Tuning of the Anion Affinity and Selectivity of Tripyrromethane-Based Receptors by Simple Structural Modification
- Authors
- Heo, Nam Jung; Yang, Ju Ho; Roh, Tae-Ho; Cho, Dong-Gyu; Kim, Sung Kuk
- Issue Date
- Dec-2023
- Publisher
- John Wiley and Sons Inc
- Keywords
- Anion Affinity; Anion Receptor; Anion Selectivity; Tripyrromethane
- Citation
- ChemistrySelect, v.8, no.47
- Indexed
- SCIE
SCOPUS
- Journal Title
- ChemistrySelect
- Volume
- 8
- Number
- 47
- URI
- https://scholarworks.gnu.ac.kr/handle/sw.gnu/69027
- DOI
- 10.1002/slct.202304567
- ISSN
- 2365-6549
2365-6549
- Abstract
- Tripyrromethane-based tripodal compounds 1–3 were synthesized as anion receptors. It was revealed by 1H NMR spectroscopic analyses carried out in CDCl3 that tripyrromethane 1 with an ester group was capable of recognizing F−, Cl−, Br−, and H2PO4− with relatively high selectivity for F−. By contrast, receptor 2 having an additional hydrogen bond donor of an amide group binds F− and H2PO4− with much improved affinity relative to receptor 1. On the other hand, receptor 3 bearing formyl groups on its two pyrrole subunits showed markedly enhanced selectivity for F− presumably due to the increased acidity of the pyrrolic NHs and the resulting strengthened intermolecular hydrogen bonds. In addition, tripodal receptors 1–3 were found to bind H2PO4−, a tetrahedral oxyanion, more efficiently than 2-dimensional macrocyclic calix[4]pyrrole 4. © 2023 Wiley-VCH GmbH.
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