Diimide-Based Assemblies

The intercalation of polycyclic aromatic compounds into duplex DNA structures was used to develop nucleic acid-based electrochemical sensors.66 For example, the bis-ferrocene-tethered naphthalene diimide (16) was used as a redox-active intercalator to probe DNA hybridization.67 The thiolated probe was assembled on a Au electrode, and the formation of the duplex DNA with the complementary analyte nucleic acid was probed by the intercalation of (16) into the double-stranded nucleic acid structure and by following the voltammetric response of the ferrocene units (Fig. 12.17a). The method enabled the analysis of the target DNA with a sensitivity that corresponded to ca. 1 x 10-20mol. 

Molecular Assemblies and Supramolecular Arrays Based on Napthalene Diimides and Sn (IV) porphyrin phenolates, PhD thesis, Monash University, Australia. 

Rybtchinski, B., Sinks, L.E., Wasielewski, M.R. 2004. Combining light-harvesting and charge separation in a self-assembled artificial photosynthetic system based on perylene-diimide chromophores. J. Am. Chem. Soc. 126, 12268-12269. 

Another, less direct, approach to manipulate molecules on a surface is through the use of chemical self-assembly principles derived from X-ray crystallographic work. A two-dimensional hydrogen bonding motif derived from crystal-engineering studies has been used to assemble a two-dimensional honeycomb lattice based on the hydrogen bonded triad motif formed between perylene tetracarboxylic acid diimide (5.1) and melamine (5.2). The honeycomb... 

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