Acidamide compound based on 2-(2'-hydroxyphenyl) benzoxazole, preparation and use thereof

Abstract

The invention relates to an acid amide compound, in particular to the compound based on ESIPT, namely the acid amide compound of 2-(2'-hydroxyphenyl) benzoxazole; the compound of the invention is obtained by adding carboxylic acid and carbonyl diimidazole into a reaction solvent and reacting for 1 to 3 hours under the temperature of 25 to 40 DEG C; then adding the amine compound of the 2-(2'-hydroxyphenyl) benzoxazole and reacting for 2 to 14 hours under the temperature of 25 to 130 DEG C, filtering and purifying. The separation and purifying operations of the preparation method of the invention are simple and convenient; the reaction has no irritation and causticity and the mono-substituted, bis-substituted and tri-substituted acid amide compounds can be directly prepared. The compound of the invention has higher decomposing temperature and excellent thermal stability and can be used for preparing organic luminous materials. The structural general formula of the invention is seen in formula I, wherein, X refers to S, O or NH; when Y is equal to 1, R refers to 7-carboxyl heptane radical, etc.; when Y is equal to 2, R refers to heptane radical, etc.; when Y is equal to 3, R is triphenyl.

Description

technical field [0001] The present invention relates to amide compounds, in particular to compounds based on excited state intramolecular proton transfer, i.e. 2-(2'-hydroxyphenyl) benzoxazole (2-(2'-hydroxyphenyl) benzoxales, HBX, X=S, O or NH) amide compound, and the preparation method of the compound and its use in the preparation of organic light-emitting materials. Background technique [0002] Amide compounds are widely used in industry, pesticide, medicine, biology and so on. In the field of medicine, biological probes with strong fluorescence have also become a hot spot in the field of medical research in the fields of immuno-optics and immuno-titration. Due to the large Stokes shift and high fluorescence intensity of the excited-state intramolecular proton transfer compound, it also has great application prospects in the research of fluorescent probes connected to biomolecules. [0003] At present, the amide compounds based on the excited state intramolecular prot...

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Problems solved by technology

Because this type of reaction involves the application of acid chloride reagents such as thionyl chloride, the reaction is more irritating and corrosive, and the generated acid chloride needs to be purified before it can undergo condensation reaction with amine, which is inconvenient to operate and generally not suitable for use.

However, for the amidation of diacids or triacids with HBX-based arylamines, this method cannot achieve complete acylation

Since the primary amine 2-(4-amino-2 hydroxyphenyl) benzoxazole compound has two active groups of hydroxyl and amino groups simultaneously, the above-mentioned method exists following for the amidation reaction of diacid or triacid and the arylamine based on HBX Two problems: (1) Although it is not necessary to protect the active group hydroxyl group in a lower boiling point solvent (tetrahydrofuran), the experimental results show that this can only prepare acylation of a single carboxyl group, that is, it is only applicable to monosubstituted 2- (2'-Hydroxyphenyl) The preparation of amide compounds of benzoxazole, (2) in the high boiling point solvent (toluene), the above method involves the protection and deprotection of hydroxyl groups, and it is impossible to prepare all carboxyl groups easily. Disubstituted and trisubstituted amides

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