(4-iodo-3-nitrophenylethynyl)trimethylsilane | 518980-41-1

• 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: (4-iodo-3-nitrophenylethynyl)trimethylsilane
• 英文别名: 2-iodo-5-trimethylsilylethynylnitrobenzene；2-(4-Iodo-3-nitrophenyl)ethynyl-trimethylsilane
• CAS: 518980-41-1
• 化学式: C₁₁H₁₂INO₂Si
• 分子量: 345.212
• InChiKey: ADVGRZYBRPSFFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  苯乙炔 、 (4-iodo-3-nitrophenylethynyl)trimethylsilane 在 三乙胺 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以85%的产率得到[3-nitro-4-(phenylethynyl)phenylethynyl]trimethylsilane
  参考文献：
  名称：

  Synthesis of nitrile-terminated potential molecular electronic devices

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)01527-2
• 作为产物：
  描述：

  2-nitro-4-((trimethylsilyl)ethynyl)aniline 在 亚硝酸特丁酯 、 三氟化硼乙醚 、 碘 、 sodium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.67h， 以75%的产率得到(4-iodo-3-nitrophenylethynyl)trimethylsilane
  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

• Fullerene/Thiol-Terminated Molecules
  作者：Yasuhiro Shirai、Jason M. Guerrero、Takashi Sasaki、Tao He、Huanjun Ding、Guillaume Vives、Byung-Chan Yu、Long Cheng、Austen K. Flatt、Priscilla G. Taylor、Yongli Gao、James M. Tour

  DOI：10.1021/jo901701j

  日期：2009.10.16

  A series of fullerene-terminated oligo(phenylene ethynylene) (OPEs) have been synthesized for potential use in electronic or optoelectronic device monolayers. Electronic properties such as the energy levels and the distribution of HOMOs and LUMOs of fullerene-terminated OPEs have been calculated using the ab initio method at the B3LYP/6-31G(d) level. The calculations have revealed the concentration of frontier orbitals on the fullerene cage and a narrow distribution of HOMO-LUMO energy gaps. Ultraviolet photoelectron spectroscopy and inverse photoemission spectroscopy studies have been performed to further examine the electronic properties of the fullerene-terminated OPEs on gold surfaces. The obtained broad photoelectron spectra Suggest that there are strong intermolecular interactions in the fullerene self-assembled monolayers, and the small bandgap (similar to 1.5 eV), determined by the photoelectron spectroscopy, indicates the unique nature of the fullerene-terminated OPEs in which the C-60 moiety can be connected to the Au surface through the conjugated OPE backbone.