,,,-tetramethylcyclotetrasiloxane and methods for their production

 

(57) Abstract:

Describes new , , , - tetramethylcyclotetrasiloxane General formula I, where M = NN, Cu, Ni, VO; R = R1= N

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and three retrieval method based on the condensation of a mixture of tetramethylethylenediamine derivative of o-phthalic or naphthalene-2,3-dicarboxylic acid. The compounds obtained are distinguished by intense absorption in the near infrared range of the spectrum, good solubility and stability in organic solvents and in polymer matrices and can be used as functional dyes, such as absorbing components of the optical filters in the near-IR range. 3 C.p. f-crystals.

The invention relates to chemistry and chemical technology, and more specifically to the synthesis of a new breed of macroheterocyclic compounds, tetrasauropus chlorine, namely , , , -tetramethylcyclotetrasiloxane.

Known the unsubstituted tetrazole (TAX) - dihydrotetrazolo, in the electronic absorption spectrum of which has a intense long-wavelength band at 678 nm [E. A. Makarova, Century, Queen, E. A. Lukyanets. J. of General chemistry, 69, 1356 (1999)]. Hydrogenation of , -one communication and is without significant intensity changes. TAX is resistant to oxidation in air in the solid state and in solutions of neutral organic solvents at room temperature or under heating, in a polar organic solvents (DMF, pyridine) observed partial oxidation even at room temperature.

With the purpose of obtaining a TAX with the longer-wavelength absorption and is more resistant to oxidation compared to the unsubstituted compound we synthesized condensed analogues TAX - , , , -tetramethylcyclotetrasiloxane derived TAX stabilized by exhaustive methylation of the C-C-bond. Method of obtaining is a mixed condensation of tetramethylcyclobutane (TSN), a very affordable product of thermal decomposition of azoisobutyronitrile, with appropriate phalaenae, primarily dinitrile aromatic o-dicarboxylic acids and their anhydrides or imides. Condensed analogues TAX not described. It Is Known [J. A. Elvidge, R. P. Linstead. J. Chem. Soc., 1955, 3536; B. N. Kapranenko, A. M. Tsygankova, E. A. Lukyanets. Oneliners. prom., 1979, vol. 5, page 1], which when mixed condensation of succinonitrile with phthalonitrile along with phthalocyanine is formed transacetalization because of the instability of obrazuyushchiesya or boiling mixtures with salts of metals (NiCl2, CuCl, VCl3and others) in the high-boiling organic solvents (quinoline, sulfolane, dimethylaminoethanol, nitrobenzene, and so on ), or in solutions of alcohols in the presence of the corresponding lithium alcoholate. Shows when boiling phthalonitrile and TMSN (ratio 1:1) dimethylaminoethanol in the presence of dimethylaminoethyl lithium is formed with a small output (about 2%) , , , -tetramethylcyclotetrasiloxane along with phthalocyanine, which is the main reaction product.

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M = NN, Cu, Ni, VO;

R = R1= H;

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In the interaction of equimolar amounts TSN and phthalonitrile with Vl3in boiling quinoline is formed a mixture of VOPc and three new compounds: VO,,,, tetramethylchroman-TAH exit 15% and farmax763 nm, VO octamethylcyclotetrasiloxane with the release of ~1% andmax898 nm and VO octamethylcyclotetrasiloxane with the release of ~1% andmax/721 nm, which were separated by chromatography on silica gel.

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Metal complexes of tetramethylchroman-TAH formed also when using as telogen other derivatives of phthalic acid, namely anhydride or imide, in the presence of urea and kacestveno also, when the interaction TMSN derivative of 2,3-naphthaleneboronic acid (anhydride, imide or 1-phenylselenenyl analogues) in boiling quinoline or sulfolane in the presence of metal salts (VCl3, NiCl2) and a catalytic amount of ammonium molybdate is formed a mixture of the corresponding metal complexes of 2,3-naphthalocyanine and , , , -tetramethylene-2,3-oil-TAH (~ 8%)max871 nm for 1-phenylseleno VO complex and 819 nm for 1-phenylseleno Ni complex. It should be noted that in the case of NiCl2in the electronic spectrum of the reaction mixture is observed bandmax900 nm, which, apparently, the Ni complex octaketide-2,3-(1-anilnetto)tetraazamacrocyclic not selected, however, in its pure form.

