1-ethynyl-2-nitro-4-phenylethynylbenzene | 421554-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-ethynyl-2-nitro-4-phenylethynylbenzene
• 英文别名: 2-ethynyl-5-phenylethynyl-1-nitrobenzene；1-Ethynyl-2-nitro-4-(2-phenylethynyl)benzene
• CAS: 421554-51-0
• 化学式: C₁₆H₉NO₂
• 分子量: 247.253
• InChiKey: ZXVUVQXLPITXOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-ethynyl-2-nitro-4-phenylethynylbenzene 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ copper(l) iodide 、 四丁基氟化铵 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 thioacetic acid S-[4-(3-oxo-1-oxy-6-phenylethynyl-3H-indol-2-yl)phenyl] ester
  参考文献：
  名称：

  Improved and new syntheses of potential molecular electronics devices

  摘要：

  New syntheses of ethyl and nitro substituted oligo(phenylene ethynylene)s (OPEs) have been developed. To further explore whether the presence of nitro functionality in OPEs leads to switching and memory capabilities, new nitro substituted OPEs have been designed and synthesized. An isatogen-based system, a structure that is isomeric to the nitro OPE, has been synthesized. Additionally, pyridine-based and chromium-based compounds have been synthesized. We surmise that redox reactions of these candidates may impart switching capabilities and electrochemical studies are shown. U-shaped OPEs were synthesized to inhibit leakage of metals deposited during formation of top contacts on self-assembled monolayers (SAMs). The OPEs contain either thiol-based moieties or isonitrile groups to enable formation of SAMs on metal substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00246-1
• 作为产物：
  描述：

  1-iodo-2-nitro-4-phenylethynyl-benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 1-ethynyl-2-nitro-4-phenylethynylbenzene
  参考文献：
  名称：

  Improved and new syntheses of potential molecular electronics devices

  摘要：

  New syntheses of ethyl and nitro substituted oligo(phenylene ethynylene)s (OPEs) have been developed. To further explore whether the presence of nitro functionality in OPEs leads to switching and memory capabilities, new nitro substituted OPEs have been designed and synthesized. An isatogen-based system, a structure that is isomeric to the nitro OPE, has been synthesized. Additionally, pyridine-based and chromium-based compounds have been synthesized. We surmise that redox reactions of these candidates may impart switching capabilities and electrochemical studies are shown. U-shaped OPEs were synthesized to inhibit leakage of metals deposited during formation of top contacts on self-assembled monolayers (SAMs). The OPEs contain either thiol-based moieties or isonitrile groups to enable formation of SAMs on metal substrates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00246-1

文献信息

• Synthesis and Preliminary Testing of Molecular Wires and Devices
  作者：James M. Tour、Adam M. Rawlett、Masatoshi Kozaki、Yuxing Yao、Raymond C. Jagessar、Shawn M. Dirk、David W. Price、Mark A. Reed、Chong-Wu Zhou、Jia Chen、Wenyong Wang、Ian Campbell

  DOI：10.1002/1521-3765(20011203)7:23<5118::aid-chem5118>3.0.co;2-1

  日期：2001.12.3

  Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups

  本文介绍了几种共轭低聚（亚苯基乙炔基）合成路线。这些低聚物中的一些不含官能团，而其他则具有供体基团，受体基团，卟啉内部以及用于各种潜在传输和数字设备应用的其他杂环内部。提出了具有各种端基的低聚（亚苯基亚乙炔基）的合成方法，该低端基用于连接许多金属探针和表面。一些功能化分子系统表现出线性，线状，电流对电压（I（V））响应，而另一些则表现出负差分电阻（NDR）和分子随机存取记忆效应的非线性I（V）曲线。最后，描述了可以在金属电极上形成自组装单分子层的功能化低聚物的合成，从而降低了肖特基势垒。肖特基势垒研究的信息可以为分子电子学中的分子鳄鱼夹优化提供有用的见解。
• MOLECULAR SCALE ELECTRONIC DEVICES
  申请人：Yale University

  公开号：EP1542869A2

  公开（公告）日：2005-06-22
• EP1542869A4
  申请人：——

  公开号：EP1542869A4

  公开（公告）日：2005-06-22
• [EN] MOLECULAR SCALE ELECTRONIC DEVICES<br/>[FR] DISPOSITIFS ELECTRONIQUES A L'ECHELLE MOLECULAIRE
  申请人：——

  公开号：WO2001027972A9

  公开（公告）日：2002-11-14

  [EN] Molecular scale electronic devices (1) are disclosed. Such devices include at least two conductive contacts (9 and 11), and a conductive path (13) bridging the contacts. The conductive path is able to be written into a perturbed state by a voltage pulse, which can be of high or low conductivity, relative to an initial state. The conductive path comprises organic molecules including at least one electron-withdrawing group. Room temperature negative differential resistance is exhibited by the devices.
  [FR] L'invention porte sur des dispositifs électroniques à l'échelle moléculaire comprenant au moins deux contacts conducteurs et un chemin conducteur enjambant les contacts. Le chemin conducteur peut être figé à l'état perturbé par une impulsion en tension correspondant à niveau de conductivité élevé ou faible par rapport à un état initial. Le chemin conducteur comprend des molécules organiques comprenant au moins un groupe suppresseur d'électrons. Ces dispositifs font preuve d'une résistance différentielle négative à température ambiante.