Metal-polymer complex of europium (eu3+) and (co)poly-(methylmethacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxy quinolyl)hydrazine

FIELD: chemistry.

SUBSTANCE: invention relates to metal-polymer complex of europium (Eu3+) and (co)poly-(methylmethacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxy quinolyl)hydrazine of formula: where: m:k = 80 - 95.5:20 - 3.9:0 - 0.6 mol %, MM from 17000 to 24000 Da, Lig denotes a low-molecular weight ligand selected from dibenzoyl methane, thenoyltrifluoroacetone, having Eu3+ ion content from 2.6 to 9.6 wt %.

EFFECT: obtaining complexes with high luminescence intensity.

2 cl, 10 ex, 1 tbl, 2 dwg

 

The invention relates to chemistry and physicochemistry of polymers, namely, metal-polymer complexes (IPC) on the basis of rare earth elements (REE), which take europium (Eu3+and (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) of hydrazine of General formula

,

where n:m:k=80-95,5:20-3,9:0-0,6 mol.%,

MM from 17000 24000 Yes,

Lig - low molecular weight ligand of the series, including dibenzoylmethane (DBM), thenoyltrifluoroacetone TTA, with the content of Eu3+from 2.6 to 9.6 wt.%.

It is known that the IPC with ions of rare-earth elements can have pronounced photo - and electroluminescent properties, characterized by a narrow band and high stability fluorescent light (red for IPC with the Eu3+). Therefore, polymer-based materials such IPC finds practical application in the creation of the laser, fluorescent, high-speed switching device 1. Lanthanide Probes in Life, Chemical and Earth Sciences. Theory and Practice / Ed. by Bunzli, J.-C.G., G.R. Choppin Amsterdam: Elsevier, 1989; 2. Okamoto, S., Vyprachticky D., H. Furuya, F. Abe, Y. Okamoto // Macromolecules. 1996. V.29. No. 10. P.3511; 3. Crescenzi V., H.G. Brittain, Yoshino N., Okamoto Y. // J. Polym. Sci., Polym. Phys. Td. 1985. V.23 supported. P.437; 4. S.I. Klink, G.A. Hebbink et al. / Sensitized near-infrared luminescence from polydentate triphenylene-functionalized Nd3+, Yb3+and Er3+complexes // Journal of Appl. Phys. 1981. V.86. P.1181-1185).

The complexes of Eu3+with polymeric ligands of different chemical article is oenia and study of their photophysical properties the subject of many publications (5. Rosendo A., Flores M, Cordoba G. et al. / Synthesis, characterization and luminescence properties of Tb3+and Eu3+- doped poly(acrylic)acid // Material Setters. 2003. V.57. P.2885-2893; 6. Ling, G., Yang, M., Wu Z. et al. / A novel high photoluminescence efficiency polymer incorporated with pendant europium complexes // Polymer. 2001. V.42. P.4605-4610. 7. Baeka N., Koa J., Kima H, Leeb Yo. / Synthesis and luminescent properties of novel Eu(III)-chelated complexes and their silicon-based copolymers // Materials Science and Engineering. 2004. C.24. P.251-255. 8. Cheng Yi., Zou X., D. Zhu, T. Zhu et al. / Synthesis and Characterization of Chiral Polymer Complexes Incorporating Polybinaphthyls, Bipyridine, and Eu(Raja Shunmugam, Gregory N. Tew III) // Journal of Polymer Science. 2007. V.45A, P.650-660. 9. Farah A.A., Veinot J.G., M. Najman, W.J. Pietro / Redox active, multi-chromophore Ru(II) polypyridyl-carbazole copolymers: synthesis and characterization // Journal Macromol. Sci., Pure appl. chem. 2000. V.A37. No. 11. P.1507-1529.). The last of these technical solutions is the closest to the essence and the achieved result.

As polymeric ligands to obtain the above-mentioned known IPC with ions of Eu3+use chain polymers produced by the method of free radical polymerization and containing lateral substituents groups are capable of forming coordination bonds with ions of rare-earth elements. This Homo - and copolymers of derivatives of styrene, acrylic acid or methacrylamide containing carboxyaniline, carboxyaniline, salicylamide and other similar fragments.

