Charge transport and electronic properties of N-heteroquinones: quadruple weak hydrogen bonds and strong π–π stacking interactions

Yang, Guochun; Si, Yanling; Geng, Yun; Yu, Fei; Wu, Qingxiu; Su, Zhong‐Min

doi:10.1007/s00214-010-0841-4

Cited by 19 publications

(17 citation statements)

References 60 publications

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“…Note that the splitting approach commonly used yields overestimated values due to the non-centrosymmetric dimeric forms found. 50 Additionally, the electronic coupling between parallel stacks can be considered small, 51 promoting indeed a high mobility anisotropy, as found also before for collinear arrays of unsubstituted pentacene. 52 When inserting the values of e ·− and corresponding V if into Eq.…”

Section: Marcus Electron Transfer Ratesupporting

confidence: 56%

Application of double-hybrid density functionals to charge transfer in N-substituted pentacenequinones

Sancho‐García

2012

The Journal of Chemical Physics

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A set of N-heteroquinones, deriving from oligoacenes, have been recently proposed as n-type organic semiconductors with high electron mobilities in thin-film transistors. Generally speaking, this class of compounds self-assembles in neighboring π -stacks linked by weak hydrogen bonds. We aim at theoretically characterizing here the sequential charge transport (hopping) process expected to take place across these arrays of molecules. To do so, we need to accurately address the preferred packing of these materials simultaneously to single-molecule properties related to charge-transfer events, carefully employing dispersion-corrected density functional theory methods to accurately extract the key molecular parameters governing this phenomenon at the nanoscale. This study confirms the great deal of interest around these compounds, since controlled functionalization of model molecules (i.e., pentacene) allows to efficiently tune the corresponding charge mobilities, and the capacity of modern quantum-chemical methods to predict it after rationalizing the underlying structure-property relationships.

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Section: Marcus Electron Transfer Ratesupporting

confidence: 56%

Application of double-hybrid density functionals to charge transfer in N-substituted pentacenequinones

Sancho‐García

2012

The Journal of Chemical Physics

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“…We will limit ourselves in the following to the study of these two systems mainly on a relative basis. We note that the electronic coupling between other crystallographic directions (parallel stacks) can be considered small, 101,102 although might however promote large anisotropy of charge carrier mobilities.…”

Section: Hole and Electron Transfer Ratesmentioning

confidence: 90%

Theoretical study of stability and charge-transport properties of coronene molecule and some of its halogenated derivatives: A path to ambipolar organic-based materials?

Sancho‐García

Pérez-Jiménez

2014

The Journal of Chemical Physics

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We have carefully investigated the structural and electronic properties of coronene and some of its fluorinated and chlorinated derivatives, including full periphery substitution, as well as the preferred orientation of the non-covalent dimer structures subsequently formed. We have paid particular attention to a set of methodological details, to first obtain single-molecule magnitudes as accurately as possible, including next the use of modern dispersion-corrected methods to tackle the corresponding non-covalently bound dimers. Generally speaking, this class of compounds is expected to self-assembly in neighboring π -stacks with dimer stabilization energies ranging from -20 to -30 kcal mol −1 at close distances around 3.0-3.3 Å. Then, in a further step, we have also calculated hole and electron transfer rates of some suitable candidates for ambipolar materials, and corresponding charge mobility values, which are known to critically depend on the supramolecular organization of the samples. For coronene and per-fluorinated coronene, we have found high values for their hopping rates, although slightly smaller for the latter due to an increase (decrease) of the reorganization energies (electronic couplings).

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“…Electron transport which is preferred in these materials was determined to be strongest along p-stacks. 259 Good electron mobilities of up to 0.373 cm 2 V À1 s…”

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confidence: 98%

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

2017

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aIn recent years, organic semiconducting materials have enabled technological innovation in the field of flexible electronics. Substantial optimization and development of new p-conjugated materials has resulted in the demonstration of several practical devices, particularly in displays and photoreceptors.However, applications of organic semiconductors in bipolar junction devices, e.g. rectifiers and inverters, are limited due to an imbalance in charge transport. The performance of p-channel organic semiconducting materials exceeds that of electron transport. In addition, electron transport in p-conjugated materials exhibits poorer atmospheric stability and dispersive transient photocurrents due to extrinsic carrier trapping. Thus development of air stable n-channel conjugated materials is required. New classes of materials with delocalized n-doped states are under development, aiming at improvement of the electron transport properties of organic semiconductors. In this review, we highlight the basic tenets related to the stability of n-channel organic semiconductors, primarily focusing on the thermodynamic stability of anions and summarizing the recent progress in the development of air stable electron transporting organic semiconductors. Molecular design strategies are analysed with theoretical investigations.

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Charge transport and electronic properties of N-heteroquinones: quadruple weak hydrogen bonds and strong π–π stacking interactions

Cited by 19 publications

References 60 publications

Application of double-hybrid density functionals to charge transfer in N-substituted pentacenequinones

Application of double-hybrid density functionals to charge transfer in N-substituted pentacenequinones

Theoretical study of stability and charge-transport properties of coronene molecule and some of its halogenated derivatives: A path to ambipolar organic-based materials?

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

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