Hydrogen bond directed self-assembly of core-substituted naphthalene bisimides with melamines in solution and at the graphite interface
- 1 January 2005
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 3 (3) , 414-422
- https://doi.org/10.1039/b414443k
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.Keywords
This publication has 48 references indexed in Scilit:
- Assembly and Processing of Hydrogen Bond Induced Supramolecular NanostructuresNano Letters, 2002
- High photovoltage multiple-heterojunction organic solar cells incorporating interfacial metallic nanoclustersApplied Physics Letters, 2002
- STM Investigations of the Two-Dimensional Ordering of Perylenetetracarboxylic Acid N-Alkyl-diimides on HOPG and MoS2 SurfacesLangmuir, 2001
- Artificial photosynthesisPublished by Royal Society of Chemistry (RSC) ,1998
- Restricted rotations in 4,6-bis- and 2,4,6-tris-(N,N-dialkylamino)-s-triazinesJournal of the Chemical Society, Perkin Transactions 2, 1996
- STM characterisation of organic molecules on H-terminated Si(111)Zeitschrift für Physik B Condensed Matter, 1995
- Tube-like Nanostructures Composed of Networks of Complementary Hydrogen BondsJournal of the American Chemical Society, 1995
- STM investigations of PTCDA and PTCDI on graphite and MoS2. A systematic study of epitaxy and STM image contrastZeitschrift für Physik B Condensed Matter, 1994
- New Varieties of Crystalline Architecture Produced by Small Changes in Molecular Structure in Tape Complexes of Melamines and BarbituratesJournal of the American Chemical Society, 1994
- Design of Organic Structures in the Solid State: Molecular Tapes Based on the Network of Hydrogen Bonds Present in the Cyanuric Acid.cntdot.Melamine ComplexJournal of the American Chemical Society, 1994