Self-assembly of amphiphilic calixarenes and resorcinarenes in water

Abstract

The calixarenes and resorcinarenes are macrocyclic phenolic molecules that can be modified ''a`fac ¸on'' and a wide range of chemical modification strategies have been published over the last 30 years. Because of their remarkable structural properties and their relative ease of chemical modification, they represent excellent and highly versatile bases to design complex building blocks capable of self-assembly and molecular recognition. They have been widely studied for their ability to form supramolecular structures targeting a wide range of applications. The possibility to regio(rim)-selectively modify these macrocycles with different polar and apolar moieties provides synthetic chemists with an unlimited range of possibilities for the design of complex amphiphiles with a high control over the position of the grafted moieties in the three dimensions. These amphiphiles have been shown to possess outstanding self-assembling and/or molecular recognition properties. This short review describes the developments of the chemistry of amphiphilic calixarenes and resorcinarenes with a clear focus on the synthetic paths used for their production and their self-assembly properties in water.

Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles

“…para-Acyl-55 calix [4]arenes on the other hand have not shown clear trend in the SLN size for different alkyl chain lengths. 25 Calix [9]arenes have larger, nine membered macrocyclic rings with enhanced conformational flexibility compared to resorcinarenes and calix [4]arenes, which can lead to different arrangement of the 60 amphiphiles during their self-assembly.…”

Biological applications of functionalized calixarenes

“…105 The recognition of toxic protein surfaces by designed ligands has become an attractive approach in drug discovery. However, the variable nature and irregular behavior of protein surfaces defy this new area of research.…”

Interfacial Binding of Divalent Cations to Calixarene-Based Langmuir Monolayers

“…Subsequently, Baglioni investigated the complexation properties of four calix [8]arene derivatives with alkaline earth metal ions; 25 all studied macrocycles showed the highest selectivity toward Ba 2+ . In 2005, the same group reported on the interaction of p-tertbutylcalix [6]arene and p-tert-butylcalix [8]arene monolayers with a range of K + salts. 26 The effect of the counterions on the structure of the films was discussed with regard to their position in the Hofmeister series.…”