gem-Dibromovinyl phthalonitriles: synthesis, structure elucidation, Hirshfeld surface analysis and energy framework calculations

Abstract

A series of versatile phthalocyanine precursors, consisting of gem-dibromovinyl phthalonitrile derivatives, were synthesized and characterized by various spectroscopic techniques. The assigned structures were further supported by X-ray crystallographic techniques. The crystal structures showed primarily C–H⋯N, C–H⋯Br, C–Br⋯N and π⋯π interactions. The overall intermolecular interactions in the structures were quantified and fully described by Hirshfeld surface analysis. In addition, energy-frame calculations were used to analyse the three-dimensional topology of the crystal packing. The dispersion energy framework of all compounds was shown to be dominant over the electrostatic framework.