Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

Anastasia Nazarova, Dmitriy Shurpik, Pavel Panda, Timur Mukhametzayanov, Peter Cragg, Ivan Stoikov

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Article number7206
Pages (from-to)1-19
Number of pages19
JournalInternational Journal of Molecular Sciences
Volume21
Issue number19
DOIs
Publication statusPublished - 29 Sep 2020

Bibliographical note

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

Keywords

  • aggregation
  • (1S)-(+)-10-camphorsulfonic acid
  • host-guest systems
  • methyl orange dye
  • amino acid
  • pillar[5]arene
  • Aggregation
  • Amino acid
  • Pillar[5]arene
  • Methyl orange dye
  • Host-guest systems

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