5-(2'-acrylamidophenyl)-15-(3',5''-di-tertiary-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraethylporphyne as coloring substance of optical filter

FIELD: organic chemistry.

SUBSTANCE: invention relates, in particular, to novel tetrapyrrole macroheterocycles - diphenyloctaalkylporphynes that can be used as a coloring substance of optical filters. Invention describes 5-(2'-acrylamidophenyl)-15-(3',5''-di-tert.-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraethylporphyne as a coloring substance of optical filters. This compound shows maximum absorption in the region 625 nm and can be used for preparing colored polymers used as optical filter.

EFFECT: valuable properties of substance.

1 ex

 

Introduction

The invention relates to the chemical industry, namely the tetrapyrrole macroheterocycles - diphenylmethylphosphine, i.e. parinam, substituted by two methodologies phenyl rings, one of which contains acrylamide Deputy, and β-the provisions of the eight alkyl substituents, particularly to new chemical compound 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetramethylpentane, which can be used as the coloring matter of optical filters.

The level of technology

Tetrapyrrole the macroheterocycles play an important role in nature and technology, entering into the structure of the respiratory pigments, enzymes, vitamins, catalysts, sensors, etc. and having a narrow, intense absorption band in the visible region, can be used as the coloring matter of optical filters.

Interest from diphenylmethylphosphine having the maximum absorption of light in the region of 625 nm in order to use them for photodynamic therapy and the creation of optical filters.

Optical filters are often painted plexiglass and can be obtained from the so-called "colored polymers, i.e. polymers having the structure of macromolecules elementary units containing chromophores. Such is aimery obtained by copolymerization of vinyl monomers, for example, derivatives of methacrylic acid with dyes containing vinyl group.

Known 5,15-diphenyl-3,7,13,17-tetramethyl-2,8,12,18-Tetra-Ethylmorphine (J.S.Manka, P.C.Lawrence // Tetrahedron Lett., 1989, Vol.30, P.6989)having a maximum absorption in organic solvents in the area of 625 nm and a structural analogue of the claimed compounds.

However, it cannot be used as the coloring matter of optical filters based on "colored polymers", because it does not contain the necessary functional groups.

The invention

The objective of the invention is the search for new compounds that are suitable for "colored polymer for use as an optical filter.

The goal is solved 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin.

The identity and structure of the claimed compounds determined in a manner similar spectral characteristics in the visible region of the spectrum of its solution in chloroform with those of his closest structural analogue,1H NMR and IR spectra.

Electronic absorption spectra of the solution of the claimed compound and its structural analogue in chloroform were recorded on a spectrophotometer Perkin Elmer Lambda 20 in quartz pryamougolnichkami thickness of 10 mm, concentration of solutions ˜10-5M. the provisions of the long-wave absorption bands of these spectra is shown below.

5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin625 nm and 573 nm, 541 nm 508 nm, 410 nm
5,15-diphenyl-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin625 nm, 574 nm, 540 nm and 508 nm and 409 nm

High analogy visible parts of the electronic absorption spectra strongly suggests that the claimed compound belongs to the class of diphenylmethylphosphine, and it is replaced by diphenylmethylphosphine.

As Deputy speaker acrylamide group. The number, location and nature of the substituents clearly derive from the structure used to produce Sinton: 5-(2-AMINOPHENYL)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin and absorption bands in the IR spectra of the claimed compounds in the field 1694 cm-1related to the stretching vibrations of the carbonyl group, and in the field 3395 cm-1related to the stretching vibrations of NHCO-group.

1H NMR spectra of the claimed compounds were recorded on a NMR spectrometer Bruker AS-200, solvent CDCl3, internal standard TMS.

Spectral parameters savlon the th connection (in ppm), with such signals, below, fully confirm attributed to him the structure.

5-(2'-acrylamidoethyl)-15-8,87d (o, m-H Ph); 7,49t (m, n-H Ph);
(3',5"-di-tert-butylphenyl)-7,09s (NHCO); 5,55m (CH2);
3,7,13,17-tetramethyl-4,90d (CH); 2,53s (3,7-CH3);
2,8,12,18-tetraarylporphyrin2,45s (13,17-CH3); 4,06q (CH2-Et);
1,77t (CH3-Et); 7,83s (o-H Ph);
7,93s (n-HPh); 1,49s (tBu);
10,24s (ms-H); -2,40bs (NH)

Thus, the set of spectral data uniquely identifies the structure of the claimed compounds as 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin.

This connection is a brownish-purple crystalline substance with a metallic sheen, not fuse up to 400°S, soluble in chloroform, pyridine, dimethylformamide and dimethyl sulfoxide with the formation of intensely colored solutions, and can be used to obtain colored polymer in order to apply the latter as an optical filter.

Information confirming the possibility of carrying out the invention

To obtain the claimed compounds are used with ewusie substances:

-5-(2'-AMINOPHENYL)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin, which was obtained by reduction of 5-(2'-nitrophenyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin method J.P.Colman et. al. // J. Am. Chem. Soc., 1973, Vol.95, N3, P.7869. In turn, 5-(2'-nitrophenyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin was obtained by the method of mixed aldehydes (Clagiraba, .Nagata, N.Ono, A.Osuka // Bull. Chem. Soc. Jpn. // 1989, Vol.62, P.3167);

the acid chloride of acrylic acid, which was obtained by fractional distillation of a mixture of acrylic acid, benzoyl chloride and hydroquinone at a moderate speed through the column height 25 cm;

- pyridin - GOST 13647;

- chloroform - GOST 20015-88;

- aluminium oxide for chromatography III degree of activity by Brockmann - TU 6-09-3916 (GOST 8136);

the methylene chloride - GOST 9968-86.

The inventive compound can be obtained, for example, as follows.

98 mg (0,129 mmol) 5-(2'-AMINOPHENYL)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin, 0.5 ml (6,298 mmol) of acid chloride of acrylic acid, 5 ml of dried pyridine and 20 ml of chloroform is stirred on a magnetic stirrer at room temperature for days. Then the solution is poured into 200 ml of water and boiled for 1 hour. Dropped the precipitate was separated by filtration, washed with water and dried at 80°C. To clean the residue is dissolved in 30 ml x is aristovo methylene and chromatographic on a column of aluminum oxide III degree of activity by Brockmann, elwira methylene chloride. The eluate evaporated to 3-5 ml and the product visidot by adding 50 ml of ethanol.

Get 71 mg (0,088 mmol) 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin. Output ˜68% of theory.

To determine the possibility of using 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin as the coloring matter optical filters received the samples of colored organic glass. This prepared solution of this compound in methyl methacrylate concentration ˜10-5M, was poured into the folding glass shape and subjected thermopolymerization at 140°C for 24 hours. Then samples of colored organic glass was removed from the forms and determined the wavelength of the long wavelength of maximum absorption.

The optical filter on the basis of 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin she is 625 nm. The achievable optical density depends on the amount of 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin included in the composition of the copolymer, and the thickness of the filter.

Thus, having a maximum absorption in the region of 625 nm, the proposed 5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tet is amatil-2,8,12,18-tetraarylporphyrin can be used as coloring substance for production of optical filters.

5-(2'-acrylamidoethyl)-15-(3',5"-di-tert-butylphenyl)-3,7,13,17-tetramethyl-2,8,12,18-tetraarylporphyrin formula

as the coloring matter of optical filters.



 

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