4-[tris(4-iodophenyl)silyl](oxyethyl) | 222417-70-1

• 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-[tris(4-iodophenyl)silyl](oxyethyl)
• 英文别名: ethoxytris(p-iodophenyl)silane；ethoxytri(p-iodophenyl)silane；Ethoxy-tris(4-iodophenyl)silane
• CAS: 222417-70-1
• 化学式: C₂₀H₁₇I₃OSi
• 分子量: 682.153
• InChiKey: GRQZNGJARDORQU-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C
• 沸点：
  485.1±40.0 °C(Predicted)
• 密度：
  1.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-[tris(4-iodophenyl)silyl](oxyethyl) 在 copper(l) iodide 、 Pd(dba)2*Ph₃P 、 四丁基氟化铵 、 叔丁基锂 、 乙酸酐 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 75.08h， 生成 S-[4-[2-[4-[bis[4-[2-(4-acetylsulfanylphenyl)ethynyl]phenyl]-(4-ethynylphenyl)silyl]phenyl]ethynyl]phenyl] ethanethioate
  参考文献：
  名称：

  Facile Convergent Route to Molecular Caltrops

  摘要：

  The convergent syntheses of molecular caltrops are described starting from tetraethyl orthosilicate and using organolithium additions and Pd/Cu-catalyzed coupling methods. The caltrop core is based on a tetrahedral silicon atom, and there are three legs each bearing sulfur-tipped feet for adhesion to metallic surfaces. The forth prong (arm) is non-sulfur-bearing for projection upward from the surface. Rigid phenyleneethynylene segments are used for the legs and arms. These organosilicon caltrops may have utility as scanning probe microscopy tips.

  DOI：

  10.1021/jo982085g
• 作为产物：
  描述：

  硅酸四乙酯 、 1,4-二碘苯 在 正丁基锂 作用下， 生成 4-[tris(4-iodophenyl)silyl](oxyethyl)
  参考文献：
  名称：

  Facile Convergent Route to Molecular Caltrops

  摘要：

  The convergent syntheses of molecular caltrops are described starting from tetraethyl orthosilicate and using organolithium additions and Pd/Cu-catalyzed coupling methods. The caltrop core is based on a tetrahedral silicon atom, and there are three legs each bearing sulfur-tipped feet for adhesion to metallic surfaces. The forth prong (arm) is non-sulfur-bearing for projection upward from the surface. Rigid phenyleneethynylene segments are used for the legs and arms. These organosilicon caltrops may have utility as scanning probe microscopy tips.

  DOI：

  10.1021/jo982085g

文献信息

• En Route to Surface-Bound Electric Field-Driven Molecular Motors
  作者：Huahua Jian、James M. Tour

  DOI：10.1021/jo034169h

  日期：2003.6.1

  Four caltrop-shaped molecules that might be useful as surface-bound electric field-driven molecular motors have been synthesized. The caltrops are comprised of a pair of electron donor-acceptor arms and a tripod base. The molecular arms are based on a carbazole or oligo(phenylene ethynylene) core with a strong net dipole. The tripod base uses a silicon atom as its core. The legs of the tripod bear

  已经合成了四种可用作表面受电场驱动的分子电动机的菱形分子。菱形体由一对电子供体-受体臂和三脚架基座组成。分子臂基于具有强净偶极子的咔唑或低聚（亚苯基乙炔基）核。三脚架底座使用硅原子作为其核心。三脚架的支脚带有硫磺键合单元，作为乙酰基保护的苄硫醇，用于键合到金表面。自组装后，三脚架底座的几何形状允许菱形从金属表面向上突出。椭偏研究表明，自立构的自组装单分子层形成在Au表面上，分子表面的厚度与所需的竖轴布置相一致。因此，
• Synthesis and Structural Analysis of Substituted Tripod-Shaped Tri- and Tetra(p-phenylene)s
  作者：Jesús Hierrezuelo、Elena Guillén、J. Manuel López-Romero、Rodrigo Rico、M. Rosa López-Ramírez、J. Carlos Otero、Chengzhi Cai

  DOI：10.1002/ejoc.201000786

  日期：2010.10

  Suzuki cross-coupling reaction of the silicon-derived core molecule with the appropriately substituted p-biphenyl moiety. This synthesis should be considered a new strategy for these compounds, as iterative coupling of the substituted p-biphenyl building blocks with the first-generation tripods will allow the homologation of the tripod legs to obtain giant tripod-shaped oligo(p-phenylene)s. Also, the

  我们在这里报告了几种三脚架形低聚（对亚苯基）的合成，腿由三个或四个亚苯基单元组成。每条腿都用碘原子或 TMS 或羧基封端，并且功能臂上存在乙氧基。含有甲基三（乙二醇）侧链的三脚架专为生物应用而设计。合成的关键步骤是 Pd 催化的硅衍生核心分子与适当取代的对联苯部分的 Suzuki 交叉偶联反应。这种合成应被视为这些化合物的新策略，因为取代的对联苯构件与第一代三脚架的迭代耦合将允许三脚架腿的同源性获得巨大的三脚架形低聚（对亚苯基） . 还，功能臂上带有乙氧基的碘封端腿允许三脚架的模块化设计以进一步功能化，这将定义三脚架纳米结构表面的应用。通过实验（拉曼光谱）和理论（DFT 计算）方法研究了一些合成三脚架的结构。
• Synthesis and Nonlinear Optical Properties of Tetrahedral Octupolar Phthalocyanine-Based Systems
  作者：Maurizio Quintiliani、Javier Pérez-Moreno、Inge Asselberghs、Purificación Vázquez、Koen Clays、Tomás Torres

  DOI：10.1021/jp100827k

  日期：2010.5.20

  have always fundamentally kept on relying on the old dipolar paradigm (even though the resulting molecular structure was octupolar - the most striking exponent of this is the octupolar 1,3,5-triamino-2,4,6-trinitrobenzene molecule, a simple octupolar expansion of the dipolar p-nitroaniline), we here present for the first time that the octupolar symmetry by itself, realized by four nondipolar moieties

  已经合成并充分表征了呈现中心碳或硅原子的两个系列的基于四面体酞菁的体系。乙炔基垫片将外围PC单元连接到中心核。一些结构包含四个相同的PC部分，而其他结构在第四个亚基中带有吸电子或电子释放基团。的合成策略包括在金属介导的偶联三-之间的反应叔-丁基乙炔基酞菁和相应的甲烷或硅烷衍生物。通过超瑞利散射测量对二阶非线性光学（NLO）进行的研究表明，通过以八极方式结合自身不具有二阶NLO活性的中心对称部分，可以实现较大的二阶NLO响应，与供体-受体NLO活性偶极基团的经典八极组合相反。特别地，C-中心四聚物表现出大的β HRS值，这是最高的迄今为八极基于PC的报道分子之间。有趣的是，以碳为中心的分子相对于以硅为中心的分子表现出更好的NLO响应，这可能是由于有效对称性不同，主要是T d对于C中心化合物，D 2d用于Si中心系统。尽管其他用于二阶NLO效应的设计策略从根本上一直依赖于旧的偶极范式（即使最终
• Characterization of Self-Assembled Monolayers of Fullerene Derivatives on Gold Surfaces:  Implications for Device Evaluations
  作者：Yasuhiro Shirai、Long Cheng、Bo Chen、James M. Tour

  DOI：10.1021/ja063451d

  日期：2006.10.1

  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.
• 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.