]

[0021] The synthesis method is as follows: 1.38g of sodium nitrite is slowly added in batches to 20ml of 98% concentrated sulfuric acid, the temperature is controlled below 20°C, stirred to dissolve completely, and then cooled to 0°C to obtain nitrosyl sulfuric acid. Then add 10ml of concentrated sulfuric acid to 3.45g (20mmol) of 2-chloro-4-nitroaniline, stir to form a paste, slowly add 20mmol of nitrosylsulfuric acid to the inside, and react at 0°C for 1 hour, then add 2.44g (20mmol) a mixed solution of 2,5-dimethylphenol and 10ml of methanol and water (the volume ratio of methanol to water is 2 / 1), react at 0°C for 1 hour, adjust the pH value to 7-8 with ammonia water and continue the reaction 2 hours. After standing overnight, filter with suction and wash with water to obtain the initial product. Then recrysta...

Embodiment 2

[0027] R is a chlorine atom, and the synthetic method of chromophore 2,5-dimethyl-4-(2'-chloro-4'-nitroazo)phenol: 1.38g sodium nitrite is slowly added to 20ml98 in batches % concentrated sulfuric acid, the temperature is controlled below 20°C, stirred to dissolve it completely, and then cooled to 0°C to obtain nitrosyl sulfuric acid. Then add 2ml of glacial acetic acid to 3.45g (20mmol) of 2-chloro-4-nitroaniline, stir to form a paste, slowly add 20mmol of nitrosylsulfuric acid inwardly, and react at 0°C for 1 hour, then add 3.66 g (30mmol) 2,5-xylenol and 100ml of methanol and water (the volume ratio of methanol to water is 2 / 1) mixed solution, reacted at 0°C for 1 hour, and adjusted the pH value to 7 with sodium carbonate solution -8 Continue to react for 2 hours. After standing overnight, filter with suction and wash with water to obtain the initial product. The mixed solvent of water and acetone is recrystallized twice to obtain the desired nonlinear optical chromophore...

Embodiment 3

[0029] R is a bromine atom, and the synthetic route of the nonlinear optical chromophore 2,5-dimethyl-4-(2'-bromo-4'-nitroazo)phenol is as follows:

[0030]

[0031] The synthesis method is as follows: 0.14g of sodium nitrite is slowly added in batches to 2ml of 98% concentrated sulfuric acid, the temperature is controlled below 20°C, stirred to dissolve completely, and then cooled to 0°C to obtain nitrosyl sulfuric acid. Add 10ml of concentrated hydrochloric acid to 0.44g (2mmol) of 2-bromo-4-nitroaniline, stir to form a paste, slowly add 2mmol of nitrosylsulfuric acid to the inside, react at 0°C for 1 hour, then add 0.24g ( 2mmol) a mixed solution of 2,5-dimethylphenol and 6ml of methanol and water (the volume ratio of methanol to water is 2 / 1), react at 0°C for 1 hour, and adjust the pH value to 7-8 with sodium hydroxide solution The reaction was continued for 2 hours. After standing overnight, filter with suction and wash with water to obtain the initial product. The ...

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Abstract

This invention discloses D- pi-A structure nonlinear optics chromophore and ts synthesizing method. Its structure general formula is shown as (1), and R is fluorin, chlorine or bromine and other halogen atoms. Nitroaniline compound contains halogen atoms is react with nitrolys-sulfuric acid to generate diazo salt, then it is coupled reacted with 2, 5-dimethyl phenol to generate the species chromophore compound. Its synthesis technique is simple, yield is high, the material is easy to get, and reaction condition is wild. This kind of compound has higher second order nonlinear optics capability and excellent light permeability at visible light wave band, it can be used to blue green wave band laser double frequency field.

Description

technical field [0001] The invention relates to a kind of D-π-A structure nonlinear optical chromophore and its synthesis method. Background technique [0002] With the development of the times, people have higher and higher requirements for information transmission, storage, exchange and processing. Due to its inherent defects, traditional electronic information transmission methods restrict the wide application of electronic information systems in the future society in terms of speed, capacity, space compatibility and information detection accuracy. In order to overcome the bottleneck effect of electronics, the use of photons instead of electrons for data collection, storage and processing has become an inevitable development trend of information science engineering in the future. For the development of photonic technology, nonlinear optics is an indispensable key subject. For more than 40 years, nonlinear optics has gradually developed into an independent branch of disc...

Claims

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Application Information

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IPC IPC(8): C07C245/08
Inventor 钱国栋崔元靖陈鹭剑高俊阔王智宇邱建荣樊先平洪樟连王民权
Owner ZHEJIANG UNIV
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