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

doi:10.1002/adma.201804032

Cited by 37 publications

(52 citation statements)

References 53 publications

(60 reference statements)

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“…The enantiomers RR ‐39 and SS ‐39 exhibited improved mobility values of 4.1–4.5 × 10 −4 cm 2 V −1 s −1 , whereas the best performance was observed for the achiral compound and meso ‐39 , µ ( h + ) = 1.7 × 10 −3 cm 2 . These results are corroborated by the ones obtained by Würthner et al with single crystal OFETs of DPP RR ‐40 , SS ‐40 , and meso ‐40 that affords mobility values of µ ( h + ) = 0.79, 0.79, and 3.4 cm 2 V −1 s −1 . Why do meso compounds give rise to higher mobility than pure isomers?…”

Section: Charge Transportsupporting

confidence: 84%

“…The optimum charge transport performances are generally obtained for 8–12 carbon atoms . Branching has evidently been explored as a strategy to enhance solubility and modulate packing, but at the eventual expenses of creating a stereogenic center . Triisopropylsylil, triethylsilyl, and triethylgermyl are among popular unconventional bulky side groups as can be seen in compounds 4 , 5a,b , 6 , 26 , and 28 .…”

Section: Charge Transportmentioning

confidence: 99%

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Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

et al. 2020

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The field of organic electronics has been prolific in the last couple of years, leading to the design and synthesis of several molecular semiconductors presenting a mobility in excess of 10 cm2 V−1 s−1. However, it is also started to recently falter, as a result of doubtful mobility extractions and reduced industrial interest. This critical review addresses the community of chemists and materials scientists to share with it a critical analysis of the best performing molecular semiconductors and of the inherent charge transport physics that takes place in them. The goal is to inspire chemists and materials scientists and to give them hope that the field of molecular semiconductors for logic operations is not engaged into a dead end. To the contrary, it offers plenty of research opportunities in materials chemistry.

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Section: Charge Transportsupporting

confidence: 84%

Section: Charge Transportmentioning

confidence: 99%

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

et al. 2020

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“…Note that the dependence on electron mobility by different chiralities of NDI derivatives, introducing those with nonlinear shapes of side‐chains in this work, is rather different from that of previous studies on chiral organic semiconductors. For example, in DPP stereoisomers with chiral branched alkyl (2‐ethylhexyl) side groups, DPP mesomers exhibit higher hole mobility than DPP enantiomers . However, the trend of electron mobility of NDI stereoisomers is not valid in this work.…”

Section: Resultsmentioning

confidence: 83%

“…(OFETs), organic photovoltaics (OPVs), chiral sensors, and perovskite solar cells (PSCs). [1][2][3][4][5][6][7][8] A change in the stereochemical purity of chiral organic semiconductors strongly influences their charge transporting properties, crystal characteristics, blend morphology, and optical responses. For example, in diketopyrrolopyrrole (DPP) stereoisomers consisting of two chiral 2-ethylhexyl side groups, DPP mesomers exhibit higher hole mobility than DPP enantiomers due to their larger area and tighter packing of π-π stacking interactions between DPP cores.…”

mentioning

confidence: 99%

“…For example, in diketopyrrolopyrrole (DPP) stereoisomers consisting of two chiral 2-ethylhexyl side groups, DPP mesomers exhibit higher hole mobility than DPP enantiomers due to their larger area and tighter packing of π-π stacking interactions between DPP cores. [3,4] In organic electronic devices, beyond achieving high device performance, simultaneous achievement of low-temperature solution processability and long-term temporal (and high-temperature) device stability is very important. High solubility of organic semiconductors generally results in enhanced solution processability.…”

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confidence: 99%

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Chiral Stereoisomer Engineering of Electron Transporting Materials for Efficient and Stable Perovskite Solar Cells

