Jump to main content
Jump to site search

Issue 7, 2011
Previous Article Next Article

Allosterically driven self-assemblies of interlocked calix[6]arene receptors

Author affiliations


The construction of self-assembled receptors based on flexible concave subunits is a challenging task and constitutes an interesting approach to mimic binding processes occurring in biological systems. The receptors studied herein are based on flexible calix[6]arene skeletons bearing three (or more) acid–base functionalities at their narrow rim. When complementary, they self-assemble in a tail-to-tail manner to give a diabolo-like complex, provided that each calixarene subunit hosts a guest. The allosterically-driven multi-recognition pattern is highly selective and leads to stable quaternary adducts. In order to evaluate the scope of this system, various polyamino and polyacidic calix[6]arenes have been studied. It is shown that modifications of the nature of the wide rim substituents do not alter the efficiency of the quaternary self-assembling process, even with the more flexible macrocycles that lack tBu substituents. On the contrary, the replacement of the latter by smaller groups led to receptors with broader scope, as larger guests such as tryptamine and dopamine derivatives were stabilized in the cavities. Implementation of extra-functionalities at the narrow rim were revealed also to be of high interest. Indeed, it is shown that secondary interactions take place between the two calix-subunits when they present additional and complementary functions such as carboxylate and ureido moieties. The ureido arms are also capable of binding the counter anion Cl of the ammonium guest, thus leading to a quinternary neutral complex. Such remarkable behavior is due to the versatility of the calix[6]arene platform, which allows the implementation of a high number of functions, leading to multiple non-covalent attractive interactions, whereas the macrocycle remains flexible, thus allowing induced-fit processes to occur.

Graphical abstract: Allosterically driven self-assemblies of interlocked calix[6]arene receptors

Back to tab navigation

Supplementary files

Article information

11 Nov 2010
22 Dec 2010
First published
16 Feb 2011

Org. Biomol. Chem., 2011,9, 2387-2396
Article type

Allosterically driven self-assemblies of interlocked calix[6]arene receptors

S. Le Gac, J. Picron, O. Reinaud and I. Jabin, Org. Biomol. Chem., 2011, 9, 2387
DOI: 10.1039/C0OB01020K

Social activity

Search articles by author