Hydrogen-Bonded 1D Chains Formed from Adamantane-Based Bisphenols and Bispyridines: Influences of Substitution Groups on Phenol Ring

Eight cocrystals were formed from three adamantane-based
bisphenols
with structurally analogous skeletons and three bispyridines. Various
1D chains were constructed through intermolecular OH/N hydrogen bonds.
Two crystals containing nonsubstituted bisphenols showed the formation
of 1D zigzag chains, which were generated from two bisphenols and
two bispyridines in one pitch of the 1D chain. Three crystals including
chlorine-substituted bisphenols indicated the generation of 1D zigzag
chains, and the pitches of these chains were longer than that of 1D
chains composed of nonsubstituted bisphenols. Three crystals containing
bromine-substituted bisphenols exhibited different shapes of 1D chains
from other crystals, which were consisted of one bisphenol and one
bispyridine in one pitch. These 1D chains assembled via intermolecular
CH/O and/or CH/π interactions. The halogen substituents on the
adamantane-based bisphenols influence on not only the shapes of 1D
chains, but also 2D and 3D structures mainly due to steric hindrances.