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

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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.

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Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalainagar, 608 002, India

    Gopal Boobalan & Samuthira Nagarajan

  2. Department of Chemistry, Islamiah College, Vaniyambadi, 635 752, India

    Predhanekar Mohamed Imran

Authors
  1. Gopal Boobalan
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  2. Predhanekar Mohamed Imran
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  3. Samuthira Nagarajan
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Correspondence to Samuthira Nagarajan.

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Boobalan, G., Imran, P.M. & Nagarajan, S. Self-Assembly, Optical, and Electrical Properties of a Novel Water-Soluble Perylene Bisimide. J. Electron. Mater. 40, 2392–2397 (2011). https://doi.org/10.1007/s11664-011-1784-9

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  • DOI: https://doi.org/10.1007/s11664-011-1784-9

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