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Thioether- and sulfone-functionalized dibenzopentalenes as n‑channel semiconductors for organic field-effect transistors

Abstract

Dibenzo[a,e]pentalenes (DBPs) are promising candidates to be used as ambipolar or n-type semiconductors in organic field-effect transistors (OFETs). For n-channel conduction, low LUMO energy levels are required. Furthermore, a close molecular packing in the solid state is advantageous. Here we present thioether-functionalized DBPs with LUMO energies down to −3.47 eV as well as a DBP sulfone with a LUMO energy of −3.94 eV. X-ray crystallography revealed 1-D π-stacking or herringbone packing in the solid state with close intramolecular distances between the DBP cores. Two thio-DBPs and the DBP sulfone showed n-channel conduction in FET measurements on well-aligned crystals with electron mobilities of up to 0.18 cm2 V−1 s−1, up to date the highest reported values for n-channel conduction in DBP derivatives. The short synthetic route will in the future allow for facile access to a variety of thio- and sulfone-DBPs for n-channel or ambipolar semiconduction.

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Publication details

The article was accepted on 18 Mar 2018 and first published on 03 Apr 2018


Article type: Paper
DOI: 10.1039/C8TC00970H
Citation: J. Mater. Chem. C, 2018, Accepted Manuscript
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    Thioether- and sulfone-functionalized dibenzopentalenes as n‑channel semiconductors for organic field-effect transistors

    M. Hermann, R. Wu, D. C. Grenz, D. Kratzert, H. Li and B. Esser, J. Mater. Chem. C, 2018, Accepted Manuscript , DOI: 10.1039/C8TC00970H

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