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Symmetry
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Recent Advances in Structural and Synthetic Supramolecular Systems
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Recent Advances in Structural and Synthetic Supramolecular Systems

A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (15 November 2021) | Viewed by 9246

Special Issue Editors

Prof. Ngong Kodiah Beyeh

E-Mail Website
Guest Editor
Department of Chemistry, Oakland University, 146 Library Drive, Rochester, MI 48309‐4479 USA
Interests: macrocycles; synthesis; weak interactions; supramolecules; host–guest complexes
Dr. John F Trant

E-Mail Website
Guest Editor
Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON N9B 3P4, Canada
Interests: chemistry

Special Issue Information

Dear Colleagues,

Macrocycles are suitable building blocks with applications in supramolecular chemistry. The range of old and new macrocycles have found applications in many section of the chemical sciences such as in soft materials, drug delivery agents, sensors etc. This prompted us to highlight this exciting new chemistry in a thematic issue Symmetry on Recent Advances in Structural and Synthetic Supramolecular Systems

In this Special Issue of Symmetry, manuscripts that report exciting new research on all kinds of macrocycles that have been the pillars in supramolecular chemistry, are also very welcome.

Potential topics for manuscripts include but are not limited to:

  • Synthesis and characterization of new macrocycles;
  • Host-guest chemistry, dynamics of guest exchange;
  • Applications of macrocycles;
  • Symmetry in supramolecular assemblies.

Prof. Ngong Kodiah Beyeh
Dr. John F Trant
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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. Symmetry is an international peer-reviewed open access monthly 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 2400 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

  • macrocycles
  • synthesis
  • weak interactions
  • supramolecules
  • host–guest complexes

Published Papers (4 papers)

