SU825523A1 - 4-/1-(4'-formylphenyl)-5-phenyl-2-pyrazolinyl-3/-naphthalic anhydride as yellow organic luminophore - Google Patents

Description

The invention relates to a novel chemical compound, specifically to 4-fl- (4-formylphenyl) -5-phenyl-2-pyrazolinyl-3-naphthalic anhydride: formulas which can be used as an organic yellow phosphor. There are 4- (1-phenyl-5-aryl-2-pyrazolip-3) -1, 8-naphthalite acids and the corresponding anhydrides, which are obtained by condensation of the corresponding 4-dinamoylnaphthalic anhydrides with fekilhydrazine when heated in an alcohol-alkaline medium. They are used for dyeing polymeric materials, as well as intermediate products for the synthesis of effective phosphors of orange-red and red luminescence. Known 4- (1-phenyl-5-aryl-2-pyrazolinyl-3) -naphthalic anhydrides luminesce in organic solvents and polymer matrices in the orange-red region of the spectrum of I-nciv luminescence in toluene 580-590. The disadvantage of these phosphors is relatively low quantum yield of fluorescence (0.30). Phosphor;. yellow luminescence (cAvndtx; fluorescence in the region of 535-560) among the known derivatives of 4- (1-phenyl-5-arrowyl-2-pyrazolinyl-3) naphthalic anhydrides is not described. Phosphors of a yellow luminescence are known, of which the most effective3. 4-methoxy-1,8 naphthoylen-1, 2-benegimidazole of the formula: C – CHAc is widely used for luminescent dyeing of plastics, having a luminescence in toluene 535 named G27. The disadvantage of this phosphor is the relatively low fluorescence quantum yield in carbohydrate solvents (the quantum yield of fluorescence in toluene is 0.34) and a greenish tint, which limits its use to produce pure yellow luminescent colors. The purpose of the invention is to obtain 4- {1-Fensch-1-5-arnp-2-11 and rasolinyl-3) -aftalene anhydrides in a series of derivatives; 3 dow of new compounds luminescent in the yellow region of the spectrum and possessing a high quantum yield of fluorescence. The goal is achieved by the fact that the new 4-G1-4-formylphenyl-5-phenyl-2-pyrazolinyl-3J-naphthalic acid hydride of formula (I) is used as an organic yellow phosphor. This compound is obtained by direct formylation of the corresponding 4- (1,5-diphenyl-2-pyrazolinyl-3) -aphthalic anhydride with dimethylformamide in the presence of phosphorus hormone at 70-100 ° C, followed by hydrolytic decomposition of the intermediate. The table shows the spectral and fluorescent characteristics of the proposed and known phosphors in terms of their structure and region of luminescence.

342 482

.

345 495

The table shows that the new phosphor 4-p- (D-formylphenyl) -5-phenyl-2-pyrazolinyl-3-naphthalic an2, 42

555

0.80 2.68

0.30

585

1.58 1.20

Claims (2)

hydride fluoresces in the spectral region, which is close to the spectral region of the known yellow luminophores 5 - 4-methoxy-1,8-naftoyylene-l, 2-6enzimidazole, but compared with the latter has a much higher quantum yield of fluorescence. However, the luminescence maximum of the proposed phosphor is shifted by 20 nm to a longer wavelength region compared to the known one, due to which its solutions are devoid of the green tint characteristic of 4-methoxy-1,8-naphthoylen-1,2-benzimide azole. . Example 1. Getting 4-fl- (4-formylphenyl) -2-pyrazolinyl-3 naphthalic anhydride. To a solution of 7.6 g of 4- (1,5-diphenyl-2-pyrazolinyl-3) -naphthalic anhydride heated to 70 ° C, 7 ml of phosphorus oxychloride was added dropwise with stirring. The reaction mixture is heated to 100 ° C and maintained at this temperature for 4 hours. The solution is cooled to room temperature and the viscous mass is poured onto 200 g of ice. Mix well and leave for 12-14 hours. The precipitate is filtered off, washed with water until neutral wash water and dried. After chromatography of the benzene solution on alumina and subsequent recrystallization from a mixture of ethanol and chlorobenzene (10: 1), the product is obtained in the form of a red crystalline powder with a melting point of 20-202 ° C. The output of 3.8 g (50%). Nayden,%: N 6.41 Calculated,%: N 6.27 IR spectrum in KBr: -IQQ (aldehyde group) 1689 cm; Ico (anhydrite group) 1740, 1780 C – N 1600 cm. toluene 482 them (long wavelength band); in 26,800 l cm; I fluorescence in toluene 555 nm; fluorescence quantum yield 0.8 .. 3 Example 2. Preparation of an aqueous solution of 4-Cl- (4-formylphenyl) -5-phenyl-2-pyrazolinyl-3} -naphthalene-1, 8-dicarboxylic acid sodium salt. 0.005 g of (4-formylphenyl) -5-fensh1-2-pyrazolinyl-37-naphthalic anhydride is added to 10 ml of 5% aqueous sodium hydroxide solution. With weak heating and stirring, it is complete dissolution. An intensely fluorescent yellow-green solution of fluorescence Emission nm is obtained. The same spectral-luminescent properties of anhydrides and corresponding salts also have compounds with 5-A-4-toliol, 4-annsyl, 4-chlorophenyl, as for l, 3, 5-triapyl-2-pyrazolinov is well known that the indicated substituents in position 5 do not affect the fluorescence region and its quantum yield. Claims of the invention 4-P- (4-Formylphenyl) -5-phenyl-2-pyrazolins-1-31-naphthalic anhydride of the formula as an organic lyumin. yellow glow. Sources of information, rintye taken into account in the examination 1. The author's certificate of the USSR 326209, cl. From 09 to 11/06, 1972. 2. USSR author's certificate J76299, cl. From 09 K 11/06, 1965 prototype).