The present invention is illustrated by the following examples.

Example 1.

Tetramethylsilane (TMSN).

Boil 10 g of azoisobutyronitrile in 250 ml of toluene. Upon completion of the reaction the reaction mass is then cooled, diluted with 300 ml of hexane and leave overnight in the refrigerator. The precipitation is filtered off, washed with hexane, air-dried. Get 7.5 g (87%) TMN with so pl. 156-158oC (hexane).

, , , -Tetramethylbenzidine room temperature and add a mixture of 0.41 g (3.2 mmol) of phthalonitrile and 0.44 g (3.2 mmol) TSN. The reaction mass is slowly heated with stirring to a boil and continue boiling, gradually adding 0.4 g (2.8 mmol) TMSN, cooled, diluted with 200 ml of water, precipitated precipitate is filtered off, washed successively with hot water, 50% aqueous ethanol, ethanol, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions with ethanol to remove impurities, then trichlorobenzene. Next, the extract was evaporated in vacuum and chromatographic on silica gel first with hexane to remove trichlorobenzene, then chloroform. Collect the blue faction and get 0.009 g (1.6%) , , , -tetramethylcyclotetrasiloxane.

An NMR spectrum1H (CDCl3), , m, D.: 1.96 (C., N, CH3), 7.88 (DD., 2H, = CH-), 8.16 (t, 2H, =CH-), 8.22 (t, 2H, =CH-), 9,04 (DD., 2H, =CH-), 9.32 (D., 2H, =CH-), 9.38 (D., 2H, =CH-).

The electronic absorption spectrum,maxnm (lg), chlorobenzene: 748 (5.07), 711 (4.32), 680 (4,19), 634 pl.(4.17), 606 (4.58), 584 pl.(4.37), 341 (4.81).

Example 2.

, , , -Tetramethylcyclotetrasiloxane Nickel.

A mixture of 0.5 g (3.7 mmol) TMSN, 0.47 g (3.7 mmol) of phthalonitrile, 0.47 g (3.7 mmol) of anhydrous NiCl2and 0.003 g of ammonium molybdate (MOA) in 5 ml of quinoline is boiled under stirring. Upon completion of the reaction reactivatable hot water, hot 50% aqueous acetone, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions with hexane, then dichlorobenzene. The hexane extract is evaporated, the residue chromatographic on silica gel with a mixture of hexane-ethyl acetate (10:1) and divided into two fractions: the first fraction 10 mg (0.9%) , , , -octamethylcyclotetrasiloxane Nickel, Rf0.51 (Silufol, hexane-ethyl acetate, 10:1),max(relative intensity) in chloroform 843 (1.0), 801 (0.33), 761 (0.16), 540 (0.42), 330 (0.33), and the second group of 12 mg (1.1%) , , , - octamethylcyclotetrasiloxane Nickel, Rf0.40 (Silufol, hexane-ethyl acetate, 10:1)max(relative intensity) in chloroform 675 (1.0), 649 (0.30), 631 (0.23), 312 (0.29). Dichlorbenzene extract evaporated in vacuum, chromatographic on silica gel with benzene and obtain 0.14 g (19%) , , , -tetramethylcyclotetrasiloxane Nickel, Rf0.37 (Silufol, benzene).

Found, %: C 66.52; H 4.63; N 17.65.

C32H24N8Ni.

Calculated, %: C 66.42; N, 4.18; N 19.38.

The electronic absorption spectrum,maxnm (lg), chlorobenzene: 727 (5.03), PL. (4.32), 667 (4.36), 593 (4.81), PL. (4.15), PL. (3.97), 415 (3.64), 325 (4.49).

Example 3.

A mixture of 0.5 g (3.7 mmol) TMSN, 1.06 g (8.3 mmol) talanar the tion of the reaction mass is then cooled, diluted with 100 ml of 50% aqueous ethanol, precipitated precipitate is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions-dichlorobenzene. The extract was evaporated in vacuum, chromatographic on silica gel with benzene and obtain 0.11 g (7.0%) , , , -tetramethylcyclotetrasiloxane Nickel, identical spectral obtained in example 2.

Example 4.

