Generation-independent dimerization behavior of quadruple hydrogen-bond-containing oligoether dendrons.

[reaction: see text] A new series of self-assembling G1-G3 dendronized dimers bearing oligoether dendrons and a dimeric 2-ureido-4-pyrimidinone (UPy) quadruple hydrogen-bonding core were prepared and characterized. It was found that the nonpolar microenvironment created by the dendrons preserved the UPy unit in its DDAA tautomeric form. As a result, the stabilities of the dimers were exceptionally strong for all three generations (K(dim) > 2 x 10(7) M(-)(1) in CDCl(3) at 25 degrees C). Furthermore, the steric size of the dendrons did not exhibit a significant effect on their dimerization behavior.