Trigonal Rigid Triphenols: Self-Assembly and Multicomponent Lattice Inclusion

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-6⊂H1 in turn binds guest molecules in the hexagonal voids to yield guest⊂guest⊂host 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.