Heterocyclic o-dicarbonitrile

 

(57) Abstract:

Describes new heterocyclic o-dicarbonitrile formula I,

where

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< / BR>
which can be used to obtain hexatriene-fluorophores, as a fragment of the donor to obtain hexatriene-bifluorophors besed and hexatriene-trifluoroprop. Such hexatriene promising for use as active media of liquid and solid lasers, scintillators, especially for indication of hard radiation, for the transformation of shortwave radiation in the long wavelength in the transmission of information through fiber-optic communication lines, to increase the power of solar panels for protection of securities, for the manufacture of billboards etc., 2 tab.

The invention relates to the field of production of new heterocyclic o-dicarbonitriles. o-Dicarbonitrile can be used to obtain hexatriene-fluorophores as a fragment of the donor to obtain hexatriene-bifluorophors besed and hexatriene-trifluoroprop. Such hexatriene promising for use as active media of liquid and solid lasers, scintillators, especially for indicating hard inlocuieste lines, to increase the power of solar panels for protection of securities, for the manufacture of billboards, etc.

Know the use of phthalonitrile together with the unsubstituted rhodamine to obtain hexatriene. (Sealing C. A., Feofanov B. N., Lambs N.N. and other Polyhexamethylene based heterocyclic diamines. // Polymer sciense ser. Conn. B. 1988 So 30 4. C. 286-291).

This hexatrien has the following spectral characteristics: band emission 540 nm when excited in the band 312 nm.

The problem solved by the present invention is the obtaining of new heterocyclic o-dicarbonitriles.

Come heterocyclic o-dicarbonitrile General formula

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where

< / BR>
The claimed compounds are: 4-(1H-1,2,3-benzotriazol-1-yl)-5-nitrophthalonitrile (I):

< / BR>
4-(1H-oil[2,3-d][1,2,3]triazole-1-yl)-5-nitrophthalonitrile (II):

< / BR>
The connection data is obtained by reaction of aromatic nucleophilic substitution of the bromine atom in the 4-bromo-5-nitrophthalonitrile on the nucleophile, which is formed in situ in the presence of potassium carbonate from the corresponding triazole according to the scheme:

< / BR>
This reaction is carried out in DMF in the presence of potassium carbonate at a temperature of 20...302CO3and 1.19 g (0.01 mol) of benzotriazole. The resulting mixture was intensively stirred at 20...30oWith over 1...1.5 h and poured into 100 ml of water. The sediment-target product is filtered off, washed with water and crystallized from DMF.

Obtain 2.85 g (83,8% of theory of 4-(1H-1,2,3-benzotriazol-1-yl)-5-nitrophthalonitrile. It is a yellow crystalline powder, MP. 234...236oC.

Found, %: C 57,77; N 2,15; N 28,62.

Calculated, %: 57,94; N 2,08; N 28,95.

EQ.327,2;

C14H6N6O2< / BR>
1H NMR ([2H6] DMSO):, M. D.: 9.05 (s, 1H), 8.79 (s, 1H), 7.96 (m, 2H, J= 16 Hz), 7.55 (m, 2H, J=16 Hz).

Example 2. The reaction is carried out analogously to example 1, except that the reagent (benzotriazole) used 1H-oil[2,3-d][1,2,3] triazole. The conditions and results of the synthesis are presented in table. 1.

Example 3. Condensation of I with rhodamine 123. In a flask equipped with stirrer, thermometer, reflux condenser and capillary to enter argon, download 2.9 g (0.01 mol) I, 3.8 g (0.01 mol) of rhodamine 123 and 10 g of phenol. The resulting mixture was slowly heated with stirring to 175... 185oC. the Resulting melt is maintained with stirring in a stream of argon to Excel is filtered off, washed with 3 ml of ethanol and dried at T=60oC for 2 h, and then in vacuum over P2ABOUT5. Get 5,76 g (93% of theory) of hexatriene.

Found, %: C 67,81; N 3,43; N 15,80.

Calculated, %: C 67,84; N 3,42; N 15,83.

WITH70H42N114O10< / BR>
The IR spectrum of hexatriene no band 2220 cm-1- CN, there is a band - 680 cm-1-C=N -.

The structural formula of hexatriene derived from I and rhodamine 123:

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Macroheterocycles derived from I and rhodamine 123 has the following spectral characteristics: the maximum of a spectrum of radiation - 398 nm at the maxima of the absorption spectrum of 351 and 390 nm.

Example 4. The reaction is carried out analogously to example 3, except that instead of phthalonitrile I used an equimolar amount of phthalonitrile II.

The conditions and results of the synthesis and spectral characteristics of the received macroheterocycles are given in table. 2.

Heterocyclic o-dicarbonitrile General formula

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where



 

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