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Issue 5, 2013
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Supersized contorted aromatics

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We describe here the synthesis and electronic device properties of a new type of polycyclic aromatic molecule, the contorted octabenzocircumbiphenyl (c-OBCB). Contorted polycyclic aromatic hydrocarbons (PAHs) are promising small active molecules for organic devices. We present two different methods to synthesize c-OBCB derivatives that allow the smooth incorporation of functional groups. The material has a highly contorted exterior with six 4-helicenes and two 5-helicenes around the exterior of the expanded core of the aromatic. With appropriate sidechains, the material is soluble in common organic solvents and forms thin films. In thin films, the tetradodecyloxy-substituted c-OBCB self-assembles to form the active layer in organic field effect transistors. It is a hole transporting organic semiconductor. In the transistors, the c-OBCB forms good contact with source and drain contacts made from graphene. The c-OBCB self-assembles into a heterojunction from solution with phenyl-C70-butyric acid methyl ester (PC70BM). We observed power conversion efficiencies of ∼2.9 % under 100 mW cm−2 illumination at a 1 : 4 weight ratio of the c-OBCB relative to PC70BM. The c-OBCB is shape complementary to the ball shaped PC70BM.

Graphical abstract: Supersized contorted aromatics

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The article was received on 07 Feb 2013, accepted on 01 Mar 2013 and first published on 08 Mar 2013

Article type: Edge Article
DOI: 10.1039/C3SC50374G
Citation: Chem. Sci., 2013,4, 2018-2023
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    Supersized contorted aromatics

    S. Xiao, S. J. Kang, Y. Wu, S. Ahn, J. B. Kim, Y. Loo, T. Siegrist, M. L. Steigerwald, H. Li and C. Nuckolls, Chem. Sci., 2013, 4, 2018
    DOI: 10.1039/C3SC50374G

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