Anion receptors based on intramolecularly bridged calix[4]arenes bearing ureido functions

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• 作者：Marké ; ta Řezanková ; ^a ; Jan Budka^a ; Jiř&iacute ; Mik&scaron ; á ; tko^a ; Vá ; clav Eigner^b ; Ivana C&iacute ; sařová ; ^c ; Petra Cuř&iacute ; nová ; ^d ; Pavel Lhotá ; k^a ; ^{lhotakp@vscht.cz}
• 关键词：Calixarene ; Reductive coupling ; 1 ; 2-Diamine ; Anion recognition ; X-ray structure
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：9 February 2017
• 年：2017
• 卷：73
• 期：6
• 页码：742-749
• 全文大小：920 K
• 卷排序：73

文摘

A novel type of anion receptor, based on the intramolecularly bridged calix[4]arene immobilized in the cone conformation, is described. The reductive coupling of a distal dialdoxime using Zn/TiCl4 led to calix[4]arene with a meso-1,2-diaminoethane-1,2-diyl bridge that was transformed into the corresponding receptors by reaction with aryl isocyanates. 1H NMR titration experiments revealed that the combination of a unique structural feature (bridge) with arylureido functional groups led to the formation of very potent anion receptors. Contrary to model non-bridged compounds, these well-preorganized receptors can efficiently bind selected anions (H2PO4−, AcO−, BzO−) via hydrogen bonding interactions even in highly competitive solvent (DMSO-d6).