Inspired by automated DNA synthesis, electron-rich dialkoxynaphthalene
(DAN) donor and electron-deficient naphthalene-tetracarboxylic diimide
(NDI) acceptor phosphodiester-linked homohexamers were synthesized
by the phosphoramidite method. Two types of hexamers were prepared,
one with only one phosphodiester between the aromatics (i.e., DAN
or NDI) and a second with two phosphodiesters around a propanediol
between the aromatics, leading to the latter more flexible and more
hydrophilic hexamers. The folding properties of these homohexamers
alone or mixed together, in water only, were studied by UV–visible
absorption spectroscopy and atomic force microscopy (AFM). AFM imaging
revealed that a 1:1 mixture of hexaDAN and hexaNDI formed fibers by
charge transfer donor–acceptor recognition leading to a hydrogel
after drying. The organization of the resulting structures is strongly
dependent on the nature of the complementary partner, leading to the
formation of mono- or multilayer hydrogel networks with different
compactness.