Synthesis and characterization of higher generation dendrons based on melamine using p-aminobenzylamine.: Evidence for molecular recognition of Cu(II)

The difference in nucleophilicity between the amines of p-aminobenzylamine can be used to synthesize dendrimers based on melamine using a convergent, orthogonal approach. The resulting molecules comprise groups that donate and accept hydrogen-bonds, limiting synthetic accessibility due to intermolecular aggregation. Dendrons with molecular weights exceeding 10 kDa can be prepared by this strategy, but yields drop off significantly at the highest generation (D5) due to difficulties in purification. The addition of Cu(II) reduces the extent of aggregation as evident in SEC traces. UV-vis spectroscopy confirms recognition. (C) 2001 Elsevier Science Ltd. All rights reserved.