Molecular stacking character and charge transport properties of tetrabenzoheptacenes derivatives: the effects of nitrogen doping and phenyl substitution

Guan, Lin; Wang, Wenliang; Shao, Rong; Liu, Fengyi; Yin, Shiwei

doi:10.1007/s00894-015-2677-2

Cited by 7 publications

(3 citation statements)

References 62 publications

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“…Herein, we simulated the hole and electron mobility of DTDHP and DTDHP-BF 2 by means of solving the master equation, which has been described in detail elsewhere. − The charge-transfer (CT) kinetics through the solid material with many possible residence sites can be described by the master equation. d p i d t = prefix− false ∑ j ≠ i false[ k i j p i false( 1 − p j false) − k j i p j false( 1 − p i false) false] where k ij is the CT rate constant from site i to site j in the crystal considering the correction of the electronic field, p i is the charge occupied density on site i , and 1 – p i is the Coulomb penalty factor, which prevents two or more charges at the same time from occupying the same site. If the CT reaches the so-called steady state, d p i /d t = 0, p i can be obtained by an efficient iterative procedure given a full set of CT constant k ij .…”

Section: Methodsmentioning

confidence: 99%

Theoretical Study on Optoelectronic Properties of 1,4-Dithiazole-5,10-dihydrophenazine and Its B ← N-Fused Derivatives

Huang,

Duan,

Lin

et al. 2024

J. Phys. Chem. A

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Recently, Liu et al. reported 1,4-dithiazole-5,10-dihydrophenazine (DTDHP) and its B ← N-fused derivative (DTHDHP-BF 2 ), which were expected to show excellent optoelectronic properties (Angew. Chem. Int. Ed. 2022, 61, e202205893). However, their charge-transport performance and luminescence emission mechanisms have not been revealed. In this work, we used density functional theory (DFT) calculations to investigate the optoelectronic properties of DTDHP and DTHDHP-BF 2 and analyzed the influence of the introduction of −BF 2 on the basic parameters governing charge transport and injection in detail. Our calculation results showed that adding −BF 2 could stabilize the frontier molecular orbitals and decrease the reorganization energies associated with electron transport due to the formation of B ← N bonds, and the intermolecular electronic couplings are greatly enhanced owing to the strong intermolecular F•••H interactions. Based on the master equation coupled with the Marcus−Hush electron transfer theory, we theoretically predicted the charge transport properties of DTDHP and DTHDHP-BF 2 . The optimum hole mobility (3.87 cm 2 V −1 S −1 ) and electron mobility (1.52 cm 2 V −1 S −1 ) of DTHDHP-BF 2 are, respectively, 3 and 9 times as high as the corresponding optimum values of compound DTDHP. Moreover, the assignments of multiple fluorescence bands in the experiment were confirmed by timedependent density functional theory (TDDFT) calculations. The simulated emission spectra indicate that the experimental fluorescence maxima at 687 nm originates from the S 1 → S 0 transition of the double proton transfer phototautomer (T 2H ) of DTDHP, and the shoulder peak at ∼660 nm may be related to the excited-state single-proton transfer phototautomer (T 1H ); for DTHDHP-BF 2 , the experimental fluorescence maxima at 687 nm should be attributed to normal Stokes shifted emission, and the shifted fluorescence with a peak at 751 nm originates from the emission of the photodissociation product of DTHDHP-BF 2 .

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Section: Methodsmentioning

confidence: 99%

Theoretical Study on Optoelectronic Properties of 1,4-Dithiazole-5,10-dihydrophenazine and Its B ← N-Fused Derivatives

Huang,

Duan,

Lin

et al. 2024

J. Phys. Chem. A

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“…Considering the weak intermolecular electronic couplings, we simulated the angleresolved charge mobility of indeno[1,2-b]fluorene-6,12-dionebased semiconducting materials B-IFD, BT-IFD and DBA-IFD (see Fig. 1) by means of solving the master equation, which has been described in detail elsewhere (Yin & Lv, 2008;Yin et al, 2012;Zhao et al, 2013Zhao et al, , 2014Guan et al, 2015;Guo et al, 2015). The charge-transfer kinetics through the solid material with many possible residence sites can be described by the master equation.…”

Section: Anisotropic Mobilitymentioning

confidence: 99%

Theoretical study of charge-transport and optical properties of indeno[1,2-b]fluorene-6,12-dione-based semiconducting materials

