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Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes
| Content Provider | MDPI |
|---|---|
| Author | Nazarova, Anastasia Shurpik, Dmitriy Padnya, Pavel Mukhametzyanov, Timur Cragg, Peter Stoikov, Ivan |
| Copyright Year | 2020 |
| Description | 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. |
| Starting Page | 7206 |
| e-ISSN | 14220067 |
| DOI | 10.3390/ijms21197206 |
| Journal | International Journal of Molecular Sciences |
| Issue Number | 19 |
| Volume Number | 21 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2020-09-29 |
| Access Restriction | Open |
| Subject Keyword | International Journal of Molecular Sciences Organic Chemistry Aggregation (1s)-(+)-10-camphorsulfonic Acid Host-guest Systems Methyl Orange Dye Amino Acid Pillar[5]arene |
| Content Type | Text |
| Resource Type | Article |