As shown by our study, a significant and obvious shortcomings of the prototype are, firstly, not high enough Ter the practical stability of polymeric ligands and IPC based on them, caused by the presence in the structure of the copolymer flexible aliphatic bridge junction -(CH2)4-secondly, the disadvantages of the prototype should include a synthetic approach chosen by the authors to obtain the IPC, which is a preliminary synthesis of low-molecular-weight complex and subsequent interaction with the polymer containing hydroxyl functional group. In addition, some of the famous IPC have relatively low intensity luminescence.

The technical task and the positive results of the present invention is the creation of materials with high luminescence intensity.

This problem was solved, first, the metal-polymer complexes on the basis of rare-earth metals, which take europium (Eu3+), and (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) of hydrazine of General formula

,

where n:m:k=80-95,5:20-3,9:0-0,6 mol.%, MM from 17000 24000 Yes, Lig - low molecular weight ligand of the series, including dibenzoylmethane (DBM), thenoyltrifluoroacetone TTA with the content of Eu3+from 2.6 to 9.6 wt.%.

Below is a General scheme for the synthesis of target compounds, including seven stages:

1. Getting 2-Peredelkino-4-carboxylic acid (I),

2. Obtaining the ethyl ester of 2-Peredelkino-4-carboxylic key is lots of (II)

3. Getting hydrazide 2-Peredelkino-4-carboxylic acid (III)

4. Getting 1-methacryloyl-2-(2-pyridyl-4-carboxyphenyl) hydrazine (IV)

5. Getting a (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) hydrazine (V)

6. Obtaining Monomeric complexes of europium (dibenzoylmethane)3or europium (thenoyltrifluoroacetone)3-Eu(DBM)3or Eu(TTA)3(VI)

7. Receiving IPC with Eu3+(VII).

The intensity of the glow is confirmed by the method of fluorescent spectroscopy. For example, when forming the IPC with ions of Eu3+as the solution of the reaction system, and the cast of his film acquire the ability to fotovozbuzhdenii intense red luminescence with a maximum luminescence at a wavelength of 615 nm (figure 1, curves 1, 2). On the other hand, the spectral characteristics of the luminescence declared IPC differ significantly from the spectra of luminescence themselves polymer ligands.

From solutions obtained with IPC REE ions in chloroform on a glass substrate cast film, which is subjected to drying at a temperature of 40°C to constant weight. The thickness of the films for photophysical studies - 5-10 microns.

The intensity of luminescence obtained IPC in solutions and films measured on the spectrophotometer LS-100 (Canada).

The obtained characteristics of the properties of the flax-based IPC with Eu 3+synthesized in different conditions given in the examples of embodiment and in table 1.

The obtained characteristics of the luminescence properties of solutions and films IPC-Eu3+the examples of specific performance in table 1 and figures 1 and 2.

Analysis of scientific-technical level did not reveal the published solution, identical in essential structural characteristics of the claimed invention. This confirms the conclusion about the relevance of the proposed solutions to this condition of patentability as "novelty". The analysis did not allow us to detect such technical solutions, which have been described copolymers based on acrylic and methacrylic acid containing in the side chain peribiliary group by hydrazide groups, and described the use of such copolymers as polymeric ligands to obtain intensely luminescent metal-polymer complexes. It was obvious the possibility of obtaining on the basis of copolymers of the claimed structure - polymer complexes, which are able to form self-supporting films with promising photoluminescent properties. Obvious is the ability of the claimed polymeric ligands selectively to form IPC with ion S3+more effective is awn luminescence, than with ions other REE. This allows to make a conclusion on compliance of the overall solution to such a condition of patentability as "inventive step (obviousness).

The structure of the obtained compounds was confirmed by spectral methods, the molecular weight of the original copolymers and MBC were determined by light scattering method.

The obtained optical characteristics are confirmed by the figures.

Figure 1 (curves 1, 2) represents the spectra of the luminescence of various Eu3+-soderjaschih IPC in the film with the same content of Eu3+(CEu3+=2.6 wt.%). On the X-axis wavelength (λ, nm). On the Y-axis light intensity in arbitrary units (cu). Curve 1 - IPC (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) of hydrazine with Eu(DBM)3. Curve (2) IPC (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) of hydrazine with Eu(TTA)3.

Figure 2 represents the magnitude of the intensity of the fluorescent glowsolutions in dimethylformamide IPC (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) of hydrazine with Eu(TTA)3at different excitation wavelengths λwosb.(nm). On the X-axis wavelength (λ, nm). On the Y-axis light intensity in arbitrary units (cu). Curve 1 - λwosb.=230. Curve 2 - λwosb.=300. It is Eva 3 - λwosb.=247. Curve 4 - λwosb.=338. Curve 5 - λwosb.=380. Curve 6 - λwosb.=365.

