Superphanes: Old Yet New Binding–Agents for Highly Selective Recognition of Fluoride by Size–Sieving Effect

28 December 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Superphanes, namely percyclophanes, have been widely investigated for the sake of their aesthetically pleasing structures with high symmetry, intriguing physical and chemical properties and synthetic challenges. Nonetheless, the host–guest chemistry of superphanes remains to be an unmet challenge. Herein, we delineate the design, preparation, characterization, and host–guest chemistry of an unprecedented superphane 15, which was evidenced by mass spectroscopy, NMR spectroscopy, X–ray crystallography, and DFT calculations. 15 features six bridges between two benzene planes, up to 18 CspH hydrogen–bonding donors well–distributed around the near–closed inner cavity in three dimensions. These allow 15 to exhibit exclusive selectivity towards F against Cl, Br, I, N3, SCN, NO3, ClO4, SO42– and HP2O73– due to the size–sieving effect. This contribution opens up new opportunities for design and synthesis of new supramolecular hosts for anions of interest with high selectivity.


anion receptors
host–guest chemistry

Supplementary materials

supporting Information


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