Synthesis and structure of intramolecularly hydrogen bonded dendrons

[GRAPHICS] A convenient synthesis of monodendrons whose conformation is restricted thr ough the intervention of intramolecular hydrogen bonding and repulsive elec trostatic interactions is described. X-ray crystal structure analysis of th e second generation dendron shows the presence of a propeller-type secondar y structure and indicates that the dendrons have assembled into a symmetric ally interdigitated dimer in the solid state. H-1 NMR and IR spectral data are in agreement with the presence of intramolecular hydrogen bonding betwe en the amides and the pyridine N throughout the dendron structure in soluti on.