Synthesis and study of electrochemical and optical properties of substituted perylenemonoimides in solutions and on solid surfaces

Abstract

A new and efficient methodology towards the synthesis of 7-pyrrolidinyl and 7,12-bispyrrolidinyl perylenemonoimide monoanhydrides (PMI monoanhydrides) and their corresponding dicarboxylic acids is devised. The high yields (70–96%) and facile synthesis of PMI monoanhydrides, as compared to traditional methodologies, make the method attractive and versatile. The reported 7,12-bispyrrolidinyl PMI monoanhydrides are a new family of peryleneimides, where both the bay-substituents are located towards the anhydride cycle. The electrochemical and optical properties of target molecules and their precursors were investigated using UV-Vis spectroscopy and differential pulse voltammetry. Atomic charges and electronic properties were calculated using density functional theory (DFT). In addition, self-assembling monolayers of the PMI monoanhydrides and their corresponding diacids were successfully formed over ZnO and TiO₂ films. The results of the current study indicate that these molecules are potentially good candidates for various applications in the fields of organic electronics and solar cells.