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135-48-8Relevant articles and documents
Photochemical synthesis of pentacene and its derivatives
Yamada, Hiroko,Yamashita, Yuko,Kikuchi, Makoto,Watanabe, Hikaru,Okujima, Tetsuo,Uno, Hidemitsu,Ogawa, Takuji,Ohara, Keishi,Ono, Noboru
, p. 6212 - 6220 (2005)
A novel α-diketone precursor of pentacene, 6,13-dihydro-6,13- ethanopentacene-15, 16-dione, was prepared and converted successfully to pentacene in 74% yield by photolysis of the precursor in toluene: Irradiation of the diketone solution in toluene with light of 460 nm under an Ar atmosphere caused the solution to change from yellow to fluorescent orange-pink within a few minutes, after which, purple precipitates appeared. After 35 min, the solution changed to colorless and the purple precipitates were filtered to give pentacene in 74% yield. By contrast, in the presence of oxygen, the color of the solution changed from yellow to pale yellow, and only 6,13-endoperoxide of pentacene was quantitatively obtained. The rate of the reaction upon photolysis was measured by observing the decay of n-π* absorption of the precursor at 460 nm, and was found to be similar in both the presence and absence of oxygen. Therefore, the photoreaction of the α-diketone precursor seemed to occur via the singlet excited state. Because the T-T absorption of pentacene was observed upon photolysis of the precursor in the nanosecond transient absorption measurement under an Ar atmosphere, the excited triplet state of the pentacene generated singlet oxygen by sensitization, and it reacted with the ground-state pentacene to give the 6,13-endoperoxide. The α-diketone deposited on glass was also converted successfully to pentacene film by photoirradiation. In addition, diketone precursors of a mixture of 2,8- and 2,9-dibromopentacene and 2,6-trianthrylene were also prepared and their photocon-version was performed.
Synthesis, structure, and photochemistry of 5,14-diketopentacene
Aotake, Tatsuya,Ikeda, Shinya,Kuzuhara, Daiki,Mori, Shigeki,Okujima, Tetsuo,Uno, Hidemitsu,Yamada, Hiroko
, p. 1723 - 1729 (2012)
5,14-α-Diketopentacene, a structural isomer of 6,13-α- diketopentacene, was prepared from pentacene in three steps. In addition to the typical n-π* absorption of the diketone moiety at around 468 nm and the anthracene-like absorption at 333, 349, and 367 nm, a broad absorption was observed at around 386 nm, which could be assigned to an intramolecular charge-transfer absorption from anthracene to the diketone moiety. 5,14-α-Diketopentacene could be converted into pentacene quantitatively by photoirradiation at 405 and 468 nm in toluene with quantum yields of 2.3 and 2.4%, respectively, and these values are higher than the quantum yield of 1.4% obtained for 6,13-α-diketopentacene irradiated at 468 nm. The quantum yields in acetonitrile were lowered to 0.33 and 0.28% with irradiation at 405 and 468 nm. The crystal structure of 5,14-α-diketopentacene showed a CH-π interaction and π-π stacking between neighbouring anthracene and benzene moieties. The lower solubility of 5,14-α-diketopentacene compared with the 6,13-isomer could be explained by this crystal structure.
Pentacene precursors for solution-processed OFETs
Uoyama, Hiroki,Yamada, Hiroko,Okujima, Tetsuo,Uno, Hidemitsu
, p. 6889 - 6894 (2010)
15-Acetoxy- and 15-hydroxy-6,13-dihydro-6,13-ethanopentacenes sublimed over 300 °C and no pentacene was formed below the temperature. The precursors bearing chlorinated epithiomethano bridges suffered complicated decomposition to give oligomeric pentacene derivatives. The precursor bearing an epithio-oxomethano bridge underwent smooth and clean conversion to pentacene by heat or light. An organic field-effect transistor fabricated by the spin-coating method of the precursor followed by light irradiation at 120 °C showed a good FET performance of μ=2.5×10-2 cm2 V -1 s-1 and on/off ratio=3.8×104.
A new type of soluble pentacene precursor for organic thin-film transistors
Chen, Kew-Yu,Hsieh, Hsing-Hung,Wu, Chung-Chih,Hwang, Jiunn-Jye,Chow, Tahsin J.
, p. 1065 - 1067 (2007)
A new type of soluble pentacene precursor is synthesized, which extrudes a unit of CO upon heating at 150°C, to produce pentacene in nearly quantitative yield. The Royal Society of Chemistry.
