A smart gel with light-regulated gel-sol transition and its application
A technology of intelligent gel and light regulation, applied in the direction of organic chemistry, can solve the problems of poor material performance and low oxidation efficiency, and achieve the effects of good mechanical properties and swelling ability, high product purity, and excellent switching performance
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[0053] One of the crosslinking agents having the above general structure, 2-bromo-4,4'-dipropargyloxyhexaarylbiimidazole, its synthesis method comprises the following steps:
[0054] (1) Mix and disperse 4,4'-dihydroxybenzil, 3-bromopropyne and acid-binding agent potassium carbonate in N,N'-dimethyl In formamide, the acid-binding agent can be one or more of potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide. React at room temperature (20-30°C) for 1-3 days, track and monitor with thin-layer chromatography during the reaction, filter to remove excess potassium carbonate after the reaction is completed, extract the remaining reaction solution with chloroform and wash with water, collect the organic layer with a cyclone The final product 4,4'-dipropargyl benzil was spin-dried in an evaporator and further purified by column chromatography; the acid-binding agent could also be sodium carbonate, potassium hydroxide or sodium hydroxide.
[0055] (2) Mix ...
Embodiment 1
[0069] This example provides a synthetic method of 2-bromo-4,4'-dipropargyloxyhexaarylbiimidazole, and its synthetic route is as follows figure 1 shown, including the following steps:
[0070] (1) Synthesis of 4,4'-dipropargylbenzil
[0071]
[0072] In a 100ml two-necked flask, 4,4'-dihydroxybenzil (2.42g, 10mmol), 3-bromopropyne (3ml, 40mmol) and potassium carbonate (5.52g, 40mmol) were dispersed in 50ml N,N '-Dimethylformamide. The reaction mixture was stirred at room temperature for 2 days. Follow and monitor with thin-layer chromatography in the reaction process, after the completion of the reaction, first filter to remove excess potassium carbonate, and the remaining reaction solution is extracted with chloroform and washed with water, and the organic layer is collected and spin-dried with a rotary evaporator and passed through column chromatography (mobile phase: first select Ethyl acetate: petroleum ether = 1:4, gradually increase the polarity to 1:1, and finally u...
Embodiment 2
[0081] This example provides a method for synthesizing smart gels using 2-bromo-4,4'-dipropargyloxyhexaarylbiimidazole prepared in Example 1 as a crosslinking agent. The synthetic route is as follows Figure 4 shown.
[0082] Select a 10ml sample tube, mix dipropynyl polyethylene glycol ether (208mg, 0.2mmol), dipropynyl o-bromohexaarylbiimidazole (24.1mg, 0.025mmol), 1,6-diazidohexane Alkane (43mg, 0.25mmol) and N,N,N',N,'N"-pentamethyldiethylenetriamine (52ul, 0.25mmol) were added, while adding 500ul N,N-dimethylformaldehyde Amide makes the reaction raw materials dissolve completely.Then utilize oil pump and high-purity nitrogen that above-mentioned reaction solution freeze-thaw cycle is cycled three times, remove the oxygen in the sample tube.At this moment, open the sample tube quickly, the catalyzer cuprous bromide (28mg, 0.2mmol) Add it and vacuumize the sample tube again to exhaust nitrogen. The catalyst is fully mixed with the reaction solution under the nitrogen atmo...
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