Solvent-tuned supramolecular assembly of fluorescent catechol/pyrene amphiphilic molecules

NADOR, FABIANA; WNUK, KAROLINA; ROSCINI, CLAUDIO; SOLORZANO, RUBEN; FARAUDO, JORDI; RUIZ-MOLINA, DANIEL; NOVIO, FERNANDO

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2018

0947-6539

The synthesis and structuration of a novel low molecularamphiphilic catechol 1 is reported. The combination of a hydrophilictail containing a catechol group and a pyrene-based hydrophobichead favors its solvent tuned supramolecular assembly. Formationof hollow nanocapsules/vesicles occurs in concentrated solutions ofboth polar protic and non-protic organic solvents, whereas in water afibril-like aggregation process is favored even at low concentrations.The emission properties of the pyrene moiety have allowed themonitoring of the self-assembly process which could be confirmedby optical and electronic microscopy. In organic solvents and at lowconcentrations, compound 1 remains on its non-assembledmonomeric form. As the concentration increases, the aggregationcontaining pre-associated pyrene moieties becomes more evidentup to a critical micellar concentration where vesicle-like structuresare formed. In contrast, nanosized twist belt-like fibers have beenobserved in water even at low concentrations, meanwhile at highconcentration microplate structures appears. The interactionsbetween molecules in different solvents have been studied bymolecular dynamics simulations, which have confirmed differentsolvent driven supramolecular interactions.