Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

Abstract

Pillar[5]arenes bearing amide and carboxylic groups have demonstrated recognition performance for some representative alkali metal ions including Li + , Na + , K + and Cs + in series cations of sand d-metals compared to pillar[5] arenes with hydroxyl, methoxy and acetone fragments. Their complexation abilities toward these cations were evaluated by UV-Vis technique. The complexation results revealed that pillar[5]arene, containing glicylglicyne groups, were the most efficient cation receptors for Li + , Na + , K + and Cs + over other synthesized and studied pillar[5]arenes. Introduction of long glycylglycide fragments into macrocycle structure allowed to increase the association constant logarithm in the case of Li + by 2 orders. In addition, in the set of macrocycles, incorporation of the additional amide fragments and carboxyl group into macrocycle structure leads to increasing the binding efficiency with alkali metal cations.

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

“…Amino acids are the main building blocks of many enzymes, proteins and peptides, and play important role in metabolic processes. Consequently, functionalization of macrocyclic compounds by amino acid fragments allows the creation of derivatives with antimicrobial activity, use them as artificial ion channels, for targeted drug delivery, or as cholinesterase inhibitors [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 36 , 37 ]. In this regard, the design of synthetic macrocyclic receptors containing amino acid residues is fascinating task for modern organic and supramolecular chemistry.…”

“…Introduction of chiral amino acid fragments into the macrocycle’s structure makes it possible to create novel water-soluble receptors based on them. A number of pillararenes containing alanine (Ala) [ 24 , 25 , 26 ], phenylalanine (Phe) [ 27 ], arginine (Arg) [ 28 ], tryptophan (Trp) [ 29 ], glycine (Gly) [ 30 , 31 ] and diglycine (Gly-Gly) [ 32 ] fragments have been reported in the literature. These compounds have been applied in various fields: from the binding of alkali metal cations and dyes to targeted drug delivery and use as ion channels.…”

Solid-Contact Potentiometric Sensors and Multisensors Based on Polyaniline and Thiacalixarene Receptors for the Analysis of Some Beverages and Alcoholic Drinks

“…This might be due to lower differentiation of the signal toward metal cations involved in supramolecular interactions with this receptor. Thus, pillar[5]arenes with amide and carboxylic groups can bind Li + , Na + , K + , and Cs + with similar association constants determined by UV-viz spectroscopy (Yakimova et al, 2017 ). The binding efficiency was increased by introduction of the glycylglycide, additional amide, and carboxylic fragments in the macrocycle moiety.…”

Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers

“…The macrocyclic compound in this case will act as a link between the “protective shell”—a nontoxic water-soluble polymer and a drug. This is due to the presence of a macrocyclic cavity in pillar[5]arenes [ 17 , 18 , 19 , 20 , 21 , 22 ], which is involved in the formation of host-guest complexes with drugs of various structures [ 18 , 21 , 22 ]. Additionally, the introduction into the structure of macrocycles of substituents complementary to the tetrazole fragments of the polymer and sensitive to pH changes will facilitate the packing of tetrazole-containing polymers into nanosized associates [ 17 , 19 ].…”

“…Pillar [n]arenes are macrocyclic compounds in which fragments of substituted hydroquinones are interconnected by methylene bridges [13]. Unlike other classes of macrocycles (calix[n]arenes, cyclodextrins, cucurbit[n]urils), pillar [n]arenes [16] are synthetically available and allow working in conditions (pH, water, and buffer systems) that are not suitable for other macrocycles [17][18][19][20][21][22]. Yang et al [23] used a water-soluble pillar [5]arene to increase biocompatibility in antibacterial polymeric materials based on cationic polyaspartamide derivatives with different side-chain lengths by creating host-guest complexes to produce new antibacterial materials with pH-sensitive characteristics.…”