bispentacenequinone | 1213766-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: bispentacenequinone
• 英文别名: 13-(13-Oxopentacen-6-ylidene)pentacen-6-one；13-(13-oxopentacen-6-ylidene)pentacen-6-one
• CAS: 1213766-58-5
• 化学式: C₄₄H₂₄O₂
• 分子量: 584.673
• InChiKey: RLTYCXUPMBCXKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  46
• 可旋转键数：
  0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bispentacenequinone 在 碘 、 methyloxirane 作用下， 以 苯 为溶剂， 反应 48.0h， 以59%的产率得到Dodecacyclo[21.19.1.12,14.03,12.04,41.05,10.016,21.024,29.031,43.033,42.035,40.022,44]tetratetraconta-1(42),2,4(41),5,7,9,11,14,16,18,20,22(44),23(43),24,26,28,30,33,35,37,39-henicosaene-13,32-dione
  参考文献：
  名称：

  Fused Bispentacenequinone and Its Unexpected Michael Addition

  摘要：

  Fused bispentacenequinone 2 was synthesized by photocyclization of bispentacenequinone 1. Unusual regioselective Michael addition was observed for 2 when excess aryl Grignard reagent was used. Subsequent acidification and oxidation in air gave diaryl-substituted bispentacenequinone 3. Tetra-aryl-substituted fused bispentacenequinone 4 was obtained from 3 after the second Michael addition followed by oxidation in air.

  DOI：

  10.1021/ol101720e
• 作为产物：
  描述：

  6,13-dihydropentacen-6-one 在 哌啶 、 吡啶 、 吡啶-N-氧化物 、 ferrous(II) sulfate heptahydrate 作用下， 反应 5.0h， 生成 bispentacenequinone
  参考文献：
  名称：

  十字形6,6'-二戊烯基：合成，固态包装及其在薄膜晶体管中的应用

  摘要：

  交叉！制备了一个十字形的6,6'-双戊烯基Dip-TIPS，作为一种独特的半导体，在晶体结构中具有二维各向同性的面对面π堆积。从气相沉积薄膜可以获得高FET迁移率。在有机半导体设计中使用十字形分子是一个新概念，有望减少分子取向对器件性能的影响。

  DOI：

  10.1002/chem.200902675

文献信息

• A soluble bispentacenequinone precursor for creation of directly 6,6′-linked bispentacenes and a tetracyanobipentacenequinodimethane
  作者：Kazuki Tanaka、Naoki Aratani、Daiki Kuzuhara、Sadaaki Sakamoto、Tetsuo Okujima、Noboru Ono、Hidemitsu Uno、Hiroko Yamada

  DOI：10.1039/c3ra41914b

  日期：——

  We have synthesized 13,13′-(3,5-bis(trifluoromethyl)phenyl)-6,6′-bipentacene from a soluble bispentacenequinone precursor. Bispentacene takes orthogonal conformation in the solid state and exhibits four reversible redox potentials. In addition, a tetracyanobipentacenequinodimethane was obtained for the first time from the pure bispentacenequinone.

  我们从可溶性双并五苯醌前体合成了 13,13â²-(3,5-双(三氟甲基)苯基)-6,6â²-双并五苯。双并五苯在固态下具有正交构象，并表现出四种可逆的氧化还原电位。此外，还首次从纯双并五苯醌中获得了四氰基双并五苯醌二甲烷。
• Supersized contorted aromatics
  作者：Shengxiong Xiao、Seok Ju Kang、Ying Wu、Seokhoon Ahn、Jong Bok Kim、Yueh-Lin Loo、Theo Siegrist、Michael L. Steigerwald、Hexing Li、Colin Nuckolls

  DOI：10.1039/c3sc50374g

  日期：——

  We describe here the synthesis and electronic device properties of a new type of polycyclic aromatic molecule, the contorted octabenzocircumbiphenyl (c-OBCB). Contorted polycyclic aromatic hydrocarbons (PAHs) are promising small active molecules for organic devices. We present two different methods to synthesize c-OBCB derivatives that allow the smooth incorporation of functional groups. The material has a highly contorted exterior with six 4-helicenes and two 5-helicenes around the exterior of the expanded core of the aromatic. With appropriate sidechains, the material is soluble in common organic solvents and forms thin films. In thin films, the tetradodecyloxy-substituted c-OBCB self-assembles to form the active layer in organic field effect transistors. It is a hole transporting organic semiconductor. In the transistors, the c-OBCB forms good contact with source and drain contacts made from graphene. The c-OBCB self-assembles into a heterojunction from solution with phenyl-C70-butyric acid methyl ester (PC70BM). We observed power conversion efficiencies of ∼2.9 % under 100 mW cm−2 illumination at a 1 : 4 weight ratio of the c-OBCB relative to PC70BM. The c-OBCB is shape complementary to the ball shaped PC70BM.

  我们在此描述了一种新型多环芳烃分子——扭曲八苯并环辛二烯（c-OBCB）的合成和电子器件特性。扭曲多环芳烃（PAHs）是有机器件中很有前景的小分子活性分子。我们提出了两种不同的c-OBCB衍生物合成方法，能够顺利地引入官能团。这种材料具有高度扭曲的外部结构，在芳香族膨胀核心的外部有六个4-螺旋烯和两个5-螺旋烯。在适当的侧链作用下，这种材料可溶于常见的有机溶剂并形成薄膜。在薄膜中，四十二烷氧基取代的c-OBCB可自组装形成有机场效应晶体管中的活性层。这是一种空穴传输有机半导体。在晶体管中，c-OBCB与石墨烯制成的源极和漏极接触良好。c-OBCB与苯基-C70-丁酸甲酯（PC70BM）在溶液中自组装成异质结。在100 mW cm-2光照下，c-OBCB与PC70BM的重量比为1：4时，我们观察到的功率转换效率约为2.9%。c-OBCB的形状与球形的PC70BM互补。
• A Cruciform 6,6′-Dipentacenyl: Synthesis, Solid-State Packing and Applications in Thin-Film Transistors
  作者：Xiaojie Zhang、Xiaoxia Jiang、Jing Luo、Chunyan Chi、Hongzheng Chen、Jishan Wu

  DOI：10.1002/chem.200902675

  日期：2010.1.11

  Get cross! A cruciform 6,6′‐dipentacenyl, Dip‐TIPS, was prepared as a unique semiconductor with two‐dimensional isotropic face‐to‐face π‐stacking in the crystal structure. High FET mobilities were obtained from the vapor‐deposited thin films. The use of cruciform molecules in the design of organic semiconductors is a new concept that is expected to diminish the effect of molecular orientation on device

  交叉！制备了一个十字形的6,6'-双戊烯基Dip-TIPS，作为一种独特的半导体，在晶体结构中具有二维各向同性的面对面π堆积。从气相沉积薄膜可以获得高FET迁移率。在有机半导体设计中使用十字形分子是一个新概念，有望减少分子取向对器件性能的影响。
• Fused Bispentacenequinone and Its Unexpected Michael Addition
  作者：Xiaojie Zhang、Jinling Li、Hemi Qu、Chunyan Chi、Jishan Wu

  DOI：10.1021/ol101720e

  日期：2010.9.3

  Fused bispentacenequinone 2 was synthesized by photocyclization of bispentacenequinone 1. Unusual regioselective Michael addition was observed for 2 when excess aryl Grignard reagent was used. Subsequent acidification and oxidation in air gave diaryl-substituted bispentacenequinone 3. Tetra-aryl-substituted fused bispentacenequinone 4 was obtained from 3 after the second Michael addition followed by oxidation in air.