Benzothiazole solid-state luminescent material as well as preparation method and application thereof
A technology of benzothiazole and luminescent materials, applied in luminescent materials, chemical instruments and methods, sustainable architecture, etc., can solve problems such as poor spectral stability of devices, and achieve strong light stability and chemical stability, color tone and saturation. Good, high luminous efficiency
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[0057] The present invention provides a method for preparing a benzothiazole-based solid-state luminescent material described in the above technical solution, comprising the following steps:
[0058] Mixing aromatic amine, organic base, benzoyl chloride and chlorinated alkane solvent for condensation reaction to obtain intermediate II; the aromatic amine includes aniline, naphthylamine or anthracenamine;
[0059] Under a protective atmosphere, the intermediate II, Lawson's reagent and a cyclic organic solvent are mixed for a thiolation reaction to obtain intermediate III;
[0060] Under an oxygen atmosphere, mix the intermediate III, 2,2,6,6-tetramethylpiperidinium oxide, and a chlorinated alkane solvent, and carry out a cyclization reaction under blue light irradiation to obtain a compound having the structure shown in formula I Benzothiazole-based solid-state luminescent materials;
[0061] The structural formulas of intermediate II and intermediate III are as follows:
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Embodiment 1
[0092]
[0093] Aniline (1.00g, 10.75mmol), triethylamine (1.41g, 13.98mmol) and dichloromethane (20.0mL) were stirred and mixed evenly, and benzoyl chloride (1.66g, 11.83mmol), after the dropwise addition was completed, the condensation reaction was carried out at room temperature for 3h, and then the mixed solvent of dichloromethane and water (the volume ratio of dichloromethane and water was 2:1) was used to extract the resulting reaction solution, and the resulting organic phase After washing and drying with saturated sodium chloride solution for a second time, the dichloromethane was distilled off, and the resulting concentrated solution was subjected to column chromatography separation and purification. The eluent was a mixed eluent of petroleum ether and ethyl acetate, petroleum ether and ethyl acetate The volume ratio of the ester was 15:1 to obtain intermediate II (white solid, yield 98%).
[0094] NMR data of intermediate Ⅱ: 1 H NMR (400MHz, D-DMSO): δ10.16(s, 1H...
Embodiment 2
[0112]
[0113] 1-Naphthylamine (1.00g, 6.99mmol), triethylamine (0.92g, 9.09mmol) and dichloromethane (20.0mL) were stirred and mixed evenly, and benzoyl chloride ( 1.08g, 7.69mmol), after the dropwise addition was completed, the condensation reaction was carried out at room temperature for 3h, and then the mixed solvent of dichloromethane and water (the volume ratio of dichloromethane and water was 2:1) was used to extract the resulting reaction solution, and the obtained After washing and drying the organic phase with saturated sodium chloride solution, dichloromethane was distilled off, and the resulting concentrated solution was separated and purified by column chromatography. The eluent was a mixed eluent of petroleum ether and ethyl acetate, petroleum ether The volume ratio to ethyl acetate was 15:1 to obtain intermediate II (white solid, yield 98%).
[0114] NMR data of intermediate Ⅱ: 1H NMR (400MHz, D-DMSO): δ=10.41(s, 1H), 8.07(d, J=7.6Hz, 2H), 7.96(t, J=7.9Hz, ...
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