Self-Assembly, Optical, and Electrical Properties of a Novel Water-Soluble Perylene Bisimide

  • Gopal Boobalan
  • Predhanekar Mohamed Imran
  • Samuthira Nagarajan
Article

Abstract

Highly fluorescent and water-soluble N,N′-bis(2-((5-((dimethylamino)methyl) furan-2-yl)methylthio)ethyl)perylene-3,4,9,10-tetracarboxylic diimide was synthesized, and characterized using various spectral techniques. The compound was highly fluorescent and exhibited strong absorption and emission in the visible spectral region. Computational studies predicted the highest occupied molecular orbital to lowest unoccupied molecular orbital band gap as 1.96 eV. The molecule self-assembled into a novel ball-like structure unlike the expected one-dimensional nanowire or nanobelt of other perylene bisimides. Molecular geometry optimization and computational studies at density functional theory as well as semiempirical levels strongly supported the observed self-assembly.

Graphical Abstract

New highly water-soluble N,N′-bis(2-((5-((dimethylamino)methyl)furan-2-yl) methylthio)ethyl)perylene-3,4,9,10-tetracarboxylic diimide molecule self-assembled as globules through π-stacking and rolling of its polar tail.

Keywords

Self-assembly PTCDI nanoparticle organic material fluorescent water soluble 

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Copyright information

© TMS 2011

Authors and Affiliations

  • Gopal Boobalan
    • 1
  • Predhanekar Mohamed Imran
    • 2
  • Samuthira Nagarajan
    • 1
  1. 1.Department of ChemistryAnnamalai UniversityAnnamalainagarIndia
  2. 2.Department of ChemistryIslamiah CollegeVaniyambadiIndia

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