Impact of 2-Ethylhexyl Stereoisomers on the Electrical Performance of Single-Crystal Field-Effect Transistors

Tao He, Pawaret Leowanawat, Christian Burschka, Vladimir Stepanenko, Matthias Stolte, Frank Würthner

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Many organic semiconductors (OSCs) inherit chiral alkyl chains, which ensure the desirable high solubility for solution-processing but may also lead to disorder, inhomogeneous film-formation, as well as interfacial defects due to the presence of mixtures of stereoisomers or diastereomers, which impair their peak performance. Here, single-crystal field-effect transistors (SCFETs) of a diketopyrrolopyrrole-based organic semiconductor with chiral 2-ethylhexyl substituents by sublimation in air and organic ribbon mask method are fabricated. Devices of the mesomer (R/S), both enantiomers (R/R, S/S), as well as mixtures of these three stereoisomers measured under ambient conditions exhibit all appreciable p-channel charge carrier mobilities of > 0.1 cm2 V−1 s−1 despite different packing arrangement in the R/S, R/R (or S/S), and racemate crystal structures. These results suggest a surprising tolerance for isomeric impurities. The highest literature-reported p-channel mobility so far for a diketopyrrolopyrrole-based OSC of 3.4 cm2 V−1 s−1 (Ion/Ioff of 1 × 106) is, however, only obtained for the pure R/S mesomer, illustrating the inherent potential of stereochemical purity. These results on SCFETs are further substantiated by studies on organic thin-film transistors (OTFTs) of pure and mixed thin films of the different stereoisomers.

Original languageEnglish (US)
Article number1804032
JournalAdvanced Materials
Volume30
Issue number44
DOIs
StatePublished - Nov 2 2018

Fingerprint

Stereoisomerism
Semiconducting organic compounds
Field effect transistors
Single crystals
Enantiomers
Carrier mobility
Sublimation
Thin film transistors
Charge carriers
Masks
Solubility
Crystal structure
Impurities
Ions
Thin films
Defects
Processing
Air

Keywords

  • chirality
  • diketopyrrolopyrroles
  • organic electronics
  • single-crystal field-effect transistors

PubMed: MeSH publication types

  • Journal Article

Cite this

Impact of 2-Ethylhexyl Stereoisomers on the Electrical Performance of Single-Crystal Field-Effect Transistors. / He, Tao; Leowanawat, Pawaret; Burschka, Christian; Stepanenko, Vladimir; Stolte, Matthias; Würthner, Frank.

In: Advanced Materials, Vol. 30, No. 44, 1804032, 02.11.2018.

Research output: Contribution to journalArticle

He, Tao ; Leowanawat, Pawaret ; Burschka, Christian ; Stepanenko, Vladimir ; Stolte, Matthias ; Würthner, Frank. / Impact of 2-Ethylhexyl Stereoisomers on the Electrical Performance of Single-Crystal Field-Effect Transistors. In: Advanced Materials. 2018 ; Vol. 30, No. 44.
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