Oligo(naphthylene–ethynylene) Molecular Rods

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Molecular rods designed for surface chirality studies have been synthesized in high yields. The molecules are composed of oligo(naphthylene–ethynylene) skeletons and functionalized at their two termini with carboxylic acids and hydrophobic groups. The molecular skeletons were constructed by means of palladium-catalyzed Sonogashira reactions between naphthyl halides and acetylenes. The triazene functionality was used as a protected iodine precursor to allow linear extension of the molecular rods during the synthe-ses. The carboxylic acid groups in the target molecules were protected as esters during the synthesis to keep the large aromatic molecules soluble during their syntheses. These rigid
oligomers were designed to form lamella-like structures when adsorbed on a surface, through which multiple distinguishable surface conformations should be obtainable. Preliminary scanning tunneling microscopy imaging confirmed
these properties.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Pages (from-to)2813-2822
Number of pages10
Publication statusPublished - May 2013

    Research areas

  • Self-assembly / Surface chirality / Surface analysis / Conformation analysis / Cross-coupling / Nanostructures

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