CN101880477A - POSS (Polyhedral Oligomeric Silsesquioxane) hybridized squarine near-infrared absorption dye and preparation method thereof - Google Patents

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

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CN101880477A
CN101880477A CN2010102037534A CN201010203753A CN101880477A CN 101880477 A CN101880477 A CN 101880477A CN 2010102037534 A CN2010102037534 A CN 2010102037534A CN 201010203753 A CN201010203753 A CN 201010203753A CN 101880477 A CN101880477 A CN 101880477A
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infrared absorption
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徐洪耀
严正权
光善仪
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Donghua University
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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

A kind of POSS hydridization side acid squarine near-infrared absorption dye and preparation method thereof
Technical field
The invention belongs near infrared absorption indolenium squaraine cyanine dye and preparation field thereof, particularly relate to a kind of POSS hydridization side acid squarine near-infrared absorption dye and preparation method thereof.
Background technology
Near infrared light is meant the hertzian wave of wavelength between 700～2500nm, i.e. the middle wave band of ultraviolet-visible and middle infrared analysis.Because it is few to absorb the material of near infrared light,, be emerging, as to have a unique function optical field so the interference that near infrared light is subjected in communication process is very little, transparent good to material.Near infrared technology is being brought into play important effect in research near infrared light and matter interaction relation in a plurality of fields such as military reconnaissance, infrared camouflage, species analysis, medical detection, sensitization, photopolymerization, nonlinear optical material, solar cells.
Indolenium squaraine cyanine dye has good photoelectric property with the zwitter-ion structure of its unique D-π-A-π-D type conjugated system, as strong absorbancy (ε 〉=10 5L mol -1Cm -1), absorption or emission wavelength ranges wide (from the visible light to the near infrared region), quantum yield occurred frequently and molecular structure be easy to design, modify, the simple grade of synthetic method causes the scholar's of lot of domestic and foreign section concern and attention.
Up to the present, design, synthesize all kinds of indolenium squaraine cyanine dye, disclose a kind of quinazolinone heterocyclic cyanine dyes that contains as CN 1511883A, absorbing wavelength is in 700～1100nm scope, and structural formula is as follows: CN 101346438A discloses the both sexes indolenium squaraine cyanine dye of substituted aniline, relates to photodynamic therapy, the near infrared fluorescent probe in biology, biological chemistry and the industrial application, and structure is as follows:
Figure BSA00000162377400012
CN 101395228A discloses en acid cyanines, the indolenium squaraine cyanine dye that replaces quinaldine red, as the sensitizing agent in photodynamic therapy and the industrial application.Its structural formula is:
Figure BSA00000162377400013
Deng; CN 101544844A discloses water-soluble near infrared luminescent quinoline squaraine dye, is applied to fields such as novel drugs exploitation, fluorescent mark and biological immune analysis, and its general molecular formula is:
Figure BSA00000162377400021
But the same with general organic dye, indolenium squaraine cyanine dye also exists poor heat stability, and high temperature easily decomposes, carbonization; Photoxidation, rotten easily takes place down in light action; Be subject to chemical reagent, especially strong nucleophilic reagent attack destroys its conjugated system, and optical property reduces greatly; Even more serious is because the sour cyanines in side have the inflexible zwitter-ion, in strong solution, two-phase system and solid-state in very easily assemble, form J-type aggregate or H-type aggregate, thus absorbing wavelength blue shift or red shift, wavelength region significantly broadens simultaneously.All these will limit the further application of indolenium squaraine cyanine dye, for this reason, also report the improvement to its stability in the document.As: K.A.Bello and M.Q.Tian etc. are respectively with hydroxyl (OH) or amino (NH 2) ortho position of the sour tetra-atomic ring in the side of being incorporated into, forming hydrogen bond with Sauerstoffatom, the protection tetra-atomic ring is subjected to the attack of nucleophilic reagent, has improved the chemical stability of square sour cyanines, but because rigidity strengthens, aggregation tendency increases; People such as S.Das propose to utilize hydrophilic, the hydrophobic effect of cyclodextrin or crown ether inner chamber, the cyanine dyes molecule packed in the supramolecule cage, and then the sour cyanines in protection side, reduce intermolecular buildup effect, but this method inevitably has reversibility; S.Anderson and E.Arunkumar etc. go out to take turns the indolenium squaraine cyanine dye of alkyl structure, and structure is:
Figure BSA00000162377400022
Because the design of dumbbell shape side acid phthalocyanine molecule, overcome the reversibility in molecule turnover hole effectively, improved cyanine dyes chemical stability, reduced the buildup effect of solid-state or solution state.But the sour cyanines matrix material in side of the hybrid inorganic-organic type of functional, high stable does not appear in the newspapers.
