12-Hydroxyoctadecanoic acid forms two kinds of supramolecular gels in nanostructured protic ionic liquids

12HSA is shown to form long-lived ionogels in ethylammonium and propylammonium nitrate ionic liquids at low concentrations via two distinct mechanisms; supramolecular, hydrogen-bond driven aggregation of the acid and amphiphilic assembly of the conjugate base. 12HSA gel structures were shown to consist of high aspect-ratio twisted crystalline fibrils assembled from H-bonded dimers, similar to organogels, while 12HS salts form an elongated rectangular ribbon of solvophobically-associated lamellar stacks with an opposite twist to the acid form. Partial neutralisation of 12HSA gels with base can generate coexisting mixtures of both types of gel in these ILs.