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Special Issue "Supramolecular Chirality"

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A special issue of Symmetry (ISSN 2073-8994).

Deadline for manuscript submissions: closed (31 July 2014)

Special Issue Editor

Guest Editor
Dr. Victor Borovkov

Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan
Fax: +81 6 6879 7923
Interests: induced chirality; chirality transfer; supramolecular chirality; chiral chromophores; circular dichroism; chiral materials and surfaces

Special Issue Information

Dear Colleagues,

Supramolecular chirality is a newly emerging interdisciplinary field of science, being an intelligent combination of supramolecular chemistry and chirality. This phenomenon deals with all aspects of chirality (generation, transfer, amplification, modulation, memorizing) upon noncovalent interactions. Supramolecular chirality is a rapidly growing area of research and directly relates to many natural processes, artificial systems and modern technologies. It is widely observable and plays a crucial role in various biological self-assemblies, such as DNA/RNA, proteins, membranes, photosynthetic apparatus, etc. Besides, this field has an immediate positive impact in such important applications as molecular and chiral recognition, asymmetric synthesis and catalysis, chemical and chiroptical sensors, chiral separation and stereochemical assignment, material sciences and nanotechnology, medicine and biomimetic investigations, among others.

The aim of this Special Issue is to highlight, as fully as possible, all aspects of supramolecular chirality as in natural/physical sciences and in modern technologies. First of all, comprehensive reviews on a particular subject and accounts of research work describing one or several scientific fields in connection with supramolecular chirality (such as “Supramolecular Chirality in …”) 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.

Dr. Victor Borovkov
Guest Editor

Submission

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. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as 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 refereed through a 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 800 CHF (Swiss Francs).

Keywords

  • supramolecular chirality
  • supramolecular chemistry
  • asymmetry
  • chirality
  • noncovalent interactions
  • host-guest chemistry
  • self-assembly
  • aggregation
  • chiroptical spectroscopy

Published Papers (11 papers)

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Research

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Open AccessArticle Determining Amino Acid Chirality in the Supernova Neutrino Processing Model
Symmetry 2014, 6(4), 909-925; doi:10.3390/sym6040909
Received: 19 July 2014 / Revised: 14 October 2014 / Accepted: 27 October 2014 / Published: 3 November 2014
PDF Full-text (479 KB) | HTML Full-text | XML Full-text
Abstract
A model is described that can be used to estimate the bulk polarization of largerotating meteoroids in the magnetic field of a neutron star. The results of this model areapplicable to the Supernova Neutrino Amino Acid Processing model, which describes onepossible way [...] Read more.
A model is described that can be used to estimate the bulk polarization of largerotating meteoroids in the magnetic field of a neutron star. The results of this model areapplicable to the Supernova Neutrino Amino Acid Processing model, which describes onepossible way in which the amino acids, known in nearly all cases to exhibit supramolecularchirality, could have become enantiomeric. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessArticle Dynamic Processes in Prochiral Solvating Agents (pro-CSAs) Studied by NMR Spectroscopy
Symmetry 2014, 6(2), 345-367; doi:10.3390/sym6020345
Received: 12 March 2014 / Revised: 7 May 2014 / Accepted: 7 May 2014 / Published: 14 May 2014
Cited by 3 | PDF Full-text (2656 KB) | HTML Full-text | XML Full-text
Abstract
Several dynamic processes, including tautomerism and macrocyclic inversion, in 1H-NMR prochiral solvating agents (pro-CSAs) are investigated. Various features of pro-CSA, including modes of interaction for complex formation, stoichiometry, binding strength and temperature effects were compared for three representative pro-CSA molecules. Structural [...] Read more.
Several dynamic processes, including tautomerism and macrocyclic inversion, in 1H-NMR prochiral solvating agents (pro-CSAs) are investigated. Various features of pro-CSA, including modes of interaction for complex formation, stoichiometry, binding strength and temperature effects were compared for three representative pro-CSA molecules. Structural effects of conjugated tetrapyrrole pro-CSA on the mechanism of enantiomeric excess determination are also discussed. Detailed analysis of species (complexes) and dynamic processes occurring in solution and their 1H-NMR spectral manifestations at various temperatures is presented. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessArticle Topological Symmetry Groups of Small Complete Graphs
Symmetry 2014, 6(2), 189-209; doi:10.3390/sym6020189
Received: 12 February 2014 / Revised: 2 April 2014 / Accepted: 2 April 2014 / Published: 8 April 2014
Cited by 2 | PDF Full-text (266 KB) | HTML Full-text | XML Full-text
Abstract
Topological symmetry groups were originally introduced to study the symmetries of non-rigid molecules, but have since been used to study the symmetries of any graph embedded in R3. In this paper, we determine for each complete graph Kn with [...] Read more.
Topological symmetry groups were originally introduced to study the symmetries of non-rigid molecules, but have since been used to study the symmetries of any graph embedded in R3. In this paper, we determine for each complete graph Kn with n ≤ 6, what groups can occur as topological symmetry groups or orientation preserving topological symmetry groups of some embedding of the graph in R3. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Review

