Novel water-soluble multifunctional pillararenes 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 pillararenes. It was shown that pillararenes 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.
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- (1S)-(+)-10-camphorsulfonic acid
- host-guest systems
- methyl orange dye
- amino acid
- Amino acid
- Methyl orange dye
- Host-guest systems
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- School of Applied Sciences - Prof. in Supramolecular Chemistry
- Centre for Precision Health and Translational Medicine
- Applied Chemical Sciences Research and Enterprise Group
- Centre for Lifelong Health