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Formation of Chiral Supramolecular Assemblies

A Special Issue of International Journal of Molecular Sciences (ISSN 1422-0067) belonging to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: 31 March 2027 | Viewed by 369

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Guest Editor
Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences in Lodz, Sienkiewicza 112, 90-363 Lodz, Poland
Interests: organic synthesis; stereochemistry; asymmetric synthesis; chiral (organo)catalysts; conductive organic polymers; organic electronics; flame retardants; organophosphorus; organosulfur and organoselenium chemistry; drug polymorphs

Special Issue Information

Dear Colleagues,

Supramolecular systems are defined as well-organized molecular assemblies composed of multiple components that maintain their self-organized architecture through non-covalent interactions, including electrostatic forces, π–π stacking interactions, hydrogen bonding, and metal–ligand coordination.

Chirality in chemical architectures is observed at the supramolecular level, as seen in the helical chirality of double-stranded DNA. Chiral molecular assemblies are exemplified by both low- and high-molecular-weight compounds, particularly chiral biomolecules such as enzymes, proteins, and nucleic acid strands, which are well-known for their biomedical applications. Additionally, examples include inclusion complexes, crown ethers, and cage-like catalysts that exhibit host–guest binding behavior, important for molecular recognition. Furthermore, chiral nanostructures and chiral polymers have been developed for their potential applications as functional materials in material sciences and organic synthesis. This Special Issue will present recent advances in the field of supramolecular chemistry regarding the self-organization of chiral molecules into well-defined systems.

Research areas for this Special Issue may include (but are not limited to) the following topics:

  • Synthesis, preparations of chiral structures for supramolecular assemblies and their applications;
  • The nature of supramolecular interactions;
  • The study of the host–guest behavior;
  • The significance of chiral supramolecular assemblies and supramolecules;
  • The self-assembly of achiral and chiral molecules;
  • Aspects of stereochemistry within these architectures, including chiral and molecular recognition;
  • The role of supramolecules in biocatalysis;
  • The function of enzymes in organic and/or asymmetric synthesis;
  • The physicochemical properties of the chiral supramolecular assembies.

Researchers working in this field are invited to submit original research papers and review articles to this Special Issue.

We look forward to receiving your contributions.

Dr. Dorota Krasowska
Guest Editor

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-anonymized peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

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Keywords

  • chiral macromolecules
  • supramolecular assemblies
  • helical chirality
  • molecular recognition
  • host–guest systems
  • self-assembly
  • self-organization
  • biomolecules
  • non-bonding interactions

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Published Papers (1 paper)

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Research

15 pages, 1962 KB  
Article
Regiospecific, Diastereo- and Enantioselective Allylboration with Methylenecyclobutylboranes: Experimental and Computational Study
by Oleg A. Mikhaylov, Angelina Kolchina, Ivan I. Murygin, Albert G. Nigmatov, Ivan S. Arteev and Ilya D. Gridnev
Int. J. Mol. Sci. 2026, 27(18), 8277; https://doi.org/10.3390/ijms27188277 (registering DOI) - 17 Sep 2026
Viewed by 136
Abstract
New methylenecyclobutane-derived allylboranes, diisopropyl(2-methylenecyclobutyl)borane and chiral (+)-diisopinocampheyl(2-methylenecyclobutyl)borane undergo rapid equilibration via facile [1,3]-B sigmatropic shifts that interconvert the endocyclic and exocyclic isomers. Both endocyclic isomers react with the Soai aldehyde, 2-(3,3-dimethylbut-1-yn-1-yl)pyrimidine-5-carbaldehyde, affording a single diastereomer of the corresponding homoallylic alcohol. With the achiral [...] Read more.
New methylenecyclobutane-derived allylboranes, diisopropyl(2-methylenecyclobutyl)borane and chiral (+)-diisopinocampheyl(2-methylenecyclobutyl)borane undergo rapid equilibration via facile [1,3]-B sigmatropic shifts that interconvert the endocyclic and exocyclic isomers. Both endocyclic isomers react with the Soai aldehyde, 2-(3,3-dimethylbut-1-yn-1-yl)pyrimidine-5-carbaldehyde, affording a single diastereomer of the corresponding homoallylic alcohol. With the achiral reagent the reaction is regio- and diastereoselective, yielding exclusively one diastereomer of the racemic alcohol in 83% yield. With the chiral reagent, the reaction is enantioselective, providing optically active (RR)-alcohol in 87% yield and 89% ee, demonstrating the synthetic potential of the new chiral organoboron reagent. The regio- and diastereospecific allylboration with the achiral reagent and the regio-, diastereo- and enantioselective allylboration with the novel chiral reagent, as well as their reactions with pyrimidinic aldehyde yielding new alcohol, were analyzed computationally, revealing the origins of high selectivity in dynamic multicomponent reaction mixtures. The exocyclic isomers are unreactive due to the universally high barriers of allylboration reactions with their participation. Relative stabilities of all intermediates and transition states are regulated by the effectiveness of weak non-covalent interactions in the corresponding species. X-Ray crystallographic analysis of the racemate, consisting of (RR) and (SS) enantiomers, confirmed its constitution and relative configuration, whereas the absolute configuration of the chiral compound was assigned on the basis of the DFT calculation results. The chiral alcohol was tested as a catalyst in the Soai reaction, which afforded a racemic product. Full article
(This article belongs to the Special Issue Formation of Chiral Supramolecular Assemblies)
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