Host–Guest Complexes of a Tribenzotriquinacene-Based Tris(catechol) with Quaternary Ammonium Salts: Variation of H-Bonding Pattern and Cationic Size on Supramolecular Architecture

Abstract

Hydrogen-bond-assisted host–guest complexation of a tris(catechol)-functionalized tribenzotriquinacene with various tetraalkylammonium halides yielded diversified supramolecular architectures ranging from octameric C3-symmetric cages and C2- and C4-symmetric channels to corrugated layers, depending on both the anionic and cationic components of the guest species. Single crystal X-ray analyses of this series of complexes revealed intricate anionic host networks formed by intermolecular O–H···O and O–H···X hydrogen-bonds involving catechol host molecules and halides, which accommodate the bulky quaternary ammonium guest ions in cavities, channels, or between corrugated sheets. With fine-tuning of the symmetry and size of the hydrophobic cationic guest and accompanying halide species, this simple “Mix and Match” of host and guest components provides an efficient route to the assembly of supramolecular architectures.