Chiral calixarenes and resorcinarenes

Abstract

Since the first synthesis of chiral calixarenes in 1979 by Gutsche enormous progress has been made in preparation techniques and applications. Many chiral calixarenes (including resorcinarenes and homocalixarenes) modified with peptides, carbohydrates, chiral amines or axially chiral groups are known. Due to their diverse conformational features, introduction of chirality into a calixarene platform is not only limited to classical chirality based on carbon stereogenic centers but also can be introduced by asymmetric/dissymmetric substitution pattern or in a non-covalent way. The main driving force for the development of chiral calixarenes is the possibility to use them as enantioselective synthetic receptors. Effective chiral receptors based on calixarenes have found applications in recognition of chiral guests in solution, as chromatography stationary phases, enantioselective membrane carriers and catalysts. Their potential has also been demonstrated in interactions with biological molecules, including protein recognition, formation of gels and antimicrobial activity. The chapter summarizes the current achievements in the field with the special emphasis on unique features of calixarenes and resorcinarenes leading to “non-classical” chirality and functionality based on chiral recognition.