10.1021/cg0601148.s001 Weijun Niu Weijun Niu Mark D. Smith Mark D. Smith John J. Lavigne John J. Lavigne Substituent Effects on the Structure and Supramolecular Assembly of Bis(dioxaborole)s Derived from 1,2,4,5-Tetrahydroxybenzene American Chemical Society 2006 CH influence dehydration reaction Supramolecular Assembly bi supramolecular assembly phenyl boronic acids target compounds result terminal phenyl rings Substituent Effects 2006-06-07 00:00:00 Dataset https://acs.figshare.com/articles/dataset/Substituent_Effects_on_the_Structure_and_Supramolecular_Assembly_of_Bis_dioxaborole_s_Derived_from_1_2_4_5_Tetrahydroxybenzene/3077239 The synthesis and structural characterization of bis(dioxaborole)s <b>1</b>−<b>3</b>, based on 1,2,4,5-tetrahydroxybenzene, are described. The target compounds result from the facile dehydration reaction between the bis-diol and substituted phenyl boronic acids. While substituents on the terminal phenyl rings do not influence the planarity of the extended π-system through the boroles, they do significantly influence the intermolecular stacking arrangements for these compounds in the solid state. A combination of several weak and medium intermolecular interactions, including traditional π-stacking, CH−O hydrogen bonding, and a consistent phenyl−boron−phenyl sandwich motif determine the nature of the supramolecular assembly for these bis(dioxaborole)s.