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Chemistry
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Supramolecular Anion Recognition: Principles and Applications
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Supramolecular Anion Recognition: Principles and Applications

A special issue of Chemistry (ISSN 2624-8549). This special issue belongs to the section "Supramolecular Chemistry".

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 19025

Special Issue Editors

Dr. Robert B. P. Elmes

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Guest Editor
Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Ireland
Interests: supramolecular chemistry; fluorescent chemosensors; nitroreductase; anion recognition; squaramides
Special Issues, Collections and Topics in MDPI journals
Dr. Stephen Butler

E-Mail Website
Guest Editor
Department of Chemistry, Loughborough University, Epinal Way, Loughborough, LE11 3TU UK
Interests: Organic Synthesis; Supramolecular Chemistry; Luminescent Probes; Cellular Imaging; Lanthanide complexes
Dr. Nick Fletcher

E-Mail Website
Guest Editor
Department of Chemistry, Lancaster University, Bailrigg, Lancaster LA1 4YW, UK
Interests: supramolecular chemistry; coordination chemistry; chirality; anion recognition

Special Issue Information

Dear Colleagues,

The field of anion recognition is one of the fundamental areas of supramolecular chemistry research. Progress is being continuously made in the synthesis of anion receptors based on a wide range of host molecules, which take advantage of a myriad of functional groups to engage in non-covalent interactions with their target anionic guest. The wide variety of host architectures ensures a rich vein of research that continues apace. Moreover, fundamental research in this area has led to many potential applications in areas such as anion sensors, anion transporters, anion-responsive materials, anion-induced molecular assembly, organocatalytic processes involving anion complexation, and even anion receptors as new drug candidates.

The aim of this Special Issue on “Supramolecular Anion Recognition: Principles and Applications” is to highlight and summarize the most innovative current research regarding the synthesis, host–guest properties, and new applications of novel anion receptors. The content will provide guidance for the future design of anion receptors and their potential applications across the chemical and biological sciences. 

Dr. Robert B. P. Elmes
Dr. Stephen Butler
Dr. Nick Fletcher
Guest Editors

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Chemistry is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • host–guest interaction
  • supramolecular chemistry
  • receptors
  • molecular recognition
  • anion receptors
  • physical organic chemistry
  • fluorescent sensors and probes
  • anion transport
  • indicator displacement assays
  • sensing arrays
  • organocatalysis

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Published Papers (6 papers)

