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Issue 19, 2019
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Triperyleno[3,3,3]propellane triimides: achieving a new generation of quasi-D3h symmetric nanostructures in organic electronics

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Abstract

Rigid three-dimensional (3D) polycyclic aromatic hydrocarbons (PAHs), in particular 3D nanographenes, have garnered interest due to their potential use in semiconductor applications and as models to study through-bond and through-space electronic interactions. Herein we report the development of a novel 3D-symmetric rylene imide building block, triperyleno[3,3,3]propellane triimides (6), that possesses three perylene monoimide subunits fused on a propellane. This building block shows several promising characteristics, including high solubility, large π-surfaces, electron-accepting capabilities, and a variety of reactive sites. Further, the building block is compatible with different reactions to readily yield quasi-D3h symmetric nanostructures (9, 11, and 13) of varied chemistries. For the 3D nanostructures we observed red-shift absorption maxima and amplification of the absorption coefficients when compared to the individual subunits, indicating intramolecular electronic coupling among the subunits. In addition, the microplates of 9 exhibit comparable mobilities in different directions in the range of 10−3 cm2 V−1 s−1, despite the rather limited intermolecular overlap of the π-conjugated moieties. These findings demonstrate that these quasi-D3h symmetric rylene imides have potential as 3D nanostructures for a range of materials applications, including in organic electronic devices.

Graphical abstract: Triperyleno[3,3,3]propellane triimides: achieving a new generation of quasi-D3h symmetric nanostructures in organic electronics

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Publication details

The article was received on 19 Feb 2019, accepted on 10 Apr 2019 and first published on 12 Apr 2019


Article type: Edge Article
DOI: 10.1039/C9SC00849G
Chem. Sci., 2019,10, 4951-4958
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Triperyleno[3,3,3]propellane triimides: achieving a new generation of quasi-D3h symmetric nanostructures in organic electronics

    L. Lv, J. Roberts, C. Xiao, Z. Jia, W. Jiang, G. Zhang, C. Risko and L. Zhang, Chem. Sci., 2019, 10, 4951
    DOI: 10.1039/C9SC00849G

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