Summary of the invention
Technical problem to be solved by this invention provides a kind of POSS hydridization side acid squarine near-infrared absorption dye and preparation method thereof, this material has stronger near infrared absorption performance, good heat, light and chemical stability, and anti-the gathering, material compatibility is good, this preparation method is simple, and is good in economic efficiency, is applicable to suitability for industrialized production.
A kind of POSS of the present invention hydridization side acid squarine near-infrared absorption dye, it is characterized in that: this dye structure is made of the oligomeric silsesquioxane POSS monomer that comprises a kind of active group at least and a kind of halo side's acid cyanines monomer with near infrared absorption function, wherein, the mol ratio of oligomeric silsesquioxane monomer and halo side acid cyanines monomer component is 2～1: 1～4.
The described oligomeric silsesquioxane POSS monomer structure general formula that comprises a kind of active group at least is (RSiO 1.5) n, wherein n is 8,10,12,14 or 16, and R is same to each other or different to each other, and R is hydrogen atom, halogen atom, hydroxyl, C 1-20Alkyl, alkenyl, alkynyl, aryl, alicyclic radical, alkoxyl group, vinyl, allyl group, styryl, alkynyl or-OSiR 1R 2R 3Deng, R 1, R 2, R 3Independent respectively is hydrogen atom, halogen atom, hydroxyl, C 1-20Alkyl, alkenyl, alkynyl, aryl, alicyclic radical or alkoxyl group etc.; Wherein, active group is vinyl, allyl group, styryl or alkynyl etc.
Described oligomeric silsesquioxane POSS monomer structure formula is:
Figure BSA00000162377400031
Described halo side acid cyanines monomer is,
Figure BSA00000162377400032
Wherein, R 1, R 2Be halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc., R 1, R 2Be same to each other or different to each other.
A kind of POSS of the present invention hydridization side acid cyanines near infrared absorption preparation methods comprises:
In nitrogen atmosphere, with above-mentioned POSS monomer and halo side's acid cyanines monomer, join in the mixed system of catalyzer, acid binding agent, part and organic solvent at 2～1: 1～4 in molar ratio, behind 130 ℃～140 ℃ additions or polyreaction 10～25h, through precipitation, filtration, dialysis, get POSS hydridization side acid cyanines near infrared absorption material again.
Described catalyzer is Pd (Ac) 2, consumption is 0.5～1mol% of POSS monomer consumption.
Described acid binding agent is triethylamine, Anhydrous potassium carbonate or potassiumphosphate, and consumption is 1.4～3.2mol% of POSS monomer consumption.
Described part is N, and N-dimethylamino acetate or triphenyl phosphorus, consumption are 1～1.2mol% of POSS monomer consumption.
Described organic solvent is selected from N-Methyl pyrrolidone, N, dinethylformamide, N, one or more in the N-diethylformamide, with the monomeric amount ratio of POSS be 25～100mL: 1mmol.
The structure type of described POSS hydridization side acid cyanines near infrared absorption material is dumbbell shape, line style, network-type or cross-linking type.
Cage modle multiaspect oligomeric silsesquioxane (Polyhedral oligomeric silsesquioxane, abbreviation POSS) unique nano effect of molecule, high heat stable property, good resistive properties and light stability, eight (or ten of its cagelike structure, or 12) different organo-functional groups can be modified in individual summit, thereby POSS is mixed on molecular level with organism, organic materials had good consistency, even can directly enter main chain and cross-linked network, prepare commixed type, copolymerization or crosslinked hybridized polymer or polymer composites.
Beneficial effect
(1) the POSS hydridization side of the present invention preparation acid cyanines near infrared absorption material is that POSS mixes with the sour phthalocyanine molecule in side on molecular level, material compatible good, and spectral absorption intensity is (ε 〉=5.4 * 10 greatly 5L mol -1Cm -1), absorbing wavelength is the near infrared hydridization dyestuff of excellent property in 650～1200nm scope;
Advantages such as (2) this POSS hydridization side acid cyanines near infrared absorption material has good heat, light and chemical stability, and anti-the gathering, and material compatibility is good; Improve and interelectrode interface performance the work-ing life of having improved material and device;
(3) this preparation method is simple, and is good in economic efficiency, is applicable to suitability for industrialized production.