Huang

Zhao

et al. 2018

Acta Crystallogr Sect B

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The conducting and optical properties of a series of indeno [1,2-b]fluorene-6,12dione (IFD)-based molecules have been systematically studied and the influences of butyl, butylthio and dibutylamino substituents on the reorganization energies, intermolecular electronic couplings and charge-injection barriers of IFD have been discussed. The quantum-chemical calculations combined with electron-transfer theory reveal that the incorporation of sulfur-linked side chains decreases reorganization energy associated with hole transfer and optimizes intermolecularstacking, which results in excellent ambipolar charge-transport properties ( h = 1.15 cm 2 V À1 s À1 and e = 0.08 cm 2 V À1 s À1 ); in comparison, addition of dibutylamino side chains increases intermolecular steric interactions and hinders perfect intermolecularstacking, which results in the weak electronic couplings and finally causes the low intrinsic hole mobility ( h = 0.01 cm 2 V À1 s À1 ). Furthermore, electronic spectra of butyl-IFD, butylthio-IFD and dibutylamino-IFD were simulated and compared with the reported experimental data. Calculations demonstrate that IFD-based molecules possess potential for developing novel infrared and near-infrared probe materials via suitable chemical modifications. research papers Acta Cryst. (2018). B74, 705-711 Jin-Dou Huang et al. IFD-based semiconducting materials 711

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“…At present, highly reliable and computationally cheap quantum chemical methods, such as density functional theory (DFT), are being widely used in the field of organic optoelectronics to validate the results of experimental studies and to predict the performance of novel organic semiconductor molecules. Based on DFT quantum chemistry, researchers have calculated and predicted the intrinsic electron and hole transport rates of organic molecular systems with various molecular structures, substituents, or hybridizations, including molecular derivatives such as thiophene, 2 bithiazole, 3 tetracene, 4 anthracene, 5,6 pentacene, [7][8][9] heptacenes, 10 diindole-diimide, 11 perylene, 12,13 triphenylene, 14,15 truxene, 16,17 coronene, 18 and phthalocyanine. 19,20 These theoretical studies on the relationship between the molecular structures of different systems and their charge transport properties are extremely useful for guiding experimental studies.…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigations on charge transport properties of tetrabenzo[a,d,j,m]coronene derivatives using different density functional theory functionals (B3LYP, M06-2X, and wB97XD)

Chen

et al. 2019

Journal of Chemical Research

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Charge transport rate is one of the key parameters determining the performance of organic electronic devices. Based on density functional theory, exchange-correlation functionals which adequately account for non-covalent interactions, such as M06-2X and wB97XD, should significantly improve the accuracy of charge transport rate calculations for large systems with non-covalent interactions. In this work, the B3LYP hybrid functional, the variant hybrid functional M06-2X, and the long-range-corrected wB97XD functional were used to perform geometry optimizations and charge transport rate calculations on 11 variants of tetrabenzo[ a,d,j,m]coronene, including tetrabenzo[ a,d,j,m]coronene itself and its tetra-substituted and octa-substituted derivatives. Our results indicate that the molecular geometries of these benzocoronene semiconductors are large quasi-planar conjugated π systems, and the incorporation of different substituents significantly affects their frontier molecular orbitals. The hole carrier mobility ( µ+) and electron carrier mobility ( µ−) of the methoxy-substituted derivatives (TBC(OCH3)4 and TBC(OCH3)8) were relatively low. The results of the tetrabenzo[ a,d,j,m]coronene molecules studied were consistent with using the aforementioned M06-2X, wB97XD, and B3LYP methods. We found that the octa-substituted derivatives (TBCF8, TBCCl8, TBC(CH3)8, and TBC(CN)8) could be used as p-type organic semiconductor materials.

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Molecular stacking character and charge transport properties of tetrabenzoheptacenes derivatives: the effects of nitrogen doping and phenyl substitution

Cited by 7 publications

References 62 publications

Theoretical Study on Optoelectronic Properties of 1,4-Dithiazole-5,10-dihydrophenazine and Its B ← N-Fused Derivatives

Theoretical Study on Optoelectronic Properties of 1,4-Dithiazole-5,10-dihydrophenazine and Its B ← N-Fused Derivatives

Theoretical study of charge-transport and optical properties of indeno[1,2-b]fluorene-6,12-dione-based semiconducting materials

Theoretical investigations on charge transport properties of tetrabenzo[a,d,j,m]coronene derivatives using different density functional theory functionals (B3LYP, M06-2X, and wB97XD)

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