A mixture of 1.0 g (7.4 mmol) TMSN, 0.47 g (3.7 mmol) of phthalonitrile, 0.63 g (4.9 mmol) of anhydrous NiCl2and 0.003 g MOA in 5 ml of quinoline is boiled under stirring. Upon completion of the reaction the reaction mass is treated as described in example 2 and obtain 0.07 g (9.9%) , , , -tetramethylcyclotetrasiloxane Nickel, identical spectral obtained in example 2. From the hexane extract allocate 0.023 g (2.1%) of a mixture of octamethylcyclotetrasiloxane Nickel and octamethylcyclotetrasiloxane Nickel.

Example 5.

A mixture of 0.25 g (1.8 mmol) TMSN, 0.24 g (1.8 mmol) of phthalonitrile, 0.24 g (1.8 mmol) of anhydrous NiCl2and 0.002 g MOA in 3 ml of dimethylaminoethanol boil while stirring. Upon completion of the reaction the reaction mass is then cooled, razbavljaem, air-dried. After extraction dichlorobenzene and chromatography benzene on silica gel get 0.011 g (3%) , , , -tetramethylcyclotetrasiloxane Nickel, identical spectral obtained in example 2.

Example 6.

A mixture of 1.0 g (7.4 mmol) TMSN, 0.94 g (7.4 mmol) of phthalonitrile, 0.95 g (7.4 mmol) of anhydrous NiCl2and 0.003 g MOA in a mixture of 7 ml of nitrobenzene and 0.5 ml of quinoline is boiled under stirring. Upon completion of the reaction the reaction mass is then cooled, diluted with hexane, the precipitated precipitate is filtered off, washed successively with hexane, hot 50% aqueous ethanol, air-dried. After extraction dichlorobenzene and chromatography benzene on silica gel obtain 0.10 g (7%) , , , -tetramethylcyclotetrasiloxane Nickel, identical spectral obtained in example 2.

Example 7.

A mixture of 1.0 g (7.4 mmol) TMSN, 1.08 g (7.4 mmol) of phthalimide, 0.95 g (7.4 mmol) of anhydrous NiCl2, 0.88 g (14.7 mmol) of urea and 0.003 g MOA in 5 ml of sulfolane is boiled under stirring. Upon completion of the reaction the reaction mass is treated as described in example 3 and obtain 0.11 g (7.4%) , , , -tetramethylcyclotetrasiloxane Nickel, identical spectral obtained in example 2.

Example 8.

See chevigny and 0.003 g MOA in 5 ml of quinoline is boiled under stirring. Upon completion of the reaction the reaction mass is treated as described in example 3 and get 0.094 g (6.3%) , , , -tetramethylcyclotetrasiloxane Nickel, identical spectral obtained in example 2.

Example 9.

, , , -Tetramethylcyclotetrasiloxane copper.

A mixture of 0.5 g (3.7 mmol) TMSN, 0.47 g (3.7 mmol) of phthalonitrile, 0.39 g (3.7 mmol) odnoklasniki copper and 0.003 g MOA in 3 ml of quinoline is boiled under stirring. Upon completion of the reaction the reaction mass is then cooled, diluted with 100 ml of 50% aqueous ethanol, precipitated precipitate is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions-dichlorobenzene 10 am, the Extract evaporated in vacuo to a volume of 10 ml, chromatographic on silica gel with benzene and obtain 0.43 g (5.4%) , , , -tetramethylcyclotetrasiloxane copper.

Found, %: C 64.96; N, 3.85; N 17.64.

WITH32H24N8C.

Calculated, %: C At 65.80; H 4.14; N, 19.18.

The electronic absorption spectrum,maxnm (relative intensity), chlorobenzene: 733 (1.0), 671 (0.22), 598 (0.53), 325 (0.59).

Example 10.

