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Symmetry
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Symmetry and Asymmetry in Host-Guest Chemistry and Supramolecular Chemistry
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Symmetry and Asymmetry in Host-Guest Chemistry and Supramolecular Chemistry

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

Deadline for manuscript submissions: closed (31 August 2019) | Viewed by 22926

Special Issue Editor

Prof. Keiji Hirose

E-Mail Website
Guest Editor
Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama Toyonaka, Osaka 560-8531, Japan
Interests: host-guest chemistry; supramolecular chemistry; molecular recognition; chiral sensors; molecular machines; mechanically interlocked molecules

Special Issue Information

Dear Colleagues,

Neologisms of Host-guest chemistry by D. J. Cram, and that of Supramolecular chemistry by J. M. Lehn showed an importance of interaction between molecules, gave tremendous influence on, and initiated huge amount of researches in science. Nobel prize of chemistry was awarded to these researchers in 1987. In the late 1980s fabrications of molecular assemblies using intermolecular interactions came under the spotlight. Typical examples are the syntheses of catenanes, rotaxanes, and molecular knots. One of the applications in this field of chemistry is to make smallest machines at molecular level by fabrications of molecular components. Nobel prize in chemistry was awarded to three researchers working in this field in 2016. There are many other researches making unique structures and properties concerning symmetry and asymmetry but are not well known out of their research field. The aim of this Special Issue is to highlight science and engineering of intermolecular interactions by all aspects of Symmetry and Asymmetry including chemical, physical, biological, natural, artificial, and artistic points of view.

First of all, comprehensive reviews on a particular subject and accounts of research work describing one or several scientific fields in connection with Host-guest chemistry or Supramolecular chemistry by all aspect of Symmetry and Asymmetry are especially welcome. However, any other kind of paper: full research paper, communication, technical note, short overview or comment will also be taken into consideration.

Prof. Keiji Hirose
Guest Editor

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

  • Symmetry
  • Asymmetry
  • Host-guest chemistry
  • Supramolecular chemistry
  • Intermolecular interactions
  • Noncovalent interations
  • Molecular-assembly
  • Aggregation
  • Chirality

Published Papers (5 papers)

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Research

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11 pages, 1903 KiB  
Article
Chiroptical Symmetry Analysis of Trianglimines: A Case Study
by Ani Ozcelik, Raquel Pereira-Cameselle, Ricardo A. Mosquera, Ángeles Peña-Gallego and J. Lorenzo Alonso-Gómez
Symmetry 2019, 11(10), 1245; https://doi.org/10.3390/sym11101245 - 04 Oct 2019
Cited by 3 | Viewed by 2050
Abstract
It is well established that chiroptical responses, based on the unique reaction to circularly polarized light by chiral non-racemic systems, are sensitive to the stereochemistry of the featuring systems. This behavior has promoted the use of chiroptical spectroscopies as a mandatory tool in [...] Read more.
It is well established that chiroptical responses, based on the unique reaction to circularly polarized light by chiral non-racemic systems, are sensitive to the stereochemistry of the featuring systems. This behavior has promoted the use of chiroptical spectroscopies as a mandatory tool in the structure determination of molecules for decades. Recently, the higher sensitivity of chiroptical techniques compared to the conventional UV/Vis absorption and fluorescence spectroscopies or electrochemistry has awakened much interest in the development of chiroptical everyday applications. While chiroptical responses could be predicted by ab initio calculations, large systems calculated at a high level of theory may have an important computational cost; therefore, more intuitive methods are desired to design systems with tailored chiroptical responses. In this regard, the exciton chirality method has been often used in conformationally stable systems incorporating at least two independent chromophores. Taking this method into consideration, in our previous work, we described the chiroptical symmetry analysis (CSA) based on symmetry selection rules. To explore the scope of the CSA, herein we perform the chiroptical symmetry analysis of diverse trianglimines and draw general conclusions to assist on the design of chiroptical systems with high symmetry. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Host-Guest Chemistry and Supramolecular Chemistry)
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11 pages, 5705 KiB  
Article
Template-Free Synthesis of a Phenanthroline-Containing [2]Rotaxane: A Reversible pH-Controllable Molecular Switch
by Masahiro Muraoka, Kakeru Aoyama, Sae Fujihara, Risa Yamane, Ichiro Hisaki, Mikiji Miyata, Michihisa Murata and Yohji Nakatsuji
Symmetry 2019, 11(9), 1137; https://doi.org/10.3390/sym11091137 - 06 Sep 2019
Cited by 2 | Viewed by 3357
Abstract
The synthesis of symmetric and asymmetric rotaxanes consisting of neutral axle and ring components without ionic templates is necessary for applications in molecular sensors and molecular switches. A phenanthroline-containing symmetric [2]rotaxane was newly synthesized by inducing hydrogen bonding and π-interaction using a template-free [...] Read more.
The synthesis of symmetric and asymmetric rotaxanes consisting of neutral axle and ring components without ionic templates is necessary for applications in molecular sensors and molecular switches. A phenanthroline-containing symmetric [2]rotaxane was newly synthesized by inducing hydrogen bonding and π-interaction using a template-free threading-followed-by-stoppering method. The obtained rotaxane serves as a reversible pH-controllable molecular switch. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Host-Guest Chemistry and Supramolecular Chemistry)
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19 pages, 3864 KiB  
Article
Symmetry in Recognition of Supramolecular Synthons–Competition between Hydrogen Bonding and Coordination Bond in Multinuclear CuII–4f Complexes with Bicompartmental Schiff Base Ligand
by Barbara Miroslaw, Dariusz Osypiuk, Beata Cristóvão and Halina Głuchowska
Symmetry 2019, 11(4), 460; https://doi.org/10.3390/sym11040460 - 02 Apr 2019
Cited by 5 | Viewed by 2729
Abstract
Classic Cu–O coordination bonds in 1 or elongated semi-coordination ones in 2 and 3 were applied to construct CuII–4f complexes composed of trinuclear subunits linked through μ-NO3− ions with formulae given as [Cu2Tm(H2tehy) [...] Read more.
Classic Cu–O coordination bonds in 1 or elongated semi-coordination ones in 2 and 3 were applied to construct CuII–4f complexes composed of trinuclear subunits linked through μ-NO3− ions with formulae given as [Cu2Tm(H2tehy)2]2(NO3)6·H2O, (1), {[Cu2Ho(H2tehy)2(NO3)2][Cu2Ho(H2tehy)2(H2O)2]}(NO3)4·2H2O, (2), and {[Cu2Er(H2tehy)2(H2O)]2([Cu2Er(H2tehy)2(NO3)]2}(NO3)10·2H2O·4CH3OH, (3), where H2tehy = C19H20N2O4 is a tetrahydroxy Schiff base ligand. Topological analysis showed that the same characteristic motif of coordination accompanied by hydrogen bonds involving the uncoordinated nitrate oxygen atom and ligand’s phenoxy O atoms is responsible for linking trinuclear subunits into a hexanuclear one as well as for bridging the hexanuclear coordination units in 3 into a 1D supramolecular polymer, with the Cu–O distance being 3.19(1) Å, much longer than the limit of a semi-coordination bond (3.07 Å). The Cambridge Structural Database was used to discuss issues of crystallographic criteria (distance and angular preferences) for the assessment of the stabilizing or destabilizing effect of hydrogen bonding on coordination. The presented results show that the symmetrically repeated arrangement of molecules may provide a useful tool for identifying higher order non-covalently bonded supramolecular aggregates. The complexes 1–3 have been characterized by X-ray diffraction, FTIR, and thermal analysis. The magnetic studies indicated the ferromagnetic interaction between CuII and HoIII ions. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Host-Guest Chemistry and Supramolecular Chemistry)
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Review

