Anion Recognition and Binding Constant Determination

Sheetz, Edward G.; Craen, David Van; Flood, Amar H.

doi:10.1002/9783527830664.ch2

Cited by 8 publications

(4 citation statements)

References 59 publications

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“…The hunt for tight binding of anions with artificial receptors is an ongoing, fascinating, but also challenging research area since various anions like chloride, mono- and dicarboxylates, nitrate, sulfate, or phosphates play essential roles in environmental processes and biological functions . The most crucial parameters which can be altered for the thrive of more efficient receptors with higher binding constants and selectivities are the nature of the interaction facilitated by the recognition unit, the number of recognition units, and especially the preorganization of the receptor. − The importance of the latter is prominently shown in fully organic shape-persistent preorganized receptors by Flood et al, which bind anions contrary to the common assumption with very high affinities by utilizing only weak CH–hydrogen bonds. − Unfortunately, the drawback of well-preorganized organic macrocycles and cages is the often time-demanding synthetic effort which limits the receptor modularity.…”

Section: Introductionmentioning

confidence: 99%

A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

2022

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The field of anion recognition chemistry is dominated by two fundamental approaches to design receptors. One relies on the formation of covalent bonds resulting in organic and often neutral host species, while the other one utilizes metal-driven self-assembly for the formation of charged receptors with well-defined nanocavities. Yet, the combination of their individual advantages in the form of charge-neutral metal-assembled bench-stable anion receptors is severely lacking. Herein, we present a fluorescent and uncharged double-stranded hydroxyquinoline-based zinc(II) helicate with the ability to bind environmentally relevant dicarboxylate anions with high fidelity in dimethyl sulfoxide (DMSO) at nanomolar concentrations. These dianions are pinned between zinc(II) centers with binding constants up to 145 000 000 M −1 . The presented investigation exemplifies a pathway to bridge the two design approaches and combine their strength in one structural motif as an efficient anion receptor.

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Section: Introductionmentioning

confidence: 99%

A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

2022

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“…Therein, the complexation‐induced changes of multiple spectroscopic signals, are used in the fitting analysis rather than just one. We also iterate between titrations recorded at different concentrations to generate a self‐consistent set of equilibrium constants that represent the complete binding model [21,29a] . We have used this method previously with systems that have involved five or six equilibria [38]…”

Section: Resultsmentioning

confidence: 99%

Solvent Acts as the Referee in a Match‐Up Between Charged and Preorganized Receptors

Bhattacharjee,

Gao,

Nathani

et al. 2023

Chemistry A European J

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The prevalence of cation‐anion contacts in biomolecular recognition under aqueous conditions suggests that ionic interactions should dominate the binding of anions in solvents across both high and low polarities. Investigations of this idea using titrations in low polarity solvents are impaired by interferences from ion pairing that prevent a clear picture of binding. To address this limitation and test the impact of ion‐ion interactions across multiple solvents, we quantified chloride binding to a cationic receptor after accounting for ion pairing. In these studies, we created a chelate receptor using aryl‐triazole CH donors and a quinolinium that directs its cationic methyl inside the binding pocket. In low‐polarity dichloromethane, the 1:1 complex (log K1:1 ~ 7.3) is more stable than neutral chelates, but fortuitously comparable to a preorganized macrocycle (log K1:1 ~ 6.9). Polar acetonitrile and DMSO diminish stabilities of the charged receptor (log K1:1 ~3.7 and 1.9) but surprisingly 100‐fold more than the macrocycle. While both receptors lose stability by dielectric screening of electrostatic stability, the cationic receptor also pays additional costs of organization. Even though the charged and disorganized receptor has stronger binding in apolar solvents, the organized but uncharged receptor has more anion affinity in polar solvents.

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“…NMR titration was conducted in CDCl 3 as follows. 105 Into an NMR tube with 0.5 ml host solution (0.004 M) aliquots of host-guest solution (0.004 M host and 0.02 M guest) were successively added. The tube was gently shaken and sonicated for 5 min prior to each NMR measurement.…”

Section: Methodsmentioning

confidence: 99%

Pillar[5]arene-based dually crosslinked supramolecular gel as a sensor for the detection of adiponitrile

Rodin,

Helle,

Kuckling

2024

Polym. Chem.

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Anion Recognition and Binding Constant Determination

Cited by 8 publications

References 59 publications

A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

Solvent Acts as the Referee in a Match‐Up Between Charged and Preorganized Receptors

Pillar[5]arene-based dually crosslinked supramolecular gel as a sensor for the detection of adiponitrile

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Anion Recognition and Binding Constant Determination

Cited by 8 publications

References 59 publications

A Charge-Neutral Self-Assembled L2Zn2 Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

A Charge-Neutral Self-Assembled L2Zn2 Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

Solvent Acts as the Referee in a Match‐Up Between Charged and Preorganized Receptors

Pillar[5]arene-based dually crosslinked supramolecular gel as a sensor for the detection of adiponitrile

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A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration

A Charge-Neutral Self-Assembled L₂Zn₂ Helicate as Bench-Stable Receptor for Anion Recognition at Nanomolar Concentration