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

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.

Catechol-Containing Schiff Bases on Thiacalixarene: Synthesis, Copper (II) Recognition, and Formation of Organic-Inorganic Copper-Based Materials

“…Synthetic macrocyclic compounds, such as calixarenes, thiacalixarenes, resorcinarenes, pillararenes, and others, have excellent complexing properties and are often selective for a certain substrate [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 ]. The introduction of fragments of Schiff bases into the structure of (thia)calixarenes makes it possible to increase both the efficiency and selectivity with respect to metal cations.…”

Quantitative analysis of nutrients for nucleosides, nucleobases, and amino acids hidden behind five distinct regions‐derived Poria cocos using ultra‐performance liquid chromatography coupled with triple‐quadrupole linear ion‐trap tandem mass spectrometry

“…The ACQUITY HSS T3 (2.1 × 100 mm, 1.7 μm) column, the ACQUITY BEH C18 (2.1 × 100 mm, 1.7 μm) column, and ACQUITY BEH amide (2.1 × 100 mm, 1.7 μm) column were compared in terms of morphology and retention time of the chromatographic peak. When the ACQUITY BEH amide (2.1 × 100 mm, 1.7 μm) column was used, amino acid, nucleoside, and nucleobases achieved excellent separation and aggregation properties [36]. Different organic phases (methanol, ACN) and aqueous phases (0.1% formic acid‐water solution, 0.1% trifluoroacetic acid‐water solution) have previously been identified but yielded poor results.…”

Surfactant Effect on the Physicochemical Characteristics of Solid Lipid Nanoparticles Based on Pillar[5]arenes

“…The use of synthetic receptors with the extra stability, selectivity and specificity is in demand. An application of synthetic receptors will have a great impact on technologies based on molecular recognition [ 4 , 5 , 6 , 7 , 8 , 9 ]. Macrocyclic compounds are promising candidates for the creation of next generation of molecular-scale porous materials due to their cavity [ 10 , 11 , 12 ].…”