tetraethyl ((((perchlorophenyl)methylene)bis(2,3,5,6-tetrachloro-4,1-phenylene))-bis(methylene))bis(phosphonate) | 1258329-48-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tetraethyl ((((perchlorophenyl)methylene)bis(2,3,5,6-tetrachloro-4,1-phenylene))-bis(methylene))bis(phosphonate)
• 英文别名: [bis(4-diethylphosphonomethyl-2,3,5,6-tetrachlorophenyl)-(2,3,4,5,6-pentachlorophenyl)]methane；1,2,4,5-Tetrachloro-3-[[diethoxy(oxido)phosphaniumyl]methyl]-6-[(2,3,4,5,6-pentachlorophenyl)-[2,3,5,6-tetrachloro-4-[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]methyl]benzene；1,2,4,5-tetrachloro-3-[[diethoxy(oxido)phosphaniumyl]methyl]-6-[(2,3,4,5,6-pentachlorophenyl)-[2,3,5,6-tetrachloro-4-[[diethoxy(oxido)phosphaniumyl]methyl]phenyl]methyl]benzene
• CAS: 1258329-48-4
• 化学式: C₂₉H₂₅Cl₁₃O₆P₂
• 分子量: 992.35
• InChiKey: WIBDWSHTOMRHDB-UHFFFAOYSA-N

物化性质

• 沸点：
  825.8±65.0 °C(Predicted)
• 密度：
  1.584±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetraethyl ((((perchlorophenyl)methylene)bis(2,3,5,6-tetrachloro-4,1-phenylene))-bis(methylene))bis(phosphonate) 、 4-乙炔基苯甲醛 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以83%的产率得到6,6'-((perchlorophenyl)methylene)bis(1,2,4,5-tetrachloro-3-((E)-4-ethynylstyryl)benzene)
  参考文献：
  名称：

  Robust Organic Radical Molecular Junctions Using Acetylene Terminated Groups for C–Au Bond Formation

  摘要：

  Organic paramagnetic and electroactive molecules are attracting interest as core components of molecular electronic and spintronic devices. Currently, further progress is hindered by the modest stability and reproducibility of the molecule/electrode contact. We report the synthesis of a persistent organic radical bearing one and two terminal alkyne groups to form Au-C sigma bonds. The formation and stability of self-assembled monolayers and the electron transport through single-molecule junctions at room temperature have been studied. The combined analysis of both systems demonstrates that this linker forms a robust covalent bond with gold and a better-defined contact when compared to traditional sulfur-based linkers. Density functional theory and quantum transport calculations support the experimental observation highlighting a reduced variability of conductance values for the C-Au based junction. Our findings advance the quest for robustness and reproducibility of devices based on electroactive molecules.

  DOI：

  10.1021/jacs.7b10019
• 作为产物：
  描述：

  4-甲基二苯甲酮 在 二氯化二硫 、 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 甲酸 、 磺酰氯 、 偶氮二异丁腈 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 67.0h， 生成 tetraethyl ((((perchlorophenyl)methylene)bis(2,3,5,6-tetrachloro-4,1-phenylene))-bis(methylene))bis(phosphonate)
  参考文献：
  名称：

  中性，低带隙，混合价多自由基的合成及电子转移特性

  摘要：

  通过Horner-Emmons反应合成了由交替的三芳基胺和全氯三苯基甲基自由基部分组成的多自由基。该化合物是第一种在NIR中显示间隔电荷转移（IV-CT）的聚合物中性混合价化合物。聚合物与参考单体的吸收光谱的比较表明，IV-CT跃迁仅限于一个重复单元。通过循环伏安法估计，HOMO和LUMO的水平相对于真空分别为-5.5和-4.5 eV。与光学带隙（1.2 eV）相比，显示出非常低的激子结合能。通过fs泵探针瞬态吸收光谱研究了溶液中聚合物的电子转移性质。在光激发之后，聚合物在ps时间范围内显示出双指数衰减。短暂的，溶剂依赖性的成分是指从IV-CT状态到基态的直接衰减，而长寿的，与溶剂无关的成分暂时归因于IV-CT状态的平衡形成和完全电荷分离状态。在有机场效应晶体管（OFET）器件的薄膜中研究了电荷传输特性。电子迁移率和空穴迁移率均约为3×10-5 cm 2 V -1 s -1，表明聚合物的双极性传输行为。

