CN101880477B - 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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CN101880477B
CN101880477B CN2010102037534A CN201010203753A CN101880477B CN 101880477 B CN101880477 B CN 101880477B CN 2010102037534 A CN2010102037534 A CN 2010102037534A CN 201010203753 A CN201010203753 A CN 201010203753A CN 101880477 B CN101880477 B CN 101880477B
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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 refers to the hertzian wave of wavelength between 700～2500nm, i.e. the middle wave band of ultraviolet-visible and middle infrared analysis., because the material that absorbs near infrared light is few,, so near infrared light is subject in communication process interference is very little, transparent good to material, be emerging, as to have a unique function optical field.Near infrared technology, in research near infrared light-matter interaction relation, plays an important role 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, with the zwitter-ion structure of its unique D-π-A-π-D type conjugated system, has good photoelectric property, 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, as CN 1511883A, disclose a kind of cyanine dyes that contains the quinazolinone heterocycle, absorbing wavelength is in 700～1100nm scope, and structural formula is as follows:
Figure BSA00000162377400011
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 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 industrial application.Its structural formula is:
Figure BSA00000162377400013
Deng; CN 101544844A discloses water-soluble near infrared luminescent quinoline squaraine dye, is applied to the 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 occurs under light action; Be subject to chemical reagent, especially strong nucleophilic reagent attack, destroy its conjugated system, and optical property reduces greatly; More seriously, due to the side's zwitter-ion of sour cyanines with rigidity, 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 document.As: K.A.Bello and M.Q.Tian philosophy are 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 due to rigidity reinforced, aggregation tendency increases; The people such as S.Das propose to utilize hydrophilic, the hydrophobic effect of cyclodextrin or crown ether inner chamber, Molecule of Cyanine Dyes 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
Due to the design of dumbbell shape side acid phthalocyanine molecule, effectively overcome the reversibility in molecule turnover hole, 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 has no report.
Summary of the invention
Technical problem to be solved by this invention is to provide 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-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 consists of the oligomeric silsesquioxane POSS monomer that comprises at least a kind of active group 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's acid cyanines monomer component is 2～1: 1～4.
The described oligomeric silsesquioxane POSS monomer structure general formula that comprises at least a kind of active group is (RSiO 1.5) n, wherein n be 8,10,12,14 or 16, R be same to each other or different to each other, 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,
Wherein, R 1, R 2For 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.
The preparation method of a kind of POSS of the present invention hydridization side acid cyanines near infrared absorption material 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, after 130 ℃～140 ℃ additions or polyreaction 10～25h,, through precipitation, filtration, dialysis, obtain 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 acetic acid or triphenyl phosphorus, consumption are 1～1.2mol% of POSS monomer consumption.
Described organic solvent is selected from N-Methyl pyrrolidone, DMF, N, one or more in the N-diethylformamide, with the amount ratio of POSS monomer 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 adulterated on molecular level with organism, organic materials had good consistency, even main chain and cross-linked network be can directly enter, commixed type, copolymerization or crosslinked hybridized polymer or polymer composites prepared.
Beneficial effect
(1) the POSS hydridization side of the present invention preparation acid cyanines near infrared absorption material is that POSS adulterates 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, in 650～1200nm scope, is the near infrared hydridization dyestuff of excellent property;
The advantages such as (2) this POSS hydridization side acid cyanines near infrared absorption material has good heat, light and chemical stability, and anti-gathering, and material compatibility is good; Improve and interelectrode interface performance the work-ing life of having improved materials and devices;
(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 octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1;
Fig. 2 is the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 1H NMR spectrogram;
Fig. 3 is the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 29Si NMR spectrogram;
Fig. 4 is the TG contrast collection of illustrative plates of the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 and precursor side's acid cyanines and POSS, and wherein, 1 is hybrid material, the 2 sour cyanines in the side of being, and 3 is POSS;
Fig. 5 is the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 and precursor side's acid cyanines absorption spectrum contrast collection of illustrative plates in DMSO solution, and wherein, 1 is hybrid material, the 2 sour cyanines in the side of being;
Fig. 6 is that the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 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 2 sour cyanines in the side of being;
Fig. 7 is the absorption spectrum contrast collection of illustrative plates of the solid film of the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 and precursor side's acid cyanines, and wherein, 1 is hybrid material, the 2 sour cyanines in the side of being;
