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Binding of Heterocycles by Cyclohexanohemicucurbiturils and Solid-Phase Extraction of Sulfur-Containing Heterocycles from Water

preprint
submitted on 21.04.2021, 08:31 and posted on 21.04.2021, 13:30 by Tatsiana Shalima, Kamini A. Mishra, Sandra Kaabel, Lukas Ustrnul, Simona Bartkova, Kaia Tõnsuaadu, Ivo Heinmaa, Riina Aav
Here we report a study on cyclohexanohemicucurbit[8]uril (cycHC[8]) binding of sulfur-, oxygen- and nitrogen-containing heterocycles in both solid state and solution, which is investigated by single crystal X-ray diffraction, NMR spectroscopy, isothermal titration calorimetry, and thermogravimetry. Potential guests include environmental pollutants, hazardous compounds, and bioactive substances. We found that cycHC[8] encapsulates five- and six-membered sulfur- and oxygen-containing unsubstituted heterocycles and can be used as a selective sorption material for the extraction of sulfur-heterocycles from water. Both cycHC[6] and cycHC[8] can remove a substituted heterocycle, α-lipoic acid, from an aqueous solution via the formation of an external complex. The results show that cycHC[n] is a promising reusable sorbent material with the potential to be employed in molecular recognition and highly specific solid-phase extraction of sulfur-heterocycles.

Funding

Estonian Research Council Grants No. PRG399, MOBJD556 and MOBJD592

ERDF (CoE 2014-2020.4.01.15-0013, and CoE TK134)

H2020-FETOPEN 828779 (INITIO)

History

Email Address of Submitting Author

riina.aav@taltech.ee

Institution

Tallinn University of Technology

Country

Estonia

ORCID For Submitting Author

0000-0001-6571-7596

Declaration of Conflict of Interest

No

Exports