A cyanine dye (2) can be orientated on boronic-acid-modified poly(L- and D-lysine)s (L- and D-1, respectively) in the presence of saccharides. The main driving-force for the association is the electrostatic attraction between cationic 2 and the anionic center developed by complexation of the boronic acid residue with saccharides. The chiral orientation can be monitored by a CD spectroscopic method: it is mainly governed by the chirality of 1 but not by the chirality of saccharides. This is a novel system to control the dye orientation which occurs owing to the cooperative action of both naturally-originated α-amino acids and saccharides.
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