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.