Jump to: Research

Open AccessReview Supramolecular Chirality in Dynamic Coordination Chemistry
Symmetry 2014, 6(4), 880-895; doi:10.3390/sym6040880
Received: 26 September 2014 / Revised: 16 October 2014 / Accepted: 17 October 2014 / Published: 24 October 2014
Cited by 4 | PDF Full-text (1117 KB) | HTML Full-text | XML Full-text
Abstract
Labile metal complexes have a useful coordination bond; which is weaker than a covalent C–C bond and is reversibly and dynamically formed and dissociated. Such labile metal complexes also can be used to construct chiral shapes and offer dynamic conversion of chiral [...] Read more.
Labile metal complexes have a useful coordination bond; which is weaker than a covalent C–C bond and is reversibly and dynamically formed and dissociated. Such labile metal complexes also can be used to construct chiral shapes and offer dynamic conversion of chiral molecular shapes in response to external stimuli. This review provides recent examples of chirality induction and describes the dynamic conversion systems produced by chiral metal complexes including labile metal centers, most of which respond to external stimuli by exhibiting sophisticated conversion phenomena. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessReview Chlorophylls, Symmetry, Chirality, and Photosynthesis
Symmetry 2014, 6(3), 781-843; doi:10.3390/sym6030781
Received: 28 July 2014 / Revised: 31 August 2014 / Accepted: 1 September 2014 / Published: 10 September 2014
Cited by 15 | PDF Full-text (23001 KB) | HTML Full-text | XML Full-text
Abstract
Chlorophylls are a fundamental class of tetrapyrroles and function as the central reaction center, accessory and photoprotective pigments in photosynthesis. Their unique individual photochemical properties are a consequence of the tetrapyrrole macrocycle, the structural chemistry and coordination behavior of the phytochlorin system, [...] Read more.
Chlorophylls are a fundamental class of tetrapyrroles and function as the central reaction center, accessory and photoprotective pigments in photosynthesis. Their unique individual photochemical properties are a consequence of the tetrapyrrole macrocycle, the structural chemistry and coordination behavior of the phytochlorin system, and specific substituent pattern. They achieve their full potential in solar energy conversion by working in concert in highly complex, supramolecular structures such as the reaction centers and light-harvesting complexes of photobiology. The biochemical function of these structures depends on the controlled interplay of structural and functional principles of the apoprotein and pigment cofactors. Chlorophylls and bacteriochlorophylls are optically active molecules with several chiral centers, which are necessary for their natural biological function and the assembly of their supramolecular complexes. However, in many cases the exact role of chromophore stereochemistry in the biological context is unknown. This review gives an overview of chlorophyll research in terms of basic function, biosynthesis and their functional and structural role in photosynthesis. It highlights aspects of chirality and symmetry of chlorophylls to elicit further interest in their role in nature. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessReview Supramolecular Chirality: Solvent Chirality Transfer in Molecular Chemistry and Polymer Chemistry
Symmetry 2014, 6(3), 677-703; doi:10.3390/sym6030677
Received: 15 July 2014 / Revised: 7 August 2014 / Accepted: 7 August 2014 / Published: 13 August 2014
Cited by 13 | PDF Full-text (4220 KB) | HTML Full-text | XML Full-text
Abstract
Controlled mirror symmetry breaking arising from chemical and physical origin is currently one of the hottest issues in the field of supramolecular chirality. The dynamic twisting abilities of solvent molecules are often ignored and unknown, although the targeted molecules and polymers in [...] Read more.