Description of drawings
Fig. 1 is the IR collection of illustrative plates of the prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material of embodiment 1;
Fig. 2 is the prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material of embodiment 1 1H NMR spectrogram;
Fig. 3 is the prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material of embodiment 1 29Si NMR spectrogram;
Fig. 4 is the prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material of embodiment 1 and the TG of precursor side's acid cyanines and POSS contrasts collection of illustrative plates, and wherein, 1 is hybrid material, the sour cyanines in 2 sides of being, and 3 is POSS;
Fig. 5 is that embodiment 1 prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material and precursor side's acid cyanines absorption spectrum in DMSO solution contrasts collection of illustrative plates, and wherein, 1 is hybrid material, the sour cyanines in 2 sides of being;
Fig. 6 is that embodiment 1 prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material and precursor side's acid cyanines contrast collection of illustrative plates at the two-phase system absorption spectrum, and wherein, 1 is hybrid material, the sour cyanines in 2 sides of being;
Fig. 7 is the prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material of embodiment 1 and the absorption spectrum of the solid film of precursor side's acid cyanines contrasts collection of illustrative plates, and wherein, 1 is hybrid material, the sour cyanines in 2 sides of being;
Fig. 8 is the prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material of embodiment 1 and the chemical stability of precursor side's acid cyanines contrasts collection of illustrative plates, wherein, the sour cyanines in 1 side of being, 2 is hybrid material;
Fig. 9 is the prepared line style eight vinyl POSS hydridization sides acid cyanines near infrared absorption material of embodiment 1 and the light stability of precursor side's acid cyanines contrasts collection of illustrative plates, wherein, the sour cyanines in 1 side of being, 2 is hybrid material.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
The preparation of line style POSS hydridization side acid cyanines near infrared absorption material, its structural formula is:
Figure BSA00000162377400051
Wherein:
Figure BSA00000162377400052
For:
Figure BSA00000162377400053
For:
Figure BSA00000162377400054
R 1, R 2Be halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
Take by weighing bromo side's acid cyanines 0.1mmol, the function POSS 0.1mmol of band active group, palladium 0.001mmol (0.27mg), N, N-dimethyl-beta-amino acids 0.0012mmol (0.13mg) or triphenyl phosphorus 0.0012mmol (0.52mg), Anhydrous potassium carbonate 0.0015mmol (0.21mg) or anhydrous triethylamine 0.0014mmol (0.27mL) or potassiumphosphate 0.0015mmol (0.32mg), place the dry flask that has stirring and reflux, under the biexhaust pipe system, vacuumize, behind the inflated with nitrogen three times, inject 5mL N, N-dimethyl pyrrolidone or N, the N-N,N-DIMETHYLACETAMIDE, reflux 10～21h under 130～140 ℃ of conditions adds 50～100mL deionized water, makes precipitation fully, filter, get thick product, thick product dialysis 24～48h in DMSO gets straight product.
Embodiment 2
The preparation of dumbbell shape POSS hydridization side acid cyanines near infrared absorption material, its structural formula is:
Figure BSA00000162377400055
Wherein:
Figure BSA00000162377400056
For:
Figure BSA00000162377400057
For: R 1, R 2Be halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
Take by weighing bromo side's acid cyanines 0.1mmol, the function POSS 0.2mmol of band active group, palladium 0.002mmol (0.54mg), N, N-dimethyl-beta-amino acids 0.0024mmol (0.25mg) or triphenyl phosphorus 0.0024mmol (1.04mg), Anhydrous potassium carbonate 0.003mmol (0.42mg) or anhydrous triethylamine 0.0028mmol (0.54mL) or potassiumphosphate 0.003mmol (0.64mg), place the dry flask that has stirring and reflux, under the biexhaust pipe system, vacuumize, behind the inflated with nitrogen three times, inject 10mL N, N-dimethyl pyrrolidone or N, the N-N,N-DIMETHYLACETAMIDE, reflux 10～21h under 130～140 ℃ of conditions adds 50～100mL deionized water, makes precipitation fully, filter, get thick product, the thick thick product of product dialysis 24～48h in DMSO gets straight product.
Embodiment 3
The preparation of network-type POSS hydridization side acid cyanines near infrared absorption material, its structural formula is:
Figure BSA00000162377400061
Wherein:
Figure BSA00000162377400062
For:
Figure BSA00000162377400063
For:
Figure BSA00000162377400064
R 1, R 2Be halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
Take by weighing bromo side's acid cyanines 0.2mmol, the function POSS 0.1mmol of band active group, palladium 0.001mmol (0.27mg), N, N-dimethyl-beta-amino acids 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 potassiumphosphate 0.003mmol (0.64mg), place the dry flask that has stirring and reflux, under the biexhaust pipe system, vacuumize, behind the inflated with nitrogen three times, inject 7.5mL N, N-dimethyl pyrrolidone or N, the N-N,N-DIMETHYLACETAMIDE, reflux 10～21h under 130～140 ℃ of conditions adds 50～100mL deionized water, makes precipitation fully, filter, get thick product, thick product dialysis 24～48h in DMSO gets straight product.
