Progress in anion receptor chemistry

Macreadie, Lauren K.; Gilchrist, Alexander M.; McNaughton, Daniel A.; Ryder, William G.; Farès, Mohamed; Gale, Philip A.

doi:10.1016/j.chempr.2021.10.029

Cited by 78 publications

(59 citation statements)

References 108 publications

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“…Understanding and harnessing the forces that bond n -methylammonium cations to anions are of importance in at least two fields of chemistry. On the one hand, wide research has been conducted in the last few decades in an attempt to design encapsulating organic cations as hosts of anions, referred to as “ammonium-based anionic receptors,” , although it has focused mainly on the R 3 N-H + group to form hydrogen bonds with anions, where R 3 represents three branches of an encapsulating polycyclic compound. An interesting case is the design of a macrocyclic receptor that recognizes ion pairs formed by a methylammonium cation and a halide …”

Section: Introductionmentioning

confidence: 99%

Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

2022

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The degree of interpenetration of the van der Waals crusts of two atoms, represented by a penetration index, is defined to better quantify the meaning of the nonbonding contact distances between two atoms, which should allow us to compare different atom pairs on the same footing. The structural trends of the intermolecular contacts between the tetramethylammonium cation (TMA) and halogen atoms are reviewed, and a computational study of model X···TMA ion pairs (X = F, Cl, Br, I, Au) is presented. The results disclose two energy minima, in each of which the anion simultaneously interacts with three hydrogen atoms. The bonding mechanisms in the two cases are discussed based on the results of the tools of the trade that provide a consistent picture in which a distribution of charges significantly varies not only around each different atom but is also strongly dependent on the distance to the central N atom. This behavior, together with some non-negligible covalent character of the interionic interaction, is not predicted from a single-molecular electrostatic potential map of the TMA cation.

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Section: Introductionmentioning

confidence: 99%

Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

2022

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“…Among the various anion receptors, calix[4]pyrroles have been the focus of interest due to their ease of synthesis and functionalization. Therefore, they were used as receptors, sensors, selective anion and ion-pair separators, and adsorbents .…”

Section: Introductionmentioning

confidence: 99%

Multiresponsive, Self-Healing, and Hierarchical Materials Constructed from Anion Recognition-Based Supramolecular Polymer Networks

Ünlü

Aydogan

2022

ACS Appl. Polym. Mater.

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3A type supramolecular monomers in which three calix[4]pyrrole units connected to a central benzene unit with varying linker lengths were synthesized through azide–alkyne click reactions between two different azide cores and an alkyne-functionalized calix[4]pyrrole. These compounds were then complexed with a BB-type monomer tetrabutylammonium suberate in chloroform and acetonitrile via hydrogen bonding between calix[4]pyrrole units of 3A monomers and carboxylate units of suberate anions, leading to the formation of anion recognition-based supramolecular polymer networks. Owing to the dynamic noncovalent interactions, the resulting systems were found to be responsive against temperature, competing anions, and pH. Rheological analyses of the supramolecular polymer networks revealed that the system with a longer distance between the benzene core and calix[4]pyrrole units exhibits transient network behavior and viscoelastic self-healing ability below 20% deformation ratio. These systems were also used for the fabrication of hierarchical materials ranging from zero-dimensional (0D) to three-dimensional (3D) by utilizing various methods. This work demonstrates for the first time the preparation of anion recognition-based supramolecular polymer networks based on calix[4]pyrroles and their utilization in the formation of multiresponsive, self-healing materials for the fabrication of hierarchical materials.

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“…Cl − binding by anion-responsive π-electronic molecules 11 would convert Cl − to softer receptor–Cl − complexing moieties. The Cl − in 1ni + -Cl − bound by dipyrrolyldiketone BF 2 complexes 12 as anion receptors resulted in modulations around Cl − in structures and electronic states.…”

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confidence: 99%

Ion-pairing assemblies of heteroporphyrin-based π-electronic cation with various counteranions

et al. 2022

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Progress in anion receptor chemistry

Cited by 78 publications

References 108 publications

Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

Tetramethylammonium Cation: Directionality and Covalency in Its Interactions with Halide Ions

Multiresponsive, Self-Healing, and Hierarchical Materials Constructed from Anion Recognition-Based Supramolecular Polymer Networks

Ion-pairing assemblies of heteroporphyrin-based π-electronic cation with various counteranions

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