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

preprint
submitted on 26.12.2020, 15:57 and posted on 28.12.2020, 13:51 by Qing He, Aimin Li, Shenglun Xiong, Wei Zhou, Huijuan Zhai, Yuanchu Liu

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.

Funding

National Natural Science Foundation of China (21901069 and 22071050)

the Science Technology Plan Project of Hunan Province, China (2019RS1018)

National Key Research and Development Project (Grant No. 2020YFC1807301)

Fundamental Research Funds for the Central Universities

History

Email Address of Submitting Author

heqing85@hnu.edu.cn

Institution

Hunan University

Country

China

ORCID For Submitting Author

0000-0003-3117-9587

Declaration of Conflict of Interest

The authors declare no conflict of interest.

Version Notes

This is the first submission.

Exports