Linear Acene Derivatives. New Routes to Pentacene and Naphthacene and the First Synthesis of a Triptycene with Two Anthracene Moieties
Luo, Jihmei,Hart, Harold
, p. 4833 - 4836 (1987)
The cycloaddition of o-xylylene to arene 1,4-endoxides was used to construct linear arene derivatives.For example, heating benzocyclobutene 4 with anthracene 1,4-endoxide (10) followed by dehydration and dehydrogenation gave pentacene in three steps and 64percent overall yield.An analogous sequence but with naphthalene 1,4-endoxides gave naphthacenes.Dehydration of the di adducts from 4 and anthracene 1,4:5,8-diendoxides (5) gave a mixture of 5,9,14,18- and 5,8,15,18-tetrahydroheptacenes 3 and 9.The previously unknown triptycene 2 was synthesized from 5,14-dihydropentacene (12), an intermediate in the new pentacene synthesis, in three steps and 29percent overall yield.
Synthesis, stability, and photochemistry of pentacene, hexacene, and heptacene: A matrix isolation study
Mondal, Rajib,Toenshoff, Christina,Khon, Dmitriy,Neckers, Douglas C.,Bettinger, Holger F.
, p. 14281 - 14289 (2009)
The photochemical bisdecarbonylation of bridged α-diketones (Strating-Zwanenburg reaction) to give the oligoacenes pentacene (2), hexacene (3), and heptacene (4) is investigated in solid inert gas matrices at cryogenic temperatures. The photodecomposition
An improved synthesis of pentacene: Rapid access to a benchmark organic semiconductor
Pramanik, Chandrani,Miller, Glen P.
, p. 4625 - 4633 (2012)
Pentacene is an organic semiconductor used in a variety of thin-film organic electronic devices. Although at least six separate syntheses of pentacene are known (two from dihydropentacenes, two from 6,13-pentacenedione and two from 6,13-dihydro-6,13-dihydroxypentacene), none is ideal and several utilize elevated temperatures that may facilitate the oxidation of pentacene as it is produced. Here, we present a fast (~2 min of reaction time), simple, high-yielding (≥90%), low temperature synthesis of pentacene from readily available 6,13-dihydro-6,13-dihydroxypentacene. Further, we discuss the mechanism of this highly efficient reaction. With this improved synthesis, researchers gain rapid, affordable access to high purity pentacene in excellent yield and without the need for a time consuming sublimation.
A Large Starphene Comprising Pentacene Branches
Holec, Jan,Cogliati, Beatrice,Lawrence, James,Berdonces-Layunta, Alejandro,Herrero, Pablo,Nagata, Yuuya,Banasiewicz, Marzena,Kozankiewicz, Boleslaw,Corso, Martina,de Oteyza, Dimas G.,Jancarik, Andrej,Gourdon, Andre
, p. 7752 - 7758 (2021)
Starphenes are attractive compounds due to their characteristic physicochemical properties that are inherited from acenes, making them interesting compounds for organic electronics and optics. However, the instability and low solubility of larger starphene homologs make their synthesis extremely challenging. Herein, we present a new strategy leading to pristine [16]starphene in preparative scale. Our approach is based on a synthesis of a carbonyl-protected starphene precursor that is thermally converted in a solid-state form to the neat [16]starphene, which is then characterised with a variety of analytical methods, such as 13C CP-MAS NMR, TGA, MS MALDI, UV/Vis and FTIR spectroscopy. Furthermore, high-resolution STM experiments unambiguously confirm its expected structure and reveal a moderate electronic delocalisation between the pentacene arms. Nucleus-independent chemical shifts NICS(1) are also calculated to survey its aromatic character.
Photogeneration and thermal generation of pentacene from soluble precursors for OTFT applications
Chuang, Ta-Hsien,Hsieh, Hsing-Hung,Chen, Chang-Ken,Wu, Chung-Chih,Lin, Chao-Chen,Chou, Pi-Tai,Chao, Ting-Han,Chow, Tahsin J.
, p. 2869 - 2872 (2008)
(Graph Presented) A CO adduct of pentacene with an unsymmetrical structure is synthesized; it is soluble and can be spin-coated into thin films. Pentacene is regenerated in near quantitative yield by either thermal or photoinduced elimination of CO. OTFT devices fabricated by this compound exhibit typical FET characteristics.
Analysis of molecular aggregation states in pentacene thin films prepared from soluble precursor
Akinaga, Takahiro,Yasutake, Shigekazu,Sasaki, Sono,Sakata, Osami,Otsuka, Hideyuki,Takahara, Atsushi
, p. 1162 - 1163 (2006)
Molecular packing structure in pentacene films prepared from the Afzali's precursor soluble in general organic solvents was characterized by in-plane grazing-incidence X-ray diffraction (GIXD) measurements. The crystallographic ab plane of pentacene was parallel to the surface of a Si substrate. Crystal structure of pentacene near the substrate was identified as the thin-film phase. Copyright
