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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.
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.
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.
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Bailey,Madoff
, p. 5603 (1953)
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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.
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
Fast and inexpensive synthesis of pentacene with high yield using 6,13-pentacenequinone as precursor
Mota, María L.,Rodriguez, Bibiana,Carrillo, Amanda,Ambrosio, Roberto C.,Luque, Priscy A.,Mireles, Marcela,Vivaldo, Israel,Quevedo, Manuel A.
, p. 511 - 515 (2018)
Pentacene is an important semiconductor in the field of organic electronics. In this work is presented an alternative synthesis procedure to obtain pentacene from 6,13-pentacenequinone as a precursor. Synthesis of pentacene was performed in two reactions, Diels-Adler cycloaddition of 6,13-pentacenequinone followed by 6,13-pentacenequinone reduction to pentacene, employing LiAlH4 as reducing agent. The products were characterized by Fourier Transform Infrared Spectroscopy (FTIR), 1H-Nuclear Magnetic Resonance Spectroscopy (1H-NMR), X-Ray Diffraction (XRD), Thermogravimetric Analysis (TGA) and Ultraviolet–Visible Spectroscopy (UV-VIS). In this work, 6,13-pentacenequinone was synthetized with a high yield (55%) using an alternative method. The optimization process resulted in an overall reduction of reaction time while exhibiting high yield. The method presented here provides an affordable pentacene synthesis route with high purity, which can be further applied for research and development of organic electronic applications.
Photo precursor for pentacene
Uno, Hidemitsu,Yamashita, Yuko,Kikuchi, Makoto,Watanabe, Hikaru,Yamada, Hiroko,Okujima, Tetsuo,Ogawa, Takuji,Ono, Noboru
, p. 1981 - 1983 (2005)
6,13-Dihydro-6,13-ethanopentacene-15,16-dione gave pentacene efficiently both in solid and in solution by irradiation of light.
Thermal generation of pentacene from soluble precursors through expulsion of carbon dioxide
Huang, Hsin-Hui,Hsieh, Hsing-Hung,Wu, Chung-Chih,Lin, Chao-Chen,Chou, Pi-Tai,Chuang, Ta-Hsien,Wen, Yuh-Sheng,Chow, Tahsin J.
, p. 4494 - 4497 (2008)
Highly soluble pentacene precursors possessing ketal bridges across the rings were synthesized. Pure pentacene was produced through thermal dissociation, while carbon dioxide and ethylene were extruded as volatile fragments. Thin solid film of pentacene c
Alpha-diimine ligand compound, complex and preparation method of polyolefin lubricating oil base oil
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Paragraph 0155-0158, (2020/07/24)
The present invention provides an alpha-diimine ligand compound having a structure represented by a formula (I), and further provides an alpha-diimine complex obtained from the ligand compound. In addition, the invention also provides a preparation method of polyolefin lubricating oil base oil taking the alpha-diimine complex as a catalyst and the prepared lubricant base oil. According to the ligand compound and the complex provided by the invention, a large steric hindrance group is introduced into a ligand skeleton, and the skeleton rigidity is increased, so that the chain walking capabilityof the complex as a catalyst is improved. The polyolefin lubricating oil base oil provided by the invention has high long-chain branch content and branching degree, can be used as medium-high viscosity lubricating oil base oil, simplifies the production process, reduces the production cost, is very suitable for industrial-scale production, and has excellent economic and social benefits.
