Issue 15, 2019

Highly efficient synthesis of hydrogen-bonded aromatic tetramers as macrocyclic receptors for selective recognition of lithium ions

Abstract

Persistently folded aromatic amide macrocycles comprising four monomeric units (biphenyl-cyclo[4]aramide) were synthesized with high efficiency via a one-step approach along with the larger cyclic oligomer, biphenyl-cyclo[8]aramide as a minor product. Such cyclic hydrogen-bonded aromatic tetramers feature four amide oxygens enclosing a cavity with small dimensions, enabling the selective complexation of alkali metal ions, particularly Li+, with high affinity. The cyclization efficiency and selectivity of smaller macrocycles was further improved using fragment coupling and Li+-based template approaches. In addition, the superior binding ability of biphenyl-cyclo[4]aramide towards Li+ over its acyclic analogues was observed, demonstrating a remarkable macrocyclic effect.

Graphical abstract: Highly efficient synthesis of hydrogen-bonded aromatic tetramers as macrocyclic receptors for selective recognition of lithium ions

Supplementary files

Article information

Article type
Research Article
Submitted
08 May 2019
Accepted
31 May 2019
First published
03 Jun 2019

Org. Chem. Front., 2019,6, 2654-2661

Highly efficient synthesis of hydrogen-bonded aromatic tetramers as macrocyclic receptors for selective recognition of lithium ions

X. Guo, Y. Yang, Z. Peng, Y. Cai, W. Feng and L. Yuan, Org. Chem. Front., 2019, 6, 2654 DOI: 10.1039/C9QO00612E

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