Synthetic method of phenylacetonitrile-based aromatic mechanical response fluorescent material
A fluorescent material and mechanical response technology, applied in the direction of luminescent materials, preparation of amino compounds, chemical instruments and methods, etc., can solve the problems of insignificant change in luminous color, high synthesis cost, and small change in the maximum absorption wavelength of materials, etc., to achieve Improve the effects of inconspicuous changes in fluorescence, low synthesis costs, and improved naked-eye recognition
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[0033] A method for synthesizing a phenylacetonitrile-based aromatic mechanically responsive fluorescent material, comprising the following structural formula:
[0034]
[0035] Wherein, R is a brominated intermediate, selected from aromatic compounds, including the following structures:
[0036]
[0037] , n is 1-4.
[0038] The synthetic method of described fluorescent material comprises the steps:
[0039] Step 1: 1 part of brominated intermediate R and 1 to 4 parts of 4-cyanomethylphenylboronic acid pinacol ester in 0.5% to 5% of tetrakistriphenylphosphopalladium catalyst and 3 to 12 parts of anhydrous potassium carbonate Catalyzed reaction in 1,4-dioxane and / or water through nitrogen protection, reaction temperature 50-100°C, reaction time 3-24h;
[0040] The protection reaction includes adding an organic solvent or water to the solution under nitrogen protection, and degassing for 2 to 5 times;
[0041] After degassing, reflux reaction under nitrogen protection ...
Embodiment 1
[0051] Preparation of Intermediate R: Tris-(4-bromophenyl)amine
[0052] Weigh triphenylamine (4.9g, 20mmol) in a 250mL round bottom flask, add 30mL DMF solution under ice-bath conditions to make it completely dissolved, weigh NBS (10.9g, 61mmol) again and dissolve it in 50mL DMF solution, the The solution was slowly added dropwise into the round bottom flask, the ice bath was removed, and the reaction system was stirred at room temperature for 12 h. After the reaction was carried out completely, 100 mL of water was added to the round-bottomed flask under ice-bath conditions, and a large amount of white solids were precipitated in the reaction flask, and 9 g of white solids (94%) were obtained after suction filtration and drying; the reaction formula was as follows:
[0053]
[0054] Preparation of fluorescent material 1
[0055] Weigh three-(4-bromophenyl)amine (I) (4.8g, 10mmol), 4-cyanomethylphenylboronic acid pinacol ester (7.5g, 31mmol), tetrakistriphenylphosphorous p...
Embodiment 2
[0058] Preparation of intermediates: tetra-(4-bromophenyl)ethylene
[0059] Weigh tetraphenylethylene (12g, 36mmol) in a 250mL round-bottomed flask, add 60mL of glacial acetic acid solution under ice-bath conditions and stir for 0.5h, add 60mL of dichloromethane, and then slowly add 14.8mL (269mmol) of bromine water to the circle In a bottom flask, the reaction system was heated to 50 °C and stirred for 2 h. After the reaction system was cooled to room temperature, the reaction solution was poured into ice water, and a large amount of solid was precipitated, washed several times with water, filtered with suction to obtain a filter cake, washed with methanol and dichloromethane, and dried to obtain 13.3 g of a white solid ( 76%), the reaction formula is as follows:
[0060]
[0061] Preparation of fluorescent material 2
[0062]Weigh tetrakis-(4-bromophenyl)ethylene (6.5g, 10mmol), 4-cyanomethylphenylboronic acid pinacol ester (10.0g, 41mmol), tetrakistriphenylphosphorous ...
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