Controlled mirror symmetry breaking arising from chemical and physical origin is currently one of the hottest issues in the field of supramolecular chirality. The dynamic twisting abilities of solvent molecules are often ignored and unknown, although the targeted molecules and polymers in a fluid solution are surrounded by solvent molecules. We should pay more attention to the facts that mostly all of the chemical and physical properties of these molecules and polymers in the ground and photoexcited states are significantly influenced by the surrounding solvent molecules with much conformational freedom through non-covalent supramolecular interactions between these substances and solvent molecules. This review highlights a series of studies that include: (i) historical background, covering chiral NaClO3 crystallization in the presence of d-sugars in the late 19th century; (ii) early solvent chirality effects for optically inactive chromophores/fluorophores in the 1960s–1980s; and (iii) the recent development of mirror symmetry breaking from the corresponding achiral or optically inactive molecules and polymers with the help of molecular chirality as the solvent use quantity. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessReview Autosolvation: Architecture and Selection of Chiral Conformers in Alkylcobalt Carbonyl Molecular Clocks
Symmetry 2014, 6(3), 551-565; doi:10.3390/sym6030551
Received: 29 April 2014 / Revised: 23 June 2014 / Accepted: 24 June 2014 / Published: 4 July 2014
Cited by 1 | PDF Full-text (1652 KB) | HTML Full-text | XML Full-text
Abstract
Autosolvation is an important factor in stabilizing the architecture of medium complicated molecules. It is a kind of “supramolecular force” acting in intramolecular manner, consisting of orbital-orbital interactions between polar groups, separated by more than one covalent bonds within the same molecule. [...] Read more.
Autosolvation is an important factor in stabilizing the architecture of medium complicated molecules. It is a kind of “supramolecular force” acting in intramolecular manner, consisting of orbital-orbital interactions between polar groups, separated by more than one covalent bonds within the same molecule. This effect facilitates also the development of chiral conformations. Two typical alkylcobalt carbonyl type molecules are discussed here as examples of autosolvating intramolecular interactions, leading to dramatic selection of chiral conformers and indicating also to the limits of the effect. The conformers stabilized by autosolvation and their interconversion are excellent examples of a “molecular clockwork”. Operation mode of these molecular clockworks gives some insight into the intramolecular transfer of chiral information. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessReview Chiral Liquid Crystals: Structures, Phases, Effects
Symmetry 2014, 6(2), 444-472; doi:10.3390/sym6020444
Received: 12 April 2014 / Revised: 5 June 2014 / Accepted: 10 June 2014 / Published: 16 June 2014
Cited by 18 | PDF Full-text (1632 KB) | HTML Full-text | XML Full-text
Abstract
The introduction of chirality, i.e., the lack of mirror symmetry, has a profound effect on liquid crystals, not only on the molecular scale but also on the supermolecular scale and phase. I review these effects, which are related to the formation [...] Read more.
The introduction of chirality, i.e., the lack of mirror symmetry, has a profound effect on liquid crystals, not only on the molecular scale but also on the supermolecular scale and phase. I review these effects, which are related to the formation of supermolecular helicity, the occurrence of novel thermodynamic phases, as well as electro-optic effects which can only be observed in chiral liquid crystalline materials. In particular, I will discuss the formation of helical superstructures in cholesteric, Twist Grain Boundary and ferroelectric phases. As examples for the occurrence of novel phases the Blue Phases and Twist Grain Boundary phases are introduced. Chirality related effects are demonstrated through the occurrence of ferroelectricity in both thermotropic as well as lyotropic liquid crystals. Lack of mirror symmetry is also discussed briefly for some biopolymers such as cellulose and DNA, together with its influence on liquid crystalline behavior. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessReview Hydrodynamic Helical Orientations of Nanofibers in a Vortex
Symmetry 2014, 6(2), 383-395; doi:10.3390/sym6020383
