Articolo in rivista, 2020, ENG, 10.1039/c9nj05674b

Solvent- and concentration-induced self-assembly of an amphiphilic perylene dye

Boccia, Antonella Caterina; Lukes, Vladimir; Eckstein-Andicsova, Anita; Kozma, Erika

CNR Natl Res Council; Slovak Univ Technol Bratislava; Slovak Acad Sci

A new amphiphilic perylene dye bearing two carboxylic and two amidic chains (PDA-CA) has been synthesized and the ability to form pi-pi driven aggregates or folded structures has been investigated in aqueous or organic solvents at different concentrations, by means of NMR spectroscopy, theoretical calculations and optical characterization. The H-1 NMR data showed the coexistence of supramolecular aggregates due to a synergetic effect of pi-pi stacking, hydrogen bonding and hydrophobic/hydrophilic interactions. The ratio between these species has been evaluated by concentration- and temperature-dependent H-1 NMR experiments and also by the effect of aqueous or organic solvents. UV-Vis measurements are in agreement with NMR data evidencing the presence of more organized structures in organic solvents and aggregated species in aqueous solution. The pi-stacking ability and the role intermolecular hydrogen bonds in the formation of different aggregated structures, was also estimated by density functional theory.

New journal of chemistry (1987) 44 (3), pp. 892–899

Keywords

NMR, self-assembly, Perylene dye

CNR authors

Kozma Erika, Boccia Antonella Caterina

CNR institutes

SCITEC – Istituto di Scienze e Tecnologie Chimiche "Giulio Natta"