2-Chloro-5-iodo-1,1-dimethyl-3,4-diphenyl-1H-silole | 686290-23-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-Chloro-5-iodo-1,1-dimethyl-3,4-diphenyl-1H-silole
• 英文别名: Silacyclopenta-2,4-diene, 2-chloro-5-iodo-1,1-dimethyl-3,4-diphenyl-；2-chloro-5-iodo-1,1-dimethyl-3,4-diphenylsilole
• CAS: 686290-23-3
• 化学式: C₁₈H₁₆ClISi
• 分子量: 422.768
• InChiKey: UUOXFEZNELFWBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-Chloro-5-iodo-1,1-dimethyl-3,4-diphenyl-1H-silole 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 三乙胺 、 zinc(II) chloride 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 2-[(4-iodophenyl)ethynyl]-1,1-dimethyl-3,4-diphenyl-5-(phenylethynyl)silole
  参考文献：
  名称：

  A Controlled, Iterative Synthesis and the Electronic Properties of Oligo[(p-phenyleneethynylene)-alt-(2,5-siloleneethynylene)]s

  摘要：

  An introductory series of conjugated siloleneethynylene co-oligomers has been prepared from a key 2-chloro-5-iodosilole intermediate via site-specific cross-coupling reactions. The tetramer (9) and pentamer (10) both exhibit absorption maxima matching those of the corresponding silole copolymers. Extinction coefficients for the oligomers in this series are large, and in the case of the pentamer (10) the value exceeds 180 000 M-1 cm(-1). The compounds all emit in the visible region with the greatest quantum efficiencies being 8.97 x 10(-2) (monomer) and 2.99 x 10(-2) (pentamer).

  DOI：

  10.1021/ja047983a
• 作为产物：
  描述：

  双(苯基乙炔基)二甲基硅烷 生成 2-Chloro-5-iodo-1,1-dimethyl-3,4-diphenyl-1H-silole
  参考文献：
  名称：

  Synthesis and Electronic Properties of Donor−Acceptor π-Conjugated Siloles

  摘要：

  An efficient method is presented for the synthesis of novel donor-acceptor silole chromophores through selective monohalogenation of 2,5-dimetallosiloles followed by Negishi alkyne cross-coupling reactions. The electronic properties and crystal packing of these new siloles can be controlled through judicious combinations of peripheral functional groups.

  DOI：

  10.1021/ja049758z

文献信息

• Improving Quantum Efficiencies of Siloles and Silole-Derived Butadiene Chromophores through Structural Tuning
  作者：Andrew J. Boydston、Brian L. Pagenkopf

  DOI：10.1002/anie.200461844

  日期：2004.11.26
• A Controlled, Iterative Synthesis and the Electronic Properties of Oligo[(<i>p</i>-phenyleneethynylene)-<i>a</i><i>lt</i>-(2,5-siloleneethynylene)]s
  作者：Andrew J. Boydston、Youshi Yin、Brian L. Pagenkopf

  DOI：10.1021/ja047983a

  日期：2004.8.1

  An introductory series of conjugated siloleneethynylene co-oligomers has been prepared from a key 2-chloro-5-iodosilole intermediate via site-specific cross-coupling reactions. The tetramer (9) and pentamer (10) both exhibit absorption maxima matching those of the corresponding silole copolymers. Extinction coefficients for the oligomers in this series are large, and in the case of the pentamer (10) the value exceeds 180 000 M-1 cm(-1). The compounds all emit in the visible region with the greatest quantum efficiencies being 8.97 x 10(-2) (monomer) and 2.99 x 10(-2) (pentamer).
• Synthesis and Electronic Properties of Donor−Acceptor π-Conjugated Siloles
  作者：A. J. Boydston、Youshi Yin、Brian L. Pagenkopf

  DOI：10.1021/ja049758z

  日期：2004.3.1

  An efficient method is presented for the synthesis of novel donor-acceptor silole chromophores through selective monohalogenation of 2,5-dimetallosiloles followed by Negishi alkyne cross-coupling reactions. The electronic properties and crystal packing of these new siloles can be controlled through judicious combinations of peripheral functional groups.