6,13-Bis-(phenylethinyl)-pentacen | 18826-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 并五苯
• 英文名称: 6,13-Bis-(phenylethinyl)-pentacen
• 英文别名: 6,13-bis(phenylethynyl)pentacene；6,13-bis(2-phenylethynyl)pentacene
• CAS: 18826-31-8
• 化学式: C₃₈H₂₂
• 分子量: 478.593
• InChiKey: YAPRWYONBPARJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6,13-Bis-(phenylethinyl)-pentacen 在 双氧水 、 molybdenum(VI) ion 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  镍（II）双卟啉融合的戊环具有异常高的稳定性。

  摘要：

  合成并表征了一系列主要由π扩展的多发色分子，包括交叉共轭，半交叉共轭，共轭间断和线性共轭体系。这些多发色分子系统揭示了有趣的结构-性质关系。双卟啉融合的并五苯戊烯Pen-1b和Pen- 2a显示出丰富的氧化还原化学，分别具有7和8个可观察到的氧化还原状态。线性共轭双卟啉融合并戊烯（Pen-1b和Pen- 2a）与并五苯类似物（分别为2.23和2.01 eV氧化还原）相比，具有更窄的HOMO-LUMO间隙（分别为1.65和1.42 eV氧化还原）和更高的HOMO能级，这与不稳定的十六碳烯和庚二烯类似。双卟啉融合的并五苯Pen-2 a的估计半衰期> 945小时，比其并五苯类似物的半衰期更长（BPE-P，半衰期33 h）。

  DOI：

  10.1002/anie.202008076
• 作为产物：
  描述：

  6,13-Bis-phenylethynyl-6,13-dihydro-pentacene-6,13-diol 在 tin(ll) chloride 作用下， 生成 6,13-Bis-(phenylethinyl)-pentacen
  参考文献：
  名称：

  Novel soluble pentacene and anthradithiophene derivatives for organic thin-film transistors

  摘要：

  Four new solution-processable pentacene- (PEN) and anthradithiophene- (ADT) based organic semiconductors bearing two phenylethynyl (PE-) or triethylsilylphenylethynyl (TESPE-) substituents have been synthesized, characterized, and incorporated in thin-film transistors (TFTs). The molecular structures of these four materials have been determined by single-crystal X-ray diffraction. Thin films of all four compounds have been fabricated via drop-casting and exhibited p-channel OTFT transport with hole mobilities as high as similar to 0.01 cm(2)/V s. Compared to PEN derivatives, ADT-based compounds exhibited superior device performance and photooxidative stability in ambient. The film morphologies and microstructures of these compounds have been characterized by optical microscopy and X-ray diffraction to rationalize device performance trends. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.04.029

文献信息

• Highly Active Palladium Catalyst for the Sonogashira Coupling Reaction of Unreactive Aryl Chlorides
  作者：Dong-Hwan Lee、Young-Jun Kwon、Myung-Jong Jin

  DOI：10.1002/adsc.201100747

  日期：2011.11

  communication reports on the β-diketiminatophosphane palladium-catalyzed copper-free Sonogashira coupling of aryl chlorides with alkynes. A catalyst loading of 0.5 mol% is sufficient to achieve high performance under relatively mild reaction conditions. Furthermore, dialkynylbenzenes are efficiently prepared by one-pot double Sonogashira couplings of aryl dichlorides.

  该通讯报道了β-二酮亚氨基膦烷钯钯催化的芳基氯化物与炔烃的无铜Sonogashira偶联。0.5mol％的催化剂负载量足以在相对温和的反应条件下实现高性能。此外，通过一锅二芳基二氯化物的双Sonogashira偶联有效地制备二炔基苯。
• Structure, photophysics, and photooxidation of crowded diethynyltetracenes
  作者：Jingjing Zhang、Syena Sarrafpour、Terry E. Haas、Peter Müller、Samuel W. Thomas

  DOI：10.1039/c2jm16173g

  日期：——

  This paper describes a previously unreported class of sterically crowded tetracene derivatives that have both phenyl and ethynyl substituents. The steric crowding above and below the tetracene core prevents overlap between the extended π-systems of the acenes. Substituent effects cause these tetra-substituted tetracenes to have absorbance and fluorescence spectra red shifted from either disubstituted derivatives or rubrenes, such that they have spectra similar to diarylpentacenes, but with higher quantum yields of fluorescence and greater photostability. These new molecules also undergo cycloaddition reactions with 1O2, giving regioisomeric mixtures of endoperoxides, and in contrast to longer acenes, the ethynyl substituents show only a modest stabilizing effect to photooxidation. Ethynylated tetracenes also exhibited photochromism, with their endoperoxides undergoing cycloreversion to yield the acene starting material at room temperature in the dark.

  本文描述了一类先前未报道的空间拥挤并四苯衍生物，它们同时具有苯基和乙炔基取代基。并四苯核心上方和下方的空间拥挤防止了并苯的扩展 π 系统之间的重叠。取代效应导致这些四取代并四苯的吸光度和荧光光谱从二取代衍生物或红荧烯红移，使得它们具有与二芳基并五苯相似的光谱，但具有更高的荧光量子产率和更高的光稳定性。这些新分子还与 1O2 发生环加成反应，产生内过氧化物的区域异构混合物，并且与较长的并苯相比，乙炔基取代基仅对光氧化表现出适度的稳定作用。乙炔化并四苯也表现出光致变色性，其内过氧化物在室温下在黑暗中发生环化反应以产生并苯起始材料。
• Electronic absorption and fluorescence of phenylethynyl-substituted acenes
  作者：D. R. Maulding、Bernard G. Roberts

  DOI：10.1021/jo01258a045

  日期：1969.6