Molecular recognition through divalent interactions with a self-assembled fibrillar network of a supramolecular organogel

The interaction of phenol derivatives with the self-assembled fibrillar network of two different supramolecular gels has been studied. NMR relaxometry reveals the selective interaction of resorcinol over other related molecules with a gel formed by the gelator 2 which contains terminal pyridine units. No selectivity is observed for a related gelator that contains phenyl instead of pyridine moieties. The selectivity observed by NMR experiments permits the selective suppression of the (1)H NMR signals of resorcinol. This behaviour is translated to macroscopic properties such as the thermal stability of the gels. The observed selectivity together with X-ray diffraction data and molecular modelling suggest that the gels formed by 2 present arrays of pyridine H-bond acceptor groups capable of selective multivalent interaction with phenolic substrates.