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Issue 9, 2014
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Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials

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Abstract

We report the preparation and characterization of a new class of quinoidal thienoacenes. The synthetic route is efficient, high-yielding and scalable with the potential for further functionalization. Single crystal X-ray diffraction reveals that, as size increases, the molecules pack in progressively closer 1D arrangements. The title compounds are shown to have amphoteric redox behaviour by cyclic voltammetry. The anion radicals are studied by EPR spectrometry and by computations. The electron-accepting nature, NIR absorption and the low-lying LUMO energies (ca. −4.0 eV) allude to potential use in materials applications.

Graphical abstract: Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials

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Publication details

The article was received on 15 May 2014, accepted on 16 Jun 2014 and first published on 16 Jun 2014


Article type: Edge Article
DOI: 10.1039/C4SC01432D
Citation: Chem. Sci., 2014,5, 3627-3633
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    Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials

    G. E. Rudebusch, A. G. Fix, H. A. Henthorn, C. L. Vonnegut, L. N. Zakharov and M. M. Haley, Chem. Sci., 2014, 5, 3627
    DOI: 10.1039/C4SC01432D

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