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Research

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10 pages, 2869 KiB  
Communication
Selective Recognition and Reversible “Turn-Off” Fluorescence Sensing of Acetate (CH3COO−) Anion at Ppb Level Using a Simple Quinizarin Fluorescent Dye
by Mannanthara Kunhumon Noushija, Ananthu Shanmughan, Binduja Mohan and Sankarasekaran Shanmugaraju
Chemistry 2022, 4(4), 1407-1416; https://doi.org/10.3390/chemistry4040092 - 29 Oct 2022
Cited by 7 | Viewed by 2677
Abstract
A simple and cost-effective optical sensing system based on quinizarin fluorescent dye (QZ) for the selective and reversible sensing of CH3COO− anions is reported. The anion binding affinity of QZ towards different anions was monitored using electronic absorption [...] Read more.
A simple and cost-effective optical sensing system based on quinizarin fluorescent dye (QZ) for the selective and reversible sensing of CH3COO− anions is reported. The anion binding affinity of QZ towards different anions was monitored using electronic absorption and fluorescence emission titration studies in DMSO. The UV-visible absorption spectrum of QZ showed a decrease in the intensity of the characteristic absorption peaks at λ = 280, 323, and 475 nm, while a new peak appeared at λ = 586 nm after the addition of CH3COO− anions. Similarly, the initial strong emission intensity of QZ was attenuated following titration with CH3COO− anions. Notably, similar titration using other anions, such as F−, Cl−, I−, NO3−, NO2−, and H2PO4-, caused no observable changes in both absorption and emission spectra. The selective sensing of CH3COO− anions was also reflected by a sharp visual color change from bright green to faint green under room light. Further, the binding was found to be reversible, and this makes QZ a potential optical and colorimetric sensor for selective, reversible, and ppb-level detection of CH3COO− anions in a DMSO medium. Full article
(This article belongs to the Special Issue Supramolecular Anion Recognition: Principles and Applications)
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12 pages, 3035 KiB  
Article
Head vs. Tail Squaramide–Naphthalimide Conjugates: Self-Assembly and Anion Binding Behaviour
by Anthony A. Abogunrin, Stephen A. Healy, Orla Fenelon and Robert B. P. Elmes
Chemistry 2022, 4(4), 1288-1299; https://doi.org/10.3390/chemistry4040085 - 18 Oct 2022
Cited by 4 | Viewed by 2659
Abstract
The syntheses of two squaramide–naphthalimide conjugates (SN1 and SN2) are reported; the structures of SN1 and SN2 differ by the attachment of a squaramide—either at the ‘head’ or the ‘tail’ of the naphthalimide fluorophore. Both compounds displayed weak fluorescence due to [...] Read more.
The syntheses of two squaramide–naphthalimide conjugates (SN1 and SN2) are reported; the structures of SN1 and SN2 differ by the attachment of a squaramide—either at the ‘head’ or the ‘tail’ of the naphthalimide fluorophore. Both compounds displayed weak fluorescence due to the inclusion of a nitro-aromatic squaramide which efficiently quenches the emission of the naphthalimide. Both compounds were also shown to undergo self-aggregation as studied by 1H NMR and scanning electron microscopy (SEM). Furthermore, SN1 and SN2 gave rise to stark colourimetric changes in response to basic anions such as AcO−, SO42− HPO42−, and F−. The observed colour changes are thought to be due to deprotonation of a squaramide NH. The same basic anions also result in a further quenching of the naphthalimide emission. No colour change or emission modulations were observed in the presence of Cl−; however, 1H NMR studies suggest that moderate H-bonding occurs between this anion and both SN1 and SN2. Full article
(This article belongs to the Special Issue Supramolecular Anion Recognition: Principles and Applications)
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10 pages, 1318 KiB  
Communication
A Benzimidazolium-Based Organic Cage with Antimicrobial Activity
by Sonia La Cognata, Donatella Armentano, Nicoletta Marchesi, Pietro Grisoli, Alessia Pascale, Marion Kieffer, Angelo Taglietti, Anthony P. Davis and Valeria Amendola
Chemistry 2022, 4(3), 855-864; https://doi.org/10.3390/chemistry4030061 - 26 Aug 2022
Cited by 5 | Viewed by 2691
Abstract
Considering the wide interest in (benz)imidazolium-based drugs, we here report our study on a benzimidazolium-based organic cage as potential antimicrobial and antifungal agent. Cytotoxicity studies on a human derived cell line, SH-SY5Y, showed that the cage is not cytotoxic at all at the [...] Read more.
Considering the wide interest in (benz)imidazolium-based drugs, we here report our study on a benzimidazolium-based organic cage as potential antimicrobial and antifungal agent. Cytotoxicity studies on a human derived cell line, SH-SY5Y, showed that the cage is not cytotoxic at all at the investigated concentrations. Anion binding studies demonstrated that the cage can bind anions (chloride and nitrate, in particular) both in organic solvent and 20%v D2O/CD3CN mixture. The cage was also tested as anionophore, showing a weak but measurable transport of chloride and nitrate across LUVs vesicles. Nonetheless, the compounds have antimicrobial activity towards Staphylococcus aureus (Gram-positive bacteria). This is probably the first organic cage studied as anionophore and antimicrobial agent. Full article
(This article belongs to the Special Issue Supramolecular Anion Recognition: Principles and Applications)
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12 pages, 663 KiB  
Article
Characterizing the Properties of Anion-Binding Bis(cyclopeptides) with Solvent-Independent Energy Increments
by Stefan Kubik
Chemistry 2022, 4(2), 419-430; https://doi.org/10.3390/chemistry4020031 - 12 May 2022
Cited by 1 | Viewed by 2253
Abstract
The binding energies of 121 complexes between anions and bis(cyclopeptides) differing in the structure and the number of linking units between the two cyclopeptide rings were analyzed. These Gibbs free energies were obtained in earlier work for different anions, under different conditions, and [...] Read more.
The binding energies of 121 complexes between anions and bis(cyclopeptides) differing in the structure and the number of linking units between the two cyclopeptide rings were analyzed. These Gibbs free energies were obtained in earlier work for different anions, under different conditions, and with different methods. The multiparametric analysis of a subset of 42 binding energies afforded linear relationships that allowed the relatively reliable estimation of the iodide and sulfate affinity of three structurally related bis(cyclopeptides) in water/methanol and water/acetonitrile mixtures at different solvent compositions. Three parameters were required to achieve a satisfactory correlation, namely, the Gibbs free energy of transferring the respective anion from water into the solvent mixture in which complex stability was determined, and the Kamlet–Taft parameters α and β. Based on these relationships, the anion affinities of the other bis(cyclopeptides) were evaluated, giving rise to a set of energy increments that allow quantifying the effects of the linker structure or the nature of the anion on binding affinity relative to the reference system. Full article
(This article belongs to the Special Issue Supramolecular Anion Recognition: Principles and Applications)
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Review

