Adsorptive separation of cyclohexanol and cyclohexanone by nonporous adaptive crystals of RhombicArene

Zhao, Yongye; Xiao, Hongyan; Tung, Chen‐Ho; Wu, Li‐Zhu; Cong, Huan

doi:10.1039/d1sc04728k

Cited by 48 publications

(19 citation statements)

References 53 publications

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“…Rhombicarene. In 2021, Cong's group obtained a new macrocyclic arene named rhombicarene by introducing two octahydrobinaphthol (H 8 -BINOL) subunits into the pillar [6]arene's skeleton, 88 which showed a C 2 -symmetrical structure with in-cavity hydrogen-bonding sites (Fig. 39a).…”

Section: Leaning Pillarmentioning

confidence: 99%

Recent advances in the synthesis and applications of macrocyclic arenes

2023

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Section: Leaning Pillarmentioning

confidence: 99%

Recent advances in the synthesis and applications of macrocyclic arenes

2023

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“…We have recently proposed an original concept, nonporous adaptive crystals (NACs), which are a new kind of solid adsorptive materials [25–46] . Induced by guest vapors, these nonporous crystalline materials undergo a structural transformation to accommodate guest molecules.…”

Section: Introductionmentioning

confidence: 99%

Reimplementing Guest Shape Sorting of Nonporous Adaptive Crystals via Substituent‐Size‐Dependent Solid‐Vapor Postsynthetic Modification

Zhu

Fang

et al. 2022

Angewandte Chemie

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Postsynthetic modification (PSM) has been widely used in porous crystalline materials to gain better performance in adsorptive separation of gases or hydrocarbons. We here report that guest adsorption selectivity in a kind of nonporous crystalline materials, namely nonporous adaptive crystals (NACs), can be readily and precisely tuned via a facile substituent-size-dependent solid-vapor PSM method. Before PSM, NACs of pillar-[4]arene[1]quinone EtP4Q1 show negligible selectivity for C 5 hydrocarbons. PSM with a larger substituent, cyclopentylamine, onto EtP4Q1 NACs does not improve the selectivity, while EtP4Q1 NACs after PSM with a slightly smaller substituent, cyclobutylamine, is endowed with very high preference of n-pentane over cyclopentane. Comprehensive structural analyses confirm that the intermolecular interactions among the host compounds and host-guest interactions between the adsorbent and the adsorbate are the two major factors in determining the guest selectivity.

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“…Recently, macrocycle-based nonporous adaptive crystals (NACs) have emerged as a burgeoning area in supramolecular chemistry, showing great potential in the selective separation of important chemical feedstocks. − NACs possess the merits of easy preparation, low cost, and good moisture and thermal stability. Very recently, we reported the first example of two-component adaptive macrocycle cocrystals (MCCs) by the marriage of a macrocycle and cocrystal engineering, showing vapochromic behavior to haloalkanes .…”

mentioning

confidence: 99%

Separation of Cyclohexanone and Cyclohexanol by Adaptive Pillar[5]arene Cocrystals Accompanied by Vapochromic Behavior

Li,

Wang,

Liu

et al. 2023

JACS Au

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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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Adsorptive separation of cyclohexanol and cyclohexanone by nonporous adaptive crystals of RhombicArene

Abstract: The novel macrocycle RhombicArene features excellent capability for rapid, exclusive, and recyclable vapor adsorption of cyclohexanone in the presence of cyclohexanol, showing potential for energy-saving separation of these feedstock chemicals.

Cited by 48 publications

References 53 publications

Recent advances in the synthesis and applications of macrocyclic arenes

Recent advances in the synthesis and applications of macrocyclic arenes

Reimplementing Guest Shape Sorting of Nonporous Adaptive Crystals via Substituent‐Size‐Dependent Solid‐Vapor Postsynthetic Modification

Separation of Cyclohexanone and Cyclohexanol by Adaptive Pillar[5]arene Cocrystals Accompanied by Vapochromic Behavior

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