The synthesis and ambipolar charge transport properties of 1,2,3,4-tetrafluoropentacene

Chien, Ching Ting; Chiang, Ta Chung; Watanabe, Motonori; Chao, Ting Han; Chang, Yuan Jay; Lin, Yan Duo; Lee, Hung Kai; Liu, Ching Yang; Tu, Chih Hsin; Sun, Chia Hsing; Chow, Tahsin J.

doi:10.1016/j.tetlet.2012.11.126

Cited by 13 publications

(19 citation statements)

References 16 publications

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“…In comparison with the publisheds ynthesis [40] the two-step process gives an even lower yield (26 %f or the directv ersus 22 %t hrough the two-step method), but the purity of the isolated product was increased significantly. [29,30] and Bettinger et al (b;i .OsO 4 (cat. )/NMO, acetone/H 2 O, ii.…”

Section: Synthesismentioning

confidence: 83%

“…Only the relevant reaction products are shown, the byproducts of the reaction have been discussed and characterized in previous publications. [31,33] symmetry.C orrelation of chemical shifts with data for pentacene endoperoxide (PcEP), [46] an authentic sample of dianthracene prepared following our generalm ethod for preparation of substituted dianthracenes, [47] the thermald imer of 1,2,3,4tetrafluoropentacene, [29] and diheptacene [48] (see Supporting Information,T able S1)s trongly indicates formation of the covalent dimer 13.…”

Section: Synthesismentioning

confidence: 99%

“…Overview over unit celld ata, HOMO/LUMOl evels (calculateda tt he B3LYP/6-311 + G** level of theory), formalo xidation and reduction potentials [a,b] from CV measurements and data for the S 1 and T 1 states obtained from optical spectroscopyi ns olution. Dataf or 1,2,3,4-tetrafluoropentacene is taken from Chien et al, [29] for blank spaces no data is available. Chem.E ur.J.2020, 26,3420-3434 www.chemeurj.org tion peak for 10 above + +0.9V (Supporting Information , Figure S39).…”

Section: Molecular Electrochemistrymentioning

confidence: 99%

“…Thermald imerizationr eactions of pentacene derivatives bearing substituents on the terminal rings have been reported before. [29,49,50] Although orbital-symmetryf orbidden according to the Woodward-Hoffmann rules, the thermal[ 4 + +4] cycloaddition reactionw as rationalizedb yc onsideration of packing motifs in the crystal structure as well as by molecular dynamics calculations. [50] It was suggested that a p-p stacking arrangement in the crystal is able to facilitate the solid-stated imerization by pre-aligning the reactionp artners.…”

Section: Synthesismentioning

confidence: 99%

“…[29,30] The 2-fluoro derivativew as characterized as ap -channel semiconductor, [30] whereas 1,2,3,4-tetrafluoropentacene exhibits ambipolar charge-transport behavior depending on the electrode material used. [29] The Bettinger group obtained 2,3,9,10-tetrafluoropentacene either by thermal removal of a6 ,13-etheno bridge using a1 ,2,4,5-tetrazine derivative, [31] or by Strating-Zwanenburg reaction, [32] the photoinduced bis-decarbonylation of the 6,13-bridged a-diketone (Scheme 1b). [33] The photochemical conversionsu sually give highery ields, [34] but losses of substance due to the additional two steps for preparation of the a-diketones have to be taken into account when comparing both methods.…”

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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Section: Synthesismentioning

confidence: 83%

Section: Synthesismentioning

confidence: 99%

Section: Molecular Electrochemistrymentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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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An Angular Coumarinacene and Its Characteristics

Kumar

Venkatakrishnan

2021

Asian J Org Chem

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This paper describes the synthesis of an angular coumarinacene. Its molecular structure by single-crystal Xray analysis is revealed for the first time, which noted a sandwich-dimeric herringbone arrangement. Its solution reveals visible absorption and bright yellow-orange emission. The pyranone-annulated angular coumarinacene is relatively stable, both thermally and photochemically, when compared to popular acenes. Its alignment of frontier orbital energy levels dictates its possible entry into electronics.Coumarins are widely present in nature. [1] Studies on coumarins have shown enormous potential in biochemical and pharmaceutical regimes; for example, as antidepressants, [2] antimicrobials, [3] antivirals, [4] anticancer, [5] antioxidants, [6] antiinflammatory agents, [7] antitumors [8] and anticoagulants. [9] Besides, these benzo-α-pyranones reveal strong absorption, [10] high fluorescence quantum yields, [11] and excellent photostability. [12] Hence, they act as popular laser dyes, [13] optical brighteners, [14] luminescent materials, [15] and fluorescent probes. [16] As proven bio-friendly, coumarins serve as food additives, [17] flavoring substances, and cosmetic agents. [17,18] Due to these beneficial properties, synthetic interest in coumarins has been growing consistently. Organic chemists devote considerable time and effort in developing novel synthetic methods and approaches to expand coumarin's horizon (Figure 1a). [19] However, the structural elaboration beyond benzo-annulated coumarins have been limited. With the increasing demand for polycyclic aromatic hydrocarbons (PAHs) in organic electronics and photonics, [20] Gryko et al. have developed several vertically π-expanded mono-or bis-coumarins with an aim to improve the optical properties. [19] They demonstrated the use of biscoumarins as organic semiconductors for photocatalytic oxygen reduction reactions. [21] Moorthy et al. constructed small to large helical coumarins, and derived photochromic pyrans [22] as well as chirooptical materials from them. [23] The rich chemistry of coumarins have further paved their entry into various other fields as well. Thus, functionally modified coumarin derivatives have shown promise as watersoluble dyes in bioimaging, [24] emissive materials in organic light-emitting diodes (OLEDs), [25] and strongly absorbing dyes in dye-sensitized solar cells (DSSCs). [26]

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Unilateral fluorierte Acene: Synthese und Festkörpereigenschaften

et al. 2020

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Die rasche Entwicklung der organischen Elektronik hängt eng mit der Verfügbarkeit molekularer Materialien mit spezifischen elektronischen Eigenschaften zusammen. Hier stellen wir einen neuen Syntheseweg vor, der eine unilaterale Funktionalisierung von Acenen entlang ihrer langen Seite ermöglicht. Dies wird durch die Synthese von 1,2,10,11,12,14‐Hexafluorpentacen (1) und dem verwandten 1,2,9,10,11‐Pentafluortetracen (2) demonstriert. Quantenchemische DFT‐Rechnungen in Kombination mit optischen und röntgenabsorptionsspektroskopischen Daten zeigen, dass die einzelnen molekularen Eigenschaften von 1 ein Bindeglied zwischen den organischen Halbleitermodellsystemen Pentacen (PEN) und Perfluorpentacen (PFP) darstellen. Im Gegensatz dazu zeigt die Kristallstrukturanalyse ein anderes Packungsmotiv als für diese beiden Referenzmoleküle, was mit unterschiedlichen F⋅⋅⋅H‐Wechselwirkungen in Verbindung gebracht werden kann, die in einer Hirshfeld‐Oberflächenanalyse identifiziert wurden und auch Festkörpereigenschaften wie die Exzitonenbindungsenergie und die Sublimationsenthalpie beeinflussen.

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The synthesis and ambipolar charge transport properties of 1,2,3,4-tetrafluoropentacene

Cited by 13 publications

References 16 publications

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

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

An Angular Coumarinacene and Its Characteristics

Unilateral fluorierte Acene: Synthese und Festkörpereigenschaften

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