Conservation of structure and dynamic behavior in triazine macrocycles with opportunities for subtle control of hinge motion.

Modifying the backbone of 24-atom macrocycles allows tailoring of physical properties (octanol-water partition coefficients, log ) while conserving both conformation and the barrier to dynamic, hinge-like motion. Structure is determined by 1D and 2D NMR spectroscopy. The barrier can be subtly tuned by modifications that appear to preclude fully revolute motion and efficient π-stacking of the two subunits. The log  values increase as expected across this series, and the correlation between computed and observed values reinforces the belief of common structure and behavior across this class of macrocycles.