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Issue 8, 2016
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Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character

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Abstract

Indeno[1,2-b]fluorenes (IFs), while containing 4n π-electrons, are best described as two aromatic benzene rings fused to a weakly paratropic s-indacene core. In this study, we find that replacement of the outer benzene rings of an IF with benzothiophenes allows the antiaromaticity of the central s-indacene to strongly reassert itself. Herein we report a combined synthetic, computational, structural, and materials study of anti- and syn-indacenodibenzothiophenes (IDBTs). We have developed an efficient and scalable synthesis for preparation of a series of aryl- and ethynyl-substituted IDBTs. NICS-XY scans and ACID calculations reveal an increasingly antiaromatic core from [1,2-b]IF to anti-IDBT, with syn-IDBT being nearly as antiaromatic as the parent s-indacene. As an initial evaluation, the intermolecular electronic couplings and electronic band structure of a diethynyl anti-IDBT derivative reveal the potential for hole and/or electron transport. OFETs constructed using this molecule show the highest hole mobilities yet achieved for a fully conjugated IF derivative.

Graphical abstract: Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character

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Publication details

The article was received on 01 Mar 2016, accepted on 04 May 2016 and first published on 13 May 2016


Article type: Edge Article
DOI: 10.1039/C6SC00950F
Citation: Chem. Sci., 2016,7, 5547-5558
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    Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character

    J. L. Marshall, K. Uchida, C. K. Frederickson, C. Schütt, A. M. Zeidell, K. P. Goetz, T. W. Finn, K. Jarolimek, L. N. Zakharov, C. Risko, R. Herges, O. D. Jurchescu and M. M. Haley, Chem. Sci., 2016, 7, 5547
    DOI: 10.1039/C6SC00950F

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