Trigonal rigid triphenols: self-assembly and multicomponent lattice inclusion

Abstract

The sterics introduced via methyl groups impart rigidity and inclusion behavior to trigonal C₃-symmetric triphenol hosts H1-H4. Triphenol H1 is found to mimic the O-H···O hydrogen-bonded self-assembly of trimesic acid to yield porous honeycomb nets. It is found that 18-crown-6H1 in turn binds guest molecules in the hexagonal voids to yield guestguesthost multicomponent molecular crystals. The triphenol H2 and the homologous derivatives H3 and H4 are also found to crystallize with 18-crown-6 and other guests to yield multicomponent crystals, but in these cases the 18-crown-6 is found to serve as a spacer. While the structure of H2 is determined in its guest-free form, some of the inclusion compounds of triphenols lend themselves to crystal packings that are deciphered based on network topologies. The networks observed for H1-Tol and H3-C-B-Et are unique; in the latter, the crystal packing analysis reveals organization of molecules into a pattern that is reminiscent of borromean rings.