1-(phenylethynyl)-4-(thioacetyl)benzene | 170159-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: 1-(phenylethynyl)-4-(thioacetyl)benzene
• 英文别名: 1-(phenylethynyl)-4-(thiocetyl)benzene；S-(4-(phenylethynyl)phenyl) ethanethioate；1-acetylthio-4-[(phenyl)ethynyl]benzene；SAc-OPE2；S-[4-(2-phenylethynyl)phenyl] ethanethioate
• CAS: 170159-16-7
• 化学式: C₁₆H₁₂OS
• 分子量: 252.337
• InChiKey: HLRNPXBOQZKXQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(phenylethynyl)-4-(thioacetyl)benzene 在 二乙胺 作用下， 以 氯仿 为溶剂， 生成 C₂₈H₁₈S₂
  参考文献：
  名称：

  钯催化的heck反应中的硫酚保护基：共轭芳基硫醇的高效合成

  摘要：

  对于Heck反应，已经评估了多种S-硫代苯酚保护基。其中，S-乙酰基似乎最适合在温和条件下轻松除去，以高产率提供相应的游离硫醇。

  DOI：

  10.1016/0040-4039(95)00861-6
• 作为产物：
  描述：

  苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三溴化硼 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 25.0h， 生成 1-(phenylethynyl)-4-(thioacetyl)benzene
  参考文献：
  名称：

  Formation of High-Quality Self-Assembled Monolayers of Conjugated Dithiols on Gold: Base Matters

  摘要：

  This Article reports a systematic study on the formation of self-assembled monolayers (SAMs) of conjugated molecules for molecular electronic (ME) devices. We monitored the deprotection reaction of acetyl protected dithiols of oligophenylene ethynylenes (OPEs) in solution using two different bases and studied the quality of the resulting SAMs on gold. We found that the optimal conditions to reproducibly form dense, high-quality monolayers are 9-15% triethylamine (Et3N) in THF. The deprotection base tetrabutylammonium hydroxide (Bu4NOH) leads to less dense SAMs and the incorporation of Bu4N into the monolayer. Furthermore, our results show the importance of the equilibrium concentrations of (di)thiolate in solution on the quality of the SAM. To demonstrate the relevance of these results for molecular electronics applications, large-area molecular junctions were fabricated using no base, Et3N, and Bu4NOH. The magnitude of the current-densities in these devices is highly dependent on the base. A value of beta = 0.15 angstrom(-1) for the exponential decay of the current-density of OPEs of varying length formed using Et3N was obtained.

  DOI：

  10.1021/ja110358t

文献信息

• Carbazole‐Based Tetrapodal Anchor Groups for Gold Surfaces: Synthesis and Conductance Properties
  作者：Luke J. O'Driscoll、Xintai Wang、Michael Jay、Andrei S. Batsanov、Hatef Sadeghi、Colin J. Lambert、Benjamin J. Robinson、Martin R. Bryce

  DOI：10.1002/anie.201911652

  日期：2020.1.7

  anchor groups used in fundamental conductance studies to more elaborate anchors designed with device stability in mind. This study presents a series of oligo(phenylene-ethynylene) wires with one tetrapodal anchor and a phenyl or pyridyl head group. The new anchors are designed to bind strongly to gold surfaces without disrupting the conductance pathway of the wires. Conductive probe atomic force microscopy

  随着分子规模电子学领域的成熟以及包含分子线的器件的前景变得更加可行，有必要从基础电导研究中使用的简单锚定基团发展到考虑到器件稳定性的更精细的锚定剂。这项研究提出了一系列带有一个四脚锚和一个苯基或吡啶基头部基团的低聚（亚苯基-亚乙炔基）线。新的锚固件旨在牢固地与金表面结合，而不会破坏导线的电导路径。导电探针原子力显微镜（cAFM）用于确定导线在Au-SAM-Pt和Au-SAM-石墨烯结中的自组装单层（SAMs）的电导率，由此得出每个分子的电导率。对于tolane型导线，每个分子的平均电导高达10-4。尽管与Au电极的电子耦合有限，但仍测量到37 G0（Pt）和10-3.78 G0（石墨烯），证明了这种方法的潜力。表面结合几何形状和传输性质的计算研究合理化并支持实验结果。
• 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.
• Reaction pathway change on plasmonic Au nanoparticles studied by surface-enhanced Raman spectroscopy
  作者：Ran Li、Can-Can Zhang、Dan Wang、Yan-Fang Hu、Yong-Long Li、Wei Xie

  DOI：10.1016/j.cclet.2021.02.014

  日期：2021.9
• Spontaneous Assembly of Organic Thiocyanates on Gold Sufaces. Alternative Precursors for Gold Thiolate Assemblies
  作者：Jacob W. Ciszek、Michael P. Stewart、James M. Tour

  DOI：10.1021/ja0472477

  日期：2004.10.1

  Thiolate self-assembly on gold has proven to be a valuable technique for assembling monolayers on a wide variety of substrates. However, the oxidative instability of the thiols, especially aromatic thiols and alpha,omega-dithiols, presents several difficulties. Shown here is that thiocyanates, easily synthesized stable thiol derivatives, can be directly assembled on gold surfaces with no auxiliary reagents required. Assembly is complete in 24 h and leaves a similar gold thiolate structure as seen in typical thiol self-assembled monolayers.
• Thiophenol protecting groups for the palladium-catalyzed heck reaction: Efficient syntheses of conjugated arylthoils
  作者：Richard P Hsung、Jason R Babcock、Christopher E.D Chidsey、Lawrence R Sita

  DOI：10.1016/0040-4039(95)00861-6

  日期：1995.6

  A variety of S-thiophenol protecting groups have been evaluated for the Heck reaction. Of these, the S-acetyl group appears to be the best suited for facile removal under mild conditions to provide the corresponding free thiols in high yields.

  对于Heck反应，已经评估了多种S-硫代苯酚保护基。其中，S-乙酰基似乎最适合在温和条件下轻松除去，以高产率提供相应的游离硫醇。