Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
| Autor: | D. N. Shurpik, Timur A. Mukhametzyanov, Pavel L. Padnya, Ivan I. Stoikov, Anastasia A. Nazarova, Peter J. Cragg |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Models
Molecular Circular dichroism Magnetic Resonance Spectroscopy Supramolecular chemistry Substituent methyl orange dye 010402 general chemistry 01 natural sciences Catalysis Article host-guest systems Inorganic Chemistry lcsh:Chemistry chemistry.chemical_compound Polymer chemistry Ammonium Compounds Methyl orange Moiety Physical and Theoretical Chemistry Amino Acids Molecular Biology lcsh:QH301-705.5 Spectroscopy (1S)-(+)-10-camphorsulfonic acid chemistry.chemical_classification 010405 organic chemistry Organic Chemistry aggregation Water General Medicine 0104 chemical sciences Computer Science Applications Amino acid Camphor Quaternary Ammonium Compounds chemistry lcsh:Biology (General) lcsh:QD1-999 Self-assembly Calixarenes pillar[5]arene Azo Compounds amino acid |
| Zdroj: | International Journal of Molecular Sciences Volume 21 Issue 19 International Journal of Molecular Sciences, Vol 21, Iss 7206, p 7206 (2020) |
| ISSN: | 1422-0067 |
| Popis: | Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (S-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and 1H NMR spectroscopy. This work demonstrates the first case of using S-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of S-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels. |
| Databáze: | OpenAIRE |
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