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Foldamer with a spiral perylene bisimide staircase aggregate structure

Chemical Science, ISSN: 2041-6520, Vol: 2, Issue: 11, Page: 2094-2100
2011
  • 43
    Citations
  • 0
    Usage
  • 54
    Captures
  • 0
    Mentions
  • 0
    Social Media
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Metrics Details

  • Citations
    43
    • Citation Indexes
      43
  • Captures
    54

Article Description

Although the precise control of dye-dye interactions is known to be of fundamental importance to achieve desired functional properties in π-conjugated materials, there are only sporadic examples where precise structural control of dye-dye interactions could be achieved by the attachment of the chromophores to an oligomeric or polymeric backbone. In this edge article, we introduce an oligophenylene ethynylene/perylene bisimide (PBI) dye system which is conceived by the foldamer concept. The molecular design enables folding of the π-conjugated oligomer to give a geometrically well-defined π-stack of intrastrand PBI molecules. The synthesis of the foldamer and its characterization by MALDI-TOF mass spectrometry are described, and the average size is estimated by gel permeation chromatography (GPC) and diffusion ordered NMR spectroscopy (DOSY). The folding dynamics are demonstrated by ultraviolet/visible absorption and fluorescence emission spectroscopic studies as the folded and unfolded states possess distinct optical properties. Quantum dynamic considerations revealed a good agreement of the calculated aggregate absorption spectrum with those obtained experimentally. © The Royal Society of Chemistry 2011.

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