Issue 19, 2019

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
19 feb 2019
Accepted
10 apr 2019
First published
12 apr 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 4951-4958

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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