Density functional theory calculations of charge transport properties of ‘plate-like’ coronene topological structures

Chen, Ziran; He, Zhanrong; You-hui, XU; Yu, Wenhao

doi:10.1007/s12039-017-1351-x

Cited by 18 publications

(10 citation statements)

References 33 publications

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“…The experimental mobilities based on SCFET were in accord with the theoretical calculation. Besides these reports, high FET mobilities of these PAH systems were also projected by density functional theory (DFT) calculations, made at the M06‐2X/6‐31+G(d) level [207] …”

Section: Resultsmentioning

confidence: 99%

“…With such packing and other specific physicochemical features, [130] coronene finds applications in the field of organic electronics. For example, a p‐type charge conduction was demonstrated in FET devices [131–132] . It also showed other interesting properties, such as excimer emission, [133] aggregation‐enhanced emission, [134] plasmon‐induced emission [135] and a phosphorescence lifetime of 22.4 s [136] .…”

Section: Resultsmentioning

confidence: 99%

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Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Kumar

Tao

2021

Chemistry An Asian Journal

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In recent years, a variety of new designs of coronene‐based polycyclic aromatic hydrocarbons (PAHs) with diverse functions have emerged to serve as complementary materials in organic chemistry and materials chemistry. In the present review, we highlight the modern aspects of syntheses related to or different from the strategies used in the early era of coronene research. Systematic extension and expansion of coronene backbones to wide categories of angular PAHs are covered. The substitution and extension of coronene architectures, by incorporating functional groups and by fusing small and large conjugated units, advatangeously enrich their photophysical, electrochemical, self‐assembling, and other properties, of which are discussed to demostrate their impact in materials chemistry. While the highly symmetric coronenes, tribenzocoronenes and hexabenzocoronenes conceived wide potential in charge‐transporting, electroluminescent, sensing, and other applications, other related derivatives such as dibenzo, tetrabenzo and pentabenzocoronenes also displayed their potentials as exemplified by their use as charge‐conduction channel in transistor application.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Kumar

Tao

2021

Chemistry An Asian Journal

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“…Structurally, TBC is a small segment of the well‐known two‐dimensional carbon allotrope—graphene . In this regard, TBC along with other π‐extended PAHs are deemed as “nanographenes” (NGs) for they represent the nanometer‐scale subunits of graphenes, and recently their tunable structural and band gap properties have attracted enormous interest from both industry and academia, owing to their great potential in the synthesis of NGs and application in organic optoelectronics such as semiconductors, transistors, and sensors …”

Section: Introductionmentioning

confidence: 99%

“…These challenges limit the number of TBC derivatives so far accomplished in synthesis, and further expansion of the TBC family awaits more efficient synthetic methods to be developed. Aside from the synthetic efforts, theoretical investigations based on density functional theory (DFT) calculations present another reasonable approach to gain deep understanding of TBC derivatives and other fundamentally interesting PAHs …”

Section: Introductionmentioning

confidence: 99%

Molecular structure and electronic properties of substituted tetrabenzocoronenes: DFT and TD‐DFT investigations

Qiu

Flinn

Zhao

2019

J of Physical Organic Chem

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1,2:3,4:7,8:9,10‐Tetrabenzocoronene (TBC) is a highly π‐conjugated polycyclic aromatic hydrocarbon (PAH) with an intriguing nonplanar, twisted molecular shape featuring two [4]helicene subunits on the opposite sides of the molecule. In this study, we examined the electronic substituent effects on the molecular properties of a series of TBC derivatives by density functional theory (DFT) and time‐dependent DFT (TD‐DFT) computational analysis at the B3LYP/6‐31G(d) and TD‐B3LYP/6‐311 + G(d,p) levels. The equilibrium geometries for the stable conformers of the TBC derivatives in the ground singlet state (So) and related transition states were optimized to obtain the energy barriers associated with the interconversion among these conformers. Variations of aromatic character for these compounds were evaluated by nucleus‐independent chemical shift (NICS) calculations, while the frontier molecular orbital (FMO) energies and the vertical electronic absorption and emission energies were calculated. The calculated absorption and emission spectra of these TBC derivatives show good correlations with the Hammett substituent constant (σ). Overall, our study has demonstrated that the attachment of electron‐donating/withdrawing substituents to the edges of TBC can exert significant effects on the structural, electronic, and photophysical properties. Understanding of the substitution effects on TBC provides valuable insight for the design and development of novel PAH‐based organic electronic materials and devices.

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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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Density functional theory calculations of charge transport properties of ‘plate-like’ coronene topological structures

Cited by 18 publications

References 33 publications

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Molecular structure and electronic properties of substituted tetrabenzocoronenes: DFT and TD‐DFT investigations

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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