2-nitro-4-phenylethynyl-phenylamine | 120703-28-8

• 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: 2-nitro-4-phenylethynyl-phenylamine
• 英文别名: Benzenamine, 2-nitro-4-(phenylethynyl)-；2-nitro-4-(2-phenylethynyl)aniline
• CAS: 120703-28-8
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: ONZAGAYCLKFGFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitro-4-phenylethynyl-phenylamine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 亚硝酸特丁酯 、 三氟化硼乙醚 、 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 6.17h， 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
• 作为产物：
  描述：

  4-碘-2-硝基苯胺 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以88%的产率得到2-nitro-4-phenylethynyl-phenylamine
  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

• Biphenyl- and fluorenyl-based potential molecular electronic devices
  作者：David W Price、James M Tour

  DOI：10.1016/s0040-4020(03)00334-x

  日期：2003.4

  New potential molecular electronics devices have been synthesized based on our knowledge of systems that we previously studied. Research has shown that simple molecular systems demonstrate negative differential resistance (NDR) and memory characteristics. The new molecules rely primarily on the redox properties of the compounds to improve upon the solid-state characteristics already observed. Electrochemical tests have been performed in order to evaluate the redox properties with the hope that the electrochemical results can be used as a predictive tool to evaluate the usefulness of those compounds in device configurations. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of nitrile-terminated potential molecular electronic devices
  作者：Shawn M Dirk、James M Tour

  DOI：10.1016/s0040-4020(02)01527-2

  日期：2003.1

  Several potential molecular devices have been synthesized consisting of oligo(phenylene ethynylene) (OPE) backbones containing a terminal nitrile group alligator clip as a means of attachment to a metal surface. The synthesis of four new nitrile-containing OPEs is discussed, including an improved synthesis of an intermediate used in our prior production of OPEs containing acetate-protected thiol alligator clips. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Polyquinoxaline polymers, and articles comprising same
  申请人：AT&T Corp.

  公开号：EP0299452B1

  公开（公告）日：1994-10-05
• Improved and new syntheses of potential molecular electronics devices
  作者：David W Price、Shawn M Dirk、Francisco Maya、James M Tour

  DOI：10.1016/s0040-4020(03)00246-1

  日期：2003.3

  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.