Fluorescent material 5-{[(2-hydroxyphenyl)methyl]amino}benzene-1,3-dicarboxylic acid and synthetic method thereof
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A hydroxyphenyl and dicarboxylic acid technology, which is applied in the fields of luminescent materials, imino compound preparation, organic chemical methods, etc., can solve the problem of low fluorescence efficiency and achieve the effects of simple process, strong blue fluorescence and low cost
Inactive Publication Date: 2018-07-31
SHANGRAO NORMAL UNIV
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Both salicylaldehyde and 5-aminoisophthalic acid are fluorescent organic molecules, but their fluorescence efficiency is not high. They are modified by introducing electron-donating groups, such as the formation of salicylaldehyde and 5-aminoisophthalic acid. The prototype Schiff base is expected to obtain higher fluorescence efficiency, so it has potential application prospects in fields such as OLED and biomedicine
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[0024] The molecular formula of 5-{[(2-hydroxyphenyl) methyl] amino}benzene-1,3-dicarboxylic acid involved in the present invention is: C 15 h 13 NO 5 , Molecular weight: 287.26. The crystal structure data is shown in Table 1, the bond length data is shown in Table 2, and the bond angle data is shown in Table 3.
[0025] 5-{[(2-hydroxyphenyl)methyl]amino}benzene-1,3-dicarboxylic acid is synthesized in the following steps:
[0026] (1) At room temperature, put 20mmol (3.583g) of 5-aminoisophthalic acid in a 250mL flask, add 10mL of N,N-dimethylformamide and stir to dissolve completely, then add 60mL of absolute ethanol in sequence and 20mmol (2.442g) salicylaldehyde, after continuous stirring for one day, a large amount of orange-red precipitate was separated out, then filtered and vacuum-dried to obtain Schiff base 5-{[(2-hydroxyphenyl)methylene]amino}benzene- 1,3-dicarboxylic acid 4.96g (about 87% yield).
[0027] (2) Under continuous magnetic stirring, add 20mL ethanol,...
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Abstract
The invention discloses a blue fluorescent material 5-{[(2-hydroxyphenyl)methyl]amino}benzene-1,3-dicarboxylic acid and a synthetic method thereof. The molecular formula of the 5-{[(2-hydroxyphenyl)methyl] amino}benzene-1,3-dicarboxylic acid is C15H13NO5, the molecular weight is 287.26, and the fluorescence peak of 5-{[(2-hydroxyphenyl)methyl]amino}benzene-1,3-dicarboxylic acid powder is at 444 nm. The synthesis steps are as follows: (1) after dissolving 5-aminoisophthalic acid in N,N-dimethylformamide while normal temperature stirring, sequentially adding anhydrous ethanol and salicylaldehyde, one day after, filtering, washing and drying to obtain orange-red Schiff base 5-{[(2-hydroxyphenyl) methylene] amino}benzene-1,3-dicarboxylic acid; (2) mixing and stirring a certain proportion of ethanol, NaOH, the orange-red Schiff base and a N, N-dimethylformamide solution containing NaBH4, after the reactant is whitened, adding hydrochloric acid to adjust the pH, and filtering, washing and drying to obtain white reduced Schiff base 5-{[(2-hydroxyphenyl)methyl]amino}benzene-1,3-dicarboxylic acid. The method has the advantages of simple process, low cost, good repeatability, high product purity and yield, strong fluorescence and narrow half-peak width.
Description
technical field [0001] The invention relates to an organic material 5-{[(2-hydroxyphenyl)methyl]amino}benzene-1,3-dicarboxylic acid with blue fluorescence and a synthesis method thereof. Background technique [0002] With the increasingly wide application in the fields of display lighting and biomedical fluorescent marking, luminescent materials have an increasingly important impact on people's production and life. However, at present, many luminescent materials, especially blue light materials, have problems such as low luminous efficiency or high cost. For example, despite the high luminous efficiency of noble metal complexes reported in recent years, the production cost is usually high, and the synthesis process is often complicated. Therefore, the development of strong blue light materials with low cost and relatively simple synthesis process is a difficult problem for the related research and popularization and application of advanced display lighting technologies such ...
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