1-[(p-trimethylsilyl)phenyl]-2-(2-phenanthryl)acetylene | 713093-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-[(p-trimethylsilyl)phenyl]-2-(2-phenanthryl)acetylene
• 英文别名: Trimethyl-[4-(2-phenanthren-2-ylethynyl)phenyl]silane；trimethyl-[4-(2-phenanthren-2-ylethynyl)phenyl]silane
• CAS: 713093-48-2
• 化学式: C₂₅H₂₂Si
• 分子量: 350.535
• InChiKey: VKUZEVBIBMOMAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-乙炔基菲 、 1-溴-4-(三甲基硅基)苯 在 copper(l) iodide bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 三苯基膦 作用下， 反应 5.0h， 以65%的产率得到1-[(p-trimethylsilyl)phenyl]-2-(2-phenanthryl)acetylene
  参考文献：
  名称：

  Synthesis and Properties of Si-Containing Poly(diarylacetylene)s and Their Desilylated Polymer Membranes

  摘要：

  The polymerization of 1-[(p-trimethylsilyl)phenyl]-2-(2-fluorenyl)acetylene (1c) with TaCl5-n-Bu4Sn produced a high molecular weight polymer (2c), whose M-w reached 3.4 x 10(6). 1-[(p-Trimethylsilyl)-phenyl]-2-(2-phenanthryl)acetylene (1d) and 1-[(p-trimethylsilyl)phenyl]-2-(4-biphenyl)acetylene (le) were also polymerized to give high molecular weight polymers (2d and 2e) in good yields. In contrast, the polymerization of 1-[(p-trimethylsilyl)phenyl]-2-(2-anthryl)acetylene (1f) provided no polymer probably owing to the steric reason. The formed polymers 2c and 2d were soluble in common solvents such as toluene and chloroform and afforded free-standing membranes by casting from toluene solution. The onset temperatures of weight loss of polymers 2c and 2d in air were about 430 degreesC, indicating very high thermal stability. The membranes of 2c and 2d obtained by the casting method showed high gas permeability; e.g., their oxygen permeability coefficients (Po-2) were 1650 and 460 barrers, respectively. The membranes of 2c and 2d were desilylated with trifluoroacetic acid to provide the membranes of poly [1-phenyl-2-(2-fluorenyl)acetylene] (3c) and poly[1-phenyl-2-(2-phenanthryl)acetylene] (3d). The desilylated poly(diarylacetylene)s exhibited even higher Po-2 values of 2150 and 1300 barrers, respectively. These desilylated polymers were insoluble in any solvents and showed higher thermal stability than those of 2c and 2d.

  DOI：

  10.1021/ma035993a

文献信息

• Synthesis and Properties of Si-Containing Poly(diarylacetylene)s and Their Desilylated Polymer Membranes
  作者：Toshikazu Sakaguchi、Masashi Shiotsuki、Toshio Masuda

  DOI：10.1021/ma035993a

  日期：2004.6.1

  The polymerization of 1-[(p-trimethylsilyl)phenyl]-2-(2-fluorenyl)acetylene (1c) with TaCl5-n-Bu4Sn produced a high molecular weight polymer (2c), whose M-w reached 3.4 x 10(6). 1-[(p-Trimethylsilyl)-phenyl]-2-(2-phenanthryl)acetylene (1d) and 1-[(p-trimethylsilyl)phenyl]-2-(4-biphenyl)acetylene (le) were also polymerized to give high molecular weight polymers (2d and 2e) in good yields. In contrast, the polymerization of 1-[(p-trimethylsilyl)phenyl]-2-(2-anthryl)acetylene (1f) provided no polymer probably owing to the steric reason. The formed polymers 2c and 2d were soluble in common solvents such as toluene and chloroform and afforded free-standing membranes by casting from toluene solution. The onset temperatures of weight loss of polymers 2c and 2d in air were about 430 degreesC, indicating very high thermal stability. The membranes of 2c and 2d obtained by the casting method showed high gas permeability; e.g., their oxygen permeability coefficients (Po-2) were 1650 and 460 barrers, respectively. The membranes of 2c and 2d were desilylated with trifluoroacetic acid to provide the membranes of poly [1-phenyl-2-(2-fluorenyl)acetylene] (3c) and poly[1-phenyl-2-(2-phenanthryl)acetylene] (3d). The desilylated poly(diarylacetylene)s exhibited even higher Po-2 values of 2150 and 1300 barrers, respectively. These desilylated polymers were insoluble in any solvents and showed higher thermal stability than those of 2c and 2d.