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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.

Perylene diimides with high photosensitivity and high electron mobility have attracted much attention for use in organic semiconductor devices. In this investigation, thin films of six new perylene tetracarboxylic diimides (PTCDI) were fabricated by spin coating, on glass as substrate, and their optical and electrical properties were studied. The absorption spectra of thin films of PTCDI furnished more informative bands than those of the compounds in solution. The morphology of the thin films was examined by scanning electron microscopy and x-ray diffraction. The absorption spectra and I-V characteristics of the compounds were affected by their molecular structures. HOMO-LUMO band gaps of the films were in the range 1.9-2.0 eV. Band gaps calculated by use of computational methods were comparable with experimental results.