To confirm the compliance of the claimed invention to such a condition of patentability as "industrial applicability", and to better understand the essence of the claimed invention provide examples of specific implementations of the invention, which can be exhausted its essence.

Example 1

Stage 1. Getting 2-Peredelkino-4-carboxylic acid (I)

In odnogolosy round bottom flask with a capacity of 100 ml equipped with a reflux condenser, placed 3 g (0.02 mol) of isatin, 15.6 g of a 33%solution of KOH, of 5.82 g (0,048 mol) of 2-acetylpyridine and 31.2 ml of ethanol. The solution is boiled on a water bath for 8 hours then add 30 ml of distilled water and stanol. The remaining mixture is cooled and twice extracted with ethyl ether. The product is isolated by adding to the mixture solution of hydrochloric acid, filtered off, washed with plenty of water until neutral and social product by recrystallization from acetic acid. Tpl.=308°C. the Yield 7.5 g, 90%.

Stage 2. Obtaining the ethyl ester of 2-Peredelkino-4-carboxylic acid (II)

In odnogolosy round-bottom flask with 5.3 g of 2-pyridyl-4-carboxyaniline, 53 ml of ethanol and 5.3 ml of concentrated sulfuric acid. The warm mixture on an oil bath at 100°C for 1.5 hours Then cooled, planted in water and neutralized with dry potash to pH=5. The precipitation is filtered off and dried in air. TPL=65°C. Yield 4 g, 75%.

Stage 3. Getting hydrazide 2-Peredelkino-4-carboxylic acid (III)

In odnogolosy round-bottom flask of 8.3 g of ethyl ester of 2-Peredelkino-4-carboxylic acid and 1.8 ml of hydrazine hydrate. The suspension is heated on an oil bath at 110°C for 40 hours. Target product produce by filtration. TPL=232°C. Yield 8 g, 95%.

Stage 4. Getting 1-methacryloyl-2-(2-pyridyl-4-carboxyphenyl)hydrazine (IV)

In a two-neck round bottom flask with a capacity of 100 ml equipped with a stirrer, thermometer and addition funnel, is placed 1.04 g (0,0041 mole) of the hydrazide 2-pyridyl-quinoline-4-carboxylic acid, 4 ml of N-methylpyrrolidone and 0.8 ml of triethylamine. The solution is cooled to -15°C. (ice-salt) and for 30 min was added dropwise a solution of 0.045 g (0,0045 mol) of methacrylic acid chloride acid 3.8 ml of N-methylpyrrolidone. Then the solution is stirred while cooling another 1 hour, add 0.1 ml of triethylamine and leave overnight. The solution is filtered from the salt of triethylamine and planted in 50 ml of water. Loose white flakes filtered off, washed with 200 ml of water, recrystallized from 5 ml of a mixture of ethanol - water (50:50), air-dried. Output - 0.5 g, 50%.

Stage 5. Getting a (co)poly(methyl methacrylate)-(1-methacryloyl-2(2-pyridyl)-4-carboxyphenyl) hydrazine (V)

In vials of 10 ml is placed 1.8 ml of dimethylacetamide and sprinkled 0,19 g (0,0006 mol) 1-methacryloyl-2-(2-phenyl-4-carboxyphenyl) hydrazine, 0,240 g (0,0024 mol) of methyl methacrylate and 0.006 g Deniz. The vacuum ampoule, sealed and incubated at 75°C for 120 hours. Upon completion of the polymerization, the polymer solution planted in 100 ml of a mixture of water-methanol (50:50), filtered, washed with water, methanol and dried. Out - of 0.38 g, 95%.

Stage 6. Obtaining Monomeric complexes of Eu(DBM)3and Eu(TTA)3(VI)

In a solution of 2.23 g (0,005 mol) of chloride rare earth element in 200 ml of water, add 50 ml of 95% ethanol and 6 g (0.007 mol) dibenzoylmethane (DBM) or thenoyltrifluoroacetone (TTA). The suspension is stirred on a magnetic stirrer and add 15 ml of 1M aqueous solution of ammonia. The resulting precipitate is filtered off and dried at room temperature. The recrystallization of the crude product is carried out by heating in 200 ml of ethanol. The solution is filtered hot and then cooled filtrate was added 100 ml of water and the mixture is placed in a refrigerator. The precipitated product is filtered and dried in vacuum. Excess dibenzoylmethane is removed by extraction with cyclohexane with stirring solid product at room temperature. The product is dried in vacuum at room temperature. Yield 0.47 g, 65%.