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Research

8 pages, 1555 KiB  
Article
A Concise Synthesis of a Methyl Ester 2-Resorcinarene: A Chair-Conformation Macrocycle
by Michael R. Reynolds, Fraser S. Pick, John J. Hayward and John F. Trant
Symmetry 2021, 13(4), 627; https://doi.org/10.3390/sym13040627 - 9 Apr 2021
Cited by 2 | Viewed by 2240
Abstract
Anions are important hydrogen bond acceptors in a range of biological, chemical, environmental and medical molecular recognition processes. These interactions have been exploited for the design and synthesis of ditopic resorcinarenes as the hydrogen bond strength can be tuned through the modification of [...] Read more.
Anions are important hydrogen bond acceptors in a range of biological, chemical, environmental and medical molecular recognition processes. These interactions have been exploited for the design and synthesis of ditopic resorcinarenes as the hydrogen bond strength can be tuned through the modification of the substituent at the 2-position. However, many potentially useful compounds, especially those incorporating electron-withdrawing functionalities, have not been prepared due to the challenge of their synthesis: their incorporation slows resorcinarene formation that is accessed by electrophilic aromatic substitution. As part of our broader campaign to employ resorcinarenes as selective recognition elements, we need access to these specialized materials. In this article, we report a straightforward synthetic pathway for obtaining a 2-(carboxymethyl)-resorcinarene, and resorcinarene esters in general. We discuss the unusual conformation it adopts and propose that this arises from the electron-withdrawing nature of the ester substituents that renders them better hydrogen bond acceptors than the phenols, ensuring that each of them acts as a donor only. Density Functional Theory (DFT) calculations show that this conformation arises as a consequence of the unusual configurational isomerism of this compound and interruption of the archetypal hydrogen bonding by the ester functionality. Full article
(This article belongs to the Special Issue Recent Advances in Structural and Synthetic Supramolecular Systems)
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17 pages, 3195 KiB  
Article
Solid-State Structural Transformation and Photoluminescence Properties of Supramolecular Coordination Compounds
by Dipankar Ghosh, Oddný Ragnarsdóttir, Daníel Arnar Tómasson and Krishna K. Damodaran
Symmetry 2021, 13(1), 112; https://doi.org/10.3390/sym13010112 - 11 Jan 2021
Viewed by 2210
Abstract
The combination of strong coordination bonds and hydrogen bonding interactions were used to generate a series of supramolecular coordination materials (SCMs), which was achieved by reacting a bis-pyridyl amide ligand, namely N-(4-pyridyl)nicotinamide (4PNA) with copper(II), zinc(II), and cadmium(II) benzoates. The SCMs were [...] Read more.
The combination of strong coordination bonds and hydrogen bonding interactions were used to generate a series of supramolecular coordination materials (SCMs), which was achieved by reacting a bis-pyridyl amide ligand, namely N-(4-pyridyl)nicotinamide (4PNA) with copper(II), zinc(II), and cadmium(II) benzoates. The SCMs were structurally characterized using X-ray diffraction and the key intermolecular interactions were identified via Hirshfeld surface analysis. The role of solvent molecules on the supramolecular architecture was analyzed by synthesizing the SCMs in different solvents/solvent mixtures. A solvent-mediated solid-state structural transformation was observed in copper(II) SCMs and we were able to isolate the intermediate form of the crystal-to-crystal transformation process. The luminescence experiments revealed that complexation enhanced the fluorescence properties of 4PNA in the zinc(II) and cadmium(II) SCMs, but a reverse phenomenon was observed in the copper(II) SCMs. This work demonstrated the tuning of supramolecular assembly in coordination compounds as a function of solvents for generating SCMs with diverse properties. Full article
(This article belongs to the Special Issue Recent Advances in Structural and Synthetic Supramolecular Systems)
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11 pages, 3538 KiB  
Article
Unexpected Encapsulation of Selected Polycyclic Aromatic Hydrocarbons by β-Cyclodextrin Studied Using UV-Vis Spectrophotometry, Micro-Planar Chromatography and Temperature Dependent Inclusion Chromatography
by Aleksandra Kaleniecka, Elżbieta Włodarczyk, Krzysztof Piaskowski, Lucyna Lewandowska and Paweł K. Zarzycki
Symmetry 2020, 12(12), 1967; https://doi.org/10.3390/sym12121967 - 28 Nov 2020
Cited by 2 | Viewed by 1940
Abstract
This research communication significantly extends our previous studies focusing on the temperature effects related to the unexpected chromatographic behavior of 1-acenaphthenol in the presence of native β-cyclodextrin (β-CD) additive, working under thin-layer chromatographic (TLC) conditions. We have applied complementary and orthogonal techniques including [...] Read more.
This research communication significantly extends our previous studies focusing on the temperature effects related to the unexpected chromatographic behavior of 1-acenaphthenol in the presence of native β-cyclodextrin (β-CD) additive, working under thin-layer chromatographic (TLC) conditions. We have applied complementary and orthogonal techniques including (i) temperature-controlled ultraviolet-visible (UV-VIS) spectroscopy, (ii) thermostated microplanar high-performance chromatography (micro-HPTLC) and (iii) temperature-dependent inclusion chromatography based on high-performance liquid chromatography (HPLC) to investigate the retention behavior of related host molecules. Particularly, various symmetric and asymmetric molecules were tested, such as: naphthalene and its derivatives including acenaphthylene, acenaphthene and selected dimethynaphthalenes: 1,8-DMN, 1,5-DMN, 2,3-DMN and 2,6-DMN. Reported raw experimental data, particularly performed in liquid phase and detected by UV-Vis spectrophotometry, may suggest that solubility changes of the supramolecular complexes studied and differences in total analysis time between TLC and HPLC separation can trigger strong retention of target components in planar chromatographic systems. This was also supported by principal component analysis (PCA) of the multi-source data obtained. It is hoped that the reported analyses enable the adjustment of phenomenological models describing liquid chromatography retention and the solubility behavior of low-molecular mass guest molecules, controlled by supramolecular interactions with selected macrocycles. It should be noted that the reported phenomenon, specifically supramolecular complexes precipitation, may have a number of practical applications. This can be used to improve the efficiency and selectivity of planar and/or microfluidic systems. On the other hand, precipitation via host-guest interactions may be applied for highly selective water purification technological processes that will be designed for the removal of given organic micropollutants. Full article
(This article belongs to the Special Issue Recent Advances in Structural and Synthetic Supramolecular Systems)
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8 pages, 1611 KiB  
Article
Water Soluble Host–Guest Chemistry Involving Aromatic N-Oxides and Sulfonateresorcinarene
by Kwaku Twum, Nicholas Schileru, Bianca Elias, Jordan Feder, Leena Yaqoo, Rakesh Puttreddy, Małgorzata M. Szczesniak and Ngong Kodiah Beyeh
Symmetry 2020, 12(11), 1751; https://doi.org/10.3390/sym12111751 - 22 Oct 2020
Cited by 3 | Viewed by 2085
Abstract
Resorcinarenes decorated with sulfonate groups are anionic in nature and water soluble with a hydrophobic electron-rich interior cavity. These receptors are shown to bind zwitterionic aromatic mono-N-oxides and cationic di-N-oxide salts with varying spacer lengths. Titration data fit a [...] Read more.
Resorcinarenes decorated with sulfonate groups are anionic in nature and water soluble with a hydrophobic electron-rich interior cavity. These receptors are shown to bind zwitterionic aromatic mono-N-oxides and cationic di-N-oxide salts with varying spacer lengths. Titration data fit a 1:1 binding isotherm for the mono-N-oxides and 2:1 binding isotherm for the di-N-oxides. The first binding constants for the di-N-oxides (K1: 104 M−1) are higher compared to the neutral mono-N-oxide (K: 103 M−1) due to enhanced electrostatic attraction from a receptor with an electron-rich internal cavity and cationic and electron deficient N-oxides. The interaction parameter α reveals positive cooperativity for the di-N-oxide with a four-carbon spacer and negative cooperativity for the di-N-oxides that have spacers with more four carbons. This is attributed to shape complementarity between the host and the guest. Full article
(This article belongs to the Special Issue Recent Advances in Structural and Synthetic Supramolecular Systems)
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