A novel perylenediimide molecule: Synthesis, structural property relationship and nanoarchitectonics

Abstract

A novel perylene diimide derivative (1) was synthesized by Stille coupling protocol to examine the effect of bulky group attached at bay position on the formation of nano-architectonics of PDI derivatives. The compound 1 was self-assembled by fast injection of chloroform solution in methanol to give nano-architecture. The size, shape and morphology of nano-architectonics were elucidated by combination of different experimental techniques such as UV–Vis spectrophotometer, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and X-ray diffraction (XRD). The construction of highly ordered nano and microstructures are operated by the property of π-conjugated dye molecules in more polar organic solvents due to π-π interaction between the perylene cores. From the UV–vis data, it is clear that the dye molecule shows solvatochromic behavior in low polar organic solvents and self-assembled behavior in methanol. The effect of bulky group at bay position and alkyl chain on imide position was investigated using UV–Vis absorption, differential scanning calorimetry (DSC), thermogravometric analysis (TGA), cyclic voltammetry (CV) and XRD. SEM and TEM images reveal the nano-architectonics morphology having diameter ≈400 ​nm. The d spacing values of XRD pattern has conformed π-π interactions. The effect of triphenylamine substituents on the π-π interaction between perylene molecules, the morphology of nano-architectonics and absorption properties of compound 1 are investigated by DFT calculations. On the basis of molecular orbitals, we have explained the electronic transitions and energy state in compound 1. The conjugation in compound 1 is affected by the degree of twisting in perylene ring due to the substituent at the bay positions of the perylene core.