• Media type: E-Article
  • Title: Giant Porphyrin Disks: Control of Their Self‐Assembly at Liquid–Solid Interfaces through Metal–Ligand Interactions
  • Contributor: Lensen, Marga C.; Elemans, Johannes A. A. W.; van Dingenen, Sandra J. T.; Gerritsen, Jan W.; Speller, Sylvia; Rowan, Alan E.; Nolte, Roeland J. M.
  • Published: Wiley, 2007
  • Published in: Chemistry – A European Journal, 13 (2007) 28, Seite 7948-7956
  • Language: English
  • DOI: 10.1002/chem.200700131
  • ISSN: 0947-6539; 1521-3765
  • Origination:
  • Footnote:
  • Description: AbstractThe synthesis and self‐assembly behaviour of porphyrin dodecamers 1H2 and Zn–1, which consist of twelve porphyrins that are covalently attached to a central aromatic core, is described. According to STM, 1D and 2D NMR studies, and molecular modelling calculations, the porphyrin dodecamers have a yo‐yo‐shaped structure. Their large π surface, in combination with their disk‐like shape, allows them to form self‐assembled structures, which in the case of Zn–1 can be tuned by adding bidentate ligands. The self‐assembly of the molecules at the liquid–solid interface of 1‐phenyloctane with highly oriented pyrolytic graphite or Au(111) was imaged by using STM. The porphyrin disks in the self‐assembled arrays have an edge‐on orientation on the surface. The addition of bidentate axial ligands to the Zn–1 molecules in the arrays allows their intermolecular distance to be precisely controlled.