Stage 7. Obtaining the metal-polymer complexes with Eu3+(VII)

odnogolosy round bottom flask is placed 0.1 g (9×10 -4mol) polymer, 0,0045 g (5×10-6mol) monomer complex with Eu(III) and 2.5 ml of chloroform. The solution is boiled for 30 minutes the resulting solution cast films on glass substrates and dried.

Examples 1-10 were performed under the stage 5 with the change in the proportion of comonomers and polymerization conditions.

The data of examples 1-10 are summarized in table 1. The table shows the intervals n, m and k, as well as MM and indicators luminescence intensity.

The presented data confirm the achievement of the stated objectives. The first IPC characterized by high intensity of luminescence. Moreover, examples 2, 4, 7 and 10 proves the obviousness of the solution, because the increase in the content of complex fragments in the polymer reduces the intensity of luminescence of the IPC on its basis (table 1, examples 2, 4, 7, 10).

ExampleThe composition of the copolymer, mol.%The Eu content, wt.%Concentration %The reaction temperature, °CThe ligandOutput %MM×104I loom, Rel. units
n mk
1.95,5a 3.90,62,6460TTA912,4630
2.80,020,009,6460TTA832,0510
3.95,5a 3.90,62,6660TTA802,0600
4.80,020,009,6660TTA80 2,2485
5.95,5a 3.90,62,6460DBM902,2210
6.95,5a 3.90,62,6450TTA841,8550
7.80,020,009,6450TTA761,9410
8.95,5a 3.90,62,6660DBM791,8 200
9.95,5a 3.90,62,6650TTA811,7570
10.80,020,009,6650TTA831,8320
Note. DBM - dibenzoylmethane, TTA - thenoyltrifluoroacetone

1. The metal-polymer complex of europium (Eu3+and (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) of hydrazine of General formula:
,
where n:m:k=80-95,5:20-3,9:0-0,6 mol. %MM from 17000 24000 Yes, Lig - low molecular weight ligand of the series, including dibenzoylmethane, thenoyltrifluoroacetone, with the content of Eu3+from 2.6 to 9.6 wt.%.

2. The metal-polymer complex according to claim 1, characterized in that the polymer used (co)poly(methyl methacrylate)-(1-methacryloyl-2-(2-pyridyl)-4-carboxyphenyl) hydrazine, content is the seer peribiliary group in the side chain, General formula:
,
where n:m=80-95,5:20-4,5 mol.%, MM from 17000 24000 Yes.



 

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23 cl, 9 tbl, 19 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a multifunctional polymer which contains a graft polymer formed from: a) polyolefin, b) nitrogen-containing ethylene-unsaturated aromatic or aliphatic monomer which contains from 2 to approximately 50 carbon atoms; and c) an organometallic compound capable of reacting with the said polyolefin. The invention also discloses multifunctional polymers (versions), a synthesis method thereof, and lubricating oil (versions).

EFFECT: invention enables to obtain a multifunctional polymer which acts as a dispersing agent, viscosity index improver and an antiwear additive.

62 cl, 7 ex, 3 tbl

FIELD: pharmaceuticals.

SUBSTANCE: polyvinyl alcohol and magnesium or calcium chlorides polyhydrated complexes are obtained by dissolution of polyvinyl alcohol and magnesium or calcium chlorides in water on boiling water bath. Said components are taken in the next ratio (mass%): polyvinyl alcohol 11.5-11.6; magnesium or calcium chloride 23.2-24.0; and balance: distilled water.

EFFECT: new complex compounds having antiinflammation, resolution and analgesic action.

11 ex

The invention relates to new functional derivatives of polyolefins, more particularly to polyolefin, metilirovaniem alkaline metals, the method of production mentioned polyolefins and their use

FIELD: pharmaceuticals.

SUBSTANCE: polyvinyl alcohol and magnesium or calcium chlorides polyhydrated complexes are obtained by dissolution of polyvinyl alcohol and magnesium or calcium chlorides in water on boiling water bath. Said components are taken in the next ratio (mass%): polyvinyl alcohol 11.5-11.6; magnesium or calcium chloride 23.2-24.0; and balance: distilled water.

EFFECT: new complex compounds having antiinflammation, resolution and analgesic action.

11 ex

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