SU702015A1 - 4-(5-aryloxazolyl-2) dimethylphthalate derivatives as organic luminophores - Google Patents

Description

(54) 4- (5-Aryloxazole-2) Derivatives of Dimethyl Phthalate as Organic Luminophores

The invention relates to novel chemical compounds, specifically, to 4- (5-aryloxaolyl-2) dimethyl phthalate derivative. The proposed compound possesses the properties of organic phosphors. This property suggests the possibility of using 4- (5-aryloxazolyl-2) dimethyl phthalate derivatives as luminescent components in the production of day-time fluorescent pigments and inks that are stable in pH changes in the production of organic scintillas. Trr, as optical brighteners, for dyeing polymeric materials and other purposes. The organic phosphor of 4- (5-E and iloxazolyl-2) phthalic acids fluorescent in the blue region of the spectrum (1J. These compounds, due to the presence of phthalic acid in their molecule, could easily be converted into salts. on the one hand, this is their advantage, since in the form of salts they can be successfully used as a solution of organic phosphorino qiopOB.On the other hand, this property limits their use in the production of luminescent materials, since In the 4- (5-aryloxazolyl-2) salt, phthalic acids change the color of the luminescence. In addition, they practically do not dissolve in hydrocarbon solvents, and in dimethylformamide, in which the days dissolve, they have a relatively low quantum yield (0, 1-0.4). The aim of the invention is to improve the properties of the organic phosphor, in particular, to increase the quantum yield and expand the field of use of the gamenoforoe in the national household. The goal is achieved by a new chemical structure — expressed by the general formula 1J CooCHj COOCHj; where Ar is C “, H ,, CHj — C H.,, CI -, 9 —U t. Compounds of formula 1 are well soluble in various, including carbon,

Jt PoflHHjc, solvents, and are stable under conditions of varying pif of the medium. The spectral region in which they luminesce is close to that in which the corresponding 4- (5-aryl-6xazolyl-2) phthalic acids emit light, but in terms of quantum yield they significantly exceed the latter. Thus, the absolute quantum yield of (p-chlorophenyl) oxazolyl-2 dimethyl phthalate is 0.62, while the quantum yield of (p-chlorophenyl) oxazolyl-2 phthalic acid is only 0.10. Thus, the proposed compounds have an abnormally high quantum yield, which is very significant when used as an organic phosphor.

Compounds of formula 1, 4- (5-aryloxazolyl-2) dimethyl phthalate derivatives are obtained by treating an alcohol-alkaline solution of the corresponding acid OR of the anhydride with dimethyl sulfate at 35-40 °,

Example 1. Preparation of 4- (5- 1 -phenyloxazolyl-2) dimethyl phthalate.

To (0.01 mol) suspension of 3.1 g of 4- (5-phenyloxazolyl-2) phthalic acid (or anhydride) in 30 m of ethyl alcohol was added 5 ml of dimethyl sulfate, and then with vigorous stirring and a temperature of 35-40 at the bottom are a solution of 6 g of caustic: ali in 30 ml of methyl alcohol. After adding all the alkali, the mixture is held at room temperature and for 1 hour, poured into 300 ml of WATER, the precipitate is filtered, washed with water, dried and recrystallized from methanol.

Output: Output - 2.5 g (74%), so pl. 142 °.

Found,%: C 67.2; rf 4,3; N 4, 2; .

C H NOg:

Calculated,%: C 67.6; rf 4,5; . N 4, h; : ---- - --------- - - - ---- - - -L max, luminescence in toluene is 405 nm.

J Absolute lute quantum. output in toluene - 0.63.

EXAMPLE 2. Preparation of (p-t6l} 1l) oxazolyl-2 dimethyl phthalate. - - - - - - Similar to example 1. Yield from 3.1 g. (P-tolyl) oxazolyl-2 phthalic anhydride 2.8 g (80%),

mp.131.5 °.

h1a11%,%: C 68.2; H 4.9; N 4.0.

 , .-.--- Calculated,%: C 68.4; A 4.8; N 4.0:. :: ..;.; L ... ; ; ; X max, luminescence in toluene - 412 nN-.

The absolute quantum yield in toluene is 0.67 ..,

Example 3. Preparation of 4-f5-: (p methoxy phenyl) oxazolyl-2 dimethi (talate. W.-,;

Analogic example 1. The yield of 3.3 g (p-methoxyphenyl) oxazolyl-2 ft: alev Of Of anhydride 2, 9 g (79%), so pl. 130 °.

Found: C 65.3; H 4.6; N 4.0.

C2oH ,, NO.

Calculated,%: C 65.5; And 4.6; N 3, A. max. Liu of otsentsii in toluene - 425 nm.,

The absolute quantum yield in toluene is O, 74.

Example 4. Preparation of 4-15- (p-chlorophenyl) oxazolyl-2 dimethyl phthalate.

, it; .

...

Analogously to example 1. Yield from 3.3 g (p-chlorophenyl) oxazolyl-2 phthalic anhydride 3.0 g (81%), so pl. 135 ° ..

 Found,%: C 61.5; H 3.8; From 9.8

N. 4.0,

C, H CINOj .... Calculated,%: C 61.3; H 3.8;

C, 9.6; N 3.8.

L max, luminescence in toluene - 405 nm.

The absolute quantum yield in toluene is 0.60.

Example 5. Obtaining (p-bipheny. Lil) oxazolyl-2 dimethyl phthalate. . ,

Analogously to example 1. Yield from 3.7 g (p-biphenylyl) oxazolyl-2 phthalic anhydride, 3.3 g (80%),

m.p. 170 °. : -: Found,%: C 72.9; H 4.5; N 3.3;

 five

Calculated,%: C 72.7; H 4.6; N 3,

X max, luminescence in toluene - 420 nm.

The absolute quantum yield in toluene is 0.61. . . . -:.

Example 6. Obtaining (2-naphthyloxazolyl-2 dimethyl phthalate

Analogously to Example 1. A 3,1 g (2-naphthyl) oxazolyl-2 phthalic anhydride blend of 3.1 g (80%), m.p. 139 °.

Yaydeno,%: C 71.5; And 4.6; N 3.7.

.

Calculated,%: C 71.2; H 4.4; N 3, L. max; luminescence in toluene - 429 them.

Absolute quantum yield and toluene -0.84. .:

Claims (1)

 The following table shows the luminescent characteristics of the proposed phosphors and are previously known to be similar in structure. .Cabled Chemical Compounds -NCooCH3. ,, s; # L-COOCH3 ЧХ СООСн Known compounds -N -tOOH Invention 4- (5-Aryloxazolyl-2) produced dimethylphthalate, of the general formula, / - and l.cooCH-s, 702015 COOCHJ SOUPS 1, USSR Author's Certificate No. 558914, class C 09 K 11/06, 1977.