Layered 2D Sheetlike Supramolecular Polymers Formed by O–H···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, 1H NMR spectroscopy, IR spectroscopy, and elemental analysis. The relatively predictable organization of these molecules in the solid state may be exploited for crystal engineering.