title: Hydrogen bond directed self-assembly of core-substituted naphthalene bisimides with melamines in solution and at the graphite interface.
abstract: 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.
authors.affiliation: Institut für Organische Chemie, Universität Würzburg, D-97074 Würzburg, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Thalacker
authors.forename: Atsushi
authors.initials: A
authors.lastname: Miura
authors.forename: Steven
authors.initials: S
authors.lastname: De Feyter
authors.forename: Frans C
authors.initials: FC
authors.lastname: De Schryver
authors.forename: Frank
authors.initials: F
authors.lastname: Würthner