Solid naphthalocyanine device with optical limiting properties

A naphthalocyanine, optical limiting technology, applied in the fields of instruments, optics, nonlinear optics, etc., can solve the problems of fragile anti-laser ability, etc., and achieve good anti-laser ability, good anti-laser ability, and excellent optical limiting. performance effect

Active Publication Date: 2009-10-21
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention overcomes the defects of brittleness and poor laser resistance of the solid phthalocyanine device prepared in the prior art, adopts the combination of organosilicon modification method and doping inorganic salt, and at the same time incorporates a conjugated system with larger π electrons Naphthalocyanine, which forms a continuous random chemically bonded network system of organic and inorganic components, rather than physical mixing, not only has good anti-laser ability, but also has excellent optical limiting performance

Method used

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  • Solid naphthalocyanine device with optical limiting properties
  • Solid naphthalocyanine device with optical limiting properties
  • Solid naphthalocyanine device with optical limiting properties

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 4.74g (10mmol) of 6,7-di-tert-butylphenoxy-2,3-naphthalenedicarbonitrile and 10ml of analytically pure amyl alcohol were added to a 50ml there-necked flask, heated to 60°C in an oil bath, and 1ml of 1 , 8-diazacyclo[5,4,0]undecene-7 (DBU) was used as a catalyst, and the temperature was slowly raised to 110 °C for 2 hours, and then 0.45 g of anhydrous GaCl was added. 3 And the temperature was raised to 140 ℃, after heating and refluxing for 36 hours, the heating was stopped. When the solution was cooled to room temperature, 50 ml of a mixed solution of methanol and water with a volume ratio of 1:1 was added. The product was passed through a silica gel column with a mixed solvent of dichloromethane and tetrahydrofuran (THF) in a volume ratio of 20:1 as a developing solvent to obtain a gallium naphthalocyanine compound with a yield of 62%. Ultraviolet-visible (THF) λmax: 799, 340 nm; mass spectrum (MALDI-TOF): 2001.1 (M + ), 1966.2 (M + -Cl), 1817.1 (M + -Cl-OR), 1669.0...

Embodiment 2

[0028] 4.74g (10mmol) of 6,7-di-tert-butylphenoxy-2,3-naphthalenedicarbonitrile and 10ml of analytically pure amyl alcohol were added to the there-necked flask of 50ml, and after the oil bath was heated to 60°C, 1ml of DBU was added. As a catalyst, the temperature was slowly raised to 110 °C and heated for 2 hours, and then 0.55 g of anhydrous InCl was added. 3 And the temperature was raised to 140 ℃, after heating and refluxing for 36 hours, the heating was stopped. When the solution was cooled to room temperature, 50 ml of a mixed solution of methanol and water with a volume ratio of 1:1 was added, and a yellow-green group was obtained by filtering and washing. The product was passed through a silica gel column with a mixed solvent of dichloromethane and tetrahydrofuran having a volume ratio of 20:1 as a developing solvent to obtain an indium naphthalocyanine compound with a yield of 58%. Ultraviolet-visible (THF) λmax: 802, 339 nm; mass spectrum (MALDI-TOF): 2046.2 (M + ),...

Embodiment 3

[0030] 4.74g (10mmol) of 6,7-di-tert-butylphenoxy-2,3-naphthalenedicarbonitrile, 0.46g anhydrous SnCl 2 , 10ml of 1-chloronaphthalene was added to the three-necked flask of 50ml, after the oil bath was heated to 190 ℃, the reaction was stopped after 4 hours, when the solution was cooled to room temperature, 50ml of n-hexane was added, and the yellow-green was obtained after filtration and washing. Group product, using a mixed solvent of dichloromethane and tetrahydrofuran with a volume ratio of 20:1 as a developing agent to pass through a silica gel column to obtain a tin naphthalocyanine compound with a yield of 55%. Ultraviolet-visible (THF) λmax: 821, 346 nm; mass spectrum (MALDI-TOF): 2085.6 (M +), 2014.5 (M + -2Cl), 1485.8 (M + -40R); 1 H-NMR (CDCl 3 , 400Hz): 9.54(s, 8H), 8.55(s, 8H), 7.50-7.55(d, 16H), 7.27-7.33(d, 16H), 1.44(s, 72H); elemental analysis (%): measured Found C 73.64, H 5.75, N 5.37; found C 73.44, H 5.04, N 5.83.

[0031] 2. Preparation of Solid Sta...

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Abstract

The invention relates to a solid naphthalocyanine device with excellent optical limiting properties. The device is made by the following steps: adding tetraethoxysilane, diglycidyl ether propyltrimethoxy siloxane, analytically pure ethanol and acidic aqueous solution to a reactor; stirring in an enclosed reactor for 2-3h, then opening the reactor and continuing stirring for 1-2h; adding a naphthalocyanine solution and stirring to cause the mixture to become viscous; transferring the viscous mixture to a mould, and taking out after drying to obtain the novel solid naphthalocyanine device with optical limiting properties. The device is made by an organosilicon modification method combined with doped inorganic salt, and by doping naphthalocyanine with a larger pi electron conjugated system to form a continuous random network system with bonded chemical bonds of organic components and inorganic components instead of physical hybrid. The device has good laser resistance and excellent optical limiting properties.

Description

technical field [0001] The invention belongs to the technical field of preparing solid devices by a sol-gel method, in particular to a naphthalocyanine with a larger π-electron conjugated system prepared by combining an organic silicon modification method and doping inorganic salts. Solid Naphthalocyanine Devices with Optical Limiting Properties. technical background [0002] As an important means of modern high-tech warfare, laser technology has been widely used in the military field. Among all kinds of laser weapons, laser jamming and blinding weapons have been researched and applied all over the world in the 1980s. The target of such weapons is the human eye and some important electronic communication equipment and devices. With the development of such weapons, the research on corresponding laser protective materials and devices has attracted great attention. Among them, optical limiting material is one of the important materials for laser protection, and its research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G02F1/361
Inventor 杨国强陈军王双青李沙瑜
Owner INST OF CHEM CHINESE ACAD OF SCI
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