Synthesis and structure of intramolecularly hydrogen bonded dendrons

[reaction: see text] A convenient synthesis of monodendrons whose conformation is restricted through the intervention of intramolecular hydrogen bonding and repulsive electrostatic interactions is described. X-ray crystal structure analysis of the second generation dendron shows the presence of a propeller-type secondary structure and indicates that the dendrons have assembled into a symmetrically interdigitated dimer in the solid state. 1H NMR and IR spectral data are in agreement with the presence of intramolecular hydrogen bonding between the amides and the pyridine N throughout the dendron structure in solution.