Jung

Heo

et al. 2020

Adv Funct Materials

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A series of chiral stereoisomers of electron transporting materials with two chiral substituents is rationally designed and synthesized, and the influence of stereoisomerism on their physical and electronic properties is investigated to demonstrate highly efficient and stable perovskite solar cells (PSCs). Compared to mesomeric naphthalene diimide (NDI) derivatives, which have heterochiral side groups with centrosymmetric molecular packing of symmetric‐shaped conformers in the crystalline state, enantiomeric NDI derivatives have homochiral side groups that exhibit non‐centrosymmetric molecular packing of asymmetric‐shaped conformers in the crystalline state and exhibit better solution processability based on one order of magnitude higher solubility. A similar trend is observed in different rylene diimide stereoisomers based on larger semiconducting core perylene diimide. The PSCs based on NDI enantiomers with good film‐forming ability and a very high lowest phase transition temperature (Tlowest) of 321 °C exhibit a high and uniform average power conversion efficiency (PCE) of 19.067 ± 0.654%. These PSCs also have a high temporal device stability, with less than 10% degradation of the PCE at 100 °C for 1000 h without encapsulation. Therefore, chiral stereoisomer engineering of charge transporting materials is a potential approach to achieve high solution processability, excellent performance, and significant temporal stability in organic electronic devices.

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Half‐Fused Diketopyrrolopyrrole‐Based Conjugated Donor–Acceptor Polymer for Ambipolar Field‐Effect Transistors

Shi

Liu

et al. 2020

Adv Funct Materials

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IntroductionConjugated donor-acceptor (D-A) polymers have attracted increasing attention due to their easily modified structures, good solution rheology, semiconducting properties, and A novel building block, denoted as half-fused diketopyrrolopyrrole (DPP) (9-(3-octadecylhenicosyl)-8-(thiophen-2-yl)-7H-pyrrolo[3,4-a]thieno[3,2-g] indolizine-7,10(9H)-dione), in which one of the flanking thiophene units is fused to one of the DPP rings via a carbon-carbon double bond at the N-position is reported. The half-fused DPP is successfully utilized as an electron acceptor to prepare the conjugated donor-acceptor polymer PTFDFT, which exhibits ambipolar semiconducting behavior in ambient air. Theoretical calculations and absorption spectral studies show that the backbone of PTFDFT is more planar compared to the reference polymer with conventional DPP units. As a result, PTFDFT shows a narrow bandgap and low lowest unoccupied molecular orbital level. The more planar backbone with fewer side chains favors the dense packing of the polymer chains of PTFDFT with a short π-π stacking distance (3.49 Å). Grazing-incidence wide-angle X-ray scattering data further confirm the predominant edge-on packing mode of the PTFDFT polymer chains on the substrate. As expected, the PTFDFT thin film shows excellent ambipolar semiconducting properties under ambient conditions, reaching 2.23 and 1.08 cm 2 V −1 s −1 for the n-and p-channels, respectively. In addition, complementary-like inverter with gain value as high as 141 is successfully constructed using the PTFDFT thin film. mechanical properties. [1][2][3] Accordingly, they show promising applications in largearea, lightweight, and flexible electronic devices. [4,5] Among them, ambipolar conjugated D-A polymers, which are capable of transporting both electron and hole carriers, have drawn interest due to the fact that they facilitate the fabrication of complementary-like logic circuits using singlecomponent solution processing instead of selective deposition of p-and n-channel materials, which demand advanced patterning techniques. [6] In the pursuit of high ambipolar performance polymeric field-effect transistors (FETs), various conjugated D-A polymers have been developed and investigated. Different electron acceptors, including diketopyrrolopyrrole (DPP), [2e,7,8] isoindigo, [9] and naphthalene diimide, [10] have been introduced into conjugated D-A polymers to obtain ambipolar semiconductors. [2e,6-11] Among them, DPP-based polymers have been intensively investigated as semiconducting materials for FETs. [2e,6b,7,8,12,13] However, a large number of DPP-based polymers mainly show hole mobilities. This is because of the hindrance of electron injection due to the large gaps between lowest unoccupied molecular orbitals (LUMOs) (−3.2 to −3.6 eV) of DPP-based polymers and the electrode (normally gold) W F (work function ≈ 5.1 eV), while their highest occupied molecular orbitals (HOMOs) (−5.0 to −5.5 eV) were close to the W F of gold. [12] Therefore, lowering the LUMOs of DPP-based conjuga...

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

Cited by 37 publications

References 53 publications

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

Chiral Stereoisomer Engineering of Electron Transporting Materials for Efficient and Stable Perovskite Solar Cells

Half‐Fused Diketopyrrolopyrrole‐Based Conjugated Donor–Acceptor Polymer for Ambipolar Field‐Effect Transistors

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