On-surface formation of one-dimensional polyphenylene through Bergman cyclization

J Am Chem Soc. 2013 Jun 12;135(23):8448-51. doi: 10.1021/ja404039t. Epub 2013 May 28.

Abstract

On-surface fabrication of covalently interlinked conjugated nanostructures has attracted significant attention, mainly because of the high stability and efficient electron transport ability of these structures. Here, from the interplay of scanning tunneling microscopy imaging and density functional theory calculations, we report for the first time on-surface formation of one-dimensional polyphenylene chains through Bergman cyclization followed by radical polymerization on Cu(110). The formed surface nanostructures were further corroborated by the results for the ex situ-synthesized molecular product after Bergman cyclization. These findings are of particular interest and importance for the construction of molecular electronic nanodevices on surfaces.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry
  • Cyclization
  • Microscopy, Scanning Tunneling
  • Molecular Structure
  • Polymers / chemical synthesis*
  • Polymers / chemistry*
  • Quantum Theory
  • Surface Properties

Substances

  • Polymers
  • Copper
  • polyphenylene sulfide