Supramolecular Chirality

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

Deadline for manuscript submissions: closed (31 July 2014) | Viewed by 130498

Special Issue Editor

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

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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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479 KiB  
Article
Determining Amino Acid Chirality in the Supernova Neutrino Processing Model
by Michael Famiano, Richard Boyd, Toshitaka Kajino, Takashi Onaka, Katrina Koehler and Sarah Hulbert
Symmetry 2014, 6(4), 909-925; https://doi.org/10.3390/sym6040909 - 03 Nov 2014
Cited by 11 | Viewed by 6144
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 in [...] 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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2656 KiB  
Article
Dynamic Processes in Prochiral Solvating Agents (pro-CSAs) Studied by NMR Spectroscopy
by Jan Labuta, Shinsuke Ishihara, Katsuhiko Ariga and Jonathan P. Hill
Symmetry 2014, 6(2), 345-367; https://doi.org/10.3390/sym6020345 - 14 May 2014
Cited by 11 | Viewed by 6727
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 effects [...] 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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266 KiB  
Article
Topological Symmetry Groups of Small Complete Graphs
by Dwayne Chambers and Erica Flapan
Symmetry 2014, 6(2), 189-209; https://doi.org/10.3390/sym6020189 - 08 Apr 2014
Cited by 13 | Viewed by 5654
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 n [...] 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

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1117 KiB  
Review
Supramolecular Chirality in Dynamic Coordination Chemistry
by Hiroyuki Miyake
Symmetry 2014, 6(4), 880-895; https://doi.org/10.3390/sym6040880 - 24 Oct 2014
Cited by 27 | Viewed by 8249
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 molecular [...] 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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23001 KiB  
Review
Chlorophylls, Symmetry, Chirality, and Photosynthesis
by Mathias O. Senge, Aoife A. Ryan, Kristie A. Letchford, Stuart A. MacGowan and Tamara Mielke
Symmetry 2014, 6(3), 781-843; https://doi.org/10.3390/sym6030781 - 10 Sep 2014
Cited by 167 | Viewed by 34580
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, and [...] 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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4220 KiB  
Review
Supramolecular Chirality: Solvent Chirality Transfer in Molecular Chemistry and Polymer Chemistry
by Michiya Fujiki
Symmetry 2014, 6(3), 677-703; https://doi.org/10.3390/sym6030677 - 13 Aug 2014
Cited by 72 | Viewed by 15631
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 a [...] 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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1652 KiB  
Review
Autosolvation: Architecture and Selection of Chiral Conformers in Alkylcobalt Carbonyl Molecular Clocks
by Róbert Kurdi, Attila Táborosi, Claudia Zucchi and Gyula Pályi
Symmetry 2014, 6(3), 551-565; https://doi.org/10.3390/sym6030551 - 04 Jul 2014
Cited by 6 | Viewed by 6421
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. This [...] 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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1632 KiB  
Review
Chiral Liquid Crystals: Structures, Phases, Effects
by Ingo Dierking
Symmetry 2014, 6(2), 444-472; https://doi.org/10.3390/sym6020444 - 16 Jun 2014
Cited by 157 | Viewed by 19035
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 of [...] 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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1359 KiB  
Review
Hydrodynamic Helical Orientations of Nanofibers in a Vortex
by Akihiko Tsuda
Symmetry 2014, 6(2), 383-395; https://doi.org/10.3390/sym6020383 - 20 May 2014
Cited by 8 | Viewed by 7491
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 rotary [...] 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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1066 KiB  
Review
Supramolecular Chirality in Porphyrin Chemistry
by Victor Borovkov
Symmetry 2014, 6(2), 256-294; https://doi.org/10.3390/sym6020256 - 23 Apr 2014
Cited by 63 | Viewed by 11125
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 and [...] 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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256 KiB  
Review
Metalloporphyrin Symmetry in Chiral Recognition and Enantioselective Catalysis
by Gérard Simonneaux, Hassan Srour, Paul Le Maux, Soizic Chevance and Daniel Carrie
Symmetry 2014, 6(2), 210-221; https://doi.org/10.3390/sym6020210 - 10 Apr 2014
Cited by 15 | Viewed by 8062
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 chiral [...] 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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