Simultaneous Recognition and Separation of Organic Isomers Via Cooperative Control of Pore-Inside and Pore-Outside Interactions

Shaomin Xue, Yujia Rong, Ning Ding, Chaofeng Zhao, Qi Sun, Shenghua Li*, Siping Pang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Despite the desirability of organic isomer recognition and separation, current strategies are expensive and complicated. Here, a simple strategy for simultaneously recognizing and separating organic isomers using pillararene-based charge-transfer cocrystals through the cooperative control of pore-inside and pore-outside intermolecular interactions is presented. This strategy is illustrated using 1-bromobutane (1-BBU), which is often produced as an isomeric mixture with 2-bromobutane (2-BBU). According to its structure, perethylated pillar[5]arene (EtP5) and 3,5-dinitrobenzonitrile (DNB) are strategically chosen as a donor and an acceptor. As a result, their cocrystal exhibited stronger pore-inside interactions and much weaker pore-outside interactions with 1-BBU than with 2-BBU. Consequently, nearly 100% 1-BBU selectivity is achieved in two-component mixtures, even in those containing trace 1-BBU (1%), whereas free EtP5 only achieved 89.80% selectivity. The preference for linear bromoalkanes is retained in 1-bromopentane/3-bromopentane and 1-bromohexane/2-bromohexane mixtures, demonstrating the generality of this strategy. Selective adsorption of linear bromoalkanes induced a naked-eye-detectable color change from red to white. Moreover, the cocrystal are used over multiple cycles without losing selectivity.

Original languageEnglish
Article number2204963
JournalAdvanced Science
Volume9
Issue number36
DOIs
Publication statusPublished - 28 Dec 2022

Keywords

  • intermolecular interactions
  • organic isomer
  • pillararenes
  • recognition
  • separation

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