1-iodo-3-ethyl-4-<(trimethylsilyl)ethynyl>benzene | 174753-23-2

• 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-iodo-3-ethyl-4-<(trimethylsilyl)ethynyl>benzene
• 英文别名: (2-ethyl-4-iodophenylethynyl)trimethylsilane；2-(2-Ethyl-4-iodophenyl)ethynyl-trimethylsilane
• CAS: 174753-23-2
• 化学式: C₁₃H₁₇ISi
• 分子量: 328.268
• InChiKey: AZLKJIVREKIERM-UHFFFAOYSA-N

物化性质

• 沸点：
  307.4±42.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-iodo-3-ethyl-4-<(trimethylsilyl)ethynyl>benzene 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 甲醇 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 N-ethyl-N-[[3-ethyl-4-[2-(3-ethyl-4-ethynylphenyl)ethynyl]phenyl]diazenyl]ethanamine
  参考文献：
  名称：

  Schumm, Jeffry; Pearson, Darren L.; Tour, James M., Angewandte Chemie, 1994, vol. 106, # 13, p. 1445 - 1448

  摘要：

  DOI：
• 作为产物：
  描述：

  3-ethyl-4-iodoaniline 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 nitrosonium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.33h， 生成 1-iodo-3-ethyl-4-<(trimethylsilyl)ethynyl>benzene
  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。
• Rapid Solution and Solid Phase Syntheses of Oligo(1,4-phenylene ethynylene)s with Thioester Termini:  Molecular Scale Wires with Alligator Clips. Derivation of Iterative Reaction Efficiencies on a Polymer Support
  作者：LeRoy Jones、Jeffry S. Schumm、James M. Tour

  DOI：10.1021/jo962336q

  日期：1997.3.1

  The syntheses of soluble oligo(2-alkyl-1,4-phenylene ethynylene)s via an iterative divergent/ convergent approach starting from 1-(diethyltriazyl)-3-alkyl-4-[(trimethyl are described. When the solublizing alkyl group is an ethyl substituent, the monomer, dimer, tetramer, and octamer can be synthesized. The octamer, however, is only minimally soluble. When the alkyl substituent is 3-ethylheptyl or dodecyl, the compounds are easily dissolved even at the 16-mer stage. The 16-mer is 128 Angstrom long in its near-linear extended conformation. At each stage in the iteration, the length of the framework doubles. Only three sets of reaction conditions are needed for the entire iterative synthetic sequence: an iodination, a protodesilylation, and a Pd/Cu-catalyzed cross coupling. Synthesis of the dodecyl-containing 16-mer was also achieved on Merrifield's resin using the iterative divergent/convergent approach. The oligomers were characterized spectroscopically and by mass spectrometry. The optical properties are presented which show that at the octamer stage, the optical absorbance maximum is nearly saturated. The size exclusion chromatography values for the number average weights, relative to polystyrene, illustrate the tremendous differences in the hydrodynamic volume of these rigid rod oligomers verses the random coils of polystyrene. These differences become quite apparent at the octamer stage. Equations were derived for assessing the efficiency of the polymer-supported reactions based on resin weight; differences, molar concentration differences, and elemental analysis data. Each of these methods' limitations are discussed. Attachment of thiol end groups, protected as thioacetyl moieties, was achieved. These serve as binding sites for adhesion to gold surfaces. In some cases, one end of the oligomeric chains is capped with a thiol group so that the surface attachments to gold could be studied. In other cases, thiol groups are affixed to both ends of the molecular chains so that future conduction studies could be done between proximal metallic probes. The rigid rod conjugated oligomers may act as molecular wires in molecular scale electronic devices, and they also serve as useful models for understanding analogous bulk polymers.