Organic compound containing Schiff base unit and preparation method and application thereof
A technology of organic compounds and compounds, applied in organic chemistry, chemical instruments and methods, fluorescence/phosphorescence, etc., can solve the problems of large-scale instruments, high detection costs, and limited applications, and achieve high reproducibility, high sensitivity, and post-processing Handle simple effects
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[0031] The present invention also provides the preparation method of the organic compound containing Schiff base unit shown in formula (I), comprising:
[0032] Step (1): Dissolving 5-bromosalicylaldehyde in reaction solvent I, adding hydrazine hydrate dropwise to reflux reaction to obtain compound I;
[0033] Wherein, the reaction formula of 5-bromosalicylaldehyde and hydrazine hydrate is as follows:
[0034]
[0035] The reaction solvent I is selected from one or a combination of ethanol, methanol, acetonitrile, N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), ethyl acetate and isopropanol; preferably Use ethanol, DMF or DMSO, more preferably ethanol with strong polarity and low toxicity as the reaction solvent.
[0036] In order to promote the full progress of the reaction, the ratio of the amount of 5-bromosalicylaldehyde to hydrazine hydrate is 1:1-1.5, preferably 1:1-1.3, for example 1:1.2.
[0037] Further, the molar volume ratio of the amount of 5-bromosalic...
Embodiment 1
[0074] Dissolve 5-bromosalicylaldehyde (2g, 10mmol) in 100ml of ethanol, add hydrazine hydrate (0.588g, 12mmol) dropwise, reflux for two hours, cool to room temperature, filter with suction, and dry to obtain compound Ⅰ.
[0075] Dissolve compound I (3.98g, 10mmol) and 3-boronic acid formaldehyde (3.15g, 21mmol) in 100ml of N,N-dimethylformamide (DMF), and add potassium carbonate (2.76g, 20mmol) under stirring React with tetrakistriphenylphosphinepalladium (0.347g) at 140°C for 24 hours under the protection of nitrogen. After the reaction was completed, it was cooled to room temperature, filtered with suction, and dried to obtain compound II.
[0076] Dissolve compound II (2.06g, 12mmol) and 9,10-phenanthrenequinone (5g, 24mmol) in 100ml ethanol solution, add ammonium acetate (15g, 0.195mol) at 90°C under stirring, and react for 3 hours. The mixture was cooled to room temperature, and the precipitate was filtered. The precipitate was collected, washed with water and dried in...
Embodiment 2
[0081] It is basically the same as Example 1, the only difference is:
[0082] Sodium carbonate (2.10 g, 20 mmol) was added to synthesize compound II.
[0083] The proton nuclear magnetic resonance spectrum data are basically similar to Example 1.
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