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POSS (Polyhedral Oligomeric Silsesquioxane) hybridized squarine near-infrared absorption dye and preparation method thereof

A technology for absorbing dyes and squaraine is applied in the field of POSS hybrid squaraine near-infrared absorbing dyes and their preparation, and achieves the effects of good economic benefit, improved service life and improved interface performance.

Inactive Publication Date: 2010-11-10
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, functional and highly stable organic-inorganic hybrid squarylium composite materials have not been reported

Method used

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  • POSS (Polyhedral Oligomeric Silsesquioxane) hybridized squarine near-infrared absorption dye and preparation method thereof
  • POSS (Polyhedral Oligomeric Silsesquioxane) hybridized squarine near-infrared absorption dye and preparation method thereof
  • POSS (Polyhedral Oligomeric Silsesquioxane) hybridized squarine near-infrared absorption dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of linear POSS hybrid squaraine near-infrared absorbing material, its structural formula is:

[0038]

[0039] among them: for: for: R 1 , R 2 It is halogenated phenyl, halogenated pyrrolyl, halogenated quinolinyl or halogenated indolyl and the like.

[0040] Weigh 0.1mmol of bromosquaraine, 0.1mmol of functional POSS with active group, 0.001mmol (0.27mg) of palladium acetate, 0.0012mmol (0.13mg) of N,N-dimethyl-β-amino acid or triphenyl Phosphorus 0.0012mmol (0.52mg), anhydrous potassium carbonate 0.0015mmol (0.21mg) or anhydrous triethylamine 0.0014mmol (0.27mL) or potassium phosphate 0.0015mmol (0.32mg), placed in a dry with stirring and reflux device In the flask, evacuate and fill with nitrogen for three times under the double-row tube system, then inject 5 mL of N,N-dimethylpyrrolidone or N,N-dimethylacetamide, and heat and reflux at 130~140℃ for 10~21h , Add 50-100mL deionized water to make the precipitation complete, filter to obtain the crude product...

Embodiment 2

[0042] Preparation of dumbbell-shaped POSS hybrid squaraine near-infrared absorbing material, its structural formula is:

[0043]

[0044] among them: for: for: R 1 , R 2 It is halogenated phenyl, halogenated pyrrolyl, halogenated quinolinyl or halogenated indolyl and the like.

[0045] Weigh 0.1mmol of bromosquaraine cyanine, 0.2mmol of functional POSS with active groups, 0.002mmol (0.54mg) of palladium acetate, 0.0024mmol (0.25mg) of N,N-dimethyl-β-amino acid or triphenyl Phosphorus 0.0024mmol (1.04mg), anhydrous potassium carbonate 0.003mmol (0.42mg) or anhydrous triethylamine 0.0028mmol (0.54mL) or potassium phosphate 0.003mmol (0.64mg), placed in a dry with stirring and reflux device In the flask, evacuate and fill with nitrogen for three times under the double-row tube system, then inject 10 mL of N,N-dimethylpyrrolidone or N,N-dimethylacetamide, and heat to reflux at 130~140℃ for 10~21h , Add 50-100mL deionized water to complete the precipitation, filter to obtain the cr...

Embodiment 3

[0047] Preparation of network type POSS hybrid squaraine cyanine near-infrared absorbing material, its structural formula is:

[0048]

[0049] among them: for: for: R 1 , R 2 It is halogenated phenyl, halogenated pyrrolyl, halogenated quinolinyl or halogenated indolyl and the like.

[0050] Weigh 0.2mmol bromosquaraine cyanine, 0.1mmol functional POSS with active groups, palladium acetate 0.001mmol (0.27mg), N,N-dimethyl-β-amino acid 0.0012mmol (0.13mg) or triphenyl Phosphorus 0.0012mmol (0.52mg), anhydrous potassium carbonate 0.003mmol (0.42mg) or anhydrous triethylamine 0.0028mmol (0.54mL) or potassium phosphate 0.003mmol (0.64mg), placed in a dry with stirring and reflux device In the flask, evacuated and filled with nitrogen three times under the double-row tube system, then inject 7.5 mL of N,N-dimethylpyrrolidone or N,N-dimethylacetamide, and heat to reflux at 130~140℃ for 10~ 21h, add 50-100mL deionized water to make the precipitation complete, filter to obtain the crud...

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Abstract

The invention relates to a POSS (Polyhedral Oligomeric Silsesquioxane) hybridized squarine near-infrared absorption dye, which at least comprises a POSS monomer of an active group and a halogenated squarine monomer. A preparation method of the dye comprises the following steps: in the nitrogen gas atmosphere, adding the POSS monomer and the halogenated squarine monomer in a mixed system of a catalyst, an acid-binding agent, a ligand and organic solvent; and carrying out an addition or polymerization reaction at the temperature of 130-140DEG C for 10-25h to obtain the POSS hybridized squarine near-infrared absorption dye. The POSS hybridized squarine near-infrared absorption dye has the advantages of stronger near-infrared absorbing performance, favorable heat, light and chemical stability and favorable aggregation resistance and material compatibility. The preparation method is simple and feasible, has favorable economic benefit, is applicable for industrial production and can be widely applied to the fields of nonlinear optics, photodynamic therapy, optical data storage, laser printing, biological probe, near-infrared photographing, solar cells and the like.

Description

Technical field [0001] The invention belongs to the field of near-infrared absorbing squaraine dye and its preparation, and particularly relates to a POSS hybrid squaraine near-infrared absorbing dye and a preparation method thereof. Background technique [0002] Near-infrared light refers to electromagnetic waves with wavelengths between 700 and 2500 nm, that is, the intermediate band of ultraviolet-visible and mid-infrared analysis. Since there are few materials that absorb near-infrared light, near-infrared light suffers little interference in the propagation process and has good transparency to materials. It is a new optical field with unique functions. Near-infrared technology plays an important role in the study of the interaction between near-infrared light and matter, and plays an important role in military reconnaissance, infrared camouflage, material analysis, medical detection, photosensitive, photopolymerization, nonlinear optical materials, solar cells and other fiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B69/10C09B57/00
Inventor 徐洪耀严正权光善仪
Owner DONGHUA UNIV
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