6,13-双(2-噻吩基)并五苯 | 849466-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 并五苯
• 中文名称: 6,13-双(2-噻吩基)并五苯
• 英文名称: 6,13-di(thiophen-2-yl)pentacene
• 英文别名: 6,13-di(2'-thienyl)pentacene；6,13-di(2-thienyl)-pentacene；6,13-dithien-2-ylpentacene；2-(13-thien-2-ylpentacene-6-yl)thiophene；6,13-Bis(2-thienyl)pentacene；2-(13-thiophen-2-ylpentacen-6-yl)thiophene
• CAS: 849466-79-1
• 化学式: C₃₀H₁₈S₂
• 分子量: 442.605
• InChiKey: UFJVWUVXQAZPRV-UHFFFAOYSA-N

物化性质

• 熔点：
  300-305 °C
• 沸点：
  615.0±50.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,13-双(2-噻吩基)并五苯 在 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到
  参考文献：
  名称：

  芳基取代的并五苯衍生物的光氧化和复制

  摘要：

  制备了在6,13位被芳基取代的并五苯衍生物，并研究了它们的电子性质以及与氧的光加成反应。被2-噻吩基和苯基取代的并五苯衍生物在光照下与溶液中的氧反应，得到其内过氧化物。这些一阶动力学常数经评估为1.5×10 -3  s -1和2.7×10 -3  s -1。具有五氟苯基的并五苯衍生物在溶液中相对稳定。具有2-噻吩基的内过氧化物的热解和光解在溶液中得到并五苯衍生物，其产率分别为30％和44％。另外，研究了内过氧化物薄膜的紫外线照射（254 nm），这表明并五苯衍生物的复制。

  DOI：

  10.1016/j.tet.2007.07.021
• 作为产物：
  描述：

  6,13-di(2-thienyl)-6,13-pentacenediol 在 sodium hypophosphite 、 溶剂黄146 、 sodium iodide 作用下， 反应 1.0h， 以87%的产率得到6,13-双(2-噻吩基)并五苯
  参考文献：
  名称：

  Reduction versus Rearrangement of 6,13-Dihydro-6,13-diarylpentacene-6,13-diols Affording 6,13- and 13,13′-Substituted Pentacene Derivatives

  摘要：

  并五苯具有优异的半导电特性，但在有机薄膜晶体管（OTFT）中的实际应用引发了诸多问题，主要由其对氧气的敏感性和极低的溶解度所致。为了解决使用并五苯所涉及的问题，在6位和13位引入了不同的芳基取代基。对于富电子芳基取代基，并五苯环系的形成可能伴随着起始的二氢并五苯二醇重排为13,13′-二取代的并五苯-6-酮。此外，还制备了6-单取代的并五苯。

  DOI：

  10.1055/s-2004-836055

文献信息

• Reduction versus Rearrangement of 6,13-Dihydro-6,13-diarylpentacene-6,13-diols Affording 6,13- and 13,13′-Substituted Pentacene Derivatives
  作者：Wim Dehaen、Nathalie Vets、Mario Smet

  DOI：10.1055/s-2004-836055

  日期：——

  Pentacene has excellent semi-conducting properties but its practical use in organic thin film transistors (OTFTs) gives rise to a lot of problems caused by its sensitivity to oxygen and its very low solubility. In order to solve the problems involved in the use of pentacene, different aryl substituents were introduced on the 6- and 13-positions. Formation of the pentacene ring system may be accompanied by the rearrangement of the starting dihydropentacenediol to a 13,13′-disubstituted pentacen-6-one for electron-rich aryl substituents. 6-Monosubstituted pentacenes were also prepared.

  并五苯具有优异的半导电特性，但在有机薄膜晶体管（OTFT）中的实际应用引发了诸多问题，主要由其对氧气的敏感性和极低的溶解度所致。为了解决使用并五苯所涉及的问题，在6位和13位引入了不同的芳基取代基。对于富电子芳基取代基，并五苯环系的形成可能伴随着起始的二氢并五苯二醇重排为13,13′-二取代的并五苯-6-酮。此外，还制备了6-单取代的并五苯。
• 6,13-Bis(thienyl)pentacene compounds
  申请人：Vogel E. Dennis

  公开号：US20070023748A1

  公开（公告）日：2007-02-01

  6,13-bis(thienyl)pentacene compounds are described that can be used as a semiconductor material. Semiconductor devices that contain the 6,13-bis(thienyl)pentacene compounds and methods of making such semiconductor devices are also described.

  描述了可以用作半导体材料的6,13-双(噻吩基)蒽化合物。还描述了含有6,13-双(噻吩基)蒽化合物的半导体器件以及制造这种半导体器件的方法。
• Application of Zirconacyclopentadienes (Metalla-heterocycles) and Cross-Coupling for the Convenient Preparative Method of 6,13-Disubstituted Pentacene
  作者：Tamotsu Takahashi、Zhiying Jia、Shi Li、Kiyohiko Nakajima、Ken-ichiro Kanno、Zhiyi Song

  DOI：10.3987/com-12-s(n)130

  日期：——

  Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.
• New Oligothiophene-Pentacene Hybrids as Highly Stable and Soluble Organic Semiconductors
  作者：Jing Wang、Ke Liu、Yi-Yang Liu、Cheng-Li Song、Zi-Fa Shi、Jun-Biao Peng、Hao-Li Zhang、Xiao-Ping Cao

  DOI：10.1021/ol900838a

  日期：2009.6.18

  Two series of new oligothiophene-pentacene hybrid compounds were successfully synthesized and characterized, which consist of pentacene and anthradithiophene skeletons modified by different oligothienyl groups at 6,13 sites or 5,11 sites, respectively. Their optical, thermal, and electrochemical properties show regular variations with the length change of the side groups. These materials exhibit much higher solubility and significantly improved thermal and photooxidation stabilities compared with unmodified pentacene and anthradithiophene.
• Organization of Acenes with a Cruciform Assembly Motif
  作者：Qian Miao、Xiaoliu Chi、Shengxiong Xiao、Roswitha Zeis、Michael Lefenfeld、Theo Siegrist、Michael L. Steigerwald、Colin Nuckolls

  DOI：10.1021/ja0570786

  日期：2006.2.1

  This study explores the assembly in the crystalline state of a class of pentacenes that are substituted along their long edges with aromatic rings forming rigid, cruciform molecules. The crystals were grown from the gas phase, and their structures were compared with DFT-optimized geometries. Both crystallographic and computed structures show that a planar acene core is the exception rather than the rule. In the assembly of these molecules, the phenyl groups block the herringbone motif and further guide the arrangement of the acene core into higher order structures. The packing for the phenyl-substituted derivatives is dictated by close contacts between the C-H's of the pendant aromatic rings and the carbons at the fusions in the acene backbone. Using thiciphene substituents instead of phenyls creates cofacially stacked acenes. In thin films, the thiophene-substituted derivative forms devices with good electrical properties: relatively high mobility, high ON/OFF ratios, and low threshold voltage for device activation. An unusual result is obtained for the decaphenyl pentacene when devices are fabricated on its crystalline surface. Although its acene cores are well isolated from each other, this material still exhibits good electrical properties.