Recognition-guided sulfate extraction and transport using tripodal hexaurea receptors

Si Qi Chen, Shu Na Yu, Wei Zhao*, Lin Liang, Yunyan Gong, Lifei Yuan, Juan Tang, Xiao Juan Yang, Biao Wu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The separation of sulfate anions (SO42−) from water is a great challenge due to its high hydration energy. Using synthetic receptors that are designed with a size-complementary cavity for sulfate binding, sulfate anions could be extracted from water to the organic phase via liquid-liquid extraction (LLE) method. To understand the correlation between sulfate binding (recognition chemistry) and sulfate-separation efficiency across two phases, herein we prepared a family of tripodal hexaurea receptors bearing various terminal substitutions: 4-nitrophenyl substituted L1, 4-methylphenyl substituted L2, and hexyl-chain-substituted L3. The crystal structures of [L2·SO4]2− and [L3·SO4]2− and 1H NMR titrations suggested that the sulfate-binding affinity of these receptors were terminal substitution-dependent, where the H-bonding strength and secondary C-H⋯π interactions were regulated. Comprehensive LLE studies indicated that all three receptors displayed highly efficient sulfate extraction with receptor-loading dependence and concentration independence. Relative sulfate-extraction efficiency was consistent with the sulfate-binding affinity of these receptors. Notably, using the hexyl-chain-substituted receptor L3, sulfate anions could be extracted and released by acidification for several cycles. Typical U-tube transport experiments demonstrated that over 70% of sulfate anions could be transported from the source phase to the receiving phase in 3 days across a bulk liquid membrane, which comprised the receptor L3. Our work shows a paradigm of how the sulfate-recognition property is correlated with sulfate separation via LLE, which may help to understand and promote the development of supramolecular recognition-based systems for achieving desired separations.

Original languageEnglish
Pages (from-to)6091-6101
Number of pages11
JournalInorganic Chemistry Frontiers
Volume9
Issue number23
DOIs
Publication statusPublished - 11 Oct 2022

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