Computational studies have shown interactions between anions and aromatic π-electron density may exist when the aromatic is electron deficient. Recent solid-state investigations have shown anions will bind to the face of transition metal complexed aromatics with the general structural motif [TMⁿ⁺–Ar–A^–] where TMⁿ⁺ is a transition metal with positive charge n, Ar is the aromatic, and A^– is the anion. Obviously, the complexation of the transition metal to the face of the aromatic makes the arene electron deficient and thus this approach is in agreement with the computational work. However, most of the computational work on arene-anion complexes used electron-withdrawing substituents to produce electron deficient aromatics. We will present the synthesis of a model host that allows for the investigation of anion-π interactions of aromatics that are not complexed with transition metals, but instead have aromatics with electron-withdrawing substituents. The synthesis allows for easy incorporation of variously substituted aromatics and thus the model host will be used to determine the relationship between the electron-withdrawing ability of the aromatic substituents and the capability of the substituted aromatic to bind anions in the solid-state.