Embodiment 4
The preparation of cross-linking type POSS hydridization side acid cyanines near infrared absorption material, its structural formula is:
Wherein:
Figure BSA00000162377400072
For: For:
Figure BSA00000162377400074
R 1, R 2Be halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
Take by weighing bromo side's acid cyanines 0.4mmol, the function POSS 0.1mmol of band active group, palladium 0.001mmol (0.27mg), N, N-dimethyl-beta-amino acids 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 potassiumphosphate 0.003mmol (0.64mg), place the dry flask that has stirring and reflux, under the biexhaust pipe system, vacuumize, behind the inflated with nitrogen three times, inject 10mL N, N-dimethyl pyrrolidone or N, the N-N,N-DIMETHYLACETAMIDE, reflux 10～21h under 130～140 ℃ of conditions adds 50～100mL deionized water, makes precipitation fully, filter, get thick product, thick product dialysis 24～48h in DMSO gets straight product.

Claims (10)

1. POSS hydridization side acid squarine near-infrared absorption dye, it is characterized in that: this dye structure is made of the oligomeric silsesquioxane POSS monomer that comprises a kind of active group at least and halo side's acid cyanines monomer, wherein, the mol ratio of oligomeric silsesquioxane monomer and halo side acid cyanines monomer component is 2～1: 1～4.
2. a kind of POSS according to claim 1 hydridization side acid squarine near-infrared absorption dye, it is characterized in that: the described oligomeric silsesquioxane POSS monomer structure general formula that comprises a kind of active group at least is (RSiO 1.5) n, wherein n is 8,10,12,14 or 16, and R is same to each other or different to each other, and R is hydrogen atom, halogen atom, hydroxyl, C 1-20Alkyl, alkenyl, alkynyl, aryl, alicyclic radical, alkoxyl group, vinyl, allyl group, styryl, alkynyl or-OSiR 1R 2R 3, R 1, R 2, R 3Independent respectively is hydrogen atom, halogen atom, hydroxyl, C 1-20Alkyl, alkenyl, alkynyl, aryl, alicyclic radical or alkoxyl group; Wherein, active group is vinyl, allyl group, styryl or alkynyl.
3. a kind of POSS according to claim 2 hydridization side acid squarine near-infrared absorption dye, it is characterized in that: described oligomeric silsesquioxane POSS monomer structure formula is:
Figure FSA00000162377300011
4. acid squarine near-infrared absorption dye in a kind of POSS according to claim 1 hydridization side is characterized in that: described halo side's acid cyanines monomer is,
Figure FSA00000162377300012
Wherein, R 1, R 2Be halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base, R 1, R 2Be same to each other or different to each other.
5. POSS hydridization side acid cyanines near infrared absorption preparation methods comprises:
In nitrogen atmosphere, with above-mentioned POSS monomer and halo side's acid cyanines monomer, join in the mixed system of catalyzer, acid binding agent, part and organic solvent at 2～1: 1～4 in molar ratio, behind 130 ℃～140 ℃ additions or polyreaction 10～25h, through precipitation, filtration, dialysis, get POSS hydridization side acid cyanines near infrared absorption material again.
6. a kind of POSS according to claim 5 hydridization side acid cyanines near infrared absorption preparation methods, it is characterized in that: described catalyzer is Pd (Ac) 2, consumption is 0.5～1mol% of POSS monomer consumption.
7. a kind of POSS according to claim 5 hydridization side acid cyanines near infrared absorption preparation methods, it is characterized in that: described acid binding agent is triethylamine, Anhydrous potassium carbonate or potassiumphosphate, consumption is 1.4～3.2mol% of POSS monomer consumption.
8. a kind of POSS according to claim 5 hydridization side acid cyanines near infrared absorption preparation methods, it is characterized in that: described part is N, N-dimethylamino acetate or triphenyl phosphorus, consumption are 1～1.2mol% of POSS monomer consumption.
9. a kind of POSS according to claim 5 hydridization side acid cyanines near infrared absorption preparation methods, it is characterized in that: described organic solvent is selected from N-Methyl pyrrolidone, N, dinethylformamide, N, in the N-diethylformamide one or more, with the monomeric amount ratio of POSS be 25～100mL: 1mmol.
10. a kind of POSS according to claim 5 hydridization side acid cyanines near infrared absorption preparation methods is characterized in that: the structure type of described POSS hydridization side acid cyanines near infrared absorption material is dumbbell shape, line style, network-type or cross-linking type.
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CN103534813A (en) * 2011-03-21 2014-01-22 阿克伦大学 Polyhedral oligomeric silsesquioxane-organic/polymeric dyads and its application for organic photovoltaic cells
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