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Hahn L, Maass F, Bleith T, et al. Core Halogenation as a Construction Principle in Tuning the Material Properties of Tetraazaperopyrenes. Chemistry. 2015;21(49):17691-700doi: 10.1002/chem.201503484.
Hahn, L., Maass, F., Bleith, T., Zschieschang, U., Wadepohl, H., Klauk, H., Tegeder, P., & Gade, L. H. (2015). Core Halogenation as a Construction Principle in Tuning the Material Properties of Tetraazaperopyrenes. Chemistry (Weinheim an der Bergstrasse, Germany), 21(49), 17691-700. https://doi.org/10.1002/chem.201503484
Hahn, Lena, et al. "Core Halogenation as a Construction Principle in Tuning the Material Properties of Tetraazaperopyrenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,49 (2015): 17691-700. doi: https://doi.org/10.1002/chem.201503484
Hahn L, Maass F, Bleith T, Zschieschang U, Wadepohl H, Klauk H, Tegeder P, Gade LH. Core Halogenation as a Construction Principle in Tuning the Material Properties of Tetraazaperopyrenes. Chemistry. 2015 Dec 01;21(49):17691-700. doi: 10.1002/chem.201503484. Epub 2015 Oct 28. PMID: 26507207.
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Chemistry. 2015 Dec 01;21(49):17691-700. doi: 10.1002/chem.201503484. Epub 2015 Oct 28.

Core Halogenation as a Construction Principle in Tuning the Material Properties of Tetraazaperopyrenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Lena Hahn, Friedrich Maass, Tim Bleith, Ute Zschieschang, Hubert Wadepohl, Hagen Klauk, Petra Tegeder, Lutz H Gade

Affiliations

  1. Anorganisch-Chemisches-Institut, Universität Heidelberg, Im Neuenheimer Feld?270, 69120 Heidelberg (Germany), Fax: (+49)?6221545609.
  2. Physikalisch-Chemisches-Institut, Universität Heidelberg, Im Neuenheimer Feld?253, 69120 Heidelberg (Germany).
  3. Max Planck Institute for Solid State Research, Heisenbergstrasse?1, 70569 Stuttgart (Germany).
  4. Anorganisch-Chemisches-Institut, Universität Heidelberg, Im Neuenheimer Feld?270, 69120 Heidelberg (Germany), Fax: (+49)?6221545609. [email protected].

PMID: 26507207 DOI: 10.1002/chem.201503484

Abstract

A detailed study on the effects of core halogenation of tetraazaperopyrene (TAPP) derivatives is presented. Its impact on the solid structure, as well as the photophysical and electrochemical properties, has been probed by the means of X-ray crystallography, UV/Vis and fluorescence spectroscopy, high-resolution electron energy loss spectroscopy (HREELS), cyclic voltammetry (CV), and DFT modeling. The aim was to assess the potential of this approach as a construction principle for organic electron-conducting materials of the type studied in this work. Although halogenation leads to a stabilization of the LUMOs compared to the unsubstituted parent compound, the nature of the halide barely affects the LUMO energy while strongly influencing the HOMO energies. In terms of band-gap engineering, it was demonstrated that the HOMO-LUMO gap is decreased by substitution of the TAPP core with halides, the effect being found to be most pronounced for the iodinated derivative. The performance of the recently reported core-fluorinated and core-iodinated TAPP derivatives in organic thin-film transistors (TFTs) was investigated on both a glass substrate, as well as on a flexible plastic substrate (PEN). Field-effect mobilities of up to 0.17 cm(2)  Vs(-1) and on/off current ratio of >10(6) were established.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: cyclic voltammetry; density functional calculations; electron energy loss spectroscopy; halogenation; material science

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