Understanding electron-withdrawing substituent effect on structural, electronic and charge transport properties of perylene bisimide derivatives

Chai, Shuo; Wen, Shuhao; Han, Keli

doi:10.1016/j.orgel.2011.07.008

Cited by 50 publications

(35 citation statements)

References 51 publications

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“…This is in agreement with the previous study. [48][49][50] At the same time, the energy gap also decreases mainly due to the decreasing of LUMO energy. Table 5 shows the bond-length change (∆d) of the studied derivatives during the electron transport process.…”

Section: Frontier Molecular Orbital Ionization Potentials Electron mentioning

confidence: 96%

“…According to equation (1), a large Heff would have great impacts on the final charge transfer mobility. In general, -F substituent result in an obviously increasing on λe except for 8 [50,48] and the introduced substituent groups can bring in more vibrational modes of geometric relaxation that will lead to λe increase from the aspect of normal-mode (MN). [17,48,53,54] The triple bond of -CN which was connected into the original molecular π-conjugate system makes the conjugate system a further expanded.…”

Section: Frontier Molecular Orbital Ionization Potentials Electron mentioning

confidence: 99%

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Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Hu¹,

Yin²,

Chaitanya³

et al. 2016

Croat. Chem. Acta

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Abstract:The electronic structures and charge transport properties of 1,3,5-tripyrrolebenzene (TPB) and its substituted derivatives with -F and -CN groups have been investigated by DFT calculations in combination with the Marcus hopping model. The dimer geometry was optimized by density functional theory method with dispersion force correction being included (DFT-D). Consequently, the charge transfer integral was evaluated. The calculation results show that the introduction of electron-withdrawing substituents does not significantly change the bond lengths and molecular symmetry of TPB, but lower the coplanarity between the pyrrole and benzene rings, especially in the case of CN substitution. Meanwhile, the introduction of electron-withdrawing groups can decrease the energy of the frontier molecular orbital and enhance the air stability. Fluorination makes the λe increase obviously while cyanation dose not. Generally speaking, the λe values of the title compounds are larger than their λh. Except for compounds 6 and 9, all others keep the face to face packing or have a slight slip in dimers, but the center of mass distances increase after fluorination or cyanation due to the distortion of the monomer's coplanarity. The predicted quasi-one-dimensional electron mobility of the dimers is up to 0.433 cm 2 ·V -1 ·s -1 at 298.15 K. The electron injection barriers of 2 and 7 are lower than that of TPB. The TPB derivatives of 1, 2, and 7 are potential n-channel materials with the high electron mobility.

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Section: Frontier Molecular Orbital Ionization Potentials Electron mentioning

confidence: 96%

Section: Frontier Molecular Orbital Ionization Potentials Electron mentioning

confidence: 99%

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Hu¹,

Yin²,

Chaitanya³

et al. 2016

Croat. Chem. Acta

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“…In the past decades, molecular organic semiconductors is the object of much interest because of their applications in new generations of (opto)electronic devices [1][2][3][4][5][6][7][8]. The development of single-crystal organic field effect transistors (SCOFETs) makes it possible to explore intrinsic properties of these materials [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

BODIPY derivatives as n-type organic semiconductors: Isomer effect on carrier mobility

Zhang

Chai

Zhao

2012

Organic Electronics

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“…Prior theoretical work on perylene has been performed using DFT or time-dependent DFT. For perylene monomers in solution, it was found that substituents can controllably alter stability, orbital level energetics, charge transport, and optical absorption (39), suggesting routes for impacting performance in the condensed phase. In addition, calculations of perylene in the solid state have predicted accurate lattice parameters by accounting for van der Waals interactions and have predicted a fundamental indirect bandgap (40).…”

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confidence: 99%

Low-lying excited states in crystalline perylene

Rangel

Rinn

Sharifzadeh

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Organic materials are promising candidates for advanced optoelectronics and are used in light-emitting diodes and photovoltaics. However, the underlying mechanisms allowing the formation of excited states responsible for device functionality, such as exciton generation and charge separation, are insufficiently understood. This is partly due to the wide range of existing crystalline polymorphs depending on sample preparation conditions. Here, we determine the linear optical response of thin-film single-crystal perylene samples of distinct polymorphs in transmission and reflection geometries. The sample quality allows for unprecedented high-resolution spectroscopy, which offers an ideal opportunity for judicious comparison between theory and experiment. Excellent agreement with firstprinciples calculations for the absorption based on the GW plus Bethe-Salpeter equation (GW-BSE) approach of many-body perturbation theory (MBPT) is obtained, from which a clear picture of the low-lying excitations in perylene emerges, including evidence of an exciton-polariton stopband, as well as an assessment of the commonly used Tamm-Dancoff approximation to the GW-BSE approach. Our findings on this well-controlled system can guide understanding and development of advanced molecular solids and functionalization for applications. molecular crystals | many-body perturbation theory | excited states | spectroscopy

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Understanding electron-withdrawing substituent effect on structural, electronic and charge transport properties of perylene bisimide derivatives

Cited by 50 publications

References 51 publications

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

BODIPY derivatives as n-type organic semiconductors: Isomer effect on carrier mobility

Low-lying excited states in crystalline perylene

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