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14 pages, 3591 KiB  
Review
Mechanical Chirality of Rotaxanes: Synthesis and Function
by Kazuko Nakazono and Toshikazu Takata
Symmetry 2020, 12(1), 144; https://doi.org/10.3390/sym12010144 - 10 Jan 2020
Cited by 31 | Viewed by 6810
Abstract
Mechanically chiral molecules have attracted considerable attention due to their property and function based on its unique interlocked structure. This review covers the recent advances in the synthesis and function of interlocked rotaxanes with mechanical chirality along with their dynamic and complex stereochemistry. [...] Read more.
Mechanically chiral molecules have attracted considerable attention due to their property and function based on its unique interlocked structure. This review covers the recent advances in the synthesis and function of interlocked rotaxanes with mechanical chirality along with their dynamic and complex stereochemistry. The application of mechanically chiral rotaxanes to control the polymer helical structure is also introduced, where amplification of mechanical chirality appears to cause the macroscopic polymer property change, suggesting the potential applicability of mechanical chirality in polymer systems. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Host-Guest Chemistry and Supramolecular Chemistry)
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22 pages, 9978 KiB  
Review
Exploring and Exploiting the Symmetry-Breaking Effect of Cyclodextrins in Mechanomolecules
by Carson J. Bruns
Symmetry 2019, 11(10), 1249; https://doi.org/10.3390/sym11101249 - 05 Oct 2019
Cited by 20 | Viewed by 7501
Abstract
Cyclodextrins (CDs) are cone-shaped molecular rings that have been widely employed in supramolecular/host–guest chemistry because of their low cost, high biocompatibility, stability, wide availability in multiple sizes, and their promiscuity for binding a range of molecular guests in water. Consequently, CD-based host–guest complexes [...] Read more.
Cyclodextrins (CDs) are cone-shaped molecular rings that have been widely employed in supramolecular/host–guest chemistry because of their low cost, high biocompatibility, stability, wide availability in multiple sizes, and their promiscuity for binding a range of molecular guests in water. Consequently, CD-based host–guest complexes are often employed as templates for the synthesis of mechanically bonded molecules (mechanomolecules) such as catenanes, rotaxanes, and polyrotaxanes in particular. The conical shape and cyclodirectionality of the CD “bead” gives rise to a symmetry-breaking effect when it is threaded onto a molecular “string”; even symmetrical guests are rendered asymmetric by the presence of an encircling CD host. This review focuses on the stereochemical implications of this symmetry-breaking effect in mechanomolecules, including orientational isomerism, mechanically planar chirality, and topological chirality, as well as how they support applications in regioselective and stereoselective chemical synthesis, the design of molecular machine prototypes, and the development of advanced materials. Full article
(This article belongs to the Special Issue Symmetry and Asymmetry in Host-Guest Chemistry and Supramolecular Chemistry)
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