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A pH‐Switchable Aqueous Organocatalysis with Amphiphilic Secondary Amine–Porphyrin Hybrids
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-06-15 , DOI: 10.1002/ejoc.202000648
Aitor Arlegui 1 , Pol Torres 1 , Victor Cuesta 1 , Joaquim Crusats 1, 2 , Albert Moyano 1
Affiliation  

A pH‐sensitive “Ampelmännchen”: The catalytic activity of an amphiphilic isoindoline–porphyrin hybrid for the aqueous aldol reaction can be selectively and reversibly switched on and off . In neutral solutions the anionic form of the hybrid is highly soluble, allowing aminocatalysis to take place, whereas in acidic pH the protonated porphyrin core of the hybrid affords a highly insoluble, catalytically inactive J‐aggregate.
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中文翻译:

两亲性仲胺-卟啉杂化剂的pH值转换有机有机水溶液。

pH敏感的“交通信号灯小人”:两亲性异吲哚啉卟啉混合用于含水醛醇缩合反应的催化活性可以选择性地和可逆地切换断开。在中性溶液中,杂化物的阴离子形式是高度可溶的,允许进行氨基催化,而在酸性pH下,杂化物的质子化的卟啉核可提供高度不溶的,催化惰性的J聚集体。
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更新日期:2020-07-24
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