, , , -Tetramethylcyclotetrasiloxane vanadyl.In 3 ml of quinoline is boiled under stirring. Upon completion of the reaction the reaction mass is then cooled, diluted with 100 ml of 50% aqueous ethanol, precipitated precipitate is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions with hexane, then with chlorobenzene. The hexane extract is evaporated, the residue chromatographic on silica gel with a mixture of hexane-ethyl acetate (10:1) and divided into two fractions: the first fraction 8 mg (1.0%) octamethylcyclotetrasiloxane vanadyl, Rf0.3 (Silufol, hexane-ethyl acetate, 10:1),max(relative intensity) in chloroform 891 (1.0), 840 (0.43), 802 (0.32), 573 (0.44), 335 (0.56) and the second fraction 10 mg (1.3%) octamethylcyclotetrasiloxane vanadyl, Rf0.22 (Silufol, hexane-ethyl acetate, 10:1)max(relative intensity) in chloroform 717 (1.0), 658 (0.24), 631 (0.20), 320 (0.49). Chlorbenzol extract evaporated in vacuo to a volume of 10 ml, chromatographic on silica gel with benzene and obtain 0.12 g (15.6%) , , , -tetramethylcyclotetrasiloxane vanadyl, Rf0.26 (Silufol, benzene).

Found, %: C 66.51; N, 4.18; N 18,65.

WITH32H24N8OV.

Calculated, %: C 65.40; H 4,12; N 19,08.

The electronic absorption spectrum,3and 0.003 g MOA in 2 ml of quinoline and then continue boiling. Upon completion of the reaction the reaction mass is then cooled, diluted with 100 ml of 50% aqueous ethanol, precipitated precipitate is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions with chlorobenzene, and then the solvent evaporated in vacuo to a volume of 10 ml, chromatographical on silica gel with benzene and obtain 0.16 g (20.9%) , , , -tetramethylcyclotetrasiloxane vanadyl, identical spectral obtained in example 10.

Example 12.

A solution of 0.8 g (5.9 mmol) TSN and 0.50 g (3.9 mmol) of phthalonitrile in 5 ml of sulfolane was added to the stirred and heated to boiling a mixture of 0.61 g (3.9 mmol) of anhydrous Vl3and 0.003 g MOA in 3 ml of sulfolane and then continue boiling. Upon completion of the reaction the reaction mass is then cooled, diluted with water, the precipitation is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions with chlorobenzene, and then the solvent evaporated in vacuo to a volume of 10 ml, chromatographic on silica gel with benzene example 10.

Example 13.

, , , -Tetramethylene-2,3-kattoterassin Nickel.

A mixture of 0.5 g (3.7 mmol) TMSN, 0.72 g (3.7 mmol) of imide naphthalene-2,3-dicarboxylic acid, 0.48 g (3.7 mmol) of anhydrous NiCl2, of 0.44 g (7.4 mmol) of urea and 0.003 g MOA in 5 ml of sulfolane is boiled under stirring. Upon completion of the reaction the reaction mass is then cooled, diluted with 100 ml of 50% aqueous ethanol, precipitated precipitate is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The residue is triturated, and then extracted in to conventional Soxhlet extractions with ethanol, acetone, then trichlorobenzene. Trichlorbenzene the extract is filtered through a layer of aluminum oxide, evaporated in vacuum to a volume of 5 ml, diluted with 100 ml of hexane, the precipitated precipitate is filtered off, washed with hexane and obtain 0.07 g (7.9%) , , , -tetramethylene-2,3-kattoterasilla Nickel.

Found, %: C, 71.44; H, 4.28; N, 15.10.

C44H30N8Ni

Calculated, %: C, 72.45; H, 4.15; N, 15.36.

The electronic absorption spectrum,maxnm (relative intensity), chlorobenzene: 811 (1.0), 687 (0.39), 310 (0.85).

Example 14.

, , , -Tetramethylene-2,3-(1-anilnetto)tetrazolium Nickel.

A mixture of 0.5 g (3.7 molmol) urea and 0.003 g MOA in 5 ml of sulfolane is boiled under stirring. Upon completion of the reaction the reaction mass is then cooled, diluted with 100 ml of 50% aqueous ethanol, precipitated precipitate is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The remainder chromatographic on aluminium oxide with a mixture of hexane-chloroform (1:2), collect the green faction with Rf(Alufol, hexane - chloroform, 1:2), obtain 0.06 g (5%) , , , -tetramethylene-2,3-(1-anilnetto)tetrasaccharide Nickel.

Mass spectrum, m/z: 957 (M+).

The electronic absorption spectrum,maxnm (relative intensity), chloroform: 819 (1.0), 694 (0.39), 313 (0.78).

