{2-[4-(4-Ethynyl-phenylethynyl)-phenylsulfanyl]-ethyl}-trimethyl-silane | 870274-72-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: {2-[4-(4-Ethynyl-phenylethynyl)-phenylsulfanyl]-ethyl}-trimethyl-silane
• 英文别名: 2-[4-[2-(4-Ethynylphenyl)ethynyl]phenyl]sulfanylethyl-trimethylsilane；2-[4-[2-(4-ethynylphenyl)ethynyl]phenyl]sulfanylethyl-trimethylsilane
• CAS: 870274-72-9
• 化学式: C₂₁H₂₂SSi
• 分子量: 334.557
• InChiKey: AGDXKWNSXAJEHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  437.7±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  {2-[4-(4-Ethynyl-phenylethynyl)-phenylsulfanyl]-ethyl}-trimethyl-silane 、 足球烯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 2-[4-[2-[4-[2-(9H-(C60-Ih)[5,6]fulleren-1-yl)ethynyl]phenyl]ethynyl]phenyl]sulfanylethyl-trimethylsilane
  参考文献：
  名称：

  Characterization of Self-Assembled Monolayers of Fullerene Derivatives on Gold Surfaces:  Implications for Device Evaluations

  摘要：

  The widely employed approach to self-assembly of fullerene derivatives on gold can be complicated due to multilayer formations and head-to-tail assemblies resulting from the strong fullerene-fullerene and fullerene-gold interactions. These anomalies were not examined in detail in previous studies on fullerene self-assembled monolayers (SAMs) but were clearly detected in the present work using surface characterization techniques including ellipsometry, cyclic voltammetry (CV), and X-ray photoelectron spectroscopy (XPS). This is the first time that SAMs prepared from fullerene derivatives of thiols/thiol esters/disulfides have been analyzed in detail, and the complications due to multilayer formations and head-to-tail assemblies were revealed. Specifically, we designed and synthesized several fullerene derivatives based on thiols, thiol acetates, and disulfides to address the characterization requirements, and these are described and delineated. These studies specifically address the need to properly characterize and control fullerene-thiol assemblies on gold before evaluating subsequent device performances.

  DOI：

  10.1021/ja063451d
• 作为产物：
  描述：

  (4-碘苯基乙炔)三甲基硅烷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 {2-[4-(4-Ethynyl-phenylethynyl)-phenylsulfanyl]-ethyl}-trimethyl-silane
  参考文献：
  名称：

  Characterization of Self-Assembled Monolayers of Fullerene Derivatives on Gold Surfaces:  Implications for Device Evaluations

  摘要：

  The widely employed approach to self-assembly of fullerene derivatives on gold can be complicated due to multilayer formations and head-to-tail assemblies resulting from the strong fullerene-fullerene and fullerene-gold interactions. These anomalies were not examined in detail in previous studies on fullerene self-assembled monolayers (SAMs) but were clearly detected in the present work using surface characterization techniques including ellipsometry, cyclic voltammetry (CV), and X-ray photoelectron spectroscopy (XPS). This is the first time that SAMs prepared from fullerene derivatives of thiols/thiol esters/disulfides have been analyzed in detail, and the complications due to multilayer formations and head-to-tail assemblies were revealed. Specifically, we designed and synthesized several fullerene derivatives based on thiols, thiol acetates, and disulfides to address the characterization requirements, and these are described and delineated. These studies specifically address the need to properly characterize and control fullerene-thiol assemblies on gold before evaluating subsequent device performances.

  DOI：

  10.1021/ja063451d

文献信息

• Synthesis and characterization of wire-like Ru2(ap)4-[σ-oligo(phenylene ethynyl)] compounds
  作者：Tong Ren、Damon A. Parish、Guo-Lin Xu、Martin H. Moore、Jeffrey R. Deschamps、Jie-Wen Ying、Steven K. Pollack、Terence L. Schull、Ranganathan Shashidhar

  DOI：10.1016/j.jorganchem.2005.07.057

  日期：2005.11

  Reported herein are the synthesis, electrochemical and structural characterization of wire-like Ru2-alkynyl compounds, Ru2(ap)4(Ln)x, where ap is 2-anilinopyridinate, and Ln is –(CCC6H4)nSCH2CH2SiMe3 with n = 1 (1) and 2 (2), and x can be 1 (a) and 2 (b). Reactions between Ru2(ap)4Cl and one equiv. of LiLn yielded the mono-alkynyl compound only, while the use of 4–5 equiv. of LiLn resulted in a mixture

  本文报道的是线状Ru 2-炔基化合物Ru 2（ap）4（L n）x的合成，电化学和结构表征，其中ap是2-苯胺基吡啶鎓，L n是–（CCC 6 H 4）ñ SCH 2 CH 2森达3与ñ  = 1（1）和2（2），和X可以是1（一）和2（b）。Ru 2（ap）4 Cl和1当量。LiL n的使用仅产生单炔基化合物，而使用4-5当量。LiL n的得到导致单炔基和双炔基两者的混合物。化合物1a和1b的单晶X射线衍射研究表明，其结构与Ru 2（ap）4（C 2 Ph）和Ru 2（ap）4（C 2 Ph）2相似。， 分别。磁性，光谱和伏安测量还显示，由于带有硫醇-TMSE基团（–SCH 2 CH 2 SiMe 3）的OPE配体的功能化，对电子结构的干扰最小。最显著，它可以基于的结构来估计1A，在Ru的OPE2-S-键2A是显著长于C11硫醇SAM的深度，从而使得能够插入图2a到后者。
• 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.