Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 29, Pages 12007-12012Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001125
Keywords
chalcogen bonding; cooperativity; halogen bonding; heteroditopic receptors; ion-pair receptors
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Funding
- Center of Excellence for Innovation in Chemistry (PERCH-CIC)
- Ministry of Higher Education, Science, Research and Innovation
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A series of heteroditopic receptors containing halogen bond (XB) and unprecedented chalcogen bond (ChB) donors integrated into a 3,5-bis-triazole pyridine structure covalently linked to benzo-15-crown-5 ether motifs exhibit remarkable cooperative recognition of halide anions. Multi-nuclear H-1, C-13, Te-125 and F-19 NMR, ion pair binding investigations reveal sodium cation-benzo-crown ether binding dramatically enhances the recognition of bromide and iodide halide anions, with the chalcogen bonding heteroditopic receptor notably displaying the largest enhancement of halide binding strength of over two hundred-fold, in comparison to the halogen bonding and hydrogen bonding heteroditopic receptor analogues. DFT calculations suggest crown ether sodium cation complexation induces a polarisation of the sigma hole of ChB and XB heteroditopic receptor donors as a significant contribution to the origin of the unique cooperativity exhibited by these systems.
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