(3-Ethyl-5-{3-ethyl-5-[3-ethyl-5-(3-ethyl-thiophen-2-ylethynyl)-thiophen-2-ylethynyl]-thiophen-2-ylethynyl}-thiophen-2-ylethynyl)-trimethyl-silane | 154978-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3-Ethyl-5-{3-ethyl-5-[3-ethyl-5-(3-ethyl-thiophen-2-ylethynyl)-thiophen-2-ylethynyl]-thiophen-2-ylethynyl}-thiophen-2-ylethynyl)-trimethyl-silane
• 英文别名: 2-[3-ethyl-5-[2-[3-ethyl-5-[2-[3-ethyl-5-[2-(3-ethylthiophen-2-yl)ethynyl]thiophen-2-yl]ethynyl]thiophen-2-yl]ethynyl]thiophen-2-yl]ethynyl-trimethylsilane
• CAS: 154978-35-5
• 化学式: C₃₅H₃₄S₄Si
• 分子量: 611.004
• InChiKey: JREZTFWTPIICAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.61
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3-Ethyl-5-{3-ethyl-5-[3-ethyl-5-(3-ethyl-thiophen-2-ylethynyl)-thiophen-2-ylethynyl]-thiophen-2-ylethynyl}-thiophen-2-ylethynyl)-trimethyl-silane 在 碘 、 lithium diisopropyl amide 作用下， 生成 (3-Ethyl-5-{3-ethyl-5-[3-ethyl-5-(3-ethyl-5-iodo-thiophen-2-ylethynyl)-thiophen-2-ylethynyl]-thiophen-2-ylethynyl}-thiophen-2-ylethynyl)-trimethyl-silane
  参考文献：
  名称：

  Rapid Syntheses of Oligo(2,5-thiophene ethynylene)s with Thioester Termini:  Potential Molecular Scale Wires with Alligator Clips

  摘要：

  The syntheses of soluble oligo(3-ethyl-2,5-thiophene ethynylene)s via an iterative divergent/convergent approach starting from 3-ethyl-2-(trimethylsilylethynyl)thiophene are described. The monomer, dimer, tetramer, octamer, and 16-mer were synthesized. The 16-mer is 100 Angstrom long in its minimized extended zigzag 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. 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. Attachment of thiol end groups, protected as the thioacetyl moieties, was achieved. These serve as binding sites for adhesion to gold surfaces. In some cases, one end of the oligomeric chains were capped with a thiol group so that the surface attachments to gold could be studied. In other cases, thiol groups were 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.

  DOI：

  10.1021/jo962335y
• 作为产物：
  描述：

  3-ethyl-2-iodothiophene 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 碘 、 potassium carbonate 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 78.67h， 生成 (3-Ethyl-5-{3-ethyl-5-[3-ethyl-5-(3-ethyl-thiophen-2-ylethynyl)-thiophen-2-ylethynyl]-thiophen-2-ylethynyl}-thiophen-2-ylethynyl)-trimethyl-silane
  参考文献：
  名称：

  针对分子融合电子设备应用的正交融合共轭低聚物的融合合成途径。

  摘要：

  本文介绍了针对分子规模电子设备构建项目的合成有机相。概述了向正交融合的共轭有机低聚物的聚合合成路线。最终系统应具有一条通过sigma键合网络与第二条潜在导电链垂直融合的潜在导电链。合成的核心链段之一是基于具有中心硅原子的螺二噻吩部分。它由四炔丙基硅烷的锆促进的双（双环化）形成。第二个核心是9,9'-螺双芴系统。末端卤化物基团通过Pd催化或Pd / Cu催化的交叉偶联方法提供了用于链的进一步延伸的连接点。所有四个分支臂都可以在一次操作中固定到核心，因此使合成高度收敛。在较大的官能化系统的情况下，噻吩上的烷基取代基提供可溶的物质。为了制备长度> 50Å的分子，必须使用迭代的发散/收敛方法来构建低聚（噻吩-乙炔）支链。有机钯催化的方法被广泛用于正交稠合化合物的合成。

  DOI：

  10.1021/jo960897b