An unsymmetrical pentacene derivative with ambipolar behavior in organic thin-film transistors

Etschel, Sebastian H.; Waterloo, Andreas R.; Margraf, Johannes T.; Amin, Atefeh Y.; Hampel, Frank; Jäger, Christof M.; Clark, Timothy; Halik, Marcus; Tykwinski, Rik R.

doi:10.1039/c3cc43270j

Cited by 24 publications

(38 citation statements)

References 25 publications

(23 reference statements)

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“…7) [31]. The pentacene skeleton and the anthracenyl substituent are nearly perpendicular to each other with a twist angle of ~90°.…”

Section: Resultsmentioning

confidence: 99%

Aryl substitution of pentacenes

Waterloo¹,

Sale²,

Lehnherr³

et al. 2014

Beilstein J. Org. Chem.

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SummaryA series of 11 new pentacene derivatives has been synthesized, with unsymmetrical substitution based on a trialkylsilylethynyl group at the 6-position and various aryl groups appended to the 13-position. The electronic and physical properties of the new pentacene chromophores have been analyzed by UV–vis spectroscopy (solution and thin films), thermoanalytical methods (DSC and TGA), cyclic voltammetry, as well as X-ray crystallography (for 8 derivatives). X-ray crystallography has been specifically used to study the influence of unsymmetrical substitution on the solid-state packing of the pentacene derivatives. The obtained results add to our ability to better predict substitution patterns that might be helpful for designing new semiconductors for use in solid-state devices.

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“…7) [31]. The pentacene skeleton and the anthracenyl substituent are nearly perpendicular to each other with a twist angle of ~90°.…”

Section: Resultsmentioning

confidence: 99%

Aryl substitution of pentacenes

Waterloo¹,

Sale²,

Lehnherr³

et al. 2014

Beilstein J. Org. Chem.

Self Cite

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“…The principal exceptions to this have come from Tykwinski and co‐workers, who described several years ago the preparation of unsymmetrically substituted diethynylpentacenes by controlling stoichiometry and rate of addition of ethynyllithium reagents to pentacenequinone 24–26. Earlier this year, the same group reported three 6‐anthryl‐13‐ethynylpentacene derivatives, one of which showed ambipolar behavior in thin film transistors 27…”

Section: Methodsmentioning

confidence: 99%

Combining Electronic and Steric Effects for Highly Stable Unsymmetric Pentacenes

Zhang

Pawle

Haas

et al. 2014

Chemistry A European J

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This paper describes the reactivity of unsymmetrically substituted pentacenes to photochemical oxidation. Acenes in general, and pentacenes in particular, are a key family of compounds for a variety of organic electronics applications. The instability of many pentacene derivatives, particularly to oxidation, is an important restriction in their applicability. Several substitution strategies for decreasing the reactivity of pentacene exist, but these almost always involve symmetrically substituted derivatives, restricting the chemical space of structures from which to choose. In this paper, we demonstrate that combining electronic and steric effects yields highly stable unsymmetrically substituted pentacenes.

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“…1−3 Ambi-OFETs can be fabricated using one ambipolar material 4,5 or by combining two unipolar materials (p-and n-type). 6,7 The fabrication of highly efficient ambipolar devices using one ambipolar organic material is still being researched, because achieving balanced p-and n-type charge transport in ambient conditions is very difficult with one organic material.…”

Section: ■ Introductionmentioning

confidence: 99%

Laterally-Stacked, Solution-Processed Organic Microcrystal With Ambipolar Charge Transport Behavior

Shim

Cho

Yang

et al. 2014

ACS Appl. Mater. Interfaces

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We report the formation of laterally stacked ambipolar crystal wire for high-mobility organic field-effect transistors (OFETs), along with a simple logic circuit through a solution process. A soluble pentacene derivative, 6,13-bis(triisopropylsilylethynyl)pentacene (Tips-pentacene), and N,N'-dioctyl-3,4,9,10-perylenedicarboximide (PTCDI-C8) were used as p-type and n-type organic semiconductors, respectively. The laterally stacked ambipolar crystal wire is made up of Tips-pentacene and PTCDI-C8 crystals in a structure of Tips-pentacene/PTCDI-C8/Tips-pentacene (TPT). The inner part of the crystal is made up of PTCDI-C8, and Tips-pentacene is present on both sides. These TPT crystals exhibit typical ambipolar charge transport behavior in organic electronic devices, which show very balanced hole and electron mobility as high as 0.23 cm(2)/V·s and 0.13 cm(2)/V·s, respectively. Static and dynamic operational stability of the device is investigated by measuring the device performance as a function of storage time and applying voltage pulse, respectively, and it shows good air stability. In addition, a simple logic circuit based on the TPT crystal wire has been fabricated, and the static and dynamic performance has been evaluated. The results indicate that the TPT crystals are potentially useful for miniaturized organic electronic devices.

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An unsymmetrical pentacene derivative with ambipolar behavior in organic thin-film transistors

Cited by 24 publications

References 25 publications

Aryl substitution of pentacenes

Aryl substitution of pentacenes

Combining Electronic and Steric Effects for Highly Stable Unsymmetric Pentacenes

Laterally-Stacked, Solution-Processed Organic Microcrystal With Ambipolar Charge Transport Behavior

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