Density-functional theoretical study of fluorination effect on the electronic structure and electron drift mobilities of symmetric pentacene derivatives

Lukeš, Vladimı́r; Cagardová, Denisa; Michalík, Martin; Poliak, Peter

doi:10.1016/j.synthmet.2018.03.014

Cited by 10 publications

(9 citation statements)

References 64 publications

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“…On the other hand, theoretical B3LYP l − values reported for donor-acceptor 1,8-naphthalimide derivatives are of 0.216-0.235 eV (Chai and Jin, 2016). For a smaller fl uorinated pentacene, the electron re or gani zation energy is of 0.246 eV (Lukeš et al, 2018) and for tris(8-hydroxyquinolinato)aluminum (Alq 3 ) it is of 0.296 eV (Friederich et al, 2016).…”

Section: Resultsmentioning

confidence: 99%

On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study

Cagardová

Lukeš

Matúška

et al. 2019

Acta Chimica Slovaca

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A computational study using density functional theory is reported for selected model aza[n]circulenes (n = 6, 7, 8 and 9) and their derivatives consisting of pyrrole and benzene units. Local aromaticity of central rings was discussed and analyzed using theoretical structural indices. Depending on their molecular structures, energies of the highest occupied and lowest unoccupied molecular orbitals change from –5.23 eV to –4.08 eV and from –1.97 eV to –0.41 eV, respectively. Based on B3LYP calculated optimal geometries, electronic structure of molecules and their charge transport properties resulted in the suggestion of three planar molecules containing three or four pyrrole units as potential candidates for p-type semiconductors. Hole drift mobilities for ideal stacked dimers of these potential semiconductors were calculated and they range from 0.94 cm2·V−1·s−1 to 7.33 cm2·V−1·s−1.

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Section: Resultsmentioning

confidence: 99%

On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study

Cagardová

Lukeš

Matúška

et al. 2019

Acta Chimica Slovaca

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“…Differences in crystal‐structure packing may have an immediate impact on the properties of molecular films that are of technological relevance. For example, pronounced island formation of 10 precludes its application in OFET devices, and hence the large charge‐carrier mobility predicted based on computations could not be experimentally confirmed. In contrast, isomers 11 and more so 12 show reasonably good n‐channel semiconducting properties with charge carrier mobility up to 6×10 −2 cm 2 V −1 s −1 .…”

Section: Discussionmentioning

confidence: 99%

“…In addition to these experimental investigations, there are a number of computational studies on partially fluorinated pentacenes without solubilizing side groups, and some very interesting predictions were made . Toyoda et al .…”

Section: Introductionmentioning

confidence: 99%

“…suggested that it could be possible to fabricate interfaces optimal for charge‐carrier injection by using pentacenes with a number of fluorine atoms n F less than or equal to eight. A systematic computational DFT study of symmetrical substituted fluoropentacenes ( n F =2–14) by Lukeš et al . came to the conclusion that charge‐carrier mobility is lowest in PFP, whereas 1,4,8,11‐tetrafluoropentacene should show the highest mobility of up to 7.30 cm 2 V −1 s −1 depending on the dimer configuration used for the calculations.…”

Section: Introductionmentioning

confidence: 99%

“…In this work, we describe the synthesis of two new isomers of peripherally substituted tetrafluoropentacenes with a 1,4,8,11‐ (for which computational predictions were made by Lukeš et al. ) and 1,4,9,10‐substitution pattern (Scheme c) using the 1,2,4,5‐tetrazine‐induced elimination of the 6,13‐etheno bridge. We compare the chemical, electrochemical, and photophysical properties, including singlet‐fission dynamics, as well as crystal‐structure data and OFET device performance in the series of tetrafluoropentacenes.…”

Section: Introductionmentioning

confidence: 99%

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Modulating the Electronic and Solid‐State Structure of Organic Semiconductors by Site‐Specific Substitution: The Case of Tetrafluoropentacenes

Geiger

Schundelmeier

Hummel

et al. 2020

Chemistry A European J

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The properties as well as solid‐state structures, singlet fission, and organic field‐effect transistor (OFET) performance of three tetrafluoropentacenes (1,4,8,11: 10, 1,4,9,10: 11, 2,3,9,10: 12) are compared herein. The novel compounds 10 and 11 were synthesized in high purity from the corresponding 6,13‐etheno‐bridged precursors by reaction with dimethyl 1,2,4,5‐tetrazine‐3,6‐dicarboxylate at elevated temperatures. Although most of the molecular properties of the compounds are similar, their chemical reactivity and crystal structures differ considerably. Isomer 10 undergoes the orbital symmetry forbidden thermal [4+4] dimerization, whereas 11 and 12 are much less reactive. The isomers 11 and 12 crystallize in a herringbone motif, but 10 prefers π–π stacking. Although the energy of the first electric dipole‐allowed optical transition varies only within 370 cm−1 (0.05 eV) for the neutral compounds, this amounts to roughly 1600 cm−1 (0.20 eV) for radical cations and 1300 cm−1 (0.16 eV) for dications. Transient spectroscopy of films of 11 and 12 reveals singlet‐fission time constants (91±11, 73±3 fs, respectively) that are shorter than for pentacene (112±9 fs). OFET devices constructed from 11 and 12 show close to ideal thin‐film transistor (TFT) characteristics with electron mobilities of 2×10−3 and 6×10−2 cm2 V−1 s−1, respectively.

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Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

et al. 2021

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The synthesis, experimental and theoretical study of the novel air-stable four adamantane-bearing dyes based on the transepindolidione (EPI) and trans-quinacridone (QA) cores are presented. Compared to the parent EPI and QA, the methyl-/ ethyladamantyl substitution ensures that their structural stability in crystals is preserved due to the self-organizing properties of adamantyl groups. The investigated materials are solutionprocessable in common organic solvents and possess excellent thermal stability. The very good solubility was achieved by a one-step short and easy synthesis, which resulted in moderate yields of a new family of synthesized dyes. The ethyladamantyl EPI derivative (3) exhibits a unique rise in thermal stability reaching 412 °C. The resulting electrochemical band gap carried out on thin-film evaporated on ITO-coated glass electrodes was in the range of 2.4-2.5 eV. The experimental HOMO energies range from À 6.2 to À 6.0 eV, and LUMO energies lay between À 3.7 and À 3.5 eV. The prepared compounds are characterized by strong fluorescence in solutions and in powder, suggesting a decrease in the extent of non-radiative relaxation processes.

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Density-functional theoretical study of fluorination effect on the electronic structure and electron drift mobilities of symmetric pentacene derivatives

Cited by 10 publications

References 64 publications

On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study

On local aromaticity of selected model aza-[n]circulenes (n = 6, 7, 8 and 9): Density functional theoretical study

Modulating the Electronic and Solid‐State Structure of Organic Semiconductors by Site‐Specific Substitution: The Case of Tetrafluoropentacenes

Adamantane Substitution Effects on Crystallization and Electrooptical Properties of Epindolidione and Quinacridone Dyes

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