Advances in Anion Receptor Chemistry

Chen, Li Jun; Berry, Stuart N.; Wu, Xin; Howe, Ethan N.W.; Gale, Philip A.

doi:10.1016/j.chempr.2019.12.002

Cited by 213 publications

(199 citation statements)

References 157 publications

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“…It is very important to address that variation of bond connectivity from para-arylene in corona [6]arenes to meta-arylene in i-corona [6]arenes led to the dramatic change of macrocyclic conformation. As alient feature of the structure of i-corona [6]arenes is that they all adopted noticeable 1,3,5-alternate conformation irrespective of the upper-rim and lower-rim substituents on the metaarylene segments.A romatic rings are leaning against the plane defined roughly by the bridging oxygen atoms.A dditionally, i-corona [6]arenes gave very similar hexagonal cavity Table 2: Synthesis of 3b-g from one-pot reaction of 7b-g with 8. views. Benzyl groups of 3fand all solvent moleculesa re hidden for clarity.…”

Section: Structure Of I-corona[6]arenesmentioning

confidence: 99%

Synthesis ofi‐Corona[6]arenes for Selective Anion Binding: Interdependent and Synergistic Anion–π and Hydrogen‐Bond Interactions

et al. 2020

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i‐Corona[3]arene[3]tetrazines were synthesized from the nucleophilic aromatic substitution reaction of resorcinol and its derivatives with 3,6‐dichlorotetrazine in a one‐pot fashion under mild conditions. All of the resulting macrocycles adopted 1,3,5‐alternate conformation irrespective of the nature of the substituents on both upper‐ and lower‐rims. i‐Corona[3]arene[3]tetrazine was found to self‐regulate its macrocyclic conformation and cavity to recognize anions with binding constants spanning from 26 M−1 to 2.2×103 M−1 depending on the structure of the anions. The selective binding resulted from a significant interdependent and synergistic effect between multiple tetrazine π/anion and Caryl–H/anion hydrogen bond interactions. Taking advantage of synergistic effect revealed, a cyanobenzene‐embedded i‐corona[3]arene[3]tetrazine was designedly synthesized and highly selective and very strong affinity toward nitrate with a binding constant of 2.2×105 M−1 was achieved.

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Section: Structure Of I-corona[6]arenesmentioning

confidence: 99%

Synthesis ofi‐Corona[6]arenes for Selective Anion Binding: Interdependent and Synergistic Anion–π and Hydrogen‐Bond Interactions

et al. 2020

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“…Exploiting the reversible complexation of anions, one could imagine using the binding event as allosteric stimulus to modify either the thermodynamic and/or the kinetic of the E / Z isomerization process. Despite the large body of research on supramolecular recognition of anions, the examples of photoregulated anion receptors are scarcer with respect to those designed for cations and often incorporate different switches than those deriving from azobenzenes …”

Section: Configurational Selection Following Anion Complexationmentioning

confidence: 99%

Configurational Selection in Azobenzene‐Based Supramolecular Systems Through Dual‐Stimuli Processes

Tecilla

Bonifazi

2020

ChemistryOpen

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Azobenzene is one of the most studied light-controlled molecular switches and it has been incorporated in a large variety of supramolecular systems to control their structural and functional properties. Given the peculiar isomeric distribution at the photoexcited state (PSS), azobenzene derivatives have been used as photoactive framework to build metastable supramolecular systems that are out of the thermodynamic equilibrium. This could be achieved exploiting the peculiar E/Z photoisomerization process that can lead to isomeric ratios that are unreachable in thermal equilibrium conditions. The challenge in the field is to find molecular architectures that, under given external circumstances, lead to a given isomeric ratio in a reversible and predictable manner, ensuring an ultimate control of the configurational distribution and system composition. By reviewing early and recent works in the field, this review aims at describing photoswitchable systems that, containing an azobenzene dye, display a controlled configurational equilibrium by means of a molecular recognition event. Specifically, examples include programmed photoactive molecular architectures binding cations, anions and H-bonded neutral guests. In these systems the non-covalent molecular recognition adds onto the thermal and light stimuli, equipping the supramolecular architecture with an additional external trigger to select the desired configuration composition.[a] Prof. P. Tecilla

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“…While several cation-sensing electrodes have been successfully commercialized, only a limited number of anion-sensing electrodes are commercially available. This is largely due to the challenges associated with the selectivity of ionophores towards anions [20,21]. In this work, potentiometric solid-contact ion-selective electrodes (SC-ISEs) were chosen as the sensor type for several reasons.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and application of carbazole macrocycles in anion sensors

Rüütel¹,

Yrjänä²,

Kadam³

et al. 2020

Beilstein J. Org. Chem.

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Carboxylate sensing solid-contact ion-selective electrodes (ISEs) were created to provide a proof-of-concept ISE development process covering all aspects from in silico ionophore design to functional sensor characterization. The biscarbazolylurea moiety was used to synthesize methylene-bridged macrocycles of different ring size aiming to fine tune selectivity towards different carboxylates. Cyclization was achieved with two separate strategies, using either amide synthesis to access up to –[CH2]10– macrocycles or acyl halides to access up to –[CH2]14– macrocycles. Seventy-five receptor–anion complexes were modelled and studied with COSMO-RS, in addition to all free host molecules. In order to predict initial selectivity towards carboxylates, 1H NMR relative titrations were used to quantify binding in DMSO-d 6/H2O solvent systems of two proportions – 99.5%:0.5% m/m and 90.0%:10.0% m/m, suggesting initial selectivity towards acetate. Three ionophores were selected for successful sensor prototype development and characterization. The constructed ion-selective electrodes showed higher selectivity towards benzoate than acetate, i.e., the selectivity patterns of the final sensors deviated from that predicted by the classic titration experiments. While the binding constants obtained by NMR titration in DMSO-d 6/H2O solvent systems provided important guidance for sensor development, the results obtained in this work emphasize the importance of evaluating the binding behavior of receptors in real sensor membranes.

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Advances in Anion Receptor Chemistry

Cited by 213 publications

References 157 publications

Synthesis ofi‐Corona[6]arenes for Selective Anion Binding: Interdependent and Synergistic Anion–π and Hydrogen‐Bond Interactions

Synthesis ofi‐Corona[6]arenes for Selective Anion Binding: Interdependent and Synergistic Anion–π and Hydrogen‐Bond Interactions

Configurational Selection in Azobenzene‐Based Supramolecular Systems Through Dual‐Stimuli Processes

Design, synthesis and application of carbazole macrocycles in anion sensors

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