Layered 2D Sheet like Supramolecular Polymers Formed by O-H center dot center dot center dot Anion Hydrogen Bonds

A hexahydroxyterphenyl was prepared in two steps and 77% overall yield. Co-crystallization of this ligand with a range of tetrabutylammonium salts gave [2 + 2] supramolecular macrocycles assembled through O-H...anion hydrogen bonds. These macrocycles form 2D sheetlike architectures through intermolecular hydrogen bonds between phenol groups. Bulk samples of these structures were prepared in high yields (70-100%) and were characterized by X-ray crystallography, H-1 NMR spectroscopy, IR spectroscopy, and elemental analysis. The relatively predictable organization of these molecules in the solid state may be exploited for crystal engineering.