Polyazomethine based on 5,5'-methylenebisacrylamide aldehyde and diamine fluorophore

 

(57) Abstract:

The inventive proposed new phosphors - polyazomethine based on 5,5'-methylenebisacrylamide aldehyde and 9,10-bis-(p-AMINOPHENYL)anthracene (I) or on the basis of 5.5*-methylenebisacrylamide aldehyde and chloride unsubstituted, rhodamine (II). New phosphors obtained by polycondensation of a diamine of the fluorophore with 5,5'-methylenebisacrylamide aldehyde in the environment of N-methylpyrrolidone at 140 - 150oC in a stream of argon in vacuum (100 mm RT.CT.) for 5 to 7 hours. The resulting polymers are powder light brown colour /polymer 1/ and maroon color /polymer 2/. According to the dynamic thermogravimetric analysis in air temperature of the beginning of decomposition of these substances reaches 400oC, the temperature at which deformation is 250 - 340oC. Data IR spectrometry confirmed the presence of characteristic polyazomethines strip = 1620 cm-1. table 1.

The invention relates to organic chemistry and is a new polymer-based 5,5'-methylenebisacrylamide aldehyde and diamine fluorophore General formula:

[=F=CH-C6H40-CH2-C6H40-CH=n,

where n= 6-9,

< / BR>
The claimed connection most effective is e active element in laser technology.

The specified connection, its properties are not described in literature.

Known polymer phosphors with different structures [1,2] obtained by polycondensation of diamines with dialdehyde. However, these compounds do not exhibit fluorescence in powders and solutions at room temperatures.

Known polyazomethine based on 9,10-bis-(n-lipogenic)anthracene and terephthalic aldehyde [3] which is high-efficiency phosphor, but he only soluble in formic acid and sulphuric acid, which significantly complicates its practical use.

The task of the invention to provide a new polymer soluble in aprotic organic solvents and having a high quantum yield of luminescence.

The problem is solved in that the substance of the mentioned formula is obtained by polycondensation of diamines fluorophores with 5,5'-methylenebisacrylamide aldehyde in the environment of N-methylpyrrolidone at T=140-150oC in a stream of argon, vacuum (100 mm RT. St) for 5-7 hours At the end of the reaction the reaction mixture is then poured into the precipitator, the precipitate is filtered off, periostat, dried at 100oC/1 mm RT.article within 20 am

The resulting polymers are powder the ski thermogravimetric analysis in air temperature of the beginning of decomposition of these substances reaches 400oC, the temperature at which deformation is 250-340oC. Data IR spectrometry confirmed the presence of characteristic polyazomethines strip = 1620 cm-1.

Example 1. Polyazomethine based on 5,5'-methylenebisacrylamide aldehyde and 9,10-bis-(n-AMINOPHENYL)anthracene.

In a three-neck flask equipped with thermometer, capillary to enter an inert gas, fall asleep 0,381 g (0,0011 M) 9,10-bis(n-AMINOPHENYL)anthracene and fill of 13.75 ml of N-methylpyrrolidone. By passing an inert gas is heated the reaction mass to 70oC to dissolve 9,10-bis-(p-AMINOPHENYL)anthracene. Then fall asleep 0,271 g (0,0011 M ) 5,5'-methylenebisacrylamide aldehyde and conduct the reaction at T 140-150oC for 5 h in a current of inert gas under vacuum (100 mm RT. Art.). Upon completion of the reaction, the reaction mixture was poured into ethyl alcohol, precipitated precipitate is filtered off, washed with alcohol and periostat from dimethylformamide in acetone. The polymer is dried in vacuum. Gain of 0.51 g(yield-80%) of product.

The formula of the polymer

< / BR>
where n 6-9.

The degree of polymerization (n) was determined from data on the size srednevekovoi molecular weight, obtained by the method of the unsteady sedimentation equilibrium method Archibald) [4]

The floor is alcohol, acetone is 0,028 g/DL, solubility in dimethylformamide 0.28 g/DL. The polymer prototype in these solvents do not dissolve.

Given the viscosity of the polymer solution in N-organic at 20oC of 0.14 DL/g

The data of elemental analysis (%):

Calculated With 84,82; H 4,82; N 4,82.

Found, C 79,69; H Of 5.05; N 4,00.

Example 2. Polyazomethine based on 5,5'-methylenebisacrylamide aldehyde and chloride unsubstituted rhodamine.

In a three-neck flask equipped with thermometer, capillary to enter an inert gas, fall asleep 0.50 g (0,00125 M ) chloride unsubstituted rhodamine. The reaction mass is heated to 70oC to dissolve the chloride unsubstituted rhodamine. Then fall asleep 0.32 g (0,00125 M ) 5,5'-methylenebisacrylamide aldehyde and conduct the reaction at T=140-150oC for 7 h in a current of inert gas under vacuum (100 mm RT. Art.). Upon completion of the reaction, the reaction mixture was poured into acetone, precipitated precipitate is filtered off, washed with acetone and periostat of N-methylpyrrolidone in a mixture of sulphuric ether: ethanol (2:1, by vol.). The polymer is dried in vacuum. Obtain 0.6 g(yield-82%) of product.

The formula of the polymer:

< / BR>
where n 6 9

The degree of polymerization was determined from data on the size of redliner soluble in aprotic solvents, in formic and sulfuric acids. The solubility of the polymer in ethyl alcohol, acetone is 0.025 g/DL, solubility in dimethylformamide, 0.5 g/DL. The polymer prototype in these solvents do not dissolve.

Given the viscosity of the polymer solution in N-organic at 25oC of 0.14 DL/g

Elemental analysis data.

Calculated With 71,61; H To 3.92; N 4,78.

Found, C 70,11; H Of 3.97; N 3,83.

The table shows the spectral-luminescent characteristics of the obtained polyazomethines.

Values of the quantum luminescence outputs defined for concentrations C=110(-5)-110(-3) mol/l at T=20oC.

The use of the claimed substance allows to obtain an effective y polymers, soluble in aprotic organic solvents, while similar y polyazomethine they are not soluble in Addition, the inventive polymers are characterized by high values of the quantum outputs the luminescence of solutions in aprotic solvents in the temperature range 20-50oC (see table).

Polyazomethine based on 5,5'-methylenebisacrylamide aldehyde and diamine-fluorophore General formula

< / BR>
where n 6 9;

F -

 

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