Organic fluorescent material with deep information hiding function, preparation and application
A fluorescent material and deep technology, applied in the field of organic fluorescent materials, can solve problems such as difficulties, multiple changes in fluorescence intensity or color, and achieve the effect of being conducive to identification, fluorescence intensity and color contrast.
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[0053] A method of preparing an organic fluorescent material having a deep hidden function, including the following steps:
[0054] S1, 9-hexyl-9H-carbazole, 4-formylbenzene boric acid, potassium carbonate, deionized water and ethylene glycol dimethyl ether under the conditions of palladium catalyst catalysts in a palladium catalytic agent, SUZUKI coupling Reaction, the intermediate aromatic aldehyde represented by the following structure is obtained:
[0055]
[0056] In R 1 C 6 -C 12 The saturated alkyl, 1-4 bits and 5-8 bits of carbazole were attached to 4-methylbenzaldehyde;
[0057] S2, the intermediate aromatic dialdaldehyde prepared by S1 with 1,3-indanntane in tetrahydrofuran and super dry anhydrous ethanol mixed solution under the conditions of alkaline catalyst catalyst, resulting in carbazole For the electron donor group, the phenyl group is a conjugate bridge, 1,3-indanidanone as an organic fluorescent material of the electron acceptor.
[0058] In the present embodi...
Embodiment 1
[0071] (1) Intermediate aromatic diehyde synthesis route
[0072]
[0073] 2,7-dibromo 9-hexyl-9H-carbazole (2 mmol, 0.8 g), 4-formylbenzonic acid (4.4 mmol, 0.66 g), anhydrous potassium carbonate (20 mmol, 2.76 g), four (triphenyl Phosphine) palladium (0.2 mmol, 0.23 g), deionized water 5 ml, ethylene glycol dimethyl ether 20 ml, add 100 ml of three flasks, repeated vacuum, 3 times, heating to 105 ° C, stirred vigorously for 12 h. After the reaction was completed, 80 ml of water was quenched, dichloromethane extraction, and the organic phase was dried over anhydrous magnesium sulfate, filtered. Decapulsted and evaporated, the crude product was separated by chromatography column, and the eluent was petroleum ether and ethyl acetate, and ratio 5: 1. The resulting crude product was recrystallized from anhydrous ethanol to give an intermediate aromatic metallide light yellow green powder 0.75 g, and the yield was 81%.
[0074] 1 H NMR (600MHz, CDCL 3 Δ10.10 (S, 2H), 8.21 (D, J = 8....
Embodiment 2
[0085] (1) Intermediate aromatic diehyde synthesis route
[0086]
[0087] 2,6-dibromo 9-hexyl-9H-carbazole (2 mmol, 0.8 g), 4-formylbenzonic acid (4.4 mmol, 0.66 g), potassium carbonate (20 mmol, 2.76 g), four (triphenyl Phosphine) palladium (0.2 mmol, 0.23 g), deionized water 5 ml, ethylene glycol dimethyl ether 20 ml, add 100 ml of three flasks, repeated vacuum, 3 times, heating to 105 ° C, stirred vigorously for 12 h. After the reaction was completed, 80 ml of water was quenched, dichloromethane extraction, and the organic phase was dried over anhydrous magnesium sulfate, filtered. Decapulsted and evaporated, the crude product was separated by chromatography column, and the eluent was petroleum ether and ethyl acetate, and ratio 5: 1. The resulting crude product was recrystallized with anhydrous ethanol to give an intermediate aromatic diehyde light yellow green powder 0.65 g, and the yield was 70%.
[0088] 1 H NMR (600MHz, CDCL 3 Δ10.08 (S, 2H), 8.16 (D, J = 8.0 Hz, 2H), 8...
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