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13 pages, 4372 KiB  
Review
Anion-Complexation-Induced Emission Based on Aggregation-Induced Emission Fluorophore
by Dongxing Ren, Liangliang Zhang, Hongwei Qian and Tangxin Xiao
Chemistry 2023, 5(1), 242-254; https://doi.org/10.3390/chemistry5010019 - 7 Feb 2023
Cited by 4 | Viewed by 4546
Abstract
Aggregation-induced emission (AIE) materials have attracted increasing research interest in recent years due to their excellent fluorescence properties in an aggregated state. Concurrently, anion coordination interactions have played a key role in the development of supramolecular assemblies and sensors. In the past decade, [...] Read more.
Aggregation-induced emission (AIE) materials have attracted increasing research interest in recent years due to their excellent fluorescence properties in an aggregated state. Concurrently, anion coordination interactions have played a key role in the development of supramolecular assemblies and sensors. In the past decade, investigations towards fluorescent materials or sensors based on AIE and anion coordination interactions are continuously being reported. In this minireview, we briefly summarize the burgeoning progress of AIE-based materials and sensors driven by anion coordination interactions. We believe that an increasing number of achievements in anion-coordination induced emission materials will appear in the near future and will demonstrate potential applications, including bio-imaging and bio-sensors. Full article
(This article belongs to the Special Issue Supramolecular Anion Recognition: Principles and Applications)
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13 pages, 3816 KiB  
Review
Heteroditopic Rotaxanes and Catenanes for Ion Pair Recognition
by Steven J. Nicholson, Sean R. Barlow and Nicholas H. Evans
Chemistry 2023, 5(1), 106-118; https://doi.org/10.3390/chemistry5010009 - 12 Jan 2023
Cited by 4 | Viewed by 2521
Abstract
A review of heteroditopic interlocked molecules and their application as receptors for simple inorganic ion pair species. The review details the design and ion recognition properties of the rotaxane and catenane receptors, as well as highlighting some of the experimental challenges; hence, it [...] Read more.
A review of heteroditopic interlocked molecules and their application as receptors for simple inorganic ion pair species. The review details the design and ion recognition properties of the rotaxane and catenane receptors, as well as highlighting some of the experimental challenges; hence, it provides insight into possible future avenues of research in this youthful field. Full article
(This article belongs to the Special Issue Supramolecular Anion Recognition: Principles and Applications)
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