  DOI：

  10.1021/cm102650h

文献信息

• Pyrene-Based Dyad and Triad Leading to a Reversible Chemical and Redox Optical and Magnetic Switch
  作者：Carlos Franco、Marta Mas-Torrent、Antonio Caballero、Arturo Espinosa、Pedro Molina、Jaume Veciana、Concepció Rovira

  DOI：10.1002/chem.201405993

  日期：2015.3.27

  Two new pyrene–polychlorotriphenylmethyl (PTM) dyads and triads have been synthesized and characterized by optical, magnetic, and electrochemical methods. The interplay between the different electronic states of the PTM moiety in the dyads and triads and the optical and magnetic properties of the molecules have been studied. The electronic spectra of the radicals 5. and 6. show the intramolecular charge‐transfer

  已经合成了两种新的pyr-聚氯三苯甲基（PTM）二元组和三元组，并通过光学，磁性和电化学方法对其进行了表征。已经研究了二元组和三元组中PTM部分不同电子态之间的相互作用以及分子的光学和磁性。自由基的电子光谱5 。和6 。由于PTM自由基的受体特性，在约700 nm处分子内发生了电荷转移跃迁。在抗磁性质子化衍生物3和4中，由于the而保持荧光，而在自由基5中。和6 。和相应的阴离子5 -和6 -有荧光的明显淬火，其是在基团的情况下更有效。容易还原为相应碳负离子的PTM自由基的氧化还原活性已被用于制造具有光和磁响应的电化​​学开关。
• Synthesis and Electron Transfer Characteristics of a Neutral, Low-Band-Gap, Mixed-Valence Polyradical
  作者：Dörte Reitzenstein、Tatjana Quast、Florian Kanal、Martin Kullmann、Stefan Ruetzel、Maria S. Hammer、Carsten Deibel、Vladimir Dyakonov、Tobias Brixner、Christoph Lambert

  DOI：10.1021/cm102650h

  日期：2010.12.28

  respectively, as estimated by cyclic voltammetry. A very low exciton binding energy is indicated by comparison with the optical band gap (1.2 eV). The electron transfer properties of the polymer were investigated in solution by fs-pump−probe transient absorption spectroscopy. After optical excitation, the polymer shows a biexponential decay in the ps time regime. The short-living, solvent-dependent component

  通过Horner-Emmons反应合成了由交替的三芳基胺和全氯三苯基甲基自由基部分组成的多自由基。该化合物是第一种在NIR中显示间隔电荷转移（IV-CT）的聚合物中性混合价化合物。聚合物与参考单体的吸收光谱的比较表明，IV-CT跃迁仅限于一个重复单元。通过循环伏安法估计，HOMO和LUMO的水平相对于真空分别为-5.5和-4.5 eV。与光学带隙（1.2 eV）相比，显示出非常低的激子结合能。通过fs泵探针瞬态吸收光谱研究了溶液中聚合物的电子转移性质。在光激发之后，聚合物在ps时间范围内显示出双指数衰减。短暂的，溶剂依赖性的成分是指从IV-CT状态到基态的直接衰减，而长寿的，与溶剂无关的成分暂时归因于IV-CT状态的平衡形成和完全电荷分离状态。在有机场效应晶体管（OFET）器件的薄膜中研究了电荷传输特性。电子迁移率和空穴迁移率均约为3×10-5 cm 2 V -1 s -1，表明聚合物的双极性传输行为。
• Robust Organic Radical Molecular Junctions Using Acetylene Terminated Groups for C–Au Bond Formation
  作者：Francesc Bejarano、Ignacio Jose Olavarria-Contreras、Andrea Droghetti、Ivan Rungger、Alexander Rudnev、Diego Gutiérrez、Marta Mas-Torrent、Jaume Veciana、Herre S. J. van der Zant、Concepció Rovira、Enrique Burzurı́、Núria Crivillers

  DOI：10.1021/jacs.7b10019

  日期：2018.2.7

  Organic paramagnetic and electroactive molecules are attracting interest as core components of molecular electronic and spintronic devices. Currently, further progress is hindered by the modest stability and reproducibility of the molecule/electrode contact. We report the synthesis of a persistent organic radical bearing one and two terminal alkyne groups to form Au-C sigma bonds. The formation and stability of self-assembled monolayers and the electron transport through single-molecule junctions at room temperature have been studied. The combined analysis of both systems demonstrates that this linker forms a robust covalent bond with gold and a better-defined contact when compared to traditional sulfur-based linkers. Density functional theory and quantum transport calculations support the experimental observation highlighting a reduced variability of conductance values for the C-Au based junction. Our findings advance the quest for robustness and reproducibility of devices based on electroactive molecules.