4-ethynyl(dithiobenzoic) acid 2-(trimethylsilyl)ethyl ester | 947495-12-7

• 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-ethynyl(dithiobenzoic) acid 2-(trimethylsilyl)ethyl ester
• 英文别名: 4-ethynyldithiobenzoic acid 2-(trimethylsilyl)ethyl ester；2-Trimethylsilylethyl 4-ethynylbenzenecarbodithioate；2-trimethylsilylethyl 4-ethynylbenzenecarbodithioate
• CAS: 947495-12-7
• 化学式: C₁₄H₁₈S₂Si
• 分子量: 278.514
• InChiKey: NPIYVGDWQCPXSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-ethynyl(dithiobenzoic) acid 2-(trimethylsilyl)ethyl ester 、 4-碘氰基苯 在 copper(l) iodide 、 四(三苯基膦)钯 二异丙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以57%的产率得到4-[(4-cyanophenyl)ethynyl]dithiobenzoic acid 2-(trimethylsilyl)ethyl ester
  参考文献：
  名称：

  Carbodithioate-Terminated Oligo(phenyleneethynylene)s:  Synthesis and Surface Functionalization of Gold Nanoparticles

  摘要：

  Carbodithioate-terminated bis(phenylene)ethynylenes and oligo(phenyleneethynylene)s have been synthesized from TMSE-protected 4-iododithiobenzoic acid ester (1) and 4-ethynyldithiobenzoic acid ester (3) via Pd-catalyzed cross-coupling reactions. TEM and spectroscopic studies demonstrate that the reaction of 4-(phenylethynyl)dithiobenzoate with alkylamine-protected gold nanoparticles (AuNPs) produces the corresponding organocarbodithioate-functionalized AuNPs.

  DOI：

  10.1021/ol070789j
• 作为产物：
  描述：

  4-[(trimethylsilyl)ethynyl]dithiobenzoic acid 2-(trimethylsilyl)ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.33h， 生成 4-ethynyl(dithiobenzoic) acid 2-(trimethylsilyl)ethyl ester
  参考文献：
  名称：

  Carbodithioate-Terminated Oligo(phenyleneethynylene)s:  Synthesis and Surface Functionalization of Gold Nanoparticles

  摘要：

  Carbodithioate-terminated bis(phenylene)ethynylenes and oligo(phenyleneethynylene)s have been synthesized from TMSE-protected 4-iododithiobenzoic acid ester (1) and 4-ethynyldithiobenzoic acid ester (3) via Pd-catalyzed cross-coupling reactions. TEM and spectroscopic studies demonstrate that the reaction of 4-(phenylethynyl)dithiobenzoate with alkylamine-protected gold nanoparticles (AuNPs) produces the corresponding organocarbodithioate-functionalized AuNPs.

  DOI：

  10.1021/ol070789j

文献信息

• Fast Electron Transfer Exchange at Self-Assembled Monolayers of Organometallic Ruthenium(II) σ-Arylacetylide Complexes
  作者：Andrea Mulas、Yves-Marie Hervault、Xiaoyan He、Emmanuel Di Piazza、Lucie Norel、Stéphane Rigaut、Corinne Lagrost

  DOI：10.1021/acs.langmuir.5b01629

  日期：2015.6.30

  characterized by wettability studies, infrared reflection absorption spectroscopy (IRRAS), X-ray photoelectron spectroscopy (XPS), and electrochemical analyses. By applying the Laviron’s formalism, fast electron transfer kinetics (≈104 s–1) were found at the derived self-assemblies while no significant effect could have been evidenced with variation of the bridging unit and of the anchoring moiety. Interestingly

  合成了一系列新的富钌有机金属富碳配合物，它们结合了快速的电子转移动力学并具有低氧化电位，可用于在金表面形成自组装单层（SAM）。该分子由高度共轭的钌（II）单（σ-芳基乙炔化物）或双（σ-芳基乙炔化物）络合物组成，这些络合物具有不同的桥单元，并带有对金具有高亲和力的特定（受保护）锚定基团，例如硫醇，碳二硫代和异氰化物。制备了单组分和混合SAM，并通过润湿性研究，红外反射吸收光谱（IRRAS），X射线光电子能谱（XPS）和电化学分析对其进行了全面表征。通过应用拉维龙的形式主义，快速的电子转移动力学（≈10 4个小号-1）被发现在衍生的自组装体上，而桥接单元和锚定部分的变化都没有明显的影响。有趣的是，与具有较短间隔基的未稀释复合物相比，桥接单元中具有硫醇基的己基脂肪族间隔基和用合适的非电活性硫醇稀释可导致更好的SAM组织和堆积。这些特征使这些化合物成为广泛使用的二茂铁中心的合适替代品，作为可逆电荷存储设备的氧化还原活性构建基块。
• Regulating a Benzodifuran Single Molecule Redox Switch via Electrochemical Gating and Optimization of Molecule/Electrode Coupling
  作者：Zhihai Li、Hui Li、Songjie Chen、Toni Froehlich、Chenyi Yi、Christian Schönenberger、Michel Calame、Silvio Decurtins、Shi-Xia Liu、Eric Borguet

  DOI：10.1021/ja5034606

  日期：2014.6.25

  We report a novel strategy for the regulation of charge transport through single molecule junctions via the combination of external stimuli of electrode potential, internal modulation of molecular structures, and optimization of anchoring groups. We have designed redox-active benzodifuran (BDF) compounds as functional electronic units to fabricate metal-molecule-metal (m-M-m) junction devices by scanning tunneling microscopy (STM) and mechanically controllable break junctions (MCBJ). The conductance of thiol-terminated BDF can be tuned by changing the electrode potentials showing clearly an off/on/off single molecule redox switching effect. To optimize the response, a BDF molecule tailored with carbodithioate (-CS2(-)) anchoring groups was synthesized. Our studies show that replacement of thiol by carbodithioate not only enhances the junction conductance but also substantially improves the switching effect by enhancing the on/off ratio from 2.5 to 8.
• Carbodithioate-Terminated Oligo(phenyleneethynylene)s:  Synthesis and Surface Functionalization of Gold Nanoparticles
  作者：Tae-Hong Park、Michael J. Therien

  DOI：10.1021/ol070789j

  日期：2007.7.1

  Carbodithioate-terminated bis(phenylene)ethynylenes and oligo(phenyleneethynylene)s have been synthesized from TMSE-protected 4-iododithiobenzoic acid ester (1) and 4-ethynyldithiobenzoic acid ester (3) via Pd-catalyzed cross-coupling reactions. TEM and spectroscopic studies demonstrate that the reaction of 4-(phenylethynyl)dithiobenzoate with alkylamine-protected gold nanoparticles (AuNPs) produces the corresponding organocarbodithioate-functionalized AuNPs.