Author:

Keywords:

solid-state, naphthalene-1,4,5,8-tetracarboxylic acid, mesoscopic superstructures, noncovalent synthesis, restricted rotations, stm investigations, molecular squares, electron-transfer, bis-imides, perylene, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, NONCOVALENT SYNTHESIS, SOLID-STATE, NAPHTHALENE-1,4,5,8-TETRACARBOXYLIC ACID, STM INVESTIGATIONS, ELECTRON-TRANSFER, BIS-IMIDES, PERYLENE, DYES, ARCHITECTURE, FLUORESCENT, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

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.