Publication: Chalcogen Bond Mediated Enhancement of Cooperative Ion-Pair Recognition
Issued Date
2020-01-01
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ISSN
15213773
14337851
14337851
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2-s2.0-85084454708
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Mahidol University
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SCOPUS
Bibliographic Citation
Angewandte Chemie - International Edition. (2020)
Suggested Citation
Thanthapatra Bunchuay, Andrew Docker, Utt Eiamprasert, Panida Surawatanawong, Asha Brown, Paul D. Beer Chalcogen Bond Mediated Enhancement of Cooperative Ion-Pair Recognition. Angewandte Chemie - International Edition. (2020). doi:10.1002/anie.202001125 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/56151
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Title
Chalcogen Bond Mediated Enhancement of Cooperative Ion-Pair Recognition
Abstract
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. 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 1H, 13C, 125Te and 19F 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.