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Anthracene- pentacene dyads: synthesis and OFET characterization

The synthesis of a series of unsymmetrical derivatives of pentacene appended with functionalized anthracene moieties is reported. These anthracene−pentacene dyads have been characterized by UV-vis spectroscopy and cyclic voltammetry to examine their electronic properties. X-ray crystallographic anal...

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Main Authors: Hauschild, Miriam (Author) , Chen, Lan (Author) , Etschel, Sebastian H. (Author) , Ferguson, Michael J. (Author) , Hampel, Frank (Author) , Halik, Marcus (Author) , Tykwinski, Rik R. (Author)
Format: Article (Journal)
Language:English
Published: 04 May 2020
In: ChemPlusChem
Year: 2020, Volume: 85, Issue: 5, Pages: 921-926
ISSN:2192-6506
DOI:https://doi.org/10.1002/cplu.202000233
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/cplu.202000233
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cplu.202000233
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Author Notes:Miriam Hauschild, Lan Chen, Sebastian H. Etschel, Michael J. Ferguson, Frank Hampel, Marcus Halik, and Rik R. Tykwinski
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Summary:The synthesis of a series of unsymmetrical derivatives of pentacene appended with functionalized anthracene moieties is reported. These anthracene−pentacene dyads have been characterized by UV-vis spectroscopy and cyclic voltammetry to examine their electronic properties. X-ray crystallographic analysis was used to examine the solid-state features of anthracene−pentacene dyads 1 a-d with H−, F−, Cl−, and Br− substituents on the 9-position of anthracene, and shows that the packing arrangement of anthracene−pentacene derivatives 1 b,d,e are remarkably similar irrespective of the presence of fluoride, bromide or methyl substituents. The pentacene−anthracene dyads have been incorporated into OTFTs to evaluate their semiconducting properties. The pentacene derivative 1 b shows ambipolar behavior using AlOx C14PA as the gate dielectric (electron and hole mobilities of 7.6 ⋅ 10−3 and 1.6 ⋅ 10−1 cm2 V−1 s−1), while performance of all derivatives was poor using p-doped Silicon as the substrate. These studies highlight the importance of thin-film formation over molecular structure.
Item Description:Gesehen am 23.03.2021
Physical Description:Online Resource
ISSN:2192-6506
DOI:https://doi.org/10.1002/cplu.202000233

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