The dimeric dendrons with amide branch units, alkyl periphery, and the aromatic bridging
units such as naphthyl, biphenyl, or isopropylidenebiphenyl were synthesized via a
convergent method. The self-assembly characteristics of these dimeric dendrons were
investigated not only in organic media but also at the solid−liquid interface. The gel formation
behavior of the dimeric dendrons in organic media and their nanostructures were highly
dependent on the bridging moiety. The dendrons with naphthyl and biphenyl bridges form
immobile gel in organic media such as n-octanol, while those with isopropylidenebiphenyl
unit did not form gel. The dry gel obtained via self-assembly formed either lamellae or
columnar hexagonal arrays depending on the structure of the bridge moiety. The dendron
dimer with the 1,5-naphthoxy bridging unit which formed a lamella structure in a dry gel
state also self-assembled at the solid−liquid interface in 0.1% n-octanol solution to exhibit
well-defined nanoribbons extending to several micrometers. In addition to hydrogen bonding
of the dendritic branches and van der Waals interactions of the alkyl periphery, the
architecture of the bridging moiety of the dimeric dendrons played a key role in the packing
process of the self-assembly of dimeric dendron.
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