Preparation method of spiropyrane photochromic material
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A technology of photochromic materials and spiropyrans, which is applied in the direction of color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of complex operation and unfriendly environment, and achieve simple reaction operation and high atom utilization rate , The effect of safe and low toxicity of raw materials
Active Publication Date: 2020-09-01
浙大宁波理工学院
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[0006] In addition to this route, other types of N-alkylating reagents can be used in the improved reaction, such as halogenated alkanes, dialkyl sulfates, and trifluorosulfonates, but this type of optimization work has not Fundamentally solve the problems of unfriendly environment, complicated operation and efficient response
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Embodiment 1
[0025] Example 1 Synthesis of 5'-fluoro-1',3',3'-trimethylspiro[chromene-2,2'-indoline]
[0026] In a 25mL dry three-necked flask, weigh sodium hydroxide (60mg, 1.5mmol, 3eq), 5-fluoro-2,3,3-trimethyl-3-H-indole (89mg, 0.5mmol), and use Sulfuryl fluoride replaced the gas in the reaction system; then added 1,4-dioxane (4mL), methanol (80μL, 2mmol, 4eq), and stirred at room temperature for 3 hours until the conversion of the raw materials was complete; then replaced the reaction system with nitrogen Gas, add ethanol (5mL) dehydrating agent, salicylaldehyde (52μL, 0.5mmol, 1eq), reflux and stir for 5 hours.
[0027] After the reaction was completed, it was quenched with water, extracted with dichloromethane, and the organic phase was washed with saturated brine, washed with Na 2 SO 4 Concentrated after drying, followed by silica gel column purification (PE:EA=50:1, R f =0.4) to obtain 105 mg of yellow solid, yield 71%.
[0028] 1 H NMR (500MHz, CDCl 3 )δ7.10(td, J=7.7,1.7Hz...
Embodiment 2
[0031] Example 2 Synthesis of 5'-fluoro-1',3',3'-trimethylspiro[chromene-2,2'-indoline]
[0032] The method is the same as in Example 1, except that sodium hydroxide is replaced by cesium carbonate, the solvent is dimethyl sulfoxide, and the yield is 65%.
Embodiment 3
[0033] Example 3 Synthesis of 5'-fluoro-1',3',3'-trimethylspiro[chromene-2,2'-indoline]
[0034] The method is the same as in Example 1, except that sodium hydroxide is replaced by potassium hydroxide, the solvent is dichloromethane, and the yield is 60%.
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Abstract
The invention discloses a preparation method of a spiropyrane photochromic material. The preparation method comprises the following steps: taking a 2, 3, 3-trimethyl-3H-indole compound as an initiator, taking methyl alcohol as an alkylation reagent, carrying out alkylation reaction at room temperature in the presence of a sulfuryl fluoride atmosphere, an acid-binding agent and an organic solvent,adding salicylaldehyde as shown in a formula 3 and ethanol into an obtained system after the reaction is finished, heating to reflux reaction, and separating and purifying a reaction product to obtainthe spiropyrane photochromic material as shown in a formula 1. According to the method, a safe and low-toxicity alcohol compound is used as an alkylation reagent, synthesis of the spiropyrane photochromic material is completed through a one-pot two-step reaction under in-situ activation of low-toxicity sulfuryl fluoride gas, and the method has the advantages of being mild in reaction condition, easy and convenient to operate and high in yield.
Description
technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of a spiropyran photochromic material. Background technique [0002] Photochromism materials refer to a class of substances whose color can change reversibly under the action of light. Spiropyran-based photochromic materials are currently one of the most widely studied color-changing materials, and are used in fields including "smart electrodes", light-controlled enzyme activity, light-controlled release of therapeutic agents, and photo-controlled dissolution of nanoparticles. In the spiropyran compound structure, two groups share a sp 3 The condensed ring structure of hybridized carbon atoms forms a spiro ring structure, which is orthogonal to each other and does not form a conjugated system. The specific compound structure formula 1 and the photochromic process are shown in the figure: [0003] [0004] In the existing technical route, the sy...
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