Self-assembly and photophysical properties of a minuscule tailed perylene bisimide

N,N′- Di(octyl)perylene-3,4,9,10-tetracarboxylic diimide was synthesized and its self-assembly and photophysical behavior were evaluated. Thermal stability and electrochemical behavior of the compound were analyzed using thermogravimetric analysis, differential scanning calorimetry and cyclic voltammetric (CV) techniques. The structure was optimized at the double zeta valence level of the density functional theory and the frontier orbital levels were computed and equated with experimental CV values. Natural bond orbital analysis was used to correlate electron population in the lowest unoccupied molecular orbital with stacking. The morphology of the formed molecular self-assembly was investigated by scanning electron microscopy. The results indicated the linear alkyl chains hydrophobic interaction cooperative with π–π stacking between the aromatic skeleton induced in the self-assembly. The CV and computational studies supported the materials semiconductive nature.