Example 15.

A mixture of 1.5 g (11 mmol) TMSN, 3 g (11 mmol) of anhydride 1-phenylnaphthalene-2,3-dicarboxylic acid, 1.43 g (11 mmol) of anhydrous Nil2, 1,32 g (22 mmol) of urea and 0.006 g MOA in 10 ml of sulfolane is boiled under stirring. Upon completion of the reaction the reaction mass is treated as described in example 14 and obtain 0.2 g (5.7%) , , , -tetramethylene-2,3-(1-anilnetto)tetrasaccharide Nickel, identical spectral obtained in example 14.

Example 16.

, , , -Tetramethylene-2,3-(1-anilnetto)tetrazolium vanadyl.

A mixture of 0.5 g (3.7 mmol) TMN, 1 g (3.7 mmol) of imide 1-phenylnaphthalene-2,3-dicarboxylic acid is I. Upon completion of the reaction the reaction mass is then cooled, diluted with 100 ml of 50% aqueous ethanol, precipitated precipitate is filtered off, washed successively with hot water, hot 50% aqueous acetone, air-dried. The remainder chromatographic on silica gel with a mixture of benzene-hexane (2:1), collect the green faction with Rf0.43 (Silufol, benzene-hexane, 2:1) and obtain 0.05 g (4.2%) , , , -tetramethylene-2,3-(1-anilnetto)tetrasaccharide vanadyl.

The electronic absorption spectrum,maxnm (relative intensity), chloroform: 871 (1.0), 825 (0.54),747 (0.35), 328 (0.74).

Thanks to the peculiarities of molecular structure, in particular the presence of two Quaternary carbon atoms with methyl groups outside the plane of the molecule, the compounds have good solubility in organic solvents and in polymer matrices.

They are resistant to oxidation in air in the solid form and in solution in organic solvents, including polar, both at room temperature and when heated, as evidenced by the preservation of the absorption spectrum of their solutions in a long time.

The synthesized compounds in the electronic absorption spectra have intensive bands in krasnic to a significant bathochromic shift of the long wavelength band Q - to 752, 727 and 763 nm in chloroform for tetramethylchroman-TAH and Ni and VO complexes, respectively, with a slight increase in its intensity compared with TAX, without causing significant changes of the spectrum in the UV region.

In the case of three-2,3-oil-TAH bathochromic shift of the long wavelength band is about 170 nm compared to TAX - Ni and VO complexes tetramethylene-2,3-(1-anilnetto)-TAH it is located at 819 and 871 nm, respectively.

Good solubility and stability in solution and in the polymer matrix allows the use of all the compounds as functional dyes, in particular as absorbing components of the optical filters in the near-IR range. So,,,,- tetramethylcyclotetrasiloxane and its Nickel and wandeling complexes with electronic absorption spectra in toluene solutions and polymethylmethacrylate wavelength bands with maxima at 750, 727 and 763 nm, respectively, made of liquid and solid state optical filters low pass type wavelength range from 720 to 780 nm, 700 to 760 nm and 730 nm to 800 nm. Of , , , -tetramethylene-2,3-(1-anilnetto)tetrasaccharide Nickel with long-wavelength maximum at 820 nm, manufactured the formula

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where M = HH, Cu, Ni, VO;

R = R1= H;

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2. The method of obtaining besmearing connection on p. 1, where M = NN, R = R1= H, which consists in condensing a mixture of tetramethylcyclobutane with phthalonitrile in the presence of dimethylaminoethyl lithium in dimethylaminoethanol.

3. The method of obtaining compounds on p. 1, where M = cu, Ni, VO, R = R1= H, which consists in condensing a mixture of tetramethylcyclobutane with phthalonitrile in a molar ratio from 1:2 to 2:1 in the presence of chlorides of Nickel, vanadium, or copper and catalytic amounts of ammonium molybdate in high-boiling organic solvents.

4. The method of obtaining compounds on p. 1, where M = Ni, VO, which consists in condensing a mixture of tetramethylcyclobutane derivative of o-phthalic or naphthalene-2,3-dicarboxylic acid of General formula

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where R = R1= H;

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in the presence of chlorides of Nickel or vanadium, urea and catalytic amounts of ammonium molybdate in quinoline or sulfolane.

 

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