Received: 15 April 2014 / Revised: 14 May 2014 / Accepted: 15 May 2014 / Published: 20 May 2014
Cited by 2 | PDF Full-text (1359 KB) | HTML Full-text | XML Full-text
Abstract
In this review article, I report our recent studies on spectroscopic visualizations of macroscopic helical alignments of nanofibers in vortex flows. Our designed supramolecular nanofibers, formed through self-assemblies of dye molecules, helically align in torsional flows of a vortex generated by mechanical [...] Read more.
In this review article, I report our recent studies on spectroscopic visualizations of macroscopic helical alignments of nanofibers in vortex flows. Our designed supramolecular nanofibers, formed through self-assemblies of dye molecules, helically align in torsional flows of a vortex generated by mechanical rotary stirring of the sample solutions. The nanofiber, formed through bundling of linear supramolecular polymers, aligns equally in right- and left-handed vortex flows. However, in contrast, a one-handedly twisted nanofiber, formed through helical bundling of the supramolecular polymers, shows unequal helical alignments in these torsional flows. When the helical handedness of the nanofiber matches that of the vortex flow, the nanofiber aligns more efficiently in the flowing fluid. Such phenomena are observed not only with the artificial helical supramolecular nanofibers but also with biological nanofibers such as double-stranded DNA. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessReview Supramolecular Chirality in Porphyrin Chemistry
Symmetry 2014, 6(2), 256-294; doi:10.3390/sym6020256
Received: 18 March 2014 / Revised: 18 April 2014 / Accepted: 21 April 2014 / Published: 23 April 2014
Cited by 12 | PDF Full-text (1066 KB) | HTML Full-text | XML Full-text
Abstract
Supramolecular chirality, being an intelligent combination of supramolecular chemistry and chiral science, plays a decisive role in the functioning of various natural assemblies and has attracted much attention from the scientific community, due to different applications in modern technologies, medicine, pharmacology, catalysis [...] Read more.
Supramolecular chirality, being an intelligent combination of supramolecular chemistry and chiral science, plays a decisive role in the functioning of various natural assemblies and has attracted much attention from the scientific community, due to different applications in modern technologies, medicine, pharmacology, catalysis and biomimetic research. Porphyrin molecules are of particular interest to study this phenomenon owing to their unique spectral, physico-chemical and synthetic properties. This review highlights the most important types of chiral porphyrin structures by using the best-suited representative examples, which are frequently used in the area of supramolecular chirality. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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Open AccessReview Metalloporphyrin Symmetry in Chiral Recognition and Enantioselective Catalysis
Symmetry 2014, 6(2), 210-221; doi:10.3390/sym6020210
Received: 28 February 2014 / Revised: 31 March 2014 / Accepted: 1 April 2014 / Published: 10 April 2014
Cited by 5 | PDF Full-text (256 KB) | HTML Full-text | XML Full-text
Abstract
Symmetry plays a fundamental role in chiral recognition and enantioselective catalysis. Porphyrins possess a number of structural features that make them attractive for the stereocontrol of chiral recognition and metal-catalyzed asymmetric reactions. This article is a brief account of our studies on [...] Read more.
Symmetry plays a fundamental role in chiral recognition and enantioselective catalysis. Porphyrins possess a number of structural features that make them attractive for the stereocontrol of chiral recognition and metal-catalyzed asymmetric reactions. This article is a brief account of our studies on chiral recognition and enantioselective catalysis by optically active metalloporphyrins. Some of the studies on chiral recognition and asymmetric catalysis by metalloporphyrins performed by others have also been included when useful. Full article
(This article belongs to the Special Issue Supramolecular Chirality)
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