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.

No abstract

No abstract

Silver complexes of a cation binding supramolecular host, resorcinarene bis-crown (CNBC5) with propyl, nonyl, decyl and undecyl alkyl chains were investigated by NMR titration, picrate extraction and single crystal X-ray diffraction. Binding studies showed that both 1 : 1 and 1 : 2 (host-Ag(+)) complexes are present in solution with only a slight effect of the lower rim alkyl chain length on the binding constants (log K 4.0-4.2 for 1 : 2 complexes). Solid state complexes of the resorcinarene bis-crowns bearing either C(3) or C(11) chains were obtained. Single crystal X-ray analyses showed that both derivatives bind silver ions by metal-arene and Ag···O coordination from the crown ether bridges and from the solvent, and pack in layered or bilayered fashion. Furthermore, the amphiphilic nature of C11BC5 was demonstrated using the Langmuir balance technique. Langmuir-Blodgett films of the amphiphilic C11BC5-Ag complex were transferred onto a substrate and shown to possess antibacterial activity against E. coli.

This communication demonstrates the possibility to nucleate and grow different crystalline polymorphic forms of gabapentin (GBP) using, as nucleation templates, Langmuir monolayers of an amphiphilic calixarene at different packing densities.