ArticleJACS Au2023
Separation of Cyclohexanone and Cyclohexanol by Adaptive Pillar[5]arene Cocrystals Accompanied by Vapochromic Behavior.
Article in JACS Au, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Inclusion co-crystals based on Tröger's base molecular box for thermally activated delayed fluorescence.Nature communications · 2026Article
- Hydrogen-bonded supramolecular polymer networks for effective removal of perchlorate in water via clustered hydrogen-bonding.Nature communications · 2025Article
- Fluoride Enhances Alcohol Binding Within a Trigonal-Prismatic Metal-Organic Capsule.Angewandte Chemie (International ed. in English) · 2025Article
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5 authors.
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Abstract
The separation of cyclohexanone (CHA-one) and cyclohexanol (CHA-ol) mixtures is of great importance in the chemical industry. Current technology exploits multiple steps of energy-intensive rectification due to their close boiling points. Herein, we report a new and energy-efficient adsorptive separation method employing binary adaptive macrocycle cocrystals (MCCs) built with π-electron-rich pillar[5]arene (P5) and an electron-deficient naphthalenediimide derivative (NDI) that can selectively separate CHA-one from an equimolar CHA-one/CHA-ol mixture with >99% purity. Intriguingly, this adsorptive separation process is accompanied by vapochromic behavior from pink to dark brown. Single-crystal and powder X-ray diffraction analyses reveal that the adsorptive selectivity and vapochromic property are derived from the CHA-one vapor inside the cocrystal lattice voids triggering solid-state structural transformations to yield charge-transfer (CT) cocrystals. Moreover, the reversible transformations make the cocrystalline materials highly recyclable.
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