Hydrogen bond directed self-assembly of core-substituted naphthalene bisimides with melamines in solution and at the graphite interface.
A series of red and blue highly fluorescent core-substituted naphthalene bisimide dyes has been synthesized and they have been investigated as supramolecular building blocks. NMR and UV-Vis titration experiments of these dyes with complementary melamines revealed the formation of triple hydrogen bonds (DAD-ADA arrays) in solution. At stoichiometric ratios, ditopic melamine receptors could dissolve otherwise insoluble bisimides by means of hydrogen bonding, even in aliphatic solvents. At the solution/graphite interface, one-dimensional chains of hydrogen bonded naphthalene bisimides and two-dimensional adlayers of ditopic melamines are formed for the pure compounds but little evidence for heterocomplexes between the two complementary building blocks could be obtained.
Thalacker
Christoph
C
Institut für Organische Chemie, Universität Würzburg, D-97074 Würzburg, Germany.
Miura
Atsushi
A
De Feyter
Steven
S
De Schryver
Frans C
FC
Würthner
Frank
F