PAPER: Oligo(naphthylene-ethynylene) Molecular Rods

Cramer, J. R.; Ning, Y. X.; Shen, C.; Nuermaimaiti, A.; Besenbacher, F.; Linderoth, T. R.; Gothelf, K. V.

Eur. J. Org. Chem. 2013, 2813-2822. DOI: 10.1002/ejoc.201201752

  • Sino-Danish Center for Molecular Nanostructures on Surfaces, Interdisciplinary Nanoscience Center (iNANO) and Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark, http://www.chem.au
  • Sino-Danish Center for Molecular Nanostructures on Surfaces, Interdisciplinary Nanoscience Center (iNANO) and Department of Physics and Astronomy, Aarhus University, Ny Munkegade 118, 8000 Aarhus C, Denmark, http://www.inano.au.dk

Abstract

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 syntheses. 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.

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