Fabrication of luminescent perylene bisimide nanorods

Perylene bisimides have attracted great interest as a result of their unique electrical and photophysical properties. In the present investigation a N,N'-bis(2-naphthalene-2-yl)perylene-3,4,9,10-tetracarboxylic diimide was synthesized from 2-aminonaphthalene and perylene-3,4,9,10-tetracarboxylic dianhydride. Structure and purity were confirmed by mass, NMR and other spectral techniques. Photophysical and electrochemical properties were investigated by UV-vis, fluorescence, differential scanning calorimetry and cyclic voltammetric techniques. Optical, fluorescence, scanning and transmission electron microscopies were employed in the molecular self-assembly studies. The compound self-assembled into nanorods. The competition and co-operation between the intermolecular pi-pi-stacking and hydrophilic/hydrophobic interactions are suggested for the observed nanostructure. (C) 2013 Elsevier B.V. All rights reserved.