Synthesis of Azacalixarenes and Development of Their Properties

Takemura, Hiroyuki

doi:10.3390/molecules26164885

Cited by 3 publications

(1 citation statement)

References 97 publications

(171 reference statements)

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“…As the "holy grail" of chemistry, hydroxycalixarene, specifically its derivatives, have good coordination adsorption properties and have often been used for heavy metal ion adsorption research. 8,9 However, the hydroxycalixarene molecule itself has poor water solubility, and protonated hydroxycalixarene usually needs to go through a tedious intermediate treatment process before it can effectively adsorb heavy metal ions. 10,11 Therefore, it is difficult to directly study the effect of various hydroxycalixarenes on metal ions.…”

Section: Introductionmentioning

confidence: 99%

Coordination binding of hydroxycalix[4]arene, hydroxycalix[5]arene, and hydroxycalix[6]arene to uranyl and thorium ions

Lan¹,

Wang²,

Liu³

et al. 2023

Applied Organom Chemis

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In this study, hydroxycalix[4]arene, hydroxycalix[5]arene, hydroxycalix[6]arene, and their complexes with uranyl and thorium ions were analyzed by density functional theory. The coordination ability of hydroxycalixarene ligands to uranyl and thorium ions could be analyzed by simulating the infrared and ultraviolet–visible spectra, the Wiberg bond energy levels, the energy gaps, and the binding energies. We found that various hydroxycalixarene complexes with uranyl or thorium ions had significant differences in their properties, as well as in their infrared vibrational and ultraviolet absorption spectra. More importantly, different hydroxycalixarenes can be selected based on the adsorption requirements in environments with coexisting uranium and thorium ions. For example, hydroxycalix[4]arene and hydroxycalix[5]arene had a significantly higher binding capacities for thorium than uranyl ions, while hydroxycalix[6]arene showed less of a difference for the two ions but had a good binding ability for both uranyl and thorium ions at the same time. Thus, the use of hydroxycalixarene can achieve the removal of both uranyl and thorium ions in the environment, and the use of specific hydroxycalixarenes may be able to achieve the separation of these ions. These results provide important guidance for the future research of hydroxycalixarene without requiring the synthesis of hydrophilic derivatives, and they may be directly applied to the field of heavy metals.

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Section: Introductionmentioning

confidence: 99%

Coordination binding of hydroxycalix[4]arene, hydroxycalix[5]arene, and hydroxycalix[6]arene to uranyl and thorium ions

Lan¹,

Wang²,

Liu³

et al. 2023

Applied Organom Chemis

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The literature of heterocyclic chemistry, Part XXI, 2021

Belen’kii,

Gazieva,

Evdokimenkova

et al. 2024

Advances in Heterocyclic Chemistry

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Crystallographic and Thermal Studies of the Polymorphs of Tetraoxa[4]arene with Meta-Phenylene Linkers

Ishida,

Kawasaki,

Hori

2024

Crystals

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The three isomers of the tetraoxa[4]arene derivative, C24H16O4, which consist of two m-phenylenes and two phenylenes (meta 1, para 2, ortho 3), represent not only intriguing fundamental structures that induce molecular recognition toward non-porous adaptive crystals, but also attractive candidates for crystallographic polymorphism. In this study, we crystallized isomers 2 and 3, in comparison to isomer 1, in order to understand their stable orientations and the corresponding intermolecular interactions in the crystalline state. For example, m-phenylene derivative 1 exhibits polymorphism with both prismatic and block-shaped crystals. Therefore, we prepared p-phenylene derivative 2 and o-phenylene derivative 3, and their structures were fully characterized by SC-XRD, revealing two polymorphs of derivative 2, namely prismatic crystal 2-I and block-shaped crystal 2-II, along with changes to the crystal lattice parameters (2-Ia, 2-Ib, and 2-Ic) based on temperature dependence. In all of its crystal forms, derivative 2 adopts an O-shaped planar structure, where the p-phenylene units face each other. This suggests that the packing mode during the early stages of crystallization, rather than due to any remarkable changes in the molecular structure, directly affects the bulk crystal morphology. On the other hand, derivative 3 adopts a U-shaped vent structure and, to the best of our knowledge, does not form polymorphs. The Platon and Hirshfeld surface analyses indicated that the contributions to the crystal packing were C···C (av. 37.3% for 2-Ia, av. 38.2% for 2-II, and 18.7% for 3), C···H/H···C (av. 37.3% for 2-Ia, av. 38.2% for 2-II, and 18.7% for 3), and O···H/H···O (av. 17.8% for 2-Ia, av. 19.6% for 2-II, and 19.4% for 3), highlighting significant intermolecular CH···π interactions and pseudo-hydrogen bonding forms for derivative 2 and π···π interactions for derivative 3.

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Synthesis of Azacalixarenes and Development of Their Properties

Cited by 3 publications

References 97 publications

Coordination binding of hydroxycalix[4]arene, hydroxycalix[5]arene, and hydroxycalix[6]arene to uranyl and thorium ions

Coordination binding of hydroxycalix[4]arene, hydroxycalix[5]arene, and hydroxycalix[6]arene to uranyl and thorium ions

The literature of heterocyclic chemistry, Part XXI, 2021

Crystallographic and Thermal Studies of the Polymorphs of Tetraoxa[4]arene with Meta-Phenylene Linkers

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