p-(triethylsilyl)phenylacetylene | 16116-94-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: p-(triethylsilyl)phenylacetylene
• 英文别名: 4-Triethylsilyl-phenylacetylen；4-triethylsilylphenylacetylene；Triethyl(4-ethynylphenyl)silane；triethyl-(4-ethynylphenyl)silane
• CAS: 16116-94-2
• 化学式: C₁₄H₂₀Si
• 分子量: 216.398
• InChiKey: JHLZJOKFTQGSIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6,13-五并苯醌 、 p-(triethylsilyl)phenylacetylene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Novel soluble pentacene and anthradithiophene derivatives for organic thin-film transistors

  摘要：

  Four new solution-processable pentacene- (PEN) and anthradithiophene- (ADT) based organic semiconductors bearing two phenylethynyl (PE-) or triethylsilylphenylethynyl (TESPE-) substituents have been synthesized, characterized, and incorporated in thin-film transistors (TFTs). The molecular structures of these four materials have been determined by single-crystal X-ray diffraction. Thin films of all four compounds have been fabricated via drop-casting and exhibited p-channel OTFT transport with hole mobilities as high as similar to 0.01 cm(2)/V s. Compared to PEN derivatives, ADT-based compounds exhibited superior device performance and photooxidative stability in ambient. The film morphologies and microstructures of these compounds have been characterized by optical microscopy and X-ray diffraction to rationalize device performance trends. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.04.029
• 作为产物：
  描述：

  1-溴-4-(三乙基甲硅烷基)苯 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 20.17h， 生成 p-(triethylsilyl)phenylacetylene
  参考文献：
  名称：

  Novel soluble pentacene and anthradithiophene derivatives for organic thin-film transistors

  摘要：

  Four new solution-processable pentacene- (PEN) and anthradithiophene- (ADT) based organic semiconductors bearing two phenylethynyl (PE-) or triethylsilylphenylethynyl (TESPE-) substituents have been synthesized, characterized, and incorporated in thin-film transistors (TFTs). The molecular structures of these four materials have been determined by single-crystal X-ray diffraction. Thin films of all four compounds have been fabricated via drop-casting and exhibited p-channel OTFT transport with hole mobilities as high as similar to 0.01 cm(2)/V s. Compared to PEN derivatives, ADT-based compounds exhibited superior device performance and photooxidative stability in ambient. The film morphologies and microstructures of these compounds have been characterized by optical microscopy and X-ray diffraction to rationalize device performance trends. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.04.029

文献信息

• The protection of terminal ethynyl groups in Grignard syntheses
  作者：C. Eaborn、A. R. Thompson、D. R. M. Walton

  DOI：10.1039/j39670001364

  日期：——

  The trimethylsilyl group can be used to protect a terminal ethynyl group in Grignard syntheses. For example, a Grignard reagent can be made in tetrahydrofuran from the easily prepared compound (p-bromophenylethynyl)-trimethylsilane, and carbonation gives the acid (p-carboxyphenylethynyl)trimethylsilane, which on treatment with dilute alkali gives p-ethynylbenzoic acid in 55% overall yield. The corresponding

  三甲基甲硅烷基可用于保护格利雅（Grignard）合成中的末端乙炔基。例如，格氏试剂可从四氢呋喃中由容易制备的化合物（对-溴苯基乙炔基）-三甲基硅烷制得，碳酸化可得到酸（对-羧基苯基乙炔基）三甲基硅烷，经稀碱处理后可得到55％的对-乙炔基苯甲酸。总产量。相应的元-酸可以类似地制造。
• Synthesis and Properties of F-Containing Poly(diphenylacetylene) Membranes
  作者：Toshikazu Sakaguchi、Masashi Shiotsuki、Fumio Sanda、Benny D. Freeman、Toshio Masuda

  DOI：10.1021/ma051445g

  日期：2005.10.1

  The polymerization of various silyl- and F-containing diphenylacetylenes (1a-k) with TaCl5- n-BU4Sn provided high-molecular-weight polymers. Most polymers (2a-d, 2g, and 2h) were totally soluble in common organic solvents and afforded tough free-standing membranes by casting from toluene solution, while some polymers (2e, 2f, and 2i-k) were insoluble in any organic solvents. The onset temperatures of weight loss of polymers 2a-d in air were over 400 *C, indicating very high thermal stability. The membranes of 2a-d were desilylated with trifluoroacetic acid to give desilylated polymer membranes 3a-d, which were insoluble in any solvents. The fractional free volumes (FFV) of the present membrane-forming trimethylsilyl and/or F-bearing polymers (2a-d and 3a-d) were ca. 0.28-0.31 and appreciably large, and they showed very high permeability (ca. 1400-14 000 barrers) to the six gases examined. The oxygen permeability coefficient (P-O2) of 2a was as high as 2900 barrers, which is about twice that of poly[1-(p-trimethylsilyl)phenyl-2-phenylacetylene]. The incorporation of F atoms into both poly[1-(p-trimethylsilyl)phenyl-2-phenylacetylene] and poly(diphenylacetylene) generally enhanced gas permeability.