Calix[n]arenes represent a very attractive family of macrocyclic compounds with many potential supramolecular applications. Due to their well-established chemistry and many different synthetic strategies, enabling practically any derivatization of the basic skeleton, calixarenes are among the very popular building blocks used for the design and construction of various receptors, sensors and other sophisticated supramolecular systems. Regio- and/or stereo-selective derivatization of calixarenes currently represents a very extensive set of reactions, the overview of which would fill many thick books. Therefore, this review deals with only a small part of the above-mentioned reactions, specifically describes possible ways of bridging the upper rim of calixarenes, often leading to interesting rigidified structures, and also briefly mentions the potential use of these compounds.

• Publikační typ
• časopisecké články MeSH
• přehledy MeSH

The formation of inherently chiral calix[4]arenes by the intramolecular cyclization approach suffers from a limited number of suitable substrates for these reactions. Here, we report an easy way to prepare one class of such compounds: calixquinolines, which can be obtained by the reaction of aldehydes with easily accessible aminocalix[4]arenes in acidic conditions (Doebner-Miller reaction). The synthetic procedure represents a very straightforward approach to the inherently chiral macrocyclic systems. The complexation studies revealed the ability of these compounds to complex quaternary ammonium salts with different stoichiometries depending on the guest molecules. At the same time, the ability of enantioselective complexation of chiral N-methylammonium salts was demonstrated.

• Klíčová slova
• calixarene, chiral recognition, complexation, inherent chirality, mercuration, meta-substitution, quinoline formation,
• MeSH
• aldehydy * MeSH
• chinoliny * MeSH
• cyklizace MeSH
• kvartérní amoniové sloučeniny chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• aldehydy * MeSH
• chinoliny * MeSH
• kvartérní amoniové sloučeniny MeSH

Meta/meta- and meta/para-disubstituted organomercury calix[4]arenes in the cone conformation were transformed into corresponding amino derivatives. Acylation and subsequent intramolecular cyclization using the Bischler-Napieralski reaction provided, in the case of the meta/meta-series, double bridged calixarenes possessing seven membered rings on the upper rim. A similar synthetic strategy applied to meta/para-isomers allowed for the isolation of monobridged compounds bearing an additional trifluoroacetamido group located distally to seven-membered rings. Both series represent inherently chiral systems, which were successfully resolved using preparative chiral HPLC. The pure enantiomers exhibited a recognition ability towards selected chiral guest molecules as documented by the 1H NMR titration experiments. The absolute configuration of the phenyl-substituted enantiomer (meta/meta-) was confirmed by single crystal structure determination (X-ray).

• Publikační typ
• časopisecké články MeSH