Fig. 8 is the chemical stability contrast collection of illustrative plates of the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 and precursor side's acid cyanines, wherein, the 1 sour cyanines in the side of being, 2 is hybrid material;
Fig. 9 is the light stability contrast collection of illustrative plates of the prepared line style octavinyl-POSS hydridization side acid cyanines near infrared absorption material of embodiment 1 and precursor side's acid cyanines, wherein, the 1 sour cyanines in the 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 are not used in and limit the scope of the invention for explanation the present 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 limited range 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 2For halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
take bromo side's acid cyanines 0.1mmol, function POSS 0.1mmol with 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), be placed in the dry flask with stirring and reflux, vacuumize under the biexhaust pipe system, after 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, add 50～100mL deionized water, make precipitation fully, filter, obtain thick product, thick product dialysis 24～48h in DMSO, obtain 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: For:
Figure BSA00000162377400057
For:
Figure BSA00000162377400058
R 1, R 2For halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
take bromo side's acid cyanines 0.1mmol, function POSS 0.2mmol with 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), be placed in the dry flask with stirring and reflux, vacuumize under the biexhaust pipe system, after 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, add 50～100mL deionized water, make precipitation fully, filter, obtain thick product, thick product coarse product dialysis 24～48h in DMSO, obtain 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 2For halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
take bromo side's acid cyanines 0.2mmol, function POSS 0.1mmol with 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), be placed in the dry flask with stirring and reflux, vacuumize under the biexhaust pipe system, after 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, add 50～100mL deionized water, make precipitation fully, filter, obtain thick product, thick product dialysis 24～48h in DMSO, obtain straight product.
Embodiment 4
The preparation of cross-linking type POSS hydridization side acid cyanines near infrared absorption material, its structural formula is:
Figure BSA00000162377400071
Wherein: For:
Figure BSA00000162377400073
For:
Figure BSA00000162377400074
R 1, R 2For halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base etc.
take bromo side's acid cyanines 0.4mmol, function POSS 0.1mmol with 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), be placed in the dry flask with stirring and reflux, vacuumize under the biexhaust pipe system, after 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, add 50～100mL deionized water, make precipitation fully, filter, obtain thick product, thick product dialysis 24～48h in DMSO, obtain straight product.

Claims (6)

1. POSS hydridization side acid squarine near-infrared absorption dye, it is characterized in that: the structure type of POSS hydridization side acid cyanines near infrared absorption material is line style, this dye structure consists of the oligomeric silsesquioxane POSS monomer that comprises at least a kind of active group and halo side's acid cyanines monomer, wherein, the mol ratio of oligomeric silsesquioxane monomer and halo side's acid cyanines monomer component is 1:1; Described oligomeric silsesquioxane POSS monomer structure formula is:
Or
Figure FDA00003249808500012
Described halo side's acid cyanines monomer is:
Figure FDA00003249808500013
Wherein, R 1, R 2For halogenophenyl, halogenated pyrrole base, halogenated quinoline base or halogeno indole base, R 1, R 2Be same to each other or different to each other.
2. the preparation method of a kind of POSS according to claim 1 hydridization side acid cyanines near infrared absorption material comprises:
In nitrogen atmosphere, with above-mentioned POSS monomer and halo side's acid cyanines monomer, 1:1 joins in the mixed system of catalyzer, acid binding agent, part and organic solvent in molar ratio, after 130 ℃～140 ℃ additions or polyreaction 10～25h, again through precipitation, filtration, dialysis, obtain POSS hydridization side acid cyanines near infrared absorption material, wherein the structure type of gained POSS hydridization side acid cyanines near infrared absorption material is line style.
3. the preparation method of a kind of POSS according to claim 2 hydridization side acid cyanines near infrared absorption material, it is characterized in that: described catalyzer is Pd (Ac) 2, consumption be POSS monomer consumption molar weight 0.5～1%.
4. the preparation method of a kind of POSS according to claim 2 hydridization side acid cyanines near infrared absorption material, it is characterized in that: described acid binding agent is triethylamine, Anhydrous potassium carbonate or potassiumphosphate, consumption be POSS monomer consumption molar weight 1.4～3.2%.
5. the preparation method of a kind of POSS according to claim 2 hydridization side acid cyanines near infrared absorption material, it is characterized in that: described part is N, N-dimethylamino acetic acid or triphenyl phosphorus, consumption be POSS monomer consumption molar weight 1～1.2%.
6. the preparation method of a kind of POSS according to claim 2 hydridization side acid cyanines near infrared absorption material, it is characterized in that: described organic solvent is selected from N-Methyl pyrrolidone, N, dinethylformamide, N, one or more in the N-diethylformamide, with the amount ratio of POSS monomer be 25～100mL:1mmol.
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