Method for preparing trapezoidal broadband absorption carbene squaraine dye with one-step method

A polyalkyne squaraine and broadband technology is applied in the field of one-step preparation of trapezoidal broadband absorption polyalkyne squaraine dyes, which can solve the problems of not being able to achieve broadband absorption at the same time, complex synthesis steps, and single absorption band, etc. It is beneficial to large-scale industrial production, the reaction is simple and feasible, and the preparation process is simple.

Inactive Publication Date: 2012-08-01
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] 1. The absorption band is single, and it only has absorption in the ultraviolet-visible band or near-infrared band, and cannot achieve broad-band absorption at the same time;
[0015] 2. The synthesis process is complicated, the separation and purification are cumbersome, and it is difficult to carry out industrial production
At present, the synthesis steps of most broadband absorbing materials are relatively complicated, and the separation and purification are separated by means of column chromatography, which is very difficult to separate and purify.
Difficult to mass produce

Method used

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  • Method for preparing trapezoidal broadband absorption carbene squaraine dye with one-step method
  • Method for preparing trapezoidal broadband absorption carbene squaraine dye with one-step method
  • Method for preparing trapezoidal broadband absorption carbene squaraine dye with one-step method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Weigh 861mg (1mmol reactive group) P2 (see the reaction formula for specific structure) and 45.6mg squaraine (0.4mmol) respectively, put them in a 50mL round bottom flask, add 7.5mL n-butanol and 7.5mL toluene, and mix thoroughly Reflux reaction (ultraviolet-visible absorption spectrum tracking reaction process, such as image 3 As shown), the color of the solution gradually turns red, and finally begins to turn slightly green again; the absorption spectrum has strong absorption in the visible-near infrared region, and the reaction is terminated after 48 hours of reaction. After cooling to room temperature, suction filtration under reduced pressure yields crude product. The crude product was repeatedly washed with deionized water to remove squaraine, and a gray-green polymer product was obtained.

[0041] The reaction formula is as follows:

[0042]

[0043] where X=1, Y=5.

Embodiment 2

[0045]Weigh 811mg (1mmol reactive group) P2 (see the reaction formula for the specific structure) and 45.6mg squaraine (0.4mmol) respectively, place them in a 50mL round bottom flask, add 7.5mL n-butanol and 7.5mL toluene, and mix thoroughly Reflux reaction (ultraviolet-visible absorption spectrum tracking reaction process), the color of the solution gradually turns red, and finally begins to turn greenish; the absorption spectrum has strong absorption in the visible-near infrared region, the reaction is terminated after 48 hours, and the room temperature is cooled Afterwards, suction filtration under reduced pressure to obtain a crude product. The crude product was repeatedly washed with deionized water to remove squaraine, and a brown-red polymer product was obtained.

[0046] Reaction formula:

[0047]

[0048] where X=1, Y=5.

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Abstract

The invention relates to a method for preparing a trapezoidal broadband absorption carbene squaraine dye with a one-step method. The method comprises the following steps of: fully mixing functional carbine, a squaric acid, a ligand and a solvent at the room temperature; undergoing a reflowing reaction at the temperature of 60-130 DEG C for 10-120 hours; and after the reaction, purifying to obtain the carbene squaraine dye, wherein the mass ratio of the functional carbine to the squaric acid is (20-10):(4-1). The preparation method provided by the invention is easy and practicable, has a good economic benefit, and is suitable for industrial production; and the carbene squaraine dye prepared with the method can be widely applied in the fields of nonlinear optics, photodynamics therapy, optical database storage, laser printing, biological probes, near infrared mapping, solar cells, and the like.

Description

technical field [0001] The invention belongs to the field of preparation of ultraviolet-visible-near-infrared wide-band squaraine absorbing materials, in particular to a method for preparing trapezoidal wide-band absorbing polyacetylene squaraine dyes in one step. Background technique [0002] Ultraviolet-visible light refers to electromagnetic waves with a wavelength between 200-700nm, and the near-infrared light region refers to electromagnetic waves between 700-1500nm. Molecules with ultraviolet-visible-near-infrared three-band absorption function can be widely used in military, infrared camouflage, material analysis, medical detection, photosensitive, Photopolymerization, nonlinear optical materials, solar cells and other fields. [0003] Since Cohen S et al first reported the synthesis of squaraine in J.A.C.S of the American Chemical Society in 1959, a large number of non-squaraine dyes have been synthesized from it. Since then, the development of squaraine dyes has b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B69/10C09B57/00
Inventor 徐洪耀冯益虎李林峰光善仪
Owner DONGHUA UNIV
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