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Issue 16, 2007
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Synthesis of fluorinated anti-fluorenacenedione and the structural, electronic, and field-effect properties

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Abstract

Fluorinated anti-fluorenacenedione 6 was newly synthesized by oxidation of a dehydro[12]annulene fused with tetrafluorobenzene 4. X-Ray crystallography of 6 demonstrated a totally planar structure and shorter intramolecular distances for F⋯I, F⋯O, and I⋯O than the corresponding sums of van der Waals (vdW) radii. In the packing structure, molecules are arranged in a π-stacked motif, and the intermolecular distances between heavy atoms (C⋯I, C⋯F, C⋯O, F⋯I, and F⋯O) of the adjacent columns are also shorter than the corresponding sums of vdW radii, indicating highly dense packing for the crystal structure of 6. In the 19F NMR spectrum of 6, a signal for the fluorine atom adjacent to iodine exhibited downfield shift by 29–40 ppm as compared with the other three signals. This is attributed to the intramolecular short contact between F and I atoms, which is supposed to cause a donor–acceptor interaction. Cyclic voltammetry of 6 exhibited two reversible reduction waves at E1/2 = −0.91 and −1.45 V vs. Fc/Fc+. A thin film of 6 was prepared by vacuum deposition and was applied to a field-effect transistor (FET) device, which exhibited n-type transistor responses although the mobility was not very high.

Graphical abstract: Synthesis of fluorinated anti-fluorenacenedione and the structural, electronic, and field-effect properties

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Publication details

The article was received on 02 May 2007, accepted on 13 Jun 2007 and first published on 04 Jul 2007


Article type: Paper
DOI: 10.1039/B706621J
Citation: Org. Biomol. Chem., 2007,5, 2592-2598
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    Synthesis of fluorinated anti-fluorenacenedione and the structural, electronic, and field-effect properties

    Y. Miyata, T. Minari, T. Nemoto, S. Isoda and K. Komatsu, Org. Biomol. Chem., 2007, 5, 2592